2079:
1688:, 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. 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.
1984:
42:
1873:
1866:
825:
802:
1889:
1163:
1810:. The synthesis took six steps. A modern, greener technique with fewer waste byproducts for the synthesis involves only three steps was developed in the 1980s by the Celanese Chemical Company. The synthesis is initiated with the acylation of isobutylbenzene using the recyclable Lewis acid catalyst hydrogen fluoride. The following catalytic hydrogenation of isobutylacetophenone is performed with either Raney nickel or palladium on carbon to lead into the key-step, the
1768:
51:
6842:
6862:
1882:
1171:
6852:
12582:
3336:
3296:
2179:. 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.
5859:
1474:, although the frequency of life-threatening complications from ibuprofen overdose is low. Human responses in cases of overdose range from an absence of symptoms to a fatal outcome despite intensive-care treatment. Most symptoms are an excess of the pharmacological action of ibuprofen and include abdominal pain, nausea,
1441:
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
5757:
Seibel K, Schaffler K, Reeh P, Reitmeir P (2004). "Comparison of two different preparations of ibuprofen with regard to the time course of their analgesic effect. A randomised, placebo-controlled, double-blind cross-over study using laser somatosensory evoked potentials obtained from UW-irritated
4217:
Kakuta H, Zheng X, Oda H, Harada S, Sugimoto Y, Sasaki K, et al. (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".
2265:
Ibuprofen lysine is sold for rapid pain relief; given in the form of its lysine salt, absorption is much quicker (35 minutes for the salt compared to 90–120 minutes for ibuprofen). However, a clinical trial with 351 participants in 2020, funded by Sanofi, found no significant difference between
1758:
After oral administration, peak serum concentration is reached after 1–2 hours, and up to 99% of the drug is bound to plasma proteins. The majority of ibuprofen is metabolized and eliminated within 24 hours in the urine; however, 1% of the unchanged drug is removed through biliary
1538:
have been reported. 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.
1573:
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. Purposeful vomiting is not recommended. Most ibuprofen ingestions produce only mild effects, and the management of overdose is
1248:(FDA) for closure of patent ductus arteriosus in premature infants weighing between 500 and 1,500 g (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.
1318:, may occur. 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 people who are hospitalized, or assist in a medicolegal death investigation. A
4630:
5410:
Miguel-Álvarez M, Santos-Lozano A, Sanchis-Gomar F, Fiuza-Luces C, Pareja-Galeano H, Garatachea N, et al. (February 2015). "Non-steroidal anti-inflammatory drugs as a treatment for
Alzheimer's disease: a systematic review and meta-analysis of treatment effect".
9052:
2852:
2108:(USAN). In the United States, it has been sold under the brand-names Motrin and Advil since 1974 and 1984, respectively. Ibuprofen is commonly available in the United States up to the FDA's 1984 dose limit OTC, rarely used higher by prescription.
2062:
In recognition of the pioneering research work, here on
Pennyfoot Street, by Dr Stewart Adams and Dr John Nicholson in the Research Department of Boots which led to the discovery of ibuprofen used by millions worldwide for the relief of
9045:
2049:
In recognition of the work during the 1980s by The Boots
Company PLC on the development of ibuprofen which resulted in its move from prescription only status to over the counter sale, therefore expanding its use to millions of people
3455:
9038:
5221:
12166:
12027:
11808:
2010:
during the 1960s. The name is derived from the 3 functional groups: isobutyl (ibu) propionic acid (pro) phenyl (fen). Its discovery was the result of research during the 1950s and 1960s to find a safer alternative to
2860:
1582:
is theoretically beneficial. However, because ibuprofen is highly protein-bound in the blood, the kidneys' excretion of the unchanged drug is minimal. Forced alkaline diuresis is, therefore, of limited benefit.
5854:
12143:
1743:-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.
4376:
Nakagita T, Taketani C, Narukawa M, Hirokawa T, Kobayashi T, Misaka T (November 2020). "Ibuprofen, a
Nonsteroidal Anti-Inflammatory Drug, is a Potent Inhibitor of the Human Sweet Taste Receptor".
3833:
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".
6898:
1241:(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.
4804:
Caldwell J, Hutt AJ, Fournel-Gigleux S (January 1988). "The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences".
3313:
1446:
aspirin. If ibuprofen is taken only occasionally without the recommended timing, though, the reduction of the cardioprotection and stroke prevention of a daily aspirin regimen is minimal.
1206:. About 60% of people respond to any NSAID; those who do not respond well to a particular one may respond to another. A Cochrane medical review of 51 trials of NSAIDs for the treatment of
3443:
3521:
3735:
9827:
5033:
3396:"Risk of myocardial infarction in patients taking cyclo-oxygenase-2 inhibitors or conventional non-steroidal anti-inflammatory drugs: population based nested case-control analysis"
3273:
5123:
5489:
Chen H, Jacobs E, Schwarzschild MA, McCullough ML, Calle EE, Thun MJ, et al. (December 2005). "Nonsteroidal antiinflammatory drug use and the risk for
Parkinson's disease".
1561:
Treatment to address an ibuprofen overdose is based on how the symptoms present. In cases presenting early, decontamination of the stomach is recommended. This is achieved using
5454:
Wang J, Tan L, Wang HF, Tan CC, Meng XF, Wang C, et al. (2015). "Anti-inflammatory drugs and risk of
Alzheimer's disease: an updated systematic review and meta-analysis".
5199:
5165:
3488:
2042:
1988:
3760:
2498:
2186:
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
5673:
Gleason JM, Slezak JM, Jung H, Reynolds K, Van den Eeden SK, Haque R, et al. (April 2011). "Regular nonsteroidal anti-inflammatory drug use and erectile dysfunction".
10138:
6891:
9198:
5857:, Stewart Sanders Adams & John Stuart Nicholson, "Anti-Inflammatory Agents", published 1964-09-30, assigned to Boots Pure Drug Co Ltd
4084:
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".
1103:
is unclear, it appears to be harmful in later pregnancy, so it is not recommended during that period. Like other NSAIDs, it works by inhibiting the production of
10279:
2416:
12642:
12148:
7422:
4584:
2755:
6884:
6845:
310:
5261:
5914:
4748:
3662:
Ward KE, Archambault R, Mersfelder TL (February 2010). "Severe adverse skin reactions to nonsteroidal antiinflammatory drugs: A review of the literature".
3444:"FDA Drug Safety Communication: FDA strengthens warning that non-aspirin nonsteroidal anti-inflammatory drugs (NSAIDs) can cause heart attacks or strokes"
3515:
2030:
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
12346:
11039:
11009:
10840:
5275:
1322:
relating ibuprofen plasma concentration, time since ingestion, and risk of developing renal toxicity in people who have overdosed has been published.
12127:
12006:
11787:
10045:
9665:
12462:
12181:
10892:
10872:
10428:
10378:
6262:
4882:
Hutt AJ, Caldwell J (November 1983). "The metabolic chiral inversion of 2-arylpropionic acids--a novel route with pharmacological consequences".
5803:"A Randomized, Double-Blind, Placebo-Controlled Trial of Ibuprofen Lysinate in Comparison to Ibuprofen Acid for Acute Postoperative Dental Pain"
12384:
12354:
12331:
12326:
12311:
12226:
12201:
11198:
10663:
10553:
10548:
10533:
10468:
10418:
10373:
9938:
9030:
8620:
7721:
3113:"Individual NSAIDs and upper gastrointestinal complications: a systematic review and meta-analysis of observational studies (the SOS project)"
1603:
than those not taking the medications. However, an
Israeli study found no increased risk of miscarriage in the group of mothers using NSAIDs.
12627:
12321:
12266:
12231:
11605:
11436:
11426:
10850:
10528:
10508:
10493:
10483:
10463:
10458:
10413:
10388:
10353:
10199:
10030:
9808:
9706:
9645:
9606:
9405:
9395:
9303:
9191:
3510:
2774:
The selection and use of essential medicines 2023: web annex A: World Health
Organization model list of essential medicines: 23rd list (2023)
183:
3743:
3562:
888:
12359:
12052:
11635:
11630:
11595:
11570:
11431:
11292:
11149:
10750:
10745:
10543:
10523:
10518:
10513:
10498:
10488:
10478:
10453:
10443:
10438:
10433:
10423:
10408:
10403:
10363:
10322:
10302:
10259:
10254:
10239:
10229:
10224:
10209:
10088:
10010:
9965:
9879:
9855:
9845:
9293:
954:
5023:
1826:
catalyst, at around 50 bar of CO pressure, in the presence of HCl (10%). The reaction presumably proceeds through the intermediacy of the
12652:
12467:
12291:
12286:
12281:
12082:
12072:
11911:
11906:
11843:
11620:
11575:
11386:
11332:
11317:
11166:
10877:
10825:
10710:
10558:
10503:
10473:
10448:
10398:
10393:
10383:
10368:
10317:
10312:
10269:
10204:
10194:
10164:
10108:
10078:
10035:
10025:
9874:
9798:
9650:
9563:
9360:
7669:
6561:
6337:
5867:
5297:
Wong RC, Kang S, Heezen JL, Voorhees JJ, Ellis CN (December 1984). "Oral ibuprofen and tetracycline for the treatment of acne vulgaris".
5131:
12117:
12112:
11981:
11771:
11625:
11600:
11590:
11441:
11416:
11401:
11366:
11342:
11337:
11088:
10538:
10358:
10292:
10264:
10249:
10244:
10219:
9835:
9803:
9783:
9726:
9611:
9534:
9529:
9524:
9519:
9355:
9350:
6277:
6237:
5892:
3868:
Vale JA, Meredith TJ (January 1986). "Acute poisoning due to non-steroidal anti-inflammatory drugs. Clinical features and management".
2667:
1830:
derivative (acidic elimination of the alcohol) and (1-chloroethyl)benzene derivative (Markovnikow addition of HCl to the double bond).
4681:
Tracy TS, Hall SD (March–April 1992). "Metabolic inversion of (R)-ibuprofen. Epimerization and hydrolysis of ibuprofenyl-coenzyme A".
4337:"Exploring the potential of RhoA inhibitors to improve exercise-recoverable spinal cord injury: A systematic review and meta-analysis"
1349:(heart attack), particularly among those chronically using higher doses. On 9 July 2015, the U.S. FDA toughened warnings of increased
12477:
12457:
12437:
12432:
12256:
11991:
11888:
11762:
11728:
11645:
11361:
11307:
11302:
10337:
10184:
10093:
10050:
9601:
9514:
9400:
9380:
9375:
9370:
5187:
5153:
3477:
2704:
Halford GM, Lordkipanidzé M, Watson SP (2012). "50th anniversary of the discovery of ibuprofen: an interview with Dr
Stewart Adams".
1542:
Correlation between severity of symptoms and measured ibuprofen plasma levels is weak. Toxic effects are unlikely at doses below 100
1329:
to be updated for all NSAID medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid.
