text:
Ibuprofen
From Wikipedia, the free encyclopedia
Jump to: navigation, search
Ibuprofen
Clinical data
Pronunciation
/ˈaɪbjuːproʊfɛn/, /aɪbjuːˈproʊfən/, EYE-bew-PROH-fən
Trade names
Advil, Motrin, Nurofen, others
Synonyms
isobutylphenylpropionic acid
AHFS/Drugs.com
Monograph
MedlinePlus
a682159
License data
EU EMA: by INN
US FDA: Ibuprofen
Pregnancy
category
AU: C
US: C (Risk not ruled out)
D (US) at ≥30 weeks of gestation, due to the potential for premature closure of the ductus arteriosus
Routes of
administration
by mouth, rectal, topical, and intravenous
ATC code
C01EB16 (WHO) G02CC01 (WHO) M01AE01 (WHO) M02AA13 (WHO) R02AX02 (WHO)
Legal status
Legal status
AU: S2 (Pharmacy only) to Prescription Only (S4)
CA: OTC
UK: General sales list (GSL, OTC)
US: OTC / Rx-only
Pharmacokinetic data
Bioavailability
87–100% (oral), 87% (rectal)[1]
Protein binding
98%[1]
Metabolism
Liver (CYP2C9)[1]
Onset of action
30 min[2]
Biological half-life
1.3–3 h[1]
Excretion
Urine (95%)[1][3]
Identifiers
IUPAC name[show]
(RS)-2-(4-(2-Methylpropyl)phenyl)propanoic acid
CAS Number
15687-27-1 Y
PubChem CID
3672
IUPHAR/BPS
2713
DrugBank
DB01050 Y
ChemSpider
3544 Y
UNII
WK2XYI10QM
KEGG
D00126 Y
ChEBI
CHEBI:5855 Y
ChEMBL
CHEMBL521 Y
PDB ligand
IBP (PDBe, RCSB PDB)
ECHA InfoCard
100.036.152
Chemical and physical data
Formula
C13H18O2
Molar mass
206.29 g/mol
3D model (JSmol)
Interactive image
Chirality
Racemic mixture
Density
1.03 g/ml g/cm3
Melting point
75 to 78 °C (167 to 172 °F)
Boiling point
157 °C (315 °F)
Solubility in water
0.021 mg/mL (20 °C)
SMILES[show]
CC(C)Cc1ccc(cc1)[C@@H](C)C(=O)O
InChI[show]
InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15) Y
Key:HEFNNWSXXWATRW-UHFFFAOYSA-N Y
(verify)
Ibuprofen is a medication in the nonsteroidal anti-inflammatory drug (NSAID) class that is used for treating pain, fever, and inflammation.[4] This includes painful menstrual periods, migraines, and rheumatoid arthritis.[4] About 60% of people improve with any given NSAID, and it is recommended that if one does not work then another should be tried.[5] It may also be used to close a patent ductus arteriosus in a premature baby.[4] It can be used by mouth or intravenously.[4] It typically begins working within an hour.[4]
Common side effects include heartburn and a rash.[4] Compared to other NSAIDs it may have fewer side effects such as gastrointestinal bleeding.[5] It increases the risk of heart failure, kidney failure, and liver failure.[4] At low doses, it does not appear to increase the risk of heart attack; however, at higher doses it may.[5] Ibuprofen can also result in worsened asthma.[5] While it is unclear if it is safe in early pregnancy,[4] it appears to be harmful in later pregnancy and therefore is not recommended.[6] Like other NSAIDs, it works by inhibiting the production of prostaglandins by decreasing the activity of the enzyme cyclooxygenase.[4] Ibuprofen might be a weaker anti-inflammatory than other NSAIDs.[5]
Ibuprofen was discovered in 1961 by Stewart Adams and initially marketed as Brufen.[7] It is available under a number of trade names, including Advil and Motrin.[4][8] It was first marketed in 1969 in the United Kingdom and in the United States in 1974.[4][7] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[9] It is available as a generic medication.[4] The wholesale cost in the developing world is between 0.01 and 0.04 USD per dose.[10] In the United States it costs about 0.05 USD per dose.[4]
Contents
[hide]
1 Medical uses
1.1 Ibuprofen lysine
2 Adverse effects
2.1 Cardiovascular risk
2.2 Skin
2.3 Interactions
2.4 Overdose
2.5 Miscarriage
3 Pharmacology
4 Chemistry
4.1 Stereochemistry
5 History
6 Society and culture
6.1 Marketing
6.2 North America
7 Research
8 References
9 External links
Medical uses[edit]
200-mg ibuprofen tablets
Ibuprofen is used primarily to treat fever (including postimmunisation fever), mild to moderate pain (including pain relief after surgery), painful menstruation, osteoarthritis, dental pain, headaches, and pain from kidney stones. About 60% of people respond to any NSAID; those who do not respond well to a particular one may respond to another.[11]
It is used for inflammatory diseases such as juvenile idiopathic arthritis and rheumatoid arthritis.[12][13] It is also used for pericarditis and patent ductus arteriosus.[14]
Ibuprofen lysine[edit]
In some countries, ibuprofen lysine (the lysine salt of ibuprofen, sometimes called "ibuprofen lysinate") is licensed for treatment of the same conditions as ibuprofen; the lysine salt is used because it is more water-soluble.[15] In 2006, ibuprofen lysine was approved in the US by the Food and Drug Administration (FDA) for closure of patent ductus arteriosus in premature infants weighing between 500 and 1,500 grams (1 and 3 lb), who are no more than 32 weeks gestational age when usual medical management (such as fluid restriction, diuretics, and respiratory support) is not effective.[16]
Adverse effects[edit]
Adverse effects include nausea, dyspepsia, diarrhea, constipation, gastrointestinal ulceration/bleeding, headache, dizziness, rash, salt and fluid retention, and hypertension.[13][17]
Infrequent adverse effects include esophageal ulceration, heart failure, hyperkalemia, renal impairment, confusion, and bronchospasm.[13] Ibuprofen can exacerbate asthma, sometimes fatally.[18]
Ibuprofen may be quantified in blood, plasma, or serum to demonstrate the presence of the drug in a person having experienced an anaphylactic reaction, confirm a diagnosis of poisoning in hospitalized patients, or assist in a medicolegal death investigation. A monograph relating ibuprofen plasma concentration, time since ingestion, and risk of developing renal toxicity in overdose patients has been published.[19]
Cardiovascular risk[edit]
Along with several other NSAIDs, chronic ibuprofen use has been found correlated with risk of hypertension[20] and myocardial infarction (heart attack),[21] particularly among those treated chronically using high doses. In older hypertensive patients treated with hydrochlorothiazide, ibuprofen at a high daily dose was found to significantly increase systolic blood pressure.[22] On 9 July 2015, the US FDA toughened warnings of increased heart attack and stroke risk associated with ibuprofen and related NSAIDs; the NSAID aspirin is not included in this warning.[23]
Skin[edit]
Along with other NSAIDs, ibuprofen has been associated with the onset of bullous pemphigoid or pemphigoid-like blistering.[24] As with other NSAIDs, ibuprofen has been reported to be a photosensitising agent,[25] but it is considered a weak photosensitising agent compared to other members of the 2-arylpropionic acid class. Like other NSAIDs, ibuprofen is an extremely rare cause of the autoimmune disease Stevens–Johnson syndrome (SJS).[26][27] Ibuprofen is also an extremely rare cause of Lyell's Syndrome (toxic epidermal necrolysis).[28]
Interactions[edit]
Drinking alcohol when taking ibuprofen may increase the risk of stomach bleeding.[29]
According to the US Food and Drug Administration (FDA), "ibuprofen can interfere with the antiplatelet effect of low-dose aspirin, potentially rendering aspirin less effective when used for cardioprotection and stroke prevention." Allowing sufficient time between doses of ibuprofen and immediate-release (IR) aspirin can avoid this problem. The recommended elapsed time between a dose of ibuprofen and a dose of aspirin depends on which is taken first. It would be 30 minutes or more for ibuprofen taken after IR aspirin, and eight hours or more for ibuprofen taken before IR aspirin. However, this timing cannot be recommended for enteric-coated aspirin. But, if ibuprofen is taken only occasionally without the recommended timing, the reduction of the cardioprotection and stroke prevention of a daily aspirin regimen is minimal.[30]
Overdose[edit]
Ibuprofen overdose has become common since it was licensed for OTC use. Many overdose experiences are reported in the medical literature, although the frequency of life-threatening complications from ibuprofen overdose is low.[31] Human response in cases of overdose ranges from absence of symptoms to fatal outcome despite intensive-care treatment. Most symptoms are an excess of the pharmacological action of ibuprofen, and include abdominal pain, nausea, vomiting, drowsiness, dizziness, headache, tinnitus, and nystagmus. Rarely, more severe symptoms, such as gastrointestinal bleeding, seizures, metabolic acidosis, hyperkalaemia, hypotension, bradycardia, tachycardia, atrial fibrillation, coma, liver dysfunction, acute renal failure, cyanosis, respiratory depression, and cardiac arrest have been reported.[32] The severity of symptoms varies with the ingested dose and the time elapsed; however, individual sensitivity also plays an important role. Generally, the symptoms observed with an overdose of ibuprofen are similar to the symptoms caused by overdoses of other NSAIDs.
Correlation between severity of symptoms and measured ibuprofen plasma levels is weak. Toxic effects are unlikely at doses below 100 mg/kg, but can be severe above 400 mg/kg (around 150 tablets of 200 mg units for an average man);[33] however, large doses do not indicate the clinical course is likely to be lethal.[34] A precise lethal dose is difficult to determine, as it may vary with age, weight, and concomitant conditions of the individual person.
Therapy is largely symptomatic. In cases presenting early, gastric decontamination is recommended. This is achieved using activated charcoal; charcoal adsorbs the drug before it can enter the systemic circulation. Gastric lavage is now rarely used, but can be considered if the amount ingested is potentially life-threatening, and it can be performed within 60 minutes of ingestion. Emesis is not recommended.[35] The majority of ibuprofen ingestions produce only mild effects and the management of overdose is straightforward. Standard measures to maintain normal urine output should be instituted and renal function monitored.[33] Since ibuprofen has acidic properties and is also excreted in the urine, forced alkaline diuresis is theoretically beneficial. However, because ibuprofen is highly protein-bound in the blood, renal excretion of unchanged drug is minimal. Forced alkaline diuresis is, therefore, of limited benefit.[36] Symptomatic therapy for hypotension, gastrointestinal bleeding, acidosis, and renal toxicity may be indicated. On occasion, close monitoring in an intensive-care unit for several days is necessary. A patient who survives the acute intoxication usually experiences no late sequelae.
Miscarriage[edit]
A study of pregnant women suggests those taking any type or amount of NSAIDs (including ibuprofen, diclofenac and naproxen) were 2.4 times more likely to miscarry than those not taking the drugs.[37] However, an Israeli study found no increased risk of miscarriage in the group of mothers using NSAIDs.[38]
Pharmacology[edit]
NSAIDs such as ibuprofen work by inhibiting the cyclooxygenase (COX) enzymes, which convert arachidonic acid to prostaglandin H2 (PGH2). PGH2, in turn, is converted by other enzymes to several other prostaglandins (which are mediators of pain, inflammation, and fever) and to thromboxane A2 (which stimulates platelet aggregation, leading to the formation of blood clots).
Like aspirin and indomethacin, ibuprofen is a nonselective COX inhibitor, in that it inhibits two isoforms of cyclooxygenase, COX-1 and COX-2. The analgesic, antipyretic, and anti-inflammatory activity of NSAIDs appears to operate mainly through inhibition of COX-2, which decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever, and swelling. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Inhibition of COX-1 instead would be responsible for unwanted effects on the gastrointestinal tract.[39] However, the role of the individual COX isoforms in the analgesic, anti-inflammatory, and gastric damage effects of NSAIDs is uncertain and different compounds cause different degrees of analgesia and gastric damage.[40]
Ibuprofen is administered as a racemic mixture. The R-enantiomer undergoes extensive interconversion to the S-enantiomer in vivo. The S-enantiomer is believed to be the more pharmacologically active enantiomer.[41] The R-enantiomer is converted through a series of three main enzymes. These enzymes include acyl-CoA-synthetase, which converts the R-enantiomer to (-)-R-ibuprofen I-CoA; 2-arylpropionyl-CoA epimerase, which converts (-)-R-ibuprofen I-CoA to (+)-S-Ibuprofen I-CoA; and hydrolase, which converts (+)-S-ibuprofen I-CoA to the S-enantiomer.[28] In addition to the conversion of ibuprofen to the S-enantiomer, the body can metabolize ibuprofen to several other compounds, including numerous hydroxyl, carboxyl and glucuronyl metabolites. Virtually all of these have no pharmacological effects.[28]
Chemistry[edit]
Ibuprofen is practically insoluble in water, but very soluble in most organic solvents like ethanol (66.18 g/100mL at 40°C for 90% EtOH), methanol, acetone and dichloromethane.[42]
The original synthesis of ibuprofen by the Boots Group started with the compound 2-methylpropylbenzene. The synthesis took six steps. A modern, greener technique for the synthesis involves only three steps.[43]
Stereochemistry[edit]
(R)-ibuprofen (S)-ibuprofen
It is an optically active compound with both S and R-isomers, of which the S (dextrorotatory) isomer is the more biologically active; this isomer has also been isolated and used medically (see dexibuprofen for details).[42]
Ibuprofen is produced industrially as a racemate. The compound, like other 2-arylpropionate derivatives (including ketoprofen, flurbiprofen, naproxen, etc.), does contain a stereocenter in the α-position of the propionate moiety. So two enantiomers of ibuprofen occur, with the potential for different biological effects and metabolism for each enantiomer. Indeed, the (S)-(+)-ibuprofen (dexibuprofen) was found to be the active form both in vitro and in vivo.[citation needed]
An isomerase (alpha-methylacyl-CoA racemase) converts (R)-ibuprofen to the active (S)-enantiomer.[44][45][46]
History[edit]
Ibuprofen was derived from propionic acid by the research arm of Boots Group during the 1960s.[47] Its discovery was the result of research during the 1950s and 1960s to find a safer alternative to aspirin.[7][48] It was discovered by a team led by Stewart Adams and the patent application was filed in 1961.[7] Adams initially tested the drug as treatment for his hangover.[49] The drug was launched as a treatment for rheumatoid arthritis in the United Kingdom in 1969, and in the United States in 1974. Later, in 1983 and 1984, it became the first NSAID (other than aspirin) to be available over the counter (OTC) in these two countries.[7][48] Dr. Adams was subsequently awarded an OBE in 1987. Boots was awarded the Queen's Award for Technical Achievement for the development of the drug in 1987.[7]
Society and culture[edit]
Marketing[edit]
See also: Ibuprofen brand names
A bottle of generic ibuprofen
Ibuprofen was made available under prescription in the United Kingdom in 1969, and in the United States in 1974.[50] In the years since, the good tolerability profile, along with extensive experience in the population, as well as in so-called phase-IV trials (postapproval studies), have resulted in the availability of ibuprofen OTC in pharmacies worldwide, as well as in supermarkets and other general retailers.[citation needed] Ibuprofen is its INN, BAN, AAN and USAN approved name. Advil is manufactured by Pfizer and has been on the market since 1984.
North America[edit]
Ibuprofen is commonly available in the United States up to the FDA's 1984 dose limit OTC, rarely used higher by prescription.[51] In 2009, the first injectable formulation of ibuprofen was approved in the United States, under the trade name Caldolor.[52][53]
Research[edit]
This section needs to be updated. Please update this article to reflect recent events or newly available information.
Last update: PMID 25227314, PMID 25644018 (November 2017)
Ibuprofen is sometimes used for the treatment of acne because of its anti-inflammatory properties, and has been sold in Japan in topical form for adult acne.[54][55] As with other NSAIDs, ibuprofen may be useful in the treatment of severe orthostatic hypotension (low blood pressure when standing up).[56] In some studies, ibuprofen showed superior results compared with a placebo in the prevention of Alzheimer's disease, when given in low doses over a long time.[57][58]
Ibuprofen has been associated with a lower risk of Parkinson's disease, and may delay or prevent it. Aspirin, other NSAIDs, and paracetamol (acetaminophen) had no effect on the risk for Parkinson's.[59] In March 2011, researchers at Harvard Medical School announced in Neurology that ibuprofen had a neuroprotective effect against the risk of developing Parkinson's disease.[60][61][62] People regularly consuming ibuprofen were reported to have a 38% lower risk of developing Parkinson's disease, but no such effect was found for other pain relievers, such as aspirin and paracetamol. Use of ibuprofen to lower the risk of Parkinson's disease in the general population would not be problem-free, given the possibility of adverse effects on the urinary and digestive systems.[63]
Some dietary supplements might be dangerous to take along with ibuprofen and other NSAIDs, but as of 2016 more research needs to be conducted to be certain. These supplements include those that can prevent platelet aggregation, including ginkgo, garlic, ginger, bilberry, dong quai, feverfew, ginseng, turmeric, meadowsweet and willow, those that contain coumarin, including chamomile, horse chestnut, fenugreek and red clover, and those that increase the risk of bleeding, like tamarind.[64]
References[edit]
^ Jump up to: a b c d e Davies, NM (February 1998). "Clinical pharmacokinetics of ibuprofen. The first 30 years". Clinical Pharmacokinetics. 34 (2): 101–54. doi:10.2165/00003088-199834020-00002. PMID 9515184.
Jump up ^ "ibuprofen". Archived from the original on 13 January 2015. Retrieved 31 January 2015.
Jump up ^ "Brufen Tablets And Syrup" (PDF). Therapeutic Goods Administration. 31 July 2012. Archived from the original on 20 August 2016. Retrieved 8 May 2014.
^ Jump up to: a b c d e f g h i j k l m "Ibuprofen". The American Society of Health-System Pharmacists. Archived from the original on 8 September 2017. Retrieved 12 October 2016.
^ Jump up to: a b c d e Bnf : march 2014-september 2014 (2014 ed.). London: British Medical Assn. 2014. pp. 686–688. ISBN 0857110861.
Jump up ^ "Ibuprofen Pregnancy and Breastfeeding Warnings". Drugs.com. Archived from the original on 8 September 2017. Retrieved 22 May 2016.
^ Jump up to: a b c d e f Halford, GM; Lordkipanidzé, M; Watson, SP (2012). "50th anniversary of the discovery of ibuprofen: an interview with Dr Stewart Adams". Platelets. 23 (6): 415–22. doi:10.3109/09537104.2011.632032. PMID 22098129.
Jump up ^ "Chemistry in your cupboard | Nurofen". Archived from the original on 5 June 2014.
Jump up ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
Jump up ^ "Ibuprofen". Retrieved 12 January 2016.
Jump up ^ "10.1.1 Non-steroidal anti-inflammatory drugs". : British National Formulary. Archived from the original on 17 November 2016. Retrieved 13 April 2016.
Jump up ^ Joint Formulary Committee (2013). British National Formulary (BNF) (65 ed.). London, UK: Pharmaceutical Press. pp. 665, 671. ISBN 978-0-85711-084-8.
^ Jump up to: a b c Rossi, S, ed. (2013). Australian Medicines Handbook (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. ISBN 978-0-9805790-9-3.
Jump up ^ "Ibuprofen". The American Society of Health-System Pharmacists. Archived from the original on 23 December 2010. Retrieved 3 April 2011.
Jump up ^ Beaver, WT (2003). "Review of the analgesic efficacy of ibuprofen". Int J Clin Pract Suppl (135): 13–7. PMID 12723741.
Jump up ^ Fanos, V; Antonucci, R; Zaffanello, M (2010). "Ibuprofen and acute kidney injury in the newborn". Turk. J. Pediatr. 52 (3): 231–8. PMID 20718179.
Jump up ^ Castellsague, Dr Jordi; Riera-Guardia, Nuria; Calingaert, Brian; Varas-Lorenzo, Cristina; Fourrier-Reglat, Annie; Nicotra, Federica; Sturkenboom, Miriam; Perez-Gutthann, Susana; Project, Safety of Non-Steroidal Anti-Inflammatory Drugs (SOS) (2012-12-13). "Individual NSAIDs and Upper Gastrointestinal Complications". Drug Safety. 35 (12): 1127–1146. doi:10.1007/BF03261999. ISSN 0114-5916. PMC 3714137  . PMID 23137151.
Jump up ^ Ayres, JG; Fleming, D; Whittington, R (9 May 1987). "Asthma death due to ibuprofen". Lancet. 1 (8541): 1082. doi:10.1016/S0140-6736(87)90499-5. PMID 2883408.
Jump up ^ Baselt, R (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, USA: Biomedical Publications. pp. 758–761.
Jump up ^ Forman, JP; Stampfer, MJ; Curhan, GC (September 2005). "Non-narcotic analgesic dose and risk of incident hypertension in US women". Hypertension. 46 (3): 500–7. doi:10.1161/01.HYP.0000177437.07240.70. PMID 16103274.
Jump up ^ Hippisley-Cox, J; Coupland, C (11 June 2005). "Risk of myocardial infarction in patients taking cyclo-oxygenase-2 inhibitors or conventional non-steroidal anti-inflammatory drugs: population based nested case-control analysis". British Medical Journal. 330 (7504): 1366. doi:10.1136/bmj.330.7504.1366. PMC 558288  . PMID 15947398.
Jump up ^ Gurwitz, JH; Everitt, DE; Monane, M; Glynn, RJ; Choodnovskiy, I; Beaudet, MP; Avorn, J (March 1996). "The impact of ibuprofen on the efficacy of antihypertensive treatment with hydrochlorothiazide in elderly persons". The Journals of Gerontology. Series A, Biological Sciences and Medical sciences. 51 (2): M74–9. doi:10.1093/gerona/51A.2.M74. PMID 8612107.
Jump up ^ Staff (9 July 2015). "FDA Strengthens Warning of Heart Attack and Stroke Risk for Non-Steroidal Anti-Inflammatory Drugs". FDA. Archived from the original on 11 July 2015. Retrieved 9 July 2015.
Jump up ^ Chan, LS (12 June 2014). Hall, R; Vinson, RP; Nunley, JR; Gelfand, JM; Elston, DM, eds. "Bullous Pemphigoid Clinical Presentation". Medscape Reference. United States: WebMD. Archived from the original on 10 November 2011.
Jump up ^ Bergner, T; Przybilla, B (January 1992). "Photosensitization caused by ibuprofen". Journal of the American Academy of Dermatology. 26 (1): 114–6. doi:10.1016/0190-9622(92)70018-b. PMID 1531054.
Jump up ^ Raksha, MP; Marfatia, YS (2008). "Clinical study of cutaneous drug eruptions in 200 patients". Indian J Dermatol Venereol Leprol. 74 (1): 80. doi:10.4103/0378-6323.38431. PMID 18193504.
Jump up ^ Ward, KE; Archambault, R; Mersfelder, TL (1 February 2010). "Severe adverse skin reactions to nonsteroidal antiinflammatory drugs: A review of the literature". American Journal of Health-System Pharmacy. 67 (3): 206–13. doi:10.2146/ajhp080603. PMID 20101062.
^ Jump up to: a b c Rainsford, K.D. (2012). Ibuprofen: Pharmacology, Therapeutics and Side Effects. London: Springer.
Jump up ^ "Ibuprofen". Drugs.com. Archived from the original on 6 August 2011.
Jump up ^ "Information for Healthcare Professionals: Concomitant Use of Ibuprofen and Aspirin". U.S. Food and Drug Administration. September 2006. Archived from the original on 13 November 2010. Retrieved 22 November 2010.