12452:
12442:
12374:
12306:
12107:
11507:
11411:
11406:
10214:
10179:
10055:
10015:
9184:
6855:
5907:
4749:"Molecular cloning and expression of a 2-arylpropionyl-coenzyme A epimerase: a key enzyme in the inversion metabolism of ibuprofen"
2491:
10297:
10146:
1554:
mg units for an average adult male); however, large doses do not indicate the clinical course is likely to be lethal. A precise
8952:
1715:-enantiomer is converted through a series of three main enzymes. These enzymes include acyl-CoA-synthetase, which converts the
1091:, and it can exacerbate the condition of patients with heart failure. At low doses, it does not appear to increase the risk of
4049:
Hall AH, Smolinske SC, Conrad FL, Wruk KM, Kulig KW, Dwelle TL, et al. (November 1986). "Ibuprofen overdose: 126 cases".
8996:
8564:
6820:
5084:
4536:"Early Industrial Roots of Green Chemistry and the history of the BHC Ibuprofen process invention and its Quality connection"
2958:
2928:
2805:
1143:
2644:
2551:
7172:
6928:
5923:
3111:
Castellsague J, Riera-Guardia N, Calingaert B, Varas-Lorenzo C, Fourrier-Reglat A, Nicotra F, et al. (December 2012).
3026:
Rostas SE, McPherson CC (2016). "Pharmacotherapy for Patent Ductus Arteriosus: Current Options and Outstanding Questions".
2683:
Stewart Adams and his associate John Nicholson invented a pharmaceutical drug known as 2-(4-isobutylphenyl) propionic acid.
1750:
and may be useful in recovery from spinal-cord injury. Another unusual activity is inhibition of the sweet taste receptor.
5532:
Bower JH, Ritz B (March 2011). "Is the answer for Parkinson disease already in the medicine cabinet?: Unfortunately not".
8180:
7741:
7709:
6501:
5900:
2111:
In 2009, the first injectable formulation of ibuprofen was approved in the United States, under the brand name Caldolor.
1013:
302:
12153:
1971:
to offer the active (S)-enantiomer. That is, when the ibuprofen is administered as a racemate the distomer is converted
1442:
aspirin, and 8 hours or more for ibuprofen taken before IR aspirin. However, this timing cannot be recommended for
8613:
5058:
4646:"Highly active supported palladium catalyst for the regioselective synthesis of 2-arylpropionic acids by carbonylation"
2620:
5109:
2420:
2093:
999:
974:
234:
145:
11740:
2747:
2078:
9013:
8581:
4490:
2035:
4264:
3274:"FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications"
10174:
5253:
3721:
1591:
A Canadian study of pregnant women suggests that those taking any type or amount of NSAIDs (including ibuprofen,
1558:
is difficult to determine, as it may vary with age, weight, and concomitant conditions of the individual person.
547:
380:
215:
9060:
4787:
12161:
12022:
11803:
5124:"Written submission to the NDAC meeting on risks of NSAIDs presented by the International Ibuprofen Foundation"
1929:(dextrorotatory) isomer is the more biologically active; this isomer has been isolated and used medically (see
4628:, Elango V, Murphy MA, Smith BL, Davenport KG, "Method for producing ibuprofen", issued 1991-01-01
4585:"Life Cycle Assessment of an Enzymatic Ibuprofen Production Process with Automatic Recycling and Purification"
622:
11755:
8967:
8606:
5239:
2086:
Ibuprofen was made available by prescription in the United Kingdom in 1969 and in the United States in 1974.
1941:
1747:
1214:
168:
1142:. Ibuprofen was first marketed in 1969 in the United Kingdom and in 1974 in the United States. It is on the
12558:
12422:
11721:
8957:
8036:
7679:
5283:
5279:
5257:
5225:
5193:
5159:
5127:
3766:
3739:
3449:
3319:
3279:
1389:
1245:
820:
673:
12412:
2975:
1210:
found that "NSAIDs are effective for short-term symptomatic relief in patients with acute low back pain".
12647:
12602:
9313:
9256:
2297:"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"
1277:
781:
5922:
4178:"Evolution of nonsteroidal anti-inflammatory drugs (NSAIDs): cyclooxygenase (COX) inhibition and beyond"
2142:(low blood pressure when standing up). NSAIDs are of unclear utility in the prevention and treatment of
12572:
9736:
9621:
9544:
9437:
8982:
8947:
7699:
4464:
2105:
1393:
11678:
1150:. In 2022, it was the 33rd most commonly prescribed medication in the United States, with more than 17
742:
12637:
12097:
11971:
9419:
9238:
9073:
8972:
6876:
4973:
3482:
2769:
2581:
2296:
1487:
1362:
1337:
Along with several other NSAIDs, chronic ibuprofen use is correlated with the risk of progression to
1080:
4968:
497:
ibuprofen glucuronide, 2-hydroxyibuprofen, 3-hydroxyibuprofen, carboxy-ibuprofen, 1-hydroxyibuprofen
12632:
11748:
11515:
11496:
11451:
9893:
8774:
8414:
8375:
7165:
6799:
2101:
1296:
1226:
1041:
797:
4286:
Kopp MA, Liebscher T, Niedeggen A, Laufer S, Brommer B, Jungehulsing GJ, et al. (July 2012).
9221:
9001:
8569:
8285:
7689:
7345:
6824:
5879:
4512:
3544:
2139:
2016:
1115:
271:
162:
2920:
2914:
2019:, with a patent application filed in 1961. Adams initially tested the drug as treatment for his
1983:
12336:
11946:
11941:
11853:
11557:
11477:
9069:
8333:
7289:
3084:
Fanos V, Antonucci R, Zaffanello M (2010). "Ibuprofen and acute kidney injury in the newborn".
2176:
2162:
2150:
2143:
763:
468:
286:
17:
5332:"In Japan, an OTC ibuprofen ointment (Fukidia) for alleviating adult acne has been launched".
4583:
Grimaldi F, Tran NN, Sarafraz MM, Lettieri P, Morales-Gonzalez OM, Hessel V (4 October 2021).
2266:
ibuprofen and ibuprofen lysine concerning the eventual onset of action or analgesic efficacy.
12622:
12617:
11931:
11534:
9990:
9227:
8962:
8092:
7786:
7704:
7694:
7406:
7349:
6804:
6794:
6789:
6779:
2097:
2073:
2031:
2023:. In 1985, Boots' worldwide patent for ibuprofen expired and generic products were launched.
1467:
1346:
1092:
899:
722:
613:
403:
282:
2883:
2325:
Davanzo R, Bua J, Paloni G, Facchina G (November 2014). "Breastfeeding and migraine drugs".
1963:, harbors the desired therapeutic activity. Interestingly, the inactive (R)-enantiomer, the
1775:
Ibuprofen is practically insoluble in water, but very soluble in most organic solvents like
1574:
straightforward. Standard measures to maintain normal urine output should be instituted and
12607:
11818:
11673:
10795:
10648:
10118:
8977:
8303:
8264:
8097:
8087:
8082:
7909:
7714:
7630:
7272:
6774:
6751:
6232:
6104:
2027:
1566:
1523:
1483:
1382:
1381:
agent, but it is considered a weak photosensitizing agent compared to other members of the
1218:
1037:
682:
577:
516:
9956:
9865:
2576:
662:
8:
10623:
9082:
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7684:
7513:
7414:
7353:
7240:
7229:
7158:
6828:
6784:
6701:
6079:
5028:
3963:
Seifert SA, Bronstein AC, McGuire T (2000). "Massive ibuprofen ingestion with survival".
2373:
Davies NM (February 1998). "Clinical pharmacokinetics of ibuprofen. The first 30 years".
2223:
2183:
2167:
2161:(acetaminophen) had no effect on the risk for Parkinson's. In March 2011, researchers at
2119:
2115:
1515:
1377:
or pemphigoid-like blistering. As with other NSAIDs, ibuprofen has been reported to be a
1053:
1049:
568:
290:
278:
5626:"Parkinson disease: Could over-the-counter treatment protect against Parkinson disease?"
3003:
982:
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)
824:
801:
11779:
11485:
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8660:
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8057:
7955:
7626:
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6691:
6624:
5827:
5802:
5783:
5739:
5655:
5601:
5576:
5557:
5514:
5436:
5357:
4950:
4938:
4907:
4895:
4864:
4779:
4565:
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4412:
4312:
4287:
4153:
4128:
4109:
4031:
3988:
3940:
3915:
3893:
3810:
3785:
3371:
3354:
3231:
3204:
3185:
3137:
3112:
2729:
2468:
2443:
2398:
2350:
2055:
1992:
1562:
1495:
1386:
1374:
1147:
415:
245:
41:
5310:
4999:
Rainsford KD (April 2003). "Discovery, mechanisms of action and safety of ibuprofen".
4062:
3846:
3420:
3395:
3173:
1872:
1865:
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11019:
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10658:
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9065:
8713:
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8274:
8129:
8117:
8004:
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6861:
6721:
6571:
6134:
6109:
5884:
5832:
5775:
5731:
5726:
5709:
5690:
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207:
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5518:
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4911:
4868:
4113:
3992:
3897:
3736:"Information for Healthcare Professionals: Concomitant Use of Ibuprofen and Aspirin"
3543:
Chan LS (12 June 2014). Hall R, Vinson RP, Nunley JR, Gelfand JM, Elston DM (eds.).
3189:
2733:
2354:
1578:
monitored. Since ibuprofen has acidic properties and is also excreted in the urine,
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11688:
10992:
10578:
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5596:
5588:
5541:
5498:
5463:
5420:
5409:
5388:
5384:
5375:
Zawada ET (May 1982). "Renal consequences of nonsteroidal antiinflammatory drugs".
5341:
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4934:
4891:
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4813:
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1968:
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941:
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450:
363:
353:
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323:
109:
68:
9176:
5787:
4783:
4625:
4603:
4129:"Fetal exposure to nonsteroidal anti-inflammatory drugs and spontaneous abortions"
3160:
Ayres JG, Fleming DM, Whittington RM (May 1987). "Asthma death due to ibuprofen".
2797:
12612:
12586:
11549:
11481:
11391:
11066:
11044:
11014:
9711:
8535:
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6865:
6603:
6593:
6551:
6017:
5935:
5592:
5545:
3931:
3576:
Bergner T, Przybilla B (January 1992). "Photosensitization caused by ibuprofen".
2827:
2717:
2636:
2547:
2283:
2172:
1914:
1807:
1806:
The original synthesis of ibuprofen by the Boots Group started with the compound
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1443:
1207:
904:
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193:
7189:
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5931:
5927:
4714:
Biochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology
3110:
1711:-enantiomer is believed to be the more pharmacologically active enantiomer. The
11898:
11071:
11024:
10589:
10151:
9210:
9007:
8832:
8693:
8575:
8530:
8293:
8173:
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8009:
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3411:
2615:(2014 ed.). London: British Medical Association. 2014. pp. 686–688.