Jump up ^ McElwee, NE; Veltri, JC; Bradford, DC; Rollins, DE (June 1990). "A prospective, population-based study of acute ibuprofen overdose: complications are rare and routine serum levels not warranted". Annals of Emergency Medicine. 19 (6): 657–62. doi:10.1016/S0196-0644(05)82471-0. PMID 2188537.
Jump up ^ Vale, JA; Meredith, TJ (January 1986). "Acute poisoning due to non-steroidal anti-inflammatory drugs. Clinical features and management". Medical Toxicology. 1 (1): 12–31. PMID 3537613.
^ Jump up to: a b Volans, G; Hartley, V; McCrea, S; Monaghan, J (March–April 2003). "Non-opioid analgesic poisoning". Clinical Medicine. 3 (2): 119–23. doi:10.7861/clinmedicine.3-2-119. PMID 12737366.
Jump up ^ Seifert, SA; Bronstein, AC; McGuire, T (2000). "Massive ibuprofen ingestion with survival". Journal of Toxicology. Clinical Toxicology. 38 (1): 55–7. doi:10.1081/clt-100100917. PMID 10696926.
Jump up ^ American Academy Of Clinical Toxico (2004). "Position paper: Ipecac syrup". Journal of Toxicology. Clinical Toxicology. 42 (2): 133–143. doi:10.1081/CLT-120037421. PMID 15214617.
Jump up ^ Hall, AH; Smolinske, SC; Conrad, FL; Wruk, KM; Kulig, KW; Dwelle, TL; Rumack, BH (November 1986). "Ibuprofen overdose: 126 cases". Annals of Emergency Medicine. 15 (11): 1308–13. doi:10.1016/S0196-0644(86)80617-5. PMID 3777588.
Jump up ^ Verma, P; Clark, CA; Spitzer, KA; Laskin, CA; Ray, J; Koren, G (July 2012). "Use of non-aspirin NSAIDs during pregnancy may increase the risk of spontaneous abortion". Evidence-Based Nursing. 15 (3): 76–7. doi:10.1136/ebnurs-2011-100439. PMID 22411163.
Jump up ^ Daniel, S; Koren, G; Lunenfeld, E; Bilenko, N; Ratzon, R; Levy, A (March 2014). "Fetal exposure to nonsteroidal anti-inflammatory drugs and spontaneous abortions". Canadian Medical Association Journal. 186 (5): E177–82. doi:10.1503/cmaj.130605. PMC 3956584  . PMID 24491470.
Jump up ^ Rao, P; Knaus, EE (20 September 2008). "Evolution of nonsteroidal anti-inflammatory drugs (NSAIDs): cyclooxygenase (COX) inhibition and beyond". Journal of Pharmacy & Pharmaceutical Sciences. 11 (2): 81s–110s. PMID 19203472.
Jump up ^ Kakuta, H; Zheng, X; Oda, H; Harada, S; Sugimoto, Y; Sasaki, K; Tai, A (24 April 2008). "Cyclooxygenase-1-selective inhibitors are attractive candidates for analgesics that do not cause gastric damage. design and in vitro/in vivo evaluation of a benzamide-type cyclooxygenase-1 selective inhibitor". Journal of Medicinal Chemistry. 51 (8): 2400–11. doi:10.1021/jm701191z. PMID 18363350.
Jump up ^ "Ibuprofen: Pharmacology: Mechanism of Action. Updated on September 16, 2013". DrugBank, Open Data Drug & Drug Target Database. Archived from the original on 21 July 2014. Retrieved 24 July 2014.
^ Jump up to: a b Brayfield, A, ed. (14 January 2014). "Ibuprofen". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 26 June 2014.
Jump up ^ "The Synthesis of Ibuprofen". Royal Society of Chemistry. Archived from the original on 18 April 2016. Retrieved 14 November 2016.
Jump up ^ Tracy, TS; Hall, SD (March–April 1992). "Metabolic inversion of (R)-ibuprofen. Epimerization and hydrolysis of ibuprofenyl-coenzyme A". Drug metabolism and disposition: the biological fate of chemicals. 20 (2): 322–7. PMID 1352228.
Jump up ^ Chen, CS; Shieh, WR; Lu, PH; Harriman, S; Chen, CY (12 July 1991). "Metabolic stereoisomeric inversion of ibuprofen in mammals". Biochimica et Biophysica Acta. 1078 (3): 411–7. doi:10.1016/0167-4838(91)90164-U. PMID 1859831.
Jump up ^ Reichel, C; Brugger, R; Bang, H; Geisslinger, G; Brune, K (April 1997). "Molecular cloning and expression of a 2-arylpropionyl-coenzyme A epimerase: a key enzyme in the inversion metabolism of ibuprofen". Molecular Pharmacology. 51 (4): 576–82. PMID 9106621.
Jump up ^ Adams, SS (April 1992). "The propionic acids: a personal perspective". Journal of Clinical Pharmacology. 32 (4): 317–23. doi:10.1002/j.1552-4604.1992.tb03842.x. PMID 1569234.
^ Jump up to: a b Rainsford, KD (April 2003). "Discovery, mechanisms of action and safety of ibuprofen". International Journal of Clinical Practice. Supplement (135): 3–8. PMID 12723739.
Jump up ^ Lambert, Victoria (8 October 2007). "Dr Stewart Adams: 'I tested ibuprofen on my hangover'". The Daily Telegraph. UK. Archived from the original on 18 November 2015. Retrieved 23 October 2015.
Jump up ^ "Written submission to the NDAC meeting on risks of NSAIDs presented by the International Ibuprofen Foundation". International Ibuprofen Foundation. August 2002. Archived from the original on 15 August 2013. Retrieved 20 March 2014.
Jump up ^ "Ibuprofen". U.S. Food and Drug Administration (FDA). Archived from the original on 16 September 2011.
Jump up ^ "Drug Approval Package: Caldolor (Ibuprofen) NDA #022348". U.S. Food and Drug Administration (FDA). 11 March 2010. Archived from the original on 19 October 2012.
Jump up ^ "FDA Approves Injectable Form of Ibuprofen" (Press release). U.S. Food and Drug Administration (FDA). 11 June 2009. Archived from the original on 18 October 2012.
Jump up ^ Wong, RC; Kang, S; Heezen, JL; Voorhees, JJ; Ellis, CN (December 1984). "Oral ibuprofen and tetracycline for the treatment of acne vulgaris". Journal of the American Academy of Dermatology. 11 (6): 1076–81. doi:10.1016/S0190-9622(84)80192-9. PMID 6239884.
Jump up ^ &Na; (25 March 2006). "In Japan, an OTC ibuprofen ointment (Fukidia) for alleviating adult acne has been launched". Inpharma. Adis. 1 (1530): 18. doi:10.2165/00128413-200615300-00043. ISSN 1173-8324.
Jump up ^ Zawada ET, Jr (May 1982). "Renal consequences of nonsteroidal antiinflammatory drugs". Postgraduate Medicine. 71 (5): 223–30. PMID 7041104.
Jump up ^ Townsend, KP; Praticò, D (October 2005). "Novel therapeutic opportunities for Alzheimer's disease: focus on nonsteroidal anti-inflammatory drugs". FASEB Journal. 19 (12): 1592–601. doi:10.1096/fj.04-3620rev. PMID 16195368.
Jump up ^ Vlad, SC; Miller, DR; Kowall, NW; Felson, DT (6 May 2008). "Protective effects of NSAIDs on the development of Alzheimer disease". Neurology. 70 (19): 1672–7. doi:10.1212/01.wnl.0000311269.57716.63. PMC 2758242  . PMID 18458226.
Jump up ^ Chen, H; Jacobs, E; Schwarzschild, MA; McCullough, ML; Calle, EE; Thun, MJ; Ascherio, A (December 2005). "Nonsteroidal antiinflammatory drug use and the risk for Parkinson's disease". Annals of Neurology. 58 (6): 963–7. doi:10.1002/ana.20682. PMID 16240369.
Jump up ^ Bower, JH; Ritz, B (8 March 2011). "Is the answer for Parkinson disease already in the medicine cabinet?: Unfortunately not". Neurology. 76 (10): 854–5. doi:10.1212/WNL.0b013e31820f2e7a. PMID 21368280.
Jump up ^ Gao, X; Chen, H; Schwarzschild, MA; Ascherio, A (8 March 2011). "Use of ibuprofen and risk of Parkinson disease". Neurology. 76 (10): 863–9. doi:10.1212/WNL.0b013e31820f2d79. PMC 3059148  . PMID 21368281.
Jump up ^ McSharry, C (May 2011). "Parkinson disease: Could over-the-counter treatment protect against Parkinson disease?". Nature Reviews. Neurology. 7 (5): 244. doi:10.1038/nrneurol.2011.49. PMID 21555992.
Jump up ^ Gleason, JM; Slezak, JM; Jung, H; Reynolds, K; Van den Eeden, SK; Haque, R; Quinn, VP; Loo, RK; Jacobsen, SJ (April 2011). "Regular nonsteroidal anti-inflammatory drug use and erectile dysfunction". The Journal of Urology. 185 (4): 1388–93. doi:10.1016/j.juro.2010.11.092. PMID 21334642.
Jump up ^ Abebe, W. (2002-12-01). "Herbal medication: potential for adverse interactions with analgesic drugs". Journal of Clinical Pharmacy and Therapeutics. 27 (6): 391–401. doi:10.1046/j.1365-2710.2002.00444.x. ISSN 0269-4727. PMID 12472978.
External links[edit]
Wikimedia Commons has media related to Ibuprofen.
U.S. National Library of Medicine: MedlinePlus Drug Information: Ibuprofen
University of Bristol chemistry department page on Ibuprofen
U.S. National Library of Medicine: Drug Information Portal – Ibuprofen
[show]
v
t
e
Nonsteroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
Pyrazolones /
Pyrazolidines
Aminophenazone
Ampyrone
Azapropazone
Clofezone
Difenamizole
Famprofazone
Feprazone
Kebuzone
Metamizole
Mofebutazone
Morazone
Nifenazone
Oxyphenbutazone
Phenazone
Phenylbutazone
Propyphenazone
Sulfinpyrazone
Suxibuzone‡
Salicylates
Aspirin (acetylsalicylic acid)#
Aloxiprin
Benorylate
Carbasalate calcium
Diflunisal
Dipyrocetyl
Ethenzamide
Guacetisal
Magnesium salicylate
Methyl salicylate
Salsalate
Salicin
Salicylamide
Salicylic acid (salicylate)
Sodium salicylate
Acetic acid derivatives
and related substances
Aceclofenac
Acemetacin
Alclofenac
Amfenac
Bendazac
Bromfenac
Bumadizone
Bufexamac
Diclofenac
Difenpiramide
Etodolac
Felbinac
Fenclozic acid
Fentiazac
Indometacin
Indometacin farnesil
Isoxepac
Ketorolac
Lonazolac
Oxametacin
Prodolic acid
Proglumetacin
Sulindac
Tiopinac
Tolmetin
Zomepirac†
Oxicams
Ampiroxicam
Droxicam
Isoxicam
Lornoxicam
Meloxicam
Piroxicam
Tenoxicam
Propionic acid derivatives
(profens)
Alminoprofen
Benoxaprofen†
Carprofen‡
Dexibuprofen
Dexketoprofen
Fenbufen
Fenoprofen
Flunoxaprofen
Flurbiprofen
Ibuprofen#
Ibuproxam
Indoprofen†
Ketoprofen
Loxoprofen
Miroprofen
Naproxen
Oxaprozin
Pirprofen
Suprofen
Tarenflurbil
Tepoxalin‡
Tiaprofenic acid
Vedaprofen‡
COX-inhibiting nitric oxide donator: Naproxcinod
N-Arylanthranilic acids
(fenamates)
Azapropazone
Clonixin
Etofenamate
Flufenamic acid
Flunixin
Meclofenamic acid
Mefenamic acid
Morniflumate
Niflumic acid
Tolfenamic acid
Flutiazin
Coxibs
Apricoxib
Celecoxib
Cimicoxib‡
Deracoxib‡
Etoricoxib
Firocoxib‡
Lumiracoxib†
Mavacoxib‡
Parecoxib
Robenacoxib‡
Rofecoxib†
Valdecoxib†
Other
Aminopropionitrile
Benzydamine
Chondroitin sulfate
Diacerein
Fluproquazone
Glucosamine
Glycosaminoglycan
Hyperforin
Nabumetone
Nimesulide
Oxaceprol
Proquazone
Superoxide dismutase/Orgotein
Tenidap
Items listed in bold indicate initially developed compounds of specific groups. #WHO-EM †Withdrawn drugs. ‡Veterinary use medications.
[show]
v
t
e
Topical products for joint and muscular pain (M02)
Anti-inflammatory
preparations,
non-steroids
Pyrazolidines
Clofezone
Mofebutazone
Oxyphenbutazone
Phenylbutazone
Acetic acid
derivatives
Diclofenac
Fentiazac
Tolmetin
Other
Bendazac
Benzydamine
Bufexamac
Etofenamate
Felbinac
Feprazone
Flurbiprofen
Ibuprofen
Indometacin
Ketoprofen
Meclofenamic acid
Naproxen
Nifenazone
Niflumic acid
Piketoprofen
Piroxicam
Suxibuzone
Capsaicin derivatives
Zucapsaicin
Other
Dimethyl sulfoxide
Idrocilamide
Tolazoline
[show]
v
t
e
Analgesics (N02A, N02B)
Opioids
Opiates/opium
Codeine# (+paracetamol, +aspirin)
Morphine# (+naltrexone)
Opium
Laudanum
Paregoric
Semisynthetic
Acetyldihydrocodeine
Benzylmorphine
Buprenorphine (+naloxone)
Desomorphine
Diamorphine (heroin)
Dihydrocodeine (+paracetamol)
Dihydromorphine
Ethylmorphine
Hydrocodone (+paracetamol, +ibuprofen, +aspirin)
Hydromorphinol
Hydromorphone
Nicocodeine
Nicodicodeine
Nicomorphine
Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone)
Oxymorphone
Thebacon
Synthetic
Alfentanil
Alphaprodine
Anileridine
Butorphanol
Carfentanil
Dextromoramide
Dextropropoxyphene
Dezocine
Fentanyl# (+fluanisone)
Ketobemidone
Levorphanol
Lofentanil
Meptazinol
Methadone#
Nalbuphine
NFEPP
Pentazocine
Pethidine (meperidine)
Phenadoxone
Phenazocine
Piminodine
Piritramide
Propiram
Remifentanil
Sufentanil
Tapentadol
Tilidine
Tramadol
Paracetamol-type
Acetanilide‡
Bucetin‡
Butacetin‡
Paracetamol (acetaminophen)#
Parapropamol‡
Phenacetin‡
Propacetamol‡
NSAIDs
Propionates
Fenoprofen
Flurbiprofen
Ibuprofen#
Ketoprofen
Naproxen
Oxaprozin
Oxicams
Meloxicam
Piroxicam
Acetates
Diclofenac
Indometacin
Ketorolac
Nabumetone
Sulindac
Tolmetin
COX-2 inhibitors
Celecoxib
Etoricoxib
Lumiracoxib
Parecoxib
Rofecoxib ‡
Valdecoxib ‡
Fenamates
Meclofenamic acid
Mefenamic acid
Salicylates
Aspirin (acetylsalicylic acid)# (+paracetamol/caffeine)
Benorylate
Diflunisal
Ethenzamide
Magnesium salicylate
Salicin
Salicylamide
Salsalate
Wintergreen (methyl salicylate)