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1811:
1639:
1304:
1191:
1088:
931:
921:
813:
428:
5710:"Herbal medication: potential for adverse interactions with analgesic drugs"
4006:
American Academy Of Clinical Toxico (2004). "Position paper: Ipecac syrup".
3629:
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4239:
4203:
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4105:
4027:
3984:
3949:
3819:
3683:
3648:
3429:
3380:
3355:"Non-narcotic analgesic dose and risk of incident hypertension in US women"
3240:
3146:
3097:
3070:
3047:
3012:
2899:
2725:
2477:
2346:
2138:. As with other NSAIDs, ibuprofen may be useful in the treatment of severe
1930:
1851:
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1643:
1499:
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4733:
4694:
4127:
Daniel S, Koren G, Lunenfeld E, Bilenko N, Ratzon R, Levy A (March 2014).
4070:
4019:
3976:
3889:
3854:
3597:
3511:"High-dose ibuprofen (≥2400mg/day): small increase in cardiovascular risk"
3181:
2394:
1723:-ibuprofen I-CoA; 2-arylpropionyl-CoA epimerase, which converts (−)-
1162:
33:
12531:
12521:
12511:
12394:
12246:
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7369:
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7317:
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7113:
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7015:
6974:
6819:
indicates initially developed first-in-class compound of specific group;
6716:
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6650:
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6506:
6495:
6305:
6227:
6155:
6144:
6094:
6089:
4767:
4335:
Luo M, Li YQ, Lu YF, Wu Y, Liu R, Zheng YR, et al. (November 2020).
3259:
3061:
Beaver WT (April 2003). "Review of the analgesic efficacy of ibuprofen".
2953:(2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust.
2444:"The Cardiovascular Pharmacology of Nonsteroidal Anti-Inflammatory Drugs"
2158:
2007:
1888:
1767:
1685:
1600:
1555:
1511:
1507:
1503:
1455:
1373:
Along with other NSAIDs, ibuprofen has been associated with the onset of
1342:
1315:
1265:
1203:
1072:
1060:
201:
12128:
12007:
11788:
4428:
4288:"Small-molecule-induced Rho-inhibition: NSAIDs after spinal cord injury"
4256:
4144:
3221:
2782:
2041:
In November 2013, work on ibuprofen was recognized by the erection of a
1111:(COX). Ibuprofen is a weaker anti-inflammatory agent than other NSAIDs.
642:
12541:
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11857:
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6196:
6190:
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6160:
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6084:
6074:
6044:
6012:
5997:
5944:
5467:
5110:"Chemical landmark plaque honours scientific discovery past and future"
3881:
3786:"A clinical and safety review of paracetamol and ibuprofen in children"
3717:
3675:
3128:
2255:
1953:
1839:
1592:
864:
653:
492:
297:
6906:
5502:
4925:
Adams SS (April 1992). "The propionic acids: a personal perspective".
4666:
4231:
3639:
1385:
class. Like other NSAIDs, ibuprofen is an extremely rare cause of the
12251:
12186:
12067:
12057:
11878:
11640:
11580:
11312:
11270:
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11215:
11130:
11113:
11108:
11103:
10987:
10967:
10962:
10927:
10882:
10855:
10810:
10805:
10800:
10780:
10735:
10730:
10693:
10683:
10608:
10327:
10234:
10083:
10020:
9933:
9850:
9655:
9640:
9461:
9456:
9125:
9115:
8931:
8890:
8870:
8845:
8827:
8550:
8510:
8505:
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8207:
8168:
8112:
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7948:
7930:
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7887:
7866:
7861:
7856:
7815:
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7534:
7399:
7328:
7256:
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7085:
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6741:
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6655:
6645:
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6418:
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6180:
6114:
6069:
6022:
5987:
5972:
4657:
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3549:
2251:
2243:
2207:
2130:
Ibuprofen is sometimes used for the treatment of acne because of its
1937:
1881:
1681:
1668:, ibuprofen is a nonselective COX inhibitor, in that it inhibits two
1319:
1285:
1261:
1100:
1064:
588:
529:
187:
50:
5112:(Press release). Royal Society of Chemistry (RSC). 21 November 2013.
4194:
4177:
12241:
12216:
12042:
11868:
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11473:
11468:
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11154:
11093:
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10977:
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10902:
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8153:
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7251:
7236:
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7010:
6994:
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6536:
6522:
6470:
6444:
6391:
6315:
6310:
6282:
6272:
6212:
6207:
6175:
6007:
5992:
5962:
4747:
Reichel C, Brugger R, Bang H, Geisslinger G, Brune K (April 1997).
4005:
2259:
2239:
2219:
2211:
2203:
2020:
2003:
1964:
1847:
1792:
1658:
1654:
1596:
1527:
1491:
1479:
1475:
1281:
1269:
1244:
In 2006, ibuprofen lysine was approved in the United States by the
1199:
1079:. Compared to other NSAIDs, it may have other side effects such as
1033:
702:
633:
229:
11772:
2974:
Alabed S, Cabello JB, Irving GJ, Qintar M, Burls A (August 2014).
1170:
887:
769:
12427:
12062:
11610:
11421:
11188:
10715:
10668:
10613:
10159:
9141:
8926:
8799:
8759:
8731:
8525:
8500:
8370:
8355:
8102:
8032:
7664:
7636:
7459:
7374:
7219:
6915:
6756:
6357:
6170:
6119:
6063:
5488:
3339:
This article incorporates text from this source, which is in the
3299:
This article incorporates text from this source, which is in the
2215:
2154:
2012:
1827:
1796:
1776:
1746:
Unlike most other NSAIDs, ibuprofen also acts as an inhibitor of
1669:
1430:
1358:
1187:
1174:
A 150 ml bottle (100 mg/5 ml dosage) of ibuprofen, sold in Greece
1128:
911:
4375:
11996:
11371:
10572:
7305:
7207:
7198:
6297:
2668:"The Inventor of Ibuprofen Tested the Drug on His Own Hangover"
2231:
2199:
2195:
2191:
2015:. The molecule was discovered and synthesized by a team led by
1739:-enantiomer. In addition to the conversion of ibuprofen to the
1466:
Ibuprofen overdose has become common since it was licensed for
1458:
is considered generally safe in children for short-term usage.
1438:
1354:
1257:
1238:
1096:
1068:
733:
484:
3914:
Volans G, Hartley V, McCrea S, Monaghan J (March–April 2003).
3909:
3907:
136:
11183:
7539:
7246:
7211:
5800:
4746:
3558:
3205:"Ibuprofen-induced Anaphylactic Shock in Adult Saudi Patient"
2828:"Ibuprofen Drug Usage Statistics, United States, 2013 - 2022"
1677:
1673:
1433:, potentially rendering aspirin less effective when used for
1357:
risk associated with ibuprofen and related NSAIDs; the NSAID
1179:
1134:
1095:; however, at higher doses it may. Ibuprofen can also worsen
1021:
878:
713:
5574:
4710:"Metabolic stereoisomeric inversion of ibuprofen in mammals"
4582:
4285:
3832:
3613:"Clinical study of cutaneous drug eruptions in 200 patients"
786:
118:
80:
5756:
4803:
4708:
Chen CS, Shieh WR, Lu PH, Harriman S, Chen CY (July 1991).
4126:
3913:
3904:
2135:
2134:
properties, and has been sold in Japan in topical form for
2045:
at Boots' Beeston Factory site in Nottingham, which reads:
1838:
Ibuprofen, like other 2-arylpropionate derivatives such as
1519:
1183:
1126:. It is available under a number of brand names, including
1017:
693:
130:
112:
95:
89:
74:
5575:
Gao X, Chen H, Schwarzschild MA, Ascherio A (March 2011).
2919:(65 ed.). London, UK: Pharmaceutical Press. pp.
2703:
2441:
1814:
of 1-(4-isobutylphenyl)ethanol. This is achieved by a PdCl
1638:, in turn, is converted by other enzymes to several other
1295:
Infrequent adverse effects include esophageal ulceration,
5801:
Kyselovič J, Koscova E, Lampert A, Weiser T (June 2020).
5672:
5254:"Drug Approval Package: Caldolor (Ibuprofen) NDA #022348"
3761:"Information about Taking Ibuprofen and Aspirin Together"
3661:
2973:
2912:
2768:
2304:
2118:(by mouth) (as a tablet, a capsule, or a suspension) and
1470:(OTC) use. Many overdose experiences are reported in the
12133:
Tooltip Peroxisome proliferator-activated receptor gamma
12012:
Tooltip Peroxisome proliferator-activated receptor delta
11793:
Tooltip Peroxisome proliferator-activated receptor alpha
3617:
Indian Journal of Dermatology, Venereology and Leprology
3314:"NSAIDs may cause rare kidney problems in unborn babies"
3202:
3083:
2324:
1425:
According to the FDA, "ibuprofen can interfere with the
5228:(FDA). Archived from the original on 16 September 2011.
5024:"Dr Stewart Adams: 'I tested ibuprofen on my hangover'"
4643:
4083:
4048:
3962:
3159:
1699:-enantiomer undergoes extensive interconversion to the
1144:
World Health Organization's List of Essential Medicines
5296:
5001:
International Journal of Clinical Practice. Supplement
3704:
Ibuprofen: Pharmacology, Therapeutics and Side Effects
3063:
International Journal of Clinical Practice. Supplement
1311:. Ibuprofen can exacerbate asthma, sometimes fatally.
12570:
3393:
3203:
Shaikhain TA, Al-Husayni F, Elder K (December 2019).
2613:
British National Formulary, March 2014–September 2014
2550:. The American Society of Health-System Pharmacists.
2442:
Grosser T, Ricciotti E, FitzGerald GA (August 2017).
2258:; and those that increase the risk of bleeding, like
146:
133:
98:
92:
4216:
3353:
Forman JP, Stampfer MJ, Curhan GC (September 2005).
3352:
2058:, the site of the original laboratory, which reads:
2034:(OTC) in these two countries. Boots was awarded the
1731:-ibuprofen I-CoA; and hydrolase, which converts (+)-
1565:; charcoal absorbs the drug before it can enter the
1182:(including postvaccination fever), mild to moderate
127:
124:
115:
86:
83:
77:
9314:
9257:
9206:
4707:
4413:"An overview of clinical pharmacology of Ibuprofen"
3516:
Medicines and Healthcare products Regulatory Agency
3306:
2884:"Do NSAIDs help in acute or chronic low back pain?"
2881:
2289:
2149:Ibuprofen has been associated with a lower risk of
621:
121:
71:
11777:Tooltip Peroxisome proliferator-activated receptor
10595:
9737:
9622:
9545:
9438:
3478:"Ibuprofen- and dexibuprofen-containing medicines"
2497:. Therapeutic Goods Administration. 31 July 2012.
2276:
2067:
12413:
9420:
9239:
5085:"Boots Hidden Heroes - Honoring Dr Stewart Adams"
4182:Journal of Pharmacy & Pharmaceutical Sciences
3262:, USA: Biomedical Publications. pp. 758–761.
1975:into the eutomer while the latter is unaffected.
27:Medication treating pain, fever, and inflammation
12594:
11516:
11497:
11452:
9894:
5873:. National Safety Council (NSC). 26 August 2020.
5577:"Use of ibuprofen and risk of Parkinson disease"
3575:
3153:
2637:"Ibuprofen Pregnancy and Breastfeeding Warnings"
601:
5868:"Evidence for the efficacy of pain medications"
3266:
3256:Disposition of Toxic Drugs and Chemicals in Man
3025:
2026:The medication was launched as a treatment for
1413:when taking ibuprofen may increase the risk of
576:
11558:
8628:
5453:
5299:Journal of the American Academy of Dermatology
3610:
3578:Journal of the American Academy of Dermatology
2853:"10.1.1 Non-steroidal anti-inflammatory drugs"
1449:
1056:. It typically begins working within an hour.
12643:World Health Organization essential medicines
11756:
11535:
9991:
9192:
9046:
8614:
7166:
6892:
5908:
5714:Journal of Clinical Pharmacy and Therapeutics
2882:Griffin G, Tudiver F, Grant WD (April 2002).
1213:It is used for inflammatory diseases such as
10119:
4881:
3867:
3697:
3695:
3693:
3436:
2571:
2569:
559:)-2-(4-(2-Methylpropyl)phenyl)propanoic acid
233:
7180:
5276:"FDA Approves Injectable Form of Ibuprofen"
4918:
4839:Simonyi M (1984). "On chiral drug action".
4644:Jayasree S, Seayad A, Chaudhari RV (1999).
4592:ACS Sustainable Chemistry & Engineering
4410:
4251:
4249:
2983:The Cochrane Database of Systematic Reviews
2542:
2540:
2538:
2536:
1325:In October 2020, the U.S. FDA required the
11763:
11749:
9199:
9185:
9053:
9039:
8621:
8607:
7173:
7159:
6899:
6885:
5915:
5901:
5104:
5102:
4008:Journal of Toxicology. Clinical Toxicology
3965:Journal of Toxicology. Clinical Toxicology
3664:American Journal of Health-System Pharmacy
3545:"Bullous Pemphigoid Clinical Presentation"
3019:
2967:
2534:
2532:
2530:
2528:
2526:
2524:
2522:
2520:
2518:
2516:
2435:
2318:
823:
800:
661:
5826:
5725:
5641:
5600:
5531:
4998:
4994:
4992:
4969:"Molecule of the Week Archive: Ibuprofen"
4680:
4665:
4551:
4462:
4436:
4352:
4334:
4311:
4193:
4152:
3939:
3809:
3701:
3690:
3638:
3628:
3419:
3394:Hippisley-Cox J, Coupland C (June 2005).
3370:
3230:
3220:
3136:
3002:
2781:
2699:
2697:
2695:
2693:
2691:
2566:
2467:
2327:European Journal of Clinical Pharmacology
2038:in 1985 for the development of the drug.
1657:aggregation, leading to the formation of
1107:by decreasing the activity of the enzyme
1083:. Long-term use has been associated with
681:
5623:
5325:
4884:The Journal of Pharmacy and Pharmacology
4246:
4175:
2607:
2605:
2603:
2601:
2077:
1982:
1766:
1169:
1166:Example of some 200 mg ibuprofen tablets
1161:
936:157 °C (315 °F) at 4 mmHg
5666:
5099:
5021:
4838:
4469:Martindale: The Complete Drug Reference
3783:
3728:
2762:
2513:
2368:
2366:
2364:
2036:Queen's Award for Technical Achievement
1486:. Rarely, more severe symptoms such as
1365:(EMA) issued similar warnings in 2015.
796:
641:
206:
14:
12595:
10590:
8953:Clindamycin/adapalene/benzoyl peroxide
5374:
5214:
4989:
4533:
3565:from the original on 10 November 2011.
3253:
3247:
3060:
2944:
2942:
2940:
2688:
2372:
2284:Use During Pregnancy and Breastfeeding
2175:effect against the risk of developing
2043:Royal Society of Chemistry blue plaque
1989:Royal Society of Chemistry blue plaque
1332:
1288:, rash, salt and fluid retention, and
814:
437:
409:
11744:
9180:
9034:
8602:
7154:
6880:
5924:Non-steroidal anti-inflammatory drugs
5896:
5707:
5264:from the original on 19 October 2012.
5036:from the original on 18 November 2015
4924:
4458:
4456:
3742:(FDA). September 2006. Archived from
3710:
2948:
2776:. Geneva: World Health Organization.
2748:"Chemistry in your cupboard: Nurofen"
2647:from the original on 9 September 2017
2598:
2554:from the original on 9 September 2017
2282:
1361:is not included in this warning. The
1178:Ibuprofen is used primarily to treat
926:75 to 78 °C (167 to 172 °F)
762:
741:
721:
422:
224:
192:
12628:Nonsteroidal anti-inflammatory drugs
11213:Selective COX-2 inhibitors (coxibs):
6851:
5202:from the original on 28 October 2019
5188:"New Drug Application (NDA): 018989"
5168:from the original on 28 October 2019
5154:"New Drug Application (NDA): 017463"
4463:Brayfield A, ed. (14 January 2014).
3542:
3536:
3524:from the original on 28 October 2019
3491:from the original on 28 October 2019
3458:from the original on 28 October 2019
2361:
1913:The product sold in pharmacies is a
1118:and John Nicholson while working at
1114:Ibuprofen was discovered in 1961 by
768:
362:
352:
342:
332:
322:
9322:Tooltip Prostaglandin D2 receptor 2
9265:Tooltip Prostaglandin D2 receptor 1
6502:COX-inhibiting nitric oxide donator
5282:(FDA). 11 June 2009. Archived from
3724:from the original on 6 August 2011.
2937:
2906:
2808:from the original on 30 August 2024
2501:from the original on 20 August 2016
1753:
1478:, drowsiness, dizziness, headache,
1232:
1014:nonsteroidal anti-inflammatory drug
701:
592:
303:Nonsteroidal anti-inflammatory drug
24:
12653:Medicine in the United States Army
11184:AM-404 (N-arachidonoylaminophenol)
11002:Anthranilic acids (fenamic acids):
10654:Mesalazine (5-aminosalicylic acid)
9745:Tooltip Prostaglandin EP4 receptor
9630:Tooltip Prostaglandin EP3 receptor
9553:Tooltip Prostaglandin EP2 receptor
9446:Tooltip Prostaglandin EP1 receptor
5130:(FDA). August 2002. Archived from
4939:10.1002/j.1552-4604.1992.tb03842.x
4896:10.1111/j.2042-7158.1983.tb02874.x
4471:. London, UK: Pharmaceutical Press
4453:
4176:Rao P, Knaus EE (September 2008).
3372:10.1161/01.HYP.0000177437.07240.70
2913:Joint Formulary Committee (2013).
2484:
2448:Trends in Pharmacological Sciences
1833:
1546:mg/kg, but can be severe above 400
1251:
25:
12664:
12418:Tooltip Selective PPARγ modulator
11674:γ-Linolenic acid (gamolenic acid)
11020:Meclofenamic acid (meclofenamate)
9429:Tooltip Prostaglandin E2 receptor
9248:Tooltip Prostaglandin D2 receptor
8265:Tetrahydrocannabinol (dronabinol)
5847:
4267:from the original on 21 July 2014
3086:The Turkish Journal of Pediatrics
2758:from the original on 5 June 2014.
2665:
2094:International nonproprietary name
1611:NSAIDs such as ibuprofen work by
1040:. It may also be used to close a
389:
256:
12580:
11729:Leukotriene signaling modulators
11521:Tooltip Prostaglandin F synthase
11502:Tooltip Prostaglandin E synthase
11461:Tooltip Prostaglandin D synthase
9903:Tooltip Prostaglandin F receptor
6860:
6850:
6841:
6840:
5877:
5727:10.1046/j.1365-2710.2002.00444.x
5346:10.2165/00128413-200615300-00043
4927:Journal of Clinical Pharmacology
4341:Journal of Chemical Neuroanatomy
3916:"Non-opioid analgesic poisoning"
3487:. 22 May 2015. EMA/325007/2015.
3334:
3294:
3284:(Press release). 15 October 2020
3040:10.2174/157339631202160506002028
2916:British National Formulary (BNF)
2387:10.2165/00003088-199834020-00002
1887:
1880:
1871:
1864:
1599:) were 2.4 times more likely to
1550:mg/kg (around 150 tablets of 200
1016:(NSAID) that is used to relieve
848:
108:
67:
49:
40:
11040:Talinflumic acid (talinflumate)
11030:Morniflumic acid (morniflumate)
11010:Floctafenic acid (floctafenate)
10993:Tiaprofenic acid (tiaprofenate)
6752:Superoxide dismutase / orgotein
5794:
5750:
5701:
5617:
5568:
5525:
5482:
5447:
5403:
5368:
5290:
5268:
5246:
5180:
5146:
5116:
5077:
5051:
5015:
4961:
4875:
4832:
4797:
4740:
4701:
4683:Drug Metabolism and Disposition
4674:
4637:
4618:
4576:
4527:
4505:
4483:
4411:Bushra R, Aslam N (July 2010).
4404:
4369:
4328:
4279:
4210:
4169:
4120:
4077:
4042:
3999:
3956:
3861:
3826:
3777:
3655:
3611:Raksha MP, Marfatia YS (2008).
3604:
3569:
3503:
3470:
3387:
3346:
3196:
3104:
3077:
3054:
2875:
2845:
2820:
2790:
2740:
2659:
2629:
2068:Availability and administration
1691:Ibuprofen is administered as a
1606:
1399:
1341:in women, though less than for
1157:
987:Key:HEFNNWSXXWATRW-UHFFFAOYSA-N
11563:Tooltip Thromboxane A synthase
10614:Aspirin (acetylsalicylic acid)
9828:16,16-Dimethyl Prostaglandin E
8033:Aspirin (acetylsalicylic acid)
6064:Aspirin (acetylsalicylic acid)
5456:Journal of Alzheimer's Disease
5389:10.1080/00325481.1982.11716077
5059:"A brief History of Ibuprofen"
4354:10.1016/j.jchemneu.2020.101879
4220:Journal of Medicinal Chemistry
2995:10.1002/14651858.CD010652.pub2
2409:
1642:(which are mediators of pain,
1586:
1314:Allergic reactions, including
1301:high blood levels of potassium
854:
842:
398:
13:
1:
12559:Receptor/signaling modulators
11722:Receptor/signaling modulators
11544:Tooltip Prostacyclin synthase
11045:Tolfenamic acid (tolfenamate)
11015:Flufenamic acid (flufenamate)
11005:Etofenamic acid (etofenamate)
10061:Prostacyclin (prostaglandin I
10000:Tooltip Prostacyclin receptor
8968:Erythromycin/benzoyl peroxide
5758:skin in healthy volunteers".