Pyrazolones
Aminophenazone‡
Ampyrone
Metamizole (dipyrone)
Nifenazone
Phenazone
Propyphenazone (+paracetamol/caffeine)
Others
Glafenine
Cannabinoids
Cannabidiol
Cannabis
Nabilone
Nabiximols
Tetrahydrocannabinol (dronabinol)
Ion channel
modulators
Calcium blockers
Gabapentin
Gabapentin enacarbil
Pregabalin
Ziconotide
Sodium blockers
Carbamazepine
Lacosamide
Local anesthetics (e.g., cocaine, lidocaine)
Mexiletine
Nefopam
Tricyclic antidepressants (e.g., amitriptyline#)
Nav1.7/1.8-selective: DSP-2230§
Funapide§
PF-05089771§
Raxatrigine§
Potassium openers
Flupirtine
Myorelaxants
Carisoprodol
Chlorzoxazone
Cyclobenzaprine
Mephenoxalone
Methocarbamol
Orphenadrine
Others
Analgesic adjuvant
Analgecine
Camphor
Capsaicin
Clonidine
Ketamine
Menthol
Methoxyflurane
Nefopam
Proglumide
Tricyclic antidepressants (e.g., amitriptyline#)
#WHO-EM
‡Withdrawn from market
Clinical trials:
†Phase III
§Never to phase III
[show]
v
t
e
Acne-treating agents (D10)
Antibacterial
Azelaic acid
Benzoyl peroxide#
8-Hydroxyquinoline
Blue light therapy
Tea tree oil
Keratolytic
Glycolic acid
Salicylic acid#
Sulfur
Benzoyl peroxide#
Anti-inflammatory
Nicotinamide
Ibuprofen#
Aspirin#
Red light therapy
Antibiotics
Clindamycin
Dapsone
Erythromycin
Sulfacetamide
Tetracyclines (Lymecycline
Minocycline
Doxycycline)
Hormonal
Antiandrogens
Bicalutamide
Cyproterone acetate
Drospirenone
Flutamide
Spironolactone)
Estrogens
Estradiol
Ethinylestradiol
Retinoids
Adapalene
Isotretinoin
Motretinide
Tazarotene
Tretinoin
Other
Benzamycin
Epristeride
Mesulfen
Pelretin
Stridex
Tioxolone
Combinations
Adapalene/benzoyl peroxide
Benzoyl peroxide/clindamycin
Clindamycin/tretinoin
Erythromycin/isotretinoin
Sulfacetamide/sulfur
#WHO-EM
‡Withdrawn from market
Clinical trials:
†Phase III
§Never to phase III
[show]
v
t
e
Prolactin inhibitors and anti-inflammatory products for vaginal administration (G02CB–G02CC)
Prolactin inhibitors
Bromocriptine
Cabergoline
Lisuride
Metergoline
Quinagolide
Terguride
Anti-inflammatory products
for vaginal administration
Benzydamine
Ibuprofen
Flunoxaprofen
Naproxen
[show]
v
t
e
Prostanoid signaling modulators
Receptor
(ligands)
DP (D2)
DP1
Agonists: Prostaglandin D2
Treprostinil
Antagonists: Asapiprant
Laropiprant
Vidupiprant
DP2
Agonists: Indometacin
Prostaglandin D2
Antagonists: ADC-3680
AZD-1981
Bay U3405
Fevipiprant
MK-1029
MK-7246
QAV-680
Ramatroban
Setipiprant
Timapiprant
TM30089
Vidupiprant
EP (E2)
EP1
Agonists: Beraprost
Enprostil
Iloprost (ciloprost)
Latanoprost
Lubiprostone
Misoprostol
Prostaglandin E1 (alprostadil)
Prostaglandin E2 (dinoprostone)
Sulprostone
Antagonists: AH-6809
ONO-8130
SC-19220
SC-51089
SC-51322
EP2
Agonists: Butaprost
Misoprostol
Prostaglandin E1 (alprostadil)
Prostaglandin E2 (dinoprostone)
Treprostinil
Antagonists: AH-6809
PF-04418948
TG 4-155
EP3
Agonists: Beraprost
Carbacyclin
Cicaprost
Enprostil
Iloprost (ciloprost)
Isocarbacyclin
Latanoprost
Misoprostol
Prostaglandin D2
Prostaglandin E1 (alprostadil)
Prostaglandin E2 (dinoprostone)
Remiprostol
Sulprostone
Antagonists: L-798106
EP4
Agonists: Lubiprostone
Misoprostol
Prostaglandin E1 (alprostadil)
Prostaglandin E2 (dinoprostone)
TCS-2510
Antagonists: Grapiprant
GW-627368
L-161982
ONO-AE3-208
Unsorted
Agonists: 16,16-Dimethyl Prostaglandin E2
Aganepag
Carboprost
Evatanepag
Gemeprost
Nocloprost
Omidenepag
Prostaglandin F2α (dinoprost)
Simenepag
Taprenepag
FP (F2α)
Agonists: Alfaprostol
Bimatoprost
Carboprost
Cloprostenol
Enprostil
Fluprostenol
Latanoprost
Prostaglandin D2
Prostaglandin F2α (dinoprost)
Sulotroban
Tafluprost
Travoprost
Unoprostone
IP (I2)
Agonists: ACT-333679
AFP-07
Beraprost
BMY-45778
Carbacyclin
Cicaprost
Iloprost (ciloprost)
Isocarbacyclin
MRE-269
NS-304
Prostacyclin (prostaglandin I2, epoprostenol)
Prostaglandin E1 (alprostadil)
Ralinepag
Selexipag
Taprostene
TRA-418
Treprostinil
Antagonists: RO1138452
TP (TXA2)
Agonists: Carbocyclic thromboxane A2
I-BOP
Thromboxane A2
U-46619
Vapiprost
Antagonists: 12-HETE
13-APA
AA-2414
Argatroban
Bay U3405
BMS-180,291
Daltroban
Domitroban
EP-045
GR-32191
ICI-185282
ICI-192605
Ifetroban
Imitrodast
L-655240
L-670596
Linotroban
Mipitroban
ONO-3708
ONO-11120
Picotamide
Pinane thromboxane A2
Ramatroban
Ridogrel
S-145
Samixogrel
Seratrodast
SQ-28,668
SQ-29,548
Sulotroban
Terbogrel
Terutroban
TRA-418
Unsorted
Arbaprostil
Ataprost
Ciprostene
Clinprost
Cobiprostone
Delprostenate
Deprostil
Dimoxaprost
Doxaprost
Ecraprost
Eganoprost
Enisoprost
Eptaloprost
Esuberaprost
Etiproston
Fenprostalene
Flunoprost
Froxiprost
Lanproston
Limaprost
Luprostiol
Meteneprost
Mexiprostil
Naxaprostene
Nileprost
Nocloprost
Ornoprostil
Oxoprostol
Penprostene
Pimilprost
Piriprost
Posaraprost
Prostalene
Rioprostil
Rivenprost
Rosaprostol
Spiriprostil
Tiaprost
Tilsuprost
Tiprostanide
Trimoprostil
Viprostol
Enzyme
(inhibitors)
COX
(PTGS)
Salicylic acids: Aloxiprin
Aspirin (acetylsalicylic acid)
Benorilate (benorylate)
Carbasalate calcium
Diflusinal
Dipyrocetyl
Ethenzamide
Guacetisal
Magnesium salicylate
Mesalazine (5-aminosalicylic acid)
Methyl salicylate
Salacetamide
Salicin
Salicylamide
Salicylate (salicylic acid)
Salsalate
Sodium salicylate
Triflusal; Acetic acids: Aceclofenac
Acemetacin
Aclofenac
Amfenac
Alclofenac
Bendazac
Bromfenac
Bufexamac
Bumadizone
Cinmetacin
Clometacin
Diclofenac
Difenpiramide
Etodolac
Felbinac
Fenclofenac
Fentiazac
Glucametacin
Indometacin (indomethacin)
Indometacin farnesil
Ketorolac
Lonazolac
Mofezolac
Nabumetone
Oxametacin
Oxindanac
Proglumetacin
Sulindac
Sulindac sulfide
Tolmetin
Zidometacin
Zomepirac; Propionic acids: Alminoprofen
Benoxaprofen
Bucloxic acid (blucloxate)
Butibufen
Carprofen
Dexibuprofen
Dexindoprofen
Dexketoprofen
Fenbufen
Fenoprofen
Flunoxaprofen
Flurbiprofen
Ibuprofen
Ibuproxam
Indoprofen
Ketoprofen
Loxoprofen
Miroprofen
Naproxen
Naproxcinod
Oxaprozin
Pirprofen
Pranoprofen
Suprofen
Tarenflurbil
Tepoxalin
Tiaprofenic acid (tiaprofenate)
Vedaprofen; Anthranilic acids (fenamic acids): Etofenamic acid (etofenamate)
Floctafenic acid (floctafenate)
Flufenamic acid (flufenamate)
Meclofenamic acid (meclofenamate)
Mefenamic acid (mefenamate)
Morniflumic acid (morniflumate)
Niflumic acid (niflumate)
Talinflumic acid (talinflumate)
Tolfenamic acid (tolfenamate); Pyrazolones: Azapropazone
Dipyrone
Isopyrin
Oxyphenbutazone
Phenylbutazone; Enolic acids (oxicams): Ampiroxicam
Droxicam
Enolicam
Isoxicam
Lornoxicam
Meloxicam
Piroxicam
Tenoxicam; 4-Aminoquinolines: Antrafenine
Floctafenine
Glafenine; Quinazolines: Fluproquazone
Proquazone; Aminonicotinic acids: Clonixeril
Clonixin
Flunixin; Sulfonanilides: Flosulide
Nimesulide; Aminophenols (anilines): Acetanilide
AM-404 (N-arachidonoylaminophenol)
Bucetin
Paracetamol (acetaminophen)
Parapropamol
Phenacetin
Propacetamol; Selective COX-2 inhibitors (coxibs): Apricoxib
Celecoxib
Cimicoxib
Deracoxib
Etoricoxib
Firocoxib
Lumiracoxib
Mavacoxib
Parecoxib
Polmacoxib
Robenacoxib
Rofecoxib
Tilmacoxib
Valdecoxib; Others/unsorted: Anitrazafen
Clobuzarit
Curcumin
DuP-697
FK-3311
Flumizole
FR-122047
Glimepiride
Hyperforin
Itazigrel
L-655240
L-670596
Licofelone
Menatetrenone (vitamin K2)
NCX-466
NCX-4040
NS-398
Pamicogrel
Resveratrol
Romazarit
Rosmarinic acid
Rutecarpine
Satigrel
SC-236
SC-560
SC-58125
Tenidap
Tiflamizole
Timegadine
Trifenagrel
Tropesin
PGD2S
Retinoids
Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
PGES
HQL-79
PGFS
Bimatoprost
PGI2S
Tranylcypromine
TXAS
Camonagrel
Dazmegrel
Dazoxiben
Furegrelate
Isbogrel
Midazogrel
Nafagrel
Nicogrelate
Ozagrel
Picotamide
Pirmagrel
Ridogrel
Rolafagrel
Samixogrel
Terbogrel
U63557A
Others
Precursors: Linoleic acid
γ-Linolenic acid (gamolenic acid)
Dihomo-γ-linolenic acid
Diacylglycerol
Arachidonic acid
Prostaglandin G2
Prostaglandin H2
See also
Receptor/signaling modulators
Leukotriene signaling modulators
Nuclear receptor modulators
[show]
v
t
e
PPAR modulators
PPARα
Agonists: 15-HETE
15-HpETE
Aleglitazar
Aluminium clofibrate
Arachidonic acid
Bezafibrate
Clofibrate
CP-775146
Daidzein
DHEA (prasterone) (in rodents)
Elafibranor
Etomoxir
Fenofibrate
Genistein
Gemfibrozil
GW-7647
Leukotriene B4
LG-101506
LG-100754
Lobeglitazone
Muraglitazar
Oleylethanolamide
Palmitoylethanolamide
Pemafibrate
Perfluorononanoic acid
Perfluorooctanoic acid
Pioglitazone
Saroglitazar
Sodelglitazar
Tesaglitazar
Tetradecylthioacetic acid
Troglitazone
WY-14643
Antagonists: GW-6471
MK-886
PPARδ
Agonists: 15-HETE
15-HpETE
Arachidonic acid
Bezafibrate
Daidzein
Elafibranor
Fonadelpar
Genistein
GW-0742
GW-501516
L-165,041
LG-101506
MBX-8025
Sodelglitazar
Tetradecylthioacetic acid
Antagonists: FH-535
GSK-0660
GSK-3787
PPARγ
Agonists: 5-Oxo-ETE
5-Oxo-15-hydroxy-ETE
15-Deoxy-Δ12,14-prostaglandin J2
15-HETE
15-HpETE
Aleglitazar
Arachidonic acid
Balaglitazone
Berberine
Bezafibrate
Cevoglitazar
Ciglitazone
Daidzein
Darglitazone
Edaglitazone
Efatutazone
Englitazone
Etalocib
Farglitazar
Genistein
GW-1929
Ibuprofen
Imiglitazar
Indeglitazar
LG-100268
LG-100754
LG-101506
Lobeglitazone
Muraglitazar (muroglitazar)
nTZDpa
Naveglitazar
Netoglitazone
Oxeglitazar
Peliglitazar
Pemaglitazar
Perfluorononanoic acid
Pioglitazone
Prostaglandin J2
Ragaglitazar
Reglitazar
Rivoglitazone
Rosiglitazone
RS5444
Saroglitazar
Sipoglitazar
Sodelglitazar
Telmisartan
Tesaglitazar
Troglitazone
SPPARMs: BADGE
EPI-001
INT-131
MK-0533
S26948
Antagonists: FH-535
GW-9662
SR-202
T-0070907
Unknown: SR-1664
Non-selective
Agonists: Ciprofibrate
Clinofibrate
Clofibride
Englitazone
Etofibrate
Farglitazar
Netoglitazone
Ronifibrate
Rivoglitazone
Simfibrate
Unsorted
Agonists: Lanifibranor
Seladelpar
See also
Receptor/signaling modulators
Nuclear receptor modulators
Authority control
LCCN: sh97005926
GND: 4123405-4
Retrieved from "https://en.wikipedia.org/w/index.php?title=Ibuprofen&oldid=822005769"
Categories:
British inventions
Hepatotoxins
Nonsteroidal anti-inflammatory drugs
Pfizer products
Propionic acids
World Health Organization essential medicines
Analgesics
Hidden categories:
Use dmy dates from November 2014
Template:drugs.com link with non-standard subpage
ECHA InfoCard ID from Wikidata
Drug has EMA link
Drugboxes which contain changes to watched fields
All articles with unsourced statements
Articles with unsourced statements from February 2017
Articles with unsourced statements from March 2011
Wikipedia articles in need of updating from November 2017
All Wikipedia articles in need of updating
Wikipedia articles with LCCN identifiers
Wikipedia articles with GND identifiers
RTT
Pages using PMID magic links
Navigation menu
Personal tools
Not logged in
Talk
Contributions
Create account
Log in
Namespaces
Article
Talk
Variants
Views
Read
Edit
View history
More
Search
Navigation
Main page
Contents
Featured content
Current events
Random article
Donate to Wikipedia
Wikipedia store
Interaction
Help
About Wikipedia
Community portal
Recent changes
Contact page
Tools
What links here
Related changes
Upload file
Special pages
Permanent link
Page information
Wikidata item
Cite this page
Print/export
Create a book
Download as PDF
Printable version
In other projects
Wikimedia Commons
Languages
Afrikaans
العربية
تۆرکجه
Български
Bosanski
Català
Čeština
Cymraeg
Dansk
Deutsch
Eesti
Ελληνικά
Español
Euskara
فارسی
Français
한국어
Հայերեն
Hrvatski
Bahasa Indonesia
Íslenska
Italiano
עברית
Latviešu
Lietuvių
Magyar
Bahasa Melayu
Nederlands
日本語
Norsk
Occitan
ଓଡ଼ିଆ
ਪੰਜਾਬੀ
پښتو
Polski
Português
Română
Русский
Scots
Simple English
Slovenščina
کوردی
Српски / srpski
Srpskohrvatski / српскохрватски
Suomi
Svenska
தமிழ்
తెలుగు
ไทย
Türkçe
Українська
اردو
Tiếng Việt
中文
Edit links
This page was last edited on 23 January 2018, at 21:52.
Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.
Privacy policy
About Wikipedia
Disclaimers
Contact Wikipedia
Developers
Cookie statement
Mobile view
Enable previews

value: mw-page-base noprint

value: mw-head-base noprint

value: firstHeading firstHeading en

value: siteSub noprint

value: jump-to-nav mw-jump

tag: span

value: International nonproprietary name (INN): Ibuprofen

tag: caption

value: (RS)-Ibuprofen Structural Formula V1.svg

attr: colspan style

tag: tr

tag: th

attr: scope style

value:
row
padding:0.2em 0; line-height:1.2em;

value:
/wiki/List_of_ibuprofen_brand_names
mw-redirect
List of ibuprofen brand names

value: American Society of Health-System Pharmacists

value:
/wiki/U.S._Food_and_Drug_Administration
mw-redirect
U.S. Food and Drug Administration

value: Anatomical Therapeutic Chemical Classification System

value: Standard for the Uniform Scheduling of Drugs and Poisons

value: Standard for the Uniform Scheduling of Medicines and Poisons

value:
/wiki/General_sales_list
mw-redirect
General sales list

value: font-size: 105%; background: transparent; text-align: left;

value: list-style: none none; margin-left: 0px; word-break: break-all; text-align: left; padding-left: 1.5em; text-indent: -1.5em; font-size: 105%; margin-top: 0px; margin-bottom: 0px; line-height: inherit; display: none;

value:
NavFrame collapsed
border: none; padding: 0;
NavFrame1

value:
nofollow
external text
https://www.drugbank.ca/drugs/DB01050

value:
nofollow
external text
http://www.kegg.jp/entry/D00126

value:
/wiki/ECHA_InfoCard
mw-redirect
ECHA InfoCard

value: chemapps.stolaf.edu (3D interactive model)