5311:10.1016/S0190-9622(84)80192-9
4604:10.1021/acssuschemeng.1c02309
4063:10.1016/S0196-0644(86)80617-5
3847:10.1016/S0196-0644(05)82471-0
3174:10.1016/S0140-6736(87)90499-5
2976:"Colchicine for pericarditis"
2951:Australian Medicines Handbook
2269:
2153:and may delay or prevent it.
2082:A bottle of generic ibuprofen
1967:, undergoes a unidirectional
1942:alpha-methylacyl-CoA racemase
1771:Modern synthesis of ibuprofen
1619:(COX) enzymes, which convert
1237:In some countries, ibuprofen
1215:juvenile idiopathic arthritis
1186:(including pain relief after
946:0.021 mg/mL (20 °C)
10128:Tooltip Thromboxane receptor
8958:Clindamycin/benzoyl peroxide
5593:10.1212/WNL.0b013e31820f2d79
5546:10.1212/WNL.0b013e31820f2e7a
5280:Food and Drug Administration
5258:Food and Drug Administration
5226:Food and Drug Administration
5194:Food and Drug Administration
5160:Food and Drug Administration
5128:Food and Drug Administration
5022:Lambert V (8 October 2007).
4818:10.1016/0006-2952(88)90762-9
4726:10.1016/0167-4838(91)90164-U
4493:. Royal Society of Chemistry
4491:"The Synthesis of Ibuprofen"
4051:Annals of Emergency Medicine
3932:10.7861/clinmedicine.3-2-119
3835:Annals of Emergency Medicine
3784:Kanabar DJ (February 2017).
3767:Food and Drug Administration
3740:Food and Drug Administration
3590:10.1016/0190-9622(92)70018-b
3450:Food and Drug Administration
3320:Food and Drug Administration
3280:Food and Drug Administration
2718:10.3109/09537104.2011.632032
2188:prevent platelet aggregation
1762:
1246:Food and Drug Administration
1099:. While its safety in early
463:80–100% (oral), 87% (rectal)
178:isobutylphenylpropionic acid
7:
12302:Muraglitazar (muroglitazar)
11194:Paracetamol (acetaminophen)
11025:Mefenamic acid (mefenamate)
10679:Salicylate (salicylic acid)
7675:Paracetamol (acetaminophen)
6130:Salicylic acid (salicylate)
5340:(1530): 18. 25 March 2006.
2125:
1998:Ibuprofen was derived from
1461:
1450:Paracetamol (acetaminophen)
1278:gastrointestinal ulceration
10:
12669:
12154:15-Deoxy-Δ-prostaglandin J
10873:Bucloxic acid (blucloxate)
10791:Indometacin (indomethacin)
9066:anti-inflammatory products
8983:Tretinoin/benzoyl peroxide
8948:Adapalene/benzoyl peroxide
5880:"The Ibuprofen Revolution"
5819:10.1007/s40122-019-00148-1
5687:10.1016/j.juro.2010.11.092
4841:Medicinal Research Reviews
4513:"The Ibuprofen Revolution"
4098:10.1136/ebnurs-2011-100439
2857:British National Formulary
2786:. WHO/MHP/HPS/EML/2023.02.
2492:"Brufen Tablets And Syrup"
2460:10.1016/j.tips.2017.05.008
2238:spp.); those that contain
2106:United States Adopted Name
2071:
1978:
1420:
1404:
1394:toxic epidermal necrolysis
1122:and initially marketed as
832:Chemical and physical data
12550:
12486:
12126:
12098:Tetradecylthioacetic acid
12005:
11972:Tetradecylthioacetic acid
11786:
11713:
11658:
11556:
11533:
11514:
11495:
11450:
11035:Niflumic acid (niflumate)
10588:
10571:
10346:
10139:Carbocyclic thromboxane A
10117:
9989:
9892:
9817:
9735:
9620:
9543:
9436:
9418:
9312:
9255:
9237:
9220:
9134:
9081:
8991:
8973:Erythromycin/isotretinoin
8940:
8904:
8861:
8798:
8745:
8712:
8679:
8641:
8559:
8478:
8435:
8413:
8376:Tricyclic antidepressants
8332:
8284:
8273:
8235:
8190:
8139:
8023:
7990:
7939:
7875:
7839:
7749:
7740:
7649:
7447:
7265:
7206:
7197:
7122:
7103:
7003:
6973:
6940:
6927:
6836:
6813:
6765:
6684:
6602:
6515:
6351:
6296:
6143:
6053:
5943:
5708:Abebe W (December 2002).
5630:Nature Reviews. Neurology
5425:10.1007/s40266-015-0239-z
5238:: CS1 maint: unfit URL (
4974:American Chemical Society
4553:10.1007/s10698-017-9300-9
4534:Murphy MA (1 July 2018).
4304:10.1007/s00441-012-1334-7
3802:10.1007/s10787-016-0302-3
3483:European Medicines Agency
3412:10.1136/bmj.330.7504.1366
3028:Current Pediatric Reviews
2888:American Family Physician
2770:World Health Organization
2582:European Medicines Agency
2375:Clinical Pharmacokinetics
2339:10.1007/s00228-014-1748-0
1854:in the α-position of the
1719:-enantiomer to (−)-
1488:gastrointestinal bleeding
1363:European Medicines Agency
1081:gastrointestinal bleeding
1030:painful menstrual periods
995:
970:
962:CC(C)Cc1ccc(cc1)(C)C(=O)O
950:
940:
930:
920:
910:
898:
876:
863:
836:
831:
812:
780:
752:
732:
712:
692:
672:
652:
632:
612:
587:
567:
543:
538:
528:
515:
501:
491:
477:
467:
457:
449:
379:
374:
309:
296:
270:
244:
214:
200:
182:
174:
161:
62:
57:
48:
39:
11353:Menatetrenone (vitamin K
11176:Aminophenols (anilines):
7710:+propyphenazone/caffeine
6800:Naproxen/diphenhydramine
5643:10.1038/nrneurol.2011.49
5047:(Subscription required.)
4806:Biochemical Pharmacology
4540:Foundations of Chemistry
4292:Cell and Tissue Research
2102:Australian Approved Name
1735:-ibuprofen I-CoA to the
1727:-ibuprofen I-CoA to (+)-
1580:forced alkaline diuresis
1454:Ibuprofen combined with
1390:Stevens–Johnson syndrome
1256:Adverse effects include
1227:patent ductus arteriosus
1042:patent ductus arteriosus
167:Advil, Motrin, Nurofen,
11679:Dihomo-γ-linolenic acid
11076:Enolic acids (oxicams):
10619:Benorilate (benorylate)
6821:WHO-Essential Medicines
5624:McSharry C (May 2011).
4650:Chemical Communications
3630:10.4103/0378-6323.38431
2140:orthostatic hypotension
2114:Ibuprofen can be taken
1368:
1204:pain from kidney stones
1154:million prescriptions.
1146:. It is available as a
433:OTC / Rx-only
12337:Perfluorononanoic acid
11947:Perfluorooctanoic acid
11942:Perfluorononanoic acid
11478:selenium tetrachloride
9070:vaginal administration
7560:Pethidine (meperidine)
6149:and related substances
5772:10.1055/s-0031-1296997
5760:Arzneimittel-Forschung
5675:The Journal of Urology
5278:(Press release). U.S.
5260:(FDA). 11 March 2010.
5087:(Press release). Boots
5063:Pharmaceutical Journal
4853:10.1002/med.2610040304
4756:Molecular Pharmacology
4390:10.1093/chemse/bjaa057
4086:Evidence-Based Nursing
2163:Harvard Medical School
2083:
2065:
2052:
1995:
1948:)-ibuprofen into the (
1772:
1532:respiratory depression
1221:. It is also used for
1175:
1167:
11932:Palmitoylethanolamide
11147:Aminonicotinic acids:
8963:Clindamycin/tretinoin
8181:+paracetamol/caffeine
8159:Metamizole (dipyrone)
8093:Morpholine salicylate
8037:+paracetamol/caffeine
6805:Naproxen/esomeprazole
6795:Meloxicam/bupivacaine
6790:Ibuprofen/paracetamol
6780:Ibuprofen/hydrocodone
5377:Postgraduate Medicine
4020:10.1081/CLT-120037421
3977:10.1081/clt-100100917
3702:Rainsford KD (2012).
2949:Rossi S, ed. (2013).
2798:"The Top 300 of 2022"
2171:that ibuprofen had a
2098:British Approved Name
2081:
2074:Ibuprofen brand names
2060:
2047:
1986:
1770:
1522:, liver dysfunction,
1347:myocardial infarction
1345:(acetaminophen), and
1173:
1165:
12149:5-Oxo-15-hydroxy-ETE
11819:Aluminium clofibrate
10796:Indometacin farnesil
10649:Magnesium salicylate
10280:Pinane thromboxane A
10041:Iloprost (ciloprost)
9661:Iloprost (ciloprost)
9467:Iloprost (ciloprost)
9083:Prolactin inhibitors
9062:Prolactin inhibitors
8978:Sulfacetamide/sulfur
8304:Gabapentin enacarbil
8098:Potassium salicylate
8088:Magnesium salicylate
8083:Imidazole salicylate
7910:Indometacin farnesil
7306:Diamorphine (heroin)
7273:Acetyldihydrocodeine
6775:Ibuprofen/famotidine
6233:Indometacin farnesil
6105:Magnesium salicylate
5926:(NSAIDs) (primarily
5855:GB patent 971700
4768:10.1124/mol.51.4.576
4417:Oman Medical Journal
3790:Inflammopharmacology
2672:Smithsonian Magazine
2157:, other NSAIDs, and
2028:rheumatoid arthritis
1646:, and fever) and to
1524:acute kidney failure
1383:2-arylpropionic acid
1219:rheumatoid arthritis
1192:painful menstruation
1038:rheumatoid arthritis
10624:Carbasalate calcium
8818:Cyproterone acetate
8053:Carbasalate calcium
6785:Ibuprofen/oxycodone
6702:Chondroitin sulfate
6080:Carbasalate calcium
5491:Annals of Neurology
5286:on 18 October 2012.
5029:The Daily Telegraph
4598:(39): 13135–13150.
4429:10.5001/omj.2010.49
4145:10.1503/cmaj.130605
3771:. 9 September 2019.
3746:on 13 November 2010
3706:. London: Springer.