value: Simplified molecular-input line-entry system

value: word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:11px; line-height:120%;

value: list-style: none none; margin-left: 0px; word-break: break-all; font-size: 105%; margin-top: 0px; margin-bottom: 0px; line-height: inherit; display: none;

value:
NavFrame collapsed
border: none; padding: 0;
NavFrame2

value:
NavFrame collapsed
border: none; padding: 0;
NavFrame3

value:
/wiki/Premature_baby
mw-redirect
Premature baby

value: World Health Organization's List of Essential Medicines

value:
/wiki/Generic_medication
mw-redirect
Generic medication

value:
/wiki/Developing_world
mw-redirect
Developing world

value:
/wiki/Congestive_heart_failure
mw-redirect
Congestive heart failure

value:
/wiki/Renal_failure
mw-redirect
Renal failure

value:
/wiki/Heart_attack
mw-redirect
Heart attack

value: Food and Drug Administration (United States)

value:
/wiki/Pathologic_nystagmus
mw-redirect
Pathologic nystagmus

value:
/wiki/Acute_renal_failure
mw-redirect
Acute renal failure

value:
/wiki/Activated_charcoal
mw-redirect
Activated charcoal

value:
/wiki/Systemic_circulation
mw-redirect
Systemic circulation

value:
/wiki/Forced_diuresis
mw-redirect
Forced diuresis

value:
/wiki/Intensive-care_unit
mw-redirect
Intensive-care unit

value: Reliable source needed for the whole sentence (February 2017)

value:
noprint Inline-Template Template-Fact
white-space:nowrap;

value:
/wiki/Boots_Group
mw-redirect
Boots Group

value: This claim needs references to reliable sources. (March 2011)

value:
/wiki/International_Nonproprietary_Name
mw-redirect
International Nonproprietary Name

value: plainlinks metadata ambox ambox-content ambox-Update

value:
/wiki/Dietary_supplements
mw-redirect
Dietary supplements

value:
/wiki/Horse_chestnut
mw-redirect
Horse chestnut

value:
/wiki/PubMed_Identifier
mw-redirect
PubMed Identifier

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/9515184

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/22098129

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/12723741

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/20718179

value:
nofollow
external text
//doi.org/10.1007%2FBF03261999

value:
nofollow
external text
//www.worldcat.org/issn/0114-5916

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/23137151

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/2883408

value:
/wiki/Foster_City
mw-redirect
Foster City

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/16103274

value:
nofollow
external text
//doi.org/10.1136%2Fbmj.330.7504.1366

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/15947398

value:
nofollow
external text
//doi.org/10.1093%2Fgerona%2F51A.2.M74

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/8612107

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/1531054

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/18193504

value:
nofollow
external text
//doi.org/10.2146%2Fajhp080603

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/20101062

value:
nofollow
external text
https://www.drugs.com/ibuprofen.html

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/2188537

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/3537613

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/12737366

value:
nofollow
external text
//doi.org/10.1081%2Fclt-100100917

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/10696926

value:
nofollow
external text
//doi.org/10.1081%2FCLT-120037421

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/15214617

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/3777588

value:
nofollow
external text
//doi.org/10.1136%2Febnurs-2011-100439

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/22411163

value:
nofollow
external text
//doi.org/10.1503%2Fcmaj.130605

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/24491470

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/19203472

value:
nofollow
external text
//doi.org/10.1021%2Fjm701191z

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/18363350

value:
nofollow
external text
http://www.drugbank.ca/drugs/DB01050#

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/1352228

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/1859831

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/9106621

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/1569234

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/12723739

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/6239884

value:
nofollow
external text
//www.worldcat.org/issn/1173-8324

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/7041104

value:
nofollow
external text
//doi.org/10.1096%2Ffj.04-3620rev

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/16195368

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/18458226

value:
nofollow
external text
//doi.org/10.1002%2Fana.20682

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/16240369

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/21368280

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/21368281

value:
nofollow
external text
//doi.org/10.1038%2Fnrneurol.2011.49

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/21555992

value:
nofollow
external text
//doi.org/10.1016%2Fj.juro.2010.11.092

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/21334642

value:
nofollow
external text
//www.worldcat.org/issn/0269-4727

value:
nofollow
external text
//www.ncbi.nlm.nih.gov/pubmed/12472978

value: -moz-column-width: 30em; -webkit-column-width: 30em; column-width: 30em; list-style-type: decimal;

value: nowraplinks collapsible autocollapse navbox-inner

value: Template:Topical products for joint and muscular pain

value: Template talk:Topical products for joint and muscular pain

value: Oxycodone/naltrexone (page does not exist)

value:
/wiki/Ion_channel_modulator
mw-redirect
Ion channel modulator

value: nowraplinks collapsible collapsed navbox-inner

value:
/wiki/Template:Acne_agents
mw-redirect
Template:Acne agents

value:
/wiki/Template_talk:Acne_agents
mw-redirect
Template talk:Acne agents

value:
/wiki/Acne_vulgaris
mw-redirect
Acne vulgaris

value: Template:Prolactin inhibitors and anti-inflammatory products for vaginal administration

value: Template talk:Prolactin inhibitors and anti-inflammatory products for vaginal administration

value:
/wiki/Prolactin_inhibitor
mw-redirect
Prolactin inhibitor

value:
/wiki/Vaginal_administration
mw-redirect
Vaginal administration

value: Template talk:Prostanoid signaling modulators

value:
/wiki/Prostaglandin_D2_receptor_1
mw-redirect
Prostaglandin D2 receptor 1

value:
/wiki/Prostaglandin_D2_receptor_2
mw-redirect
Prostaglandin D2 receptor 2

value: 16,16-Dimethyl Prostaglandin E2 (page does not exist)

value:
/wiki/Prostaglandin_F2%CE%B1
mw-redirect
Prostaglandin F2α

value: Carbocyclic thromboxane A2 (page does not exist)

value: Pinane thromboxane A2 (page does not exist)

value:
/wiki/Prostaglandin_D_synthase
mw-redirect
Prostaglandin D synthase

value:
/wiki/Prostaglandin_F_synthase
mw-redirect
Prostaglandin F synthase

value:
/wiki/Thromboxane_A_synthase
mw-redirect
Thromboxane A synthase

value: nowraplinks hlist collapsible collapsed navbox-inner

value: Peroxisome proliferator-activated receptor alpha

value:
/wiki/15-Hydroxyicosatetraenoic_acid
mw-redirect
15-Hydroxyicosatetraenoic acid

value: 15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid (page does not exist)

value: Peroxisome proliferator-activated receptor delta

value: Peroxisome proliferator-activated receptor gamma

value: 5-Oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid (page does not exist)

value: 5-Oxo-15-hydroxy-ETE (page does not exist)

value:
/wiki/Selective_PPAR%CE%B3_modulator
mw-redirect
Selective PPARγ modulator

value:
nofollow
external text
https://d-nb.info/gnd/4123405-4

value: Category:World Health Organization essential medicines

value: Category:Use dmy dates from November 2014

value: Category:Template:drugs.com link with non-standard subpage

value: Category:Drugboxes which contain changes to watched fields

value: Category:All articles with unsourced statements

value: Category:Articles with unsourced statements from February 2017

value: Category:Articles with unsourced statements from March 2011

value: Category:Wikipedia articles in need of updating from November 2017

value: Category:All Wikipedia articles in need of updating

value: Category:Wikipedia articles with LCCN identifiers

value: Category:Wikipedia articles with GND identifiers

value: Discussion about edits from this IP address [ctrl-alt-n]

value: A list of edits made from this IP address [ctrl-alt-y]

value: You are encouraged to create an account and log in; however, it is not mandatory

value:
/wiki/Ibuprofen
View the content page [ctrl-alt-c]
c

value: Discussion about the content page [ctrl-alt-t]

value: Featured content – the best of Wikipedia

value: Find background information on current events

value:
/wiki/Special:Random
Load a random article [ctrl-alt-x]
x

value: portal navigation p-navigation p-navigation-label

value: Guidance on how to use and edit Wikipedia

value: About the project, what you can do, where to find things

value: A list of recent changes in the wiki [ctrl-alt-r]

value: portal navigation p-interaction p-interaction-label

value: List of all English Wikipedia pages containing links to this page [ctrl-alt-j]

value: Recent changes in pages linked from this page [ctrl-alt-k]

value:
/wiki/Wikipedia:File_Upload_Wizard
Upload files [ctrl-alt-u]
u

value: portal navigation p-wikibase-otherprojects p-wikibase-otherprojects-label

value:
uls-settings-trigger
Language settings
0
button
true

value: إيبوبروفين – Arabic

value: Ибупрофен – Bulgarian

value:
https://bs.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Bosnian
bs
bs
interlanguage-link-target

value: interlanguage-link interwiki-bs badge-Q17437796 badge-featuredarticle

value:
https://cs.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Czech
cs
cs
interlanguage-link-target

value:
https://cy.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Welsh
cy
cy
interlanguage-link-target

value:
https://da.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Danish
da
da
interlanguage-link-target

value:
https://de.wikipedia.org/wiki/Ibuprofen
Ibuprofen – German
de
de
interlanguage-link-target

value: Ιβουπροφαίνη – Greek

value: ایبوپروفن – Persian

value: 이부프로펜 – Korean

value: Իբուպրոֆեն – Armenian

value:
https://hr.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Croatian
hr
hr
interlanguage-link-target

value:
https://id.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Indonesian
id
id
interlanguage-link-target

value: איבופרופן – Hebrew

value:
https://ms.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Malay
ms
ms
interlanguage-link-target

value:
https://nl.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Dutch
nl
nl
interlanguage-link-target

value: イブプロフェン – Japanese

value:
https://no.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Norwegian
no
no
interlanguage-link-target

value: ଆଇବୁପ୍ରୋଫେନ୍ – Odia

value: ਇਬੂਪ੍ਰੋਫ਼ੇਨ – Punjabi

value: ايبوپروفېن – Pashto

value:
https://pl.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Polish
pl
pl
interlanguage-link-target

value:
https://ro.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Romanian
ro
ro
interlanguage-link-target

value: Ибупрофен – Russian

value:
https://sl.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Slovenian
sl
sl
interlanguage-link-target

value: Ибупрофен – Serbian

value:
https://sh.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Serbo-Croatian
sh
sh
interlanguage-link-target

value:
https://sv.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Swedish
sv
sv
interlanguage-link-target

value: ஐப்யூபுரூஃபன் – Tamil

value: ఐబుప్రోఫెన్ – Telugu

value: ไอบิวพรอเฟน – Thai

value: Ібупрофен – Ukrainian

value: آئبوپروفین – Urdu

value:
https://vi.wikipedia.org/wiki/Ibuprofen
Ibuprofen – Vietnamese
vi
vi
interlanguage-link-target

value: /static/images/wikimedia-button-1.5x.png 1.5x, /static/images/wikimedia-button-2x.png 2x

value: /static/images/poweredby_mediawiki_132x47.png 1.5x, /static/images/poweredby_mediawiki_176x62.png 2x

value: mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject page-Ibuprofen rootpage-Ibuprofen skin-vector action-view


text:
This Little Piggy
From Wikipedia, the free encyclopedia
Jump to: navigation, search
For the Family Guy episode, see This Little Piggy (Family Guy).
"This Little Piggy"
Illustration by Lilly Martin Spencer, 1857
Nursery rhyme
Published
1760
Songwriter(s)
Unknown
"This Little Piggy" or "This Little Pig" is an English language nursery rhyme and fingerplay. It has a Roud Folk Song Index number of 19297.
Contents
[hide]
1 Lyrics
2 Finger play
3 Origins
4 In today's culture
5 See also
6 References
Lyrics[edit]
Children playing This Little Pig.[1]
The most common modern version is:
Words
Fingerplay
This little piggy went to market,
This little piggy stayed home,
This little piggy had roast beef,
This little piggy had none,
And this little piggy cried "wee wee wee" all the way home.[2]
Wiggle the "big" toe
Wiggle the "long" toe
Wiggle the "middle" toe
Wiggle the "ring" toe
Wiggle the "pinky" toe and tickle the bottom of the foot
Finger play[edit]
"... This little piggy had roast beef..."
The rhyme is usually counted out on an infant or toddler's toes, each line corresponding to a different toe, usually starting with the big toe and ending with the little toe. A foot tickle is usually added during the "Wee...all the way home" section of the last line.[citation needed] The rhyme can also be seen as a counting rhyme, although the number of each toe (from one for the big toe to five for the little toe) is never stated.[citation needed]
Origins[edit]
In 1728, the first line of the rhyme appeared in a medley called "The Nurse's Song". The first known full version was recorded in The Famous Tommy Thumb's Little Story-Book, published in London about 1760.[3]
The full rhyme continued to appear, with slight variations, in many late 18th and early 19th century collections. Until the mid-20th century, the lines referred to "little pigs".[3]
In today's culture[edit]
In 2013, Australian children's music group The Wiggles wrote a song "This Little Piggy Went to Market" with the same lyrics as the original This Little Piggy with different background music. In the same year, BilinguaSing released a bilingual version of the song in English and Spanish. The song is on The Wiggles' 2014 release Apples and Bananas (DVD and CD), and the song is sung with the American journalist Lee Hawkins.[citation needed]
On Tuesday, April 29, 2014, on The Today Show, Matt Lauer played This Little Piggy on Savannah Guthrie's toes.[4]
On Monday, February 23, 2015, singer Christina Aguilera sang the rhyme in the voice of Britney Spears on "The Tonight Show starring Jimmy Fallon" in the tune and instrumental of ...Baby One More Time.[5]
In a Geico television commercial, a pig named Maxwell cried "wee wee wee" all the way home.
See also[edit]
Children's literature portal
References[edit]
Wikisource has original text related to this article:
This Little Pig
Jump up ^ Wentworth, George; Smith, David Eugene (1912). Work and Play with Numbers. Boston: Ginn & Company. p. 14.
Jump up ^ Herman, D. (2007). The Cambridge Companion to Narrative. Cambridge: Cambridge University Press. p. 9.
^ Jump up to: a b Opie, I.; Opie, P. (1951). The Oxford Dictionary of Nursery Rhymes (1997 ed.). Oxford University Press. pp. 349–50.
Jump up ^ Duerson, Meena (April 29, 2014). "Savannah, Matt play 'This Little Piggy' to teach anchor a lesson". Today. Retrieved February 12, 2016.
Jump up ^ Boardman, Madeline (24 February 2015). "Christina Aguilera Does Incredible Britney Spears Impression on The Tonight Show With Jimmy Fallon". US Weekly. Archived from the original on 25 February 2015. Retrieved 1 June 2015.
[hide]
v
t
e
Nursery rhymes (list)
"A-Tisket, A-Tasket"
"Baa, Baa, Black Sheep"
"Did You Ever See a Lassie?"
"Hey Diddle Diddle"
"Hickory Dickory Dock"
"Hot Cross Buns"
"Humpty Dumpty"
"I'm a Little Teapot"
"It's Raining, It's Pouring"
"Jack and Jill"
"Little Bo Peep"
"Little Boy Blue"
"Little Jack Horner"
"Little Miss Muffet"
"Mary Had a Little Lamb"
"Mary, Mary, Quite Contrary"
"Old King Cole"
"Old MacDonald Had a Farm"
"Old Mother Hubbard"
"Old Woman Who Lived in a Shoe"
"Peter Piper"
"Polly Put the Kettle On"
"Poor Mary"
"Pop Goes the Weasel"
"Pussy Cat Pussy Cat"
"Rain Rain Go Away"
"Roses Are Red"
"Rub-a-dub-dub"
"Simple Simon"
"Sticks and Stones"
"The Grand Old Duke of York"
"The Queen of Hearts"
"Twinkle, Twinkle, Little Star"
"Two Little Dickie Birds"
Clapping
"A Sailor Went to Sea"
"Down Down Baby"
"Mary Mack"
"Miss Susie"
"Miss Lucy"
"Pat-a-cake"
"Pretty Little Dutch Girl"
"Pease Porridge Hot"
Counting
"Duck, duck, goose"
"Eeny, meeny, miny, moe"
"One, Two, Buckle My Shoe"
"One, Two, Three, Four, Five"
"This Old Man"
"Tinker, Tailor"
Finger-
plays
"Five Little Monkeys"
"Five Little Ducks"
"Five Little Speckled Frogs"
"Itsy Bitsy Spider"
"Little Robin Redbreast"
"Round and Round the Garden"
"This Little Piggy"
Games
"London Bridge"
"The Muffin Man"
"Mulberry Bush"
"Oranges and Lemons"
"Ring a Ring o' Roses"
"The Farmer in the Dell"
Riddle
"As I was going to St Ives"
Lullabies
"Hush, Little Baby"
"Rock-a-bye Baby"
Rounds
"Ding Dong Bell"
"Frère Jacques"
"Kookaburra"
"Row, Row, Row Your Boat"
"Scotland's Burning"
"Three Blind Mice"
Retrieved from "https://en.wikipedia.org/w/index.php?title=This_Little_Piggy&oldid=820962087"
Categories:
Fictional pigs
Songs about pigs
Finger plays
English nursery rhymes
Roud Folk Song Index songs
Year of song unknown
Songwriter unknown
Hidden categories:
All articles with unsourced statements
Articles with unsourced statements from August 2013
Articles with unsourced statements from January 2016
Navigation menu
Personal tools
Not logged in
Talk
Contributions
Create account
Log in
Namespaces
Article
Talk
Variants
Views
Read
Edit
View history
More
Search
Navigation
Main page
Contents
Featured content
Current events
Random article
Donate to Wikipedia
Wikipedia store
Interaction
Help
About Wikipedia
Community portal
Recent changes
Contact page
Tools
What links here
Related changes
Upload file
Special pages
Permanent link
Page information
Wikidata item
Cite this page
Print/export
Create a book
Download as PDF
Printable version
In other projects
Wikimedia Commons
Wikisource
Languages
Add links
This page was last edited on 17 January 2018, at 16:48.
Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.
Privacy policy
About Wikipedia
Disclaimers
Contact Wikipedia
Developers
Cookie statement
Mobile view
Enable previews

tag: div

attr: id class

value: mw-page-base noprint

key: html

type: local

value: mw-head-base noprint

tag: a

attr: id class lang

value: firstHeading firstHeading en

value: siteSub noprint

value: jump-to-nav mw-jump

attr: href title

attr: role class

value:
note
hatnote navigation-not-searchable

attr: colspan class style

tag: img

attr: alt src width height srcset data-file-width data-file-height

value: This Little Pig Went to Market by Lilly Martin Spencer, 1857, oil on cut arched board - New Britain Museum of American Art - DSC09337.JPG

attr: href class

tag: td

attr: alt src width height class srcset data-file-width data-file-height

value: This claim needs references to reliable sources. (August 2013)

value:
noprint Inline-Template Template-Fact
white-space:nowrap;

value:
/wiki/Counting_rhyme
mw-redirect
Counting rhyme

value: This claim needs references to reliable sources. (January 2016)

value:
reflist mw-references-wrap
list-style-type: decimal;

value:
/wiki/Little_Bo_Peep
mw-redirect
Little Bo Peep

value: There was an Old Woman Who Lived in a Shoe

value:
navbox-image
8
width:1px;padding:0px 0px 0px 2px

value: nowraplinks collapsible autocollapse navbox-inner

value: Category:All articles with unsourced statements

value: Category:Articles with unsourced statements from August 2013

value: Category:Articles with unsourced statements from January 2016

value: Discussion about edits from this IP address [ctrl-alt-n]

value: A list of edits made from this IP address [ctrl-alt-y]

value: You are encouraged to create an account and log in; however, it is not mandatory

value: You're encouraged to log in; however, it's not mandatory. [ctrl-alt-o]

value:
/wiki/This_Little_Piggy
View the content page [ctrl-alt-c]
c

value: Discussion about the content page [ctrl-alt-t]

value: p-namespaces navigation vectorTabs p-namespaces-label

value:
p-variants
navigation
vectorMenu emptyPortlet
p-variants-label

value: Past revisions of this page [ctrl-alt-h]

value: p-views navigation vectorTabs p-views-label

value:
p-cactions
navigation
vectorMenu emptyPortlet
p-cactions-label

value:
mw-wiki-logo
/wiki/Main_Page
Visit the main page

value:
/wiki/Main_Page
Visit the main page [ctrl-alt-z]
z

value: Featured content – the best of Wikipedia

value: Find background information on current events

value:
/wiki/Special:Random
Load a random article [ctrl-alt-x]
x

value: portal navigation p-navigation p-navigation-label

value: Guidance on how to use and edit Wikipedia

value: About the project, what you can do, where to find things

value: A list of recent changes in the wiki [ctrl-alt-r]

value: portal navigation p-interaction p-interaction-label

value: List of all English Wikipedia pages containing links to this page [ctrl-alt-j]

value: Recent changes in pages linked from this page [ctrl-alt-k]

value:
/wiki/Wikipedia:File_Upload_Wizard
Upload files [ctrl-alt-u]
u

value: A list of all special pages [ctrl-alt-q]

value: Permanent link to this revision of the page

value: Link to connected data repository item [ctrl-alt-g]

value: Printable version of this page [ctrl-alt-p]

value: portal navigation p-wikibase-otherprojects p-wikibase-otherprojects-label

value:
uls-settings-trigger
Language settings
0
button
true

value:
suggestions
display: none; font-size: 13px;

value: mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject page-This_Little_Piggy rootpage-This_Little_Piggy skin-vector action-view