3222:10.7759/cureus.6425
2863:on 17 November 2016
2228:Filipendula ulmaria
2184:dietary supplements
2177:Parkinson's disease
2151:Parkinson's disease
2144:Alzheimer's disease
1959:(S)-ibuprofen, the
1672:of cyclooxygenase,
1516:atrial fibrillation
1429:effect of low-dose
1387:autoimmune diseases
1333:Cardiovascular risk
1290:high blood pressure
942:Solubility in water
36:
12648:Isobutyl compounds
12603:British inventions
11486:selenium disulfide
11118:4-Aminoquinolines:
9018:Never to phase III
8666:Blue light therapy
8661:8-Hydroxyquinoline
8632:-treating agents (
8586:Never to phase III
8491:Analgesic adjuvant
8392:1.7/1.8-selective:
8058:Choline salicylate
7485:Dextropropoxyphene
7130:Dimethyl sulfoxide
6692:Aminopropionitrile
5468:10.3233/JAD-141506
3882:10.1007/BF03259825
3870:Medical Toxicology
3676:10.2146/ajhp080603
3550:Medscape Reference
3129:10.1007/BF03261999
2423:on 13 January 2015
2084:
2056:BioCity Nottingham
1996:
1993:BioCity Nottingham
1791:°C for 90% EtOH),
1773:
1653:(which stimulates
1563:activated charcoal
1504:low blood pressure
1496:metabolic acidosis
1472:medical literature
1375:bullous pemphigoid
1176:
1168:
1148:generic medication
1048:. It can be taken
416:General sales list
32:
12568:
12567:
11927:Oleylethanolamide
11738:
11737:
11654:
11653:
10689:Sodium salicylate
10659:Methyl salicylate
10582:
10567:
10566:
9888:
9887:
9414:
9413:
9231:
9174:
9173:
9136:Anti-inflammatory
9028:
9027:
8737:Red light therapy
8714:Anti-inflammatory
8596:
8595:
8431:
8430:
8415:Potassium openers
8352:Local anesthetics
8294:Alcohol (ethanol)
8231:
8230:
8130:methyl salicylate
8118:Sodium salicylate
8005:Meclofenamic acid
7680:+aspirin/caffeine
7645:
7644:
7148:
7147:
7099:
7098:
7061:Meclofenamic acid
6929:Anti-inflammatory
6874:
6873:
6722:Glycosaminoglycan
6572:Meclofenamic acid
6135:Sodium salicylate
6110:Methyl salicylate
5503:10.1002/ana.20682
5413:Drugs & Aging
5134:on 15 August 2013
4652:(12): 1067–1068.
4232:10.1021/jm701191z
4057:(11): 1308–1313.
3920:Clinical Medicine
3254:Baselt R (2008).
2960:978-0-9805790-9-3
2930:978-0-85711-084-8
2333:(11): 1313–1324.
2132:anti-inflammatory
1911:
1910:
1664:Like aspirin and
1307:, confusion, and
1305:kidney impairment
1007:
1006:
889:Interactive image
782:CompTox Dashboard
441:
426:
413:
401:
393:
260:
227:
16:(Redirected from
12660:
12638:Racemic mixtures
12585:
12584:
12583:
12576:
12419:
12415:
12177:Arachidonic acid
12134:
12130:
12033:Arachidonic acid
12013:
12009:
11824:Arachidonic acid
11794:
11790:
11778:
11774:
11765:
11758:
11751:
11742:
11741:
11689:Arachidonic acid
11564:
11560:
11545:
11541:
11522:
11518:
11503:
11499:
11462:
11458:
11285:Others/unsorted:
10860:Propionic acids:
10841:Sulindac sulfide
10606:Salicylic acids:
10597:
10592:
10586:
10585:
10576:
10129:
10125:
10001:
9997:
9904:
9900:
9746:
9742:
9631:
9627:
9554:
9550:
9447:
9443:
9434:
9433:
9430:
9426:
9323:
9319:
9266:
9262:
9253:
9252:
9249:
9245:
9235:
9234:
9225:
9201:
9194:
9187:
9178:
9177:
9055:
9048:
9041:
9032:
9031:
8851:Ethinylestradiol
8704:Benzoyl peroxide
8656:Benzoyl peroxide
8623:
8616:
8609:
8600:
8599:
8286:Calcium blockers
8282:
8281:
8178:
8127:
7953:
7941:COX-2 inhibitors
7907:
7826:Tiaprofenic acid
7797:
7784:
7776:
7747:
7746:
7624:
7404:
7343:
7315:
7287:
7204:
7203:
7175:
7168:
7161:
7152:
7151:
6938:
6937:
6901:
6894:
6887:
6878:
6877:
6864:
6854:
6853:
6844:
6843:
6604:COX-2 inhibitors
6519:-arylanthranilic
6486:Tiaprofenic acid
5917:
5910:
5903:
5894:
5893:
5889:
5874:
5872:
5863:
5862:
5858:
5841:
5840:
5830:
5807:Pain and Therapy
5798:
5792:
5791:
5754:
5748:
5747:
5729:
5705:
5699:
5698:
5681:(4): 1388–1393.
5670:
5664:
5663:
5645:
5621:
5615:
5614:
5604:
5572:
5566:
5565:
5529:
5523:
5522:
5486:
5480:
5479:
5451:
5445:
5444:
5407:
5401:
5400:
5372:
5366:
5365:
5329:
5323:
5322:
5305:(6): 1076–1081.
5294:
5288:
5287:
5272:
5266:
5265:
5250:
5244:
5243:
5237:
5229:
5218:
5212:
5211:
5209:
5207:
5184:
5178:
5177:
5175:
5173:
5150:
5144:
5143:
5141:
5139:
5120:
5114:
5113:
5106:
5097:
5096:
5094:
5092:
5081:
5075:
5074:
5072:
5070:
5055:
5049:
5048:
5045:
5043:
5041:
5019:
5013:
5012:
4996:
4987:
4986:
4984:
4982:
4965:
4959:
4958:
4922:
4916:
4915:
4879:
4873:
4872:
4836:
4830:
4829:
4801:
4795:
4794:
4793:on 2 March 2019.
4792:
4786:. Archived from
4753:
4744:
4738:
4737:
4705:
4699:
4698:
4678:
4672:
4671:
4669:
4658:10.1039/a902541c
4641:
4635:
4634:
4633:
4629:
4622:
4616:
4615:
4589:
4580:
4574:
4573:
4555:
4531:
4525:
4524:
4522:
4520:
4509:
4503:
4502:
4500:
4498:
4487:
4481:
4480:
4478:
4476:
4460:
4451:
4450:
4440:
4408:
4402:
4401:
4373:
4367:
4366:
4356:
4332:
4326:
4325:
4315:
4283:
4277:
4276:
4274:
4272:
4253:
4244:
4243:
4226:(8): 2400–2411.
4214:
4208:
4207:
4197:
4173:
4167:
4166:
4156:
4139:(5): E177–E182.
4124:
4118:
4117:
4081:
4075:
4074:
4046:
4040:
4039:
4003:
3997:
3996:
3960:
3954:
3953:
3943:
3911:
3902:
3901:
3865:
3859:
3858:
3830:
3824:
3823:
3813:
3781:
3775:
3772:
3758:Lay summary in:
3755:
3753:
3751:
3732:
3726:
3725:
3714:
3708:
3707:
3699:
3688:
3687:
3659:
3653:
3652:
3642:
3632:
3608:
3602:
3601:
3573:
3567:
3566:
3540:
3534:
3533:
3531:
3529:
3520:. 26 June 2015.
3507:
3501:
3500:
3498:
3496:
3474:
3468:
3467:
3465:
3463:
3440:
3434:
3433:
3423:
3391:
3385:
3384:
3374:
3350:
3344:
3338:
3337:
3333:
3331:
3329:
3310:
3304:
3298:
3297:
3293:
3291:
3289:
3270:
3264:
3263:
3258:(8th ed.).
3251:
3245:
3244:
3234:
3224:
3200:
3194:
3193:
3157:
3151:
3150:
3140:
3108:
3102:
3101:
3081:
3075:
3074:
3058:
3052:
3051:
3023:
3017:
3016:
3006:
2980:
2971:
2965:
2964:
2946:
2935:
2934:
2910:
2904:
2903:
2894:(7): 1319–1321.
2879:
2873:
2872:
2870:
2868:
2859:. Archived from
2849:
2843:
2842:
2840:
2838:
2824:
2818:
2817:
2815:
2813:
2794:
2788:
2787:
2785:
2766:
2760:
2759:
2744:
2738:
2737:
2701:
2686:
2685:
2680:
2678:
2663:
2657:
2656:
2654:
2652:
2633:
2627:
2626:
2609:
2596:
2595:
2593:
2591:
2573:
2564:
2563:
2561:
2559:
2544:
2511:
2510:
2508:
2506:
2496:
2488:
2482:
2481:
2471:
2439:
2433:
2432:
2430:
2428:
2419:. Archived from
2413:
2407:
2406:
2370:
2359:
2358:
2322:
2316:
2315:
2313:
2311:
2301:nctr-crs.fda.gov
2293:
2287:
2286:
2280:
2032:over-the-counter
1969:chiral inversion
1891:
1884:
1875:
1868:
1861:
1860:
1790:
1786:
1782:
1754:Pharmacokinetics
1621:arachidonic acid
1553:
1549:
1545:
1468:over-the-counter
1435:cardioprotection
1415:stomach bleeding
1379:photosensitizing
1233:Ibuprofen lysine
1153:
1120:Boots UK Limited
1028:. This includes
1003:
1002:
891:
871:
856:
850:
844:
827:
816:
805:
804:
790:
788:
772:
766:
745:
725:
705:
685:
665:
645:
625:
605:
595:
594:
580:
520:
510:
439:
436:
431:
424:
421:
411:
408:
400:
397:
391:
388:
366:
356:
346:
336:
326:
258:
255:
237:
226:
223:
210:
196:
153:
149:
143:
142:
139:
138:
135:
132:
129:
126:
123:
120:
117:
114:
105:
104:
101:
100:
97:
94:
91:
88:
85:
82:
79:
76:
73:
53:
44:
37:
35:
31:
21:
12668:
12667:
12663:
12662:
12661:
12659:
12658:
12657:
12633:Propionic acids
12593:
12592:
12591:
12581:
12579:
12571:
12569:
12564:
12546:
12482:
12417:
12350:
12347:Prostaglandin J
12157:
12132:
12122:
12011:
12001:
11902:
11792:
11782:
11776:
11769:
11739:
11734:
11709:
11705:
11702:Prostaglandin H
11697:
11694:Prostaglandin G
11650:
11562:
11552:
11550:Tranylcypromine
11543:
11539:
11529:
11520:
11510:
11501:
11491:
11482:sodium selenite
11460:
11456:
11446:
11392:Rosmarinic acid
11356:
11164:Sulfonanilides:
11067:Oxyphenbutazone
10593:
10575:
10563:
10342:
10283:
10155:
10142:
10127:
10123:
10113:
10073:
10070:Prostaglandin E
10065:, epoprostenol)
10064:
9999:
9995:
9985:
9960:
9957:Prostaglandin F
9952:
9949:Prostaglandin D
9902:
9898:
9884:
9869:
9866:Prostaglandin F
9831:
9813:
9778:
9775:Prostaglandin E
9769:
9766:Prostaglandin E
9744:
9741:
9731:
9712:Ricinoleic acid
9701:
9698:Prostaglandin E
9692:
9689:Prostaglandin E
9684:
9681:Prostaglandin D
9629:
9626:
9616:
9586:
9583:Prostaglandin E
9577:
9574:Prostaglandin E
9552:
9549:
9539:
9499:
9496:Prostaglandin E
9490:
9487:Prostaglandin E
9445:
9442:
9428:
9424:
9410:
9341:
9338:Prostaglandin D
9321:
9318:
9308:
9279:
9276:Prostaglandin D
9264:
9261:
9247:
9243:
9224:
9216:
9205:
9175:
9170:
9139:
9130:
9077:
9059:
9029:
9024:
9023:
9008:Clinical trials
8987:
8936:
8900:
8857:
8794:
8741:
8708:
8675:
8637:
8627:
8597:
8592:
8591:
8576:Clinical trials
8555:
8536:Phenazopyridine
8474:
8455:Cyclobenzaprine
8427:
8409:
8391:
8334:Sodium blockers
8328:
8276:
8269:
8227:
8186:
8176:
8135:
8125:
8019:
8015:Tolfenamic acid
8000:Flufenamic acid
7986:
7951:
7935:
7905:
7871:
7835:
7795:
7782:
7774:
7736:
7700:+metoclopramide
7641:
7622:
7443:
7402:
7341:
7324:Dihydromorphine
7313:
7285:
7261:
7193:
7179:
7149:
7144:
7118:
7095:
6999:
6977:
6969:
6960:Oxyphenbutazone
6932:
6930:
6923:
6905:
6875:
6870:
6832:
6825:withdrawn drugs
6809:
6767:
6761:
6680:
6606:
6598:
6594:Tolfenamic acid
6552:Flufenamic acid
6520:
6511:
6355:
6347:
6292:
6148:
6139:
6049:
6018:Oxyphenbutazone
5948:
5939:
5921:
5870:
5866:
5860:
5850:
5845:
5844:
5799:
5795:
5755:
5751:
5706:
5702:
5671:
5667:
5622:
5618:
5573:
5569:
5540:(10): 854–855.