text:
Director of the United States Mint
From Wikipedia, the free encyclopedia
Jump to: navigation, search
Seal of the United States Mint.
The Director of the United States Mint is the head of the United States Mint. The position is currently vacant. Since January 20, 2017, the senior career official at the Mint has been Acting Principal Deputy Director David Motl.[1]
The office of Director has existed since the creation of the Mint by the Coinage Act of 1792. Initially appointed serving at the pleasure of the President of the United States, the Coinage Act of 1873 specified a five-year term for Directors. The Director operates with general directions provided by the United States Secretary of the Treasury.
Since the resignation of Edmund C. Moy in 2011 the mint has been without an official director. Initially Matthew Rhett Jeppson was nominated by US President Barack Obama to become the mint's 39th director and was given the temporary title of principal deputy director, however the nomination was never confirmed by the Senate.[2] Jeppson stepped down as principal deputy director in January 2017, being replaced by Acting Principal Deputy Director David Motl.[3]
List of Directors of the United States Mint[edit]
Name
Assumed Office
Left Office
President Appointed By
David Rittenhouse April 1792 June 1795 George Washington
Henry William de Saussure July 1795 October 1795
Elias Boudinot October 1795 July 1805
Robert Patterson January 1806 July 1824 Thomas Jefferson
Samuel Moore July 1824 July 1835 James Monroe
Robert M. Patterson May 1835 July 1851 Andrew Jackson
George Nicholas Eckert July 1851 April 1853 Millard Fillmore
Thomas M. Pettit April 1853 May 1853 Franklin Pierce
James Ross Snowden June 1853 May 1861
James Pollock May 1861 September 1866 Abraham Lincoln
William Millward October 1866 April 1867 Andrew Johnson
Henry Linderman April 1867 May 1869
James Pollock May 1869 March 1873 Ulysses S. Grant
Henry Linderman April 1873 December 1878
Horatio C. Burchard February 1879 June 1885 Rutherford B. Hayes
James P. Kimball July 1885 October 1889 Grover Cleveland
Edward O. Leech October 1889 May 1893 Benjamin Harrison
Robert E. Preston November 1893 February 1898 Grover Cleveland
George E. Roberts February 1898 July 1907 William McKinley
Frank A. Leach September 1907 August 1909 Theodore Roosevelt
A. Piatt Andrew November 1909 June 1910 William Howard Taft
George E. Roberts July 1910 November 1914
Robert W. Woolley March 1915 July 1916 Woodrow Wilson
F. H. von Engelken September 1916 March 1917
Raymond T. Baker March 1917 March 1922
Frank Edgar Scobey March 1922 September 1923 Warren G. Harding
Robert J. Grant November 1923 May 1933 Calvin Coolidge
Nellie Tayloe Ross May 1933 April 1953 Franklin D. Roosevelt
William H. Brett July 1954 January 1961 Dwight D. Eisenhower
Eva Adams October 1961 August 1969 John F. Kennedy
Mary Brooks September 1969 February 1977 Richard Nixon
Stella Hackel Sims November 1977 April 1981 Jimmy Carter
Donna Pope July 1981 August 1991 Ronald Reagan
David J. Ryder September 1992 November 1993 George H. W. Bush
Philip N. Diehl June 1994 March 2000 Bill Clinton
Jay W. Johnson May 2000 August 2001
Henrietta H. Fore August 2001 August 2005 George W. Bush
Edmund C. Moy September 2006 January 2011
David J. Ryder April 2018 Incumbent Donald Trump
References[edit]
Jump up ^ About the Mint at usmint.gov (retrieved 20 April 2015).
Jump up ^ Gilkes, Paul (23 January 2017). "Rhett Jeppson leaves U.S. Mint as principal deputy director". coinworld.com. Retrieved 13 April 2017.
Jump up ^ "Director's Office". US Mint. Retrieved 13 April 2017.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Director_of_the_United_States_Mint&oldid=836791366"
Categories:
Directors of the United States Mint
United States Department of the Treasury
1792 establishments in the United States
Navigation menu
Personal tools
Not logged in
Talk
Contributions
Create account
Log in
Namespaces
Article
Talk
Variants
Views
Read
Edit
View history
More
Search
Navigation
Main page
Contents
Featured content
Current events
Random article
Donate to Wikipedia
Wikipedia store
Interaction
Help
About Wikipedia
Community portal
Recent changes
Contact page
Tools
What links here
Related changes
Upload file
Special pages
Permanent link
Page information
Wikidata item
Cite this page
Print/export
Create a book
Download as PDF
Printable version
Languages
Add links
This page was last edited on 16 April 2018, at 21:26.
Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.
Privacy policy
About Wikipedia
Disclaimers
Contact Wikipedia
Developers
Cookie statement
Mobile view
Enable previews

value: mw-page-base noprint

value: mw-head-base noprint

value: firstHeading firstHeading en

value: siteSub noprint

value: jump-to-nav mw-jump

attr: href class title

attr: class style

tag: b

tag: sup

tag: p

value: Edit section: List of Directors of the United States Mint

value:
reflist mw-references-wrap
list-style-type: decimal;

value: Category:Directors of the United States Mint

value: Category:United States Department of the Treasury

value: Category:1792 establishments in the United States

value:
catlinks mw-normal-catlinks
catlinks mw-normal-catlinks
interface

value: Discussion about edits from this IP address [ctrl-alt-n]

value: A list of edits made from this IP address [ctrl-alt-y]

value: You are encouraged to create an account and log in; however, it is not mandatory

value: You're encouraged to log in; however, it's not mandatory. [ctrl-alt-o]

value: Discussion about the content page [ctrl-alt-t]

value: p-namespaces navigation vectorTabs p-namespaces-label

value:
p-variants
navigation
vectorMenu emptyPortlet
p-variants-label

value: Past revisions of this page [ctrl-alt-h]

value: p-views navigation vectorTabs p-views-label

value:
p-cactions
navigation
vectorMenu emptyPortlet
p-cactions-label

value:
mw-wiki-logo
/wiki/Main_Page
Visit the main page

value:
/wiki/Main_Page
Visit the main page [ctrl-alt-z]
z

value: Featured content – the best of Wikipedia

value: Find background information on current events

value:
/wiki/Special:Random
Load a random article [ctrl-alt-x]
x

value: /static/images/wikimedia-button-1.5x.png 1.5x, /static/images/wikimedia-button-2x.png 2x

value: /static/images/poweredby_mediawiki_132x47.png 1.5x, /static/images/poweredby_mediawiki_176x62.png 2x

value: mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject page-Director_of_the_United_States_Mint rootpage-Director_of_the_United_States_Mint skin-vector action-view


text:
AOSS
From Wikipedia, the free encyclopedia
Jump to: navigation, search
AOSS (AirStation One-Touch Secure System) is a system by Buffalo Technology which allows a secure wireless connection to be set up with the push of a button. AirStation residential gateways incorporated a button on the unit to let the user initiate this procedure. AOSS was designed to use the maximum level of security available to both connecting devices including both Wired Equivalent Privacy (WEP) and Wi-Fi Protected Access (WPA).
Contents
[hide]
1 Connection Process
2 Compatible products
3 References
4 See also
Connection Process[edit]
Association Phase: Once AOSS has been initiated on both devices via the AOSS button, the access point will change its SSID to "ESSID-AOSS" and the client will attempt to connect to it. Both devices will attempt connection for two minutes. Connection will be made using a secret 64-bit WEP key known to both devices.
Key Generation Phase: With both devices connected, the AP generates and transfers a unique key to the client where an RC4 tunnel is created. The AP creates four SSIDs and encryption keys for AES, TKIP, WEP128, and WEP64 generated from a random key script. These keys are available in the user interface of the AOSS AP to be used with non-AOSS clients.
Information Exchange Phase: The client notifies the AP of its encryption support.
Key Transfer Phase: All four encryption keys are transmitted to the client regardless of encryption support allowing the client to change the SSID if needed. The user does not have access to the keys through the client device.
Reboot Stack: The AP applies the SSID and key for the highest level of encryption supported by the client and reboots. The previously used WEP64 and RC4 tunnel are no longer used. The client adapter will automatically reboot or re-initialize and connect to the SSID using the proper encryption key.
If a subsequent AOSS process connects with a lesser wireless encryption standard, the AP will apply the lesser standard and the Reboot Stack phase will be repeated for all connected devices.[1]
Compatible products[edit]
The Nintendo Wi-Fi Connection used by the Nintendo DS, Nintendo DS Lite, Nintendo DSi and Nintendo 3DS is AOSS compatible.[2] AOSS is also included in the PlayStation 3 and in system software 2.00 for the PlayStation Portable[3] and is available for automatic setup with the PSP with firmware 2.80. The PS Vita is also AOSS compatible as of release. AOSS functionality for all Wii models is included in version 3.0U of the Wii System software, released in August 2007 along with PAL version 3.0E.[4] The technology was advertised through 2009.[5]
References[edit]
Jump up ^ "AirStation One-Touch Secure System (AOSS™): A Description of WLAN Security Challenges and Potential Solutions" (PDF). Buffalo Technology. October 2004.
Jump up ^ "Business Report 2006" (PDF). Buffalo Technology. Archived from the original (PDF) on November 22, 2009.
Jump up ^ "Buffalo Expands Its Partnership with Sony Computer Entertainment Inc. to Further the Integration of its AOSS™ Technology" (Press release). Buffalo Technology. Archived from the original on November 12, 2006.
Jump up ^ Harris, Craig (August 8, 2007). "Overlooked Wii 3.0 Update". Blog: Just One Guy. IGN. Archived from the original on April 27, 2009. Retrieved May 26, 2013.
Jump up ^ "Our Technology - AOSS™". Buffalo Technology web site. Archived from the original on March 21, 2009. Retrieved May 26, 2013.
See also[edit]
Wi-Fi Protected Setup
This computer networking article is a stub. You can help Wikipedia by expanding it.
v
t
e
This article about wireless technology is a stub. You can help Wikipedia by expanding it.
v
t
e
Retrieved from "https://en.wikipedia.org/w/index.php?title=AOSS&oldid=803922071"
Categories:
Wi-Fi
Computer network stubs
Wireless stubs
Hidden categories:
All stub articles
Navigation menu
Personal tools
Not logged in
Talk
Contributions
Create account
Log in
Namespaces
Article
Talk
Variants
Views
Read
Edit
View history
More
Search
Navigation
Main page
Contents
Featured content
Current events
Random article
Donate to Wikipedia
Wikipedia store
Interaction
Help
About Wikipedia
Community portal
Recent changes
Contact page
Tools
What links here
Related changes
Upload file
Special pages
Permanent link
Page information
Wikidata item
Cite this page
Print/export
Create a book
Download as PDF
Printable version
Languages
Español
Français
日本語
Edit links
This page was last edited on 5 October 2017, at 14:53.
Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.
Privacy policy
About Wikipedia
Disclaimers
Contact Wikipedia
Developers
Cookie statement
Mobile view
Enable previews

value: mw-page-base noprint

value: mw-head-base noprint

value: firstHeading firstHeading en

value: siteSub noprint

value: jump-to-nav mw-jump

value:
/wiki/Buffalo_Technology
mw-redirect
Buffalo Technology

value: /wiki/AirStation mw-redirect AirStation

attr: role tabindex class

value: button 0 togglelink

attr: class dir xml:lang

value: toctitle ltr en

value:
reflist mw-references-wrap
list-style-type: decimal;

value: position: absolute; right: 15px; display: none;

value:
metadata plainlinks stub
presentation
background:transparent

value: Discussion about edits from this IP address [ctrl-alt-n]

value: A list of edits made from this IP address [ctrl-alt-y]

value:
/wiki/AOSS
View the content page [ctrl-alt-c]
c

value:
/w/index.php?title=AOSS&action=edit
Edit this page [ctrl-alt-e]
e

value: portal navigation p-navigation p-navigation-label

value: Guidance on how to use and edit Wikipedia

value: About the project, what you can do, where to find things

value: A list of recent changes in the wiki [ctrl-alt-r]

value: portal navigation p-interaction p-interaction-label

value: List of all English Wikipedia pages containing links to this page [ctrl-alt-j]

value: Recent changes in pages linked from this page [ctrl-alt-k]

value:
/wiki/Wikipedia:File_Upload_Wizard
Upload files [ctrl-alt-u]
u

value: A list of all special pages [ctrl-alt-q]

value: Permanent link to this revision of the page

value: Link to connected data repository item [ctrl-alt-g]

value: Printable version of this page [ctrl-alt-p]

value:
https://es.wikipedia.org/wiki/AOSS
AOSS – Spanish
es
es
interlanguage-link-target

value: AirStation OneTouch Secure System – French

value: AirStation One-Touch Secure System – Japanese

value:
suggestions
display: none; font-size: 13px;

value: mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject page-AOSS rootpage-AOSS skin-vector action-view