5530:
5526:
5487:
5483:
5452:
5448:
5408:
5404:
5373:
5369:
5334:Inpharma Weekly
5331:
5330:
5326:
5295:
5291:
5274:
5273:
5269:
5252:
5251:
5247:
5231:
5230:
5220:
5219:
5215:
5205:
5203:
5186:
5185:
5181:
5171:
5169:
5152:
5151:
5147:
5137:
5135:
5122:
5121:
5117:
5108:
5107:
5100:
5090:
5088:
5083:
5082:
5078:
5068:
5066:
5057:
5056:
5052:
5046:
5039:
5037:
5020:
5016:
4997:
4990:
4980:
4978:
4967:
4966:
4962:
4923:
4919:
4890:(11): 693–704.
4880:
4876:
4837:
4833:
4802:
4798:
4790:
4751:
4745:
4741:
4706:
4702:
4679:
4675:
4642:
4638:
4631:
4623:
4619:
4587:
4581:
4577:
4532:
4528:
4518:
4516:
4511:
4510:
4506:
4496:
4494:
4489:
4488:
4484:
4474:
4472:
4461:
4454:
4409:
4405:
4378:Chemical Senses
4374:
4370:
4333:
4329:
4284:
4280:
4270:
4268:
4255:
4254:
4247:
4215:
4211:
4195:10.18433/J3T886
4188:(2): 81s–110s.
4174:
4170:
4125:
4121:
4082:
4078:
4047:
4043:
4004:
4000:
3961:
3957:
3912:
3905:
3866:
3862:
3831:
3827:
3782:
3778:
3759:
3749:
3747:
3734:
3733:
3729:
3716:
3715:
3711:
3700:
3691:
3660:
3656:
3609:
3605:
3574:
3570:
3541:
3537:
3527:
3525:
3509:
3508:
3504:
3494:
3492:
3476:
3475:
3471:
3461:
3459:
3454:. 9 July 2015.
3442:
3441:
3437:
3392:
3388:
3351:
3347:
3335:
3327:
3325:
3312:
3311:
3307:
3295:
3287:
3285:
3272:
3271:
3267:
3252:
3248:
3201:
3197:
3158:
3154:
3123:(12): 1127–46.
3109:
3105:
3082:
3078:
3059:
3055:
3024:
3020:
2989:(8): CD010652.
2978:
2972:
2968:
2961:
2947:
2938:
2931:
2911:
2907:
2880:
2876:
2866:
2864:
2851:
2850:
2846:
2836:
2834:
2826:
2825:
2821:
2811:
2809:
2796:
2795:
2791:
2767:
2763:
2746:
2745:
2741:
2702:
2689:
2676:
2674:
2664:
2660:
2650:
2648:
2635:
2634:
2630:
2623:
2611:
2610:
2599:
2589:
2587:
2575:
2574:
2567:
2557:
2555:
2546:
2545:
2514:
2504:
2502:
2494:
2490:
2489:
2485:
2440:
2436:
2426:
2424:
2415:
2414:
2410:
2371:
2362:
2323:
2319:
2309:
2307:
2295:
2294:
2290:
2281:
2277:
2272:
2173:neuroprotective
2128:
2076:
2070:
2054:and another at
1981:
1915:racemic mixture
1836:
1834:Stereochemistry
1825:
1821:
1817:
1808:isobutylbenzene
1801:dichloromethane
1788:
1784:
1780:
1765:
1756:
1693:racemic mixture
1651:
1637:
1633:
1628:
1625:prostaglandin H
1609:
1589:
1576:kidney function
1551:
1547:
1543:
1512:fast heart rate
1508:slow heart rate
1464:
1452:
1423:
1407:
1402:
1371:
1335:
1254:
1252:Adverse effects
1235:
1208:lower back pain
1198:, dental pain,
1160:
1151:
998:
996:
991:
988:
983:
978:
977:
966:
963:
958:
957:
905:Racemic mixture
894:
869:
859:
853:
847:
808:
784:
776:
748:
728:
708:
688:
668:
648:
628:
608:
591:
583:
563:
560:
551:
550:
518:
508:
503:Onset of action
469:Protein binding
459:Bioavailability
451:Pharmacokinetic
445:
429:
370:
273:
266:
247:
240:
151:
147:
111:
107:
70:
66:
28:
23:
22:
15:
12:
11:
5:
12666:
12656:
12655:
12650:
12645:
12640:
12635:
12630:
12625:
12620:
12615:
12610:
12605:
12590:
12589:
12566:
12565:
12563:
12562:
12555:
12551:
12548:
12547:
12545:
12544:
12539:
12534:
12529:
12524:
12519:
12514:
12509:
12504:
12499:
12490:
12488:
12484:
12483:
12481:
12480:
12471:
12470:
12465:
12460:
12455:
12446:
12445:
12440:
12435:
12430:
12425:
12408:
12407:
12402:
12397:
12392:
12387:
12382:
12377:
12372:
12367:
12362:
12357:
12352:
12348:
12344:
12339:
12334:
12329:
12324:
12319:
12314:
12309:
12304:
12299:
12294:
12289:
12284:
12279:
12274:
12269:
12264:
12259:
12254:
12249:
12244:
12239:
12234:
12229:
12224:
12219:
12214:
12209:
12204:
12199:
12194:
12189:
12184:
12179:
12174:
12169:
12164:
12159:
12155:
12151:
12146:
12137:
12135:
12124:
12123:
12121:
12120:
12115:
12110:
12101:
12100:
12095:
12090:
12085:
12080:
12075:
12070:
12065:
12060:
12055:
12050:
12045:
12040:
12035:
12030:
12025:
12016:
12014:
12003:
12002:
12000:
11999:
11994:
11985:
11984:
11979:
11974:
11969:
11964:
11959:
11954:
11949:
11944:
11939:
11934:
11929:
11924:
11919:
11914:
11909:
11904:
11900:
11896:
11891:
11886:
11881:
11876:
11871:
11866:
11861:
11860:) (in rodents)
11851:
11846:
11841:
11836:
11831:
11826:
11821:
11816:
11811:
11806:
11797:
11795:
11784:
11783:
11768:
11767:
11760:
11753:
11745:
11736:
11735:
11733:
11732:
11725:
11718:
11714:
11711:
11710:
11708:
11707:
11703:
11699:
11695:
11691:
11686:
11684:Diacylglycerol
11681:
11676:
11671:
11662:
11660:
11656:
11655:
11652:
11651:
11649:
11648:
11643:
11638:
11633:
11628:
11623:
11618:
11613:
11608:
11603:
11598:
11593:
11588:
11583:
11578:
11573:
11567:
11565:
11554:
11553:
11548:
11546:
11537:
11531:
11530:
11525:
11523:
11512:
11511:
11506:
11504:
11493:
11492:
11490:
11489:
11471:
11465:
11463:
11454:
11448:
11447:
11445:
11444:
11439:
11434:
11429:
11424:
11419:
11414:
11409:
11404:
11399:
11394:
11389:
11384:
11379:
11374:
11369:
11364:
11359:
11354:
11350:
11345:
11340:
11335:
11330:
11325:
11320:
11315:
11310:
11305:
11300:
11295:
11290:
11278:
11273:
11268:
11263:
11258:
11253:
11248:
11243:
11238:
11233:
11228:
11223:
11218:
11206:
11201:
11196:
11191:
11186:
11181:
11169:
11157:
11152:
11140:
11128:
11123:
11111:
11106:
11101:
11096:
11091:
11086:
11081:
11072:Phenylbutazone
11069:
11064:
11059:
11054:
11042:
11037:
11032:
11027:
11022:
11017:
11012:
11007:
10995:
10990:
10985:
10980:
10975:
10970:
10965:
10960:
10955:
10950:
10945:
10940:
10935:
10930:
10925:
10920:
10915:
10910:
10905:
10900:
10895:
10890:
10885:
10880:
10875:
10870:
10865:
10853:
10848:
10843:
10838:
10833:
10828:
10823:
10818:
10813:
10808:
10803:
10798:
10793:
10788:
10783:
10778:
10773:
10768:
10763:
10758:
10753:
10748:
10743:
10738:
10733:
10728:
10723:
10718:
10713:
10708:
10703:
10691:
10686:
10681:
10676:
10671:
10666:
10661:
10656:
10651:
10646:
10641:
10636:
10631:
10626:
10621:
10616:
10611:
10602:
10600:
10583:
10569:
10568:
10565:
10564:
10562:
10561:
10556:
10551:
10546:
10541:
10536:
10531:
10526:
10521:
10516:
10511:
10506:
10501:
10496:
10491:
10486:
10481:
10476:
10471:
10466:
10461:
10456:
10451:
10446:
10441:
10436:
10431:
10426:
10421:
10416:
10411:
10406:
10401:
10396:
10391:
10386:
10381:
10376:
10371:
10366:
10361:
10356:
10350:
10348:
10344:
10343:
10341:
10340:
10335:
10330:
10325:
10320:
10315:
10310:
10305:
10300:
10295:
10290:
10285:
10281:
10277:
10272:
10267:
10262:
10257:
10252:
10247:
10242:
10237:
10232:
10227:
10222:
10217:
10212:
10207:
10202:
10197:
10192:
10187:
10182:
10177:
10168:
10167:
10162:
10157:
10153:
10149:
10144:
10140:
10132:
10130:
10121:
10115:
10114:
10112:
10111:
10102:
10101:
10096:
10091:
10086:
10081:
10076:
10071:
10067:
10062:
10058:
10053:
10048:
10046:Isocarbacyclin
10043:
10038:
10033:
10028:
10023:
10018:
10013:
10004:
10002:
9993:
9987:
9986:
9984:
9983:
9978:
9973:
9968:
9963:
9958:
9954:
9950:
9946:
9941:
9936:
9931:
9926:
9921:
9916:
9907:
9905:
9896:
9890:
9889:
9886:
9885:
9883:
9882:
9877:
9872:
9867:
9863:
9858:
9853:
9848:
9843:
9838:
9833:
9829:
9821:
9819:
9815:
9814:
9812:
9811:
9806:
9801:
9796:
9787:
9786:
9781:
9779:(dinoprostone)
9776:
9772:
9767:
9763:
9758:
9749:
9747:
9739:
9733:
9732:
9730:
9729:
9720:
9719:
9714:
9709:
9704:
9702:(dinoprostone)
9699:
9695:
9690:
9686:
9682:
9678:
9673:
9668:
9666:Isocarbacyclin
9663:
9658:
9653:
9648:
9643:
9634:
9632:
9624:
9618:
9617:
9615:
9614:
9609:
9604:
9595:
9594:
9589:
9587:(dinoprostone)
9584:
9580:
9575:
9571:
9566:
9557:
9555:
9547:
9541:
9540:
9538:
9537:
9532:
9527:
9522:
9517:
9508:
9507:
9502:
9500:(dinoprostone)
9497:
9493:
9488:
9484:
9479:
9474:
9469:
9464:
9459:
9450:
9448:
9440:
9431:
9422:
9416:
9415:
9412:
9411:
9409:
9408:
9403:
9398:
9393:
9388:
9383:
9378:
9373:
9368:
9363:
9358:
9353:
9344:
9343:
9339:
9335:
9326:
9324:
9316:
9310:
9309:
9307:
9306:
9301:
9296:
9287:
9286:
9281:
9277:
9269:
9267:
9259:
9250:
9241:
9232:
9218:
9217:
9204:
9203:
9196:
9189:
9181:
9172:
9171:
9169:
9168:
9163:
9158:
9153:
9147:
9145:
9144:administration
9132:
9131:
9129:
9128:
9123:
9118:
9113:
9108:
9103:
9098:
9093:
9087:
9085:
9079:
9078:
9058:
9057:
9050:
9043:
9035:
9026:
9025:
9022:
9021:
9020:
9019:
9016:
9005:
8999:
8993:
8992:
8989:
8988:
8986:
8985:
8980:
8975:
8970:
8965:
8960:
8955:
8950:
8944:
8942:
8938:
8937:
8935:
8934:
8929:
8924:
8919:
8914:
8908:
8906:
8902:
8901:
8899:
8898:
8893:
8888:
8883:
8878:
8873:
8867:
8865:
8859:
8858:
8856:
8855:
8854:
8853:
8848:
8838:
8837:
8836:
8833:Spironolactone
8830:
8825:
8820:
8815:
8804:
8802:
8796:
8795:
8793:
8792:
8786:
8781:
8772:
8767:
8762:
8757:
8751:
8749:
8743:
8742:
8740:
8739:
8734:
8729:
8724:
8718:
8716:
8710:
8709:
8707:
8706:
8701:
8696:
8694:Salicylic acid
8691:
8685:
8683:
8677:
8676:
8674:
8673:
8668:
8663:
8658:
8653:
8647:
8645:
8639:
8638:
8626:
8625:
8618:
8611:
8603:
8594:
8593:
8590:
8589:
8588:
8587:
8584:
8573:
8567:
8561:
8560:
8557:
8556:
8554:
8553:
8548:
8543:
8538:
8533:
8531:Methoxyflurane
8528:
8523:
8518:
8513:
8508:
8503:
8498:
8493:
8488:
8482:
8480:
8476:
8475:
8473:
8472:
8467:
8462:
8457:
8452:
8447:
8441:
8439:
8433:
8432:
8429:
8428:
8426:
8425:
8419:
8417:
8411:
8410:
8408:
8407:
8402:
8397:
8389:
8384:
8383:
8373:
8368:
8363:
8349:
8344:
8338:
8336:
8330:
8329:
8327:
8326:
8321:
8316:
8311:
8306:
8301:
8296:
8290:
8288:
8279:
8271:
8270:
8268:
8267:
8262:
8257:
8252:
8247:
8241:
8239:
8233:
8232:
8229:
8228:
8226:
8225:
8220:
8215:
8210:
8205:
8200:
8194:
8192:
8188:
8187:
8185:
8184:
8174:Propyphenazone
8171:
8166:
8161:
8156:
8151:
8149:Aminophenazone
8145:
8143:
8137:
8136:
8134:
8133:
8120:
8115:
8110:
8105:
8100:
8095:
8090:
8085:
8080:
8075:
8070:
8065:
8060:
8055:
8050:
8045:
8040:
8029:
8027:
8021:
8020:
8018:
8017:
8012:
8010:Mefenamic acid
8007:
8002:
7996:
7994:
7988:
7987:
7985:
7984:
7979:
7974:
7969:
7964:
7959:
7945:
7943:
7937:
7936:
7934:
7933:
7928:
7923:
7918:
7913:
7900:
7895:
7890:
7885:
7879:
7877:
7873:
7872:
7870:
7869:
7864:
7859:
7854:
7849:
7843:
7841:
7837:
7836:
7834:
7833:
7828:
7823:
7818:
7813:
7808:
7803:
7790:
7769:
7764:
7759:
7753:
7751:
7744:
7738:
7737:
7735:
7734:
7729:
7724:
7719:
7718:
7717:
7712:
7707:
7702:
7697:
7692:
7687:
7682:
7672:
7667:
7662:
7656:
7654:
7647:
7646:
7643:
7642:
7640:
7639:
7634:
7617:
7612:
7607:
7602:
7597:
7592:
7587:
7582:
7577:
7572:
7567:
7562:
7557:
7552:
7547:
7542:
7537:
7532:
7527:
7522:
7517:
7507:
7502:
7497:
7492:
7487:
7482:
7480:Dextromoramide
7477:
7472:
7467:
7462:
7457:
7451:
7449:
7445:
7444:
7442:
7441:
7436:
7431:
7426:
7397:
7392:
7387:
7382:
7377:
7372:
7367:
7362:
7360:Hydromorphinol
7357:
7336:
7331:
7326:
7321:
7311:Dihydrocodeine
7308:
7303:
7298:
7293:
7280:
7278:Benzylmorphine
7275:
7269:
7267:
7263:
7262:
7260:
7259:
7254:
7249:
7244:
7234:
7233:
7232:
7227:
7216:
7214:
7201:
7195:
7194:
7178:
7177:
7170:
7163:
7155:
7146:
7145:
7143:
7142:
7137:
7132:
7126:
7124:
7120:
7119:
7117:
7116:
7110:
7108:
7101:
7100:
7097:
7096:
7094:
7093:
7088:
7083:
7078:
7073:
7068:
7063:
7058:
7053:
7048:
7043:
7038:
7033:
7028:
7023:
7018:
7013:
7007:
7005:
7001:
7000:
6998:
6997:
6992:
6987:
6981:
6979:
6971:
6970:
6968:
6967:
6965:Phenylbutazone
6962:
6957:
6952:
6946:
6944:
6935:
6925:
6924:
6904:
6903:
6896:
6889:
6881:
6872:
6871:
6869:
6868:
6858:
6848:
6837:
6834:
6833:
6829:veterinary use
6814:
6811:
6810:
6808:
6807:
6802:
6797:
6792:
6787:
6782:
6777:
6771:
6769:
6763:
6762:
6760:
6759:
6754:
6749:
6744:
6739:
6734:
6729:
6724:
6719:
6714:
6709:
6704:
6699:
6694:
6688:
6686:
6682:
6681:
6679:
6678:
6673:
6668:
6663:
6658:
6653:
6648:
6643:
6638:
6633:
6628:
6616:
6610:
6608:
6600:
6599:
6597:
6596:
6591:
6586:
6581:
6578:Mefenamic acid
6574:
6569:
6564:
6559:
6554:
6549:
6544:
6539:
6534:
6528:
6526:
6513:
6512:
6510:
6509:
6498:
6493:
6488:
6483:
6478:
6473:
6468:
6463:
6458:
6453:
6448:
6441:
6436:
6431:
6426:
6421:
6416:
6409:
6404:
6399:
6394:
6389:
6384:
6379:
6374:
6369:
6363:
6361:
6353:propionic acid
6349:
6348:
6346:
6345:
6340:
6335:
6328:
6323:
6318:
6313:
6308:
6302:
6300:
6294:
6293:
6291:
6290:
6285:
6280:
6275:
6270:
6265:
6260:
6255:
6250:
6245:
6240:
6235:
6230:
6225:
6220:
6218:Fenclozic acid
6215:
6210:
6205:
6200:
6193:
6188:
6183:
6178:
6173:
6168:
6163:
6158:
6152:
6150:
6141:
6140:
6138:
6137:
6132:
6127:
6122:
6117:
6112:
6107:
6102:
6097:
6092:
6087:
6082:
6077:
6072:
6067:
6059:
6057:
6051:
6050:
6048:
6047:
6042:
6040:Sulfinpyrazone
6037:
6035:Propyphenazone
6032:
6029:Phenylbutazone
6025:
6020:
6015:
6010:
6005:
6000:
5995:
5990:
5985:
5980:
5975:
5970:
5965:
5960:
5958:Aminophenazone
5954:
5952:
5941:
5940:
5920:
5919:
5912:
5905:
5897:
5891:
5890:
5875:
5864:
5849:
5848:External links
5846:
5843:
5842:
5813:(1): 249–259.
5793:
5766:(8): 444–451.
5749:
5720:(6): 391–401.
5700:
5665:
5616:
5567:
5524:
5497:(6): 963–967.
5481:
5462:(2): 385–396.
5446:
5419:(2): 139–147.
5402:
5383:(5): 223–230.
5367:
5324:
5289:
5267:
5245:
5213:
5179:
5145:
5115:
5098:
5076:
5065:. 27 July 2017
5050:
5014:
4988:
4960:
4933:(4): 317–323.
4917:
4874:
4847:(3): 359–413.
4831:
4812:(1): 105–114.
4796:
4762:(4): 576–582.
4739:
4720:(3): 411–417.
4700:
4689:(2): 322–327.
4673:
4636:
4617:
4575:
4546:(2): 121–165.
4526:
4504:
4482:
4452:
4423:(3): 155–161.
4403:
4384:(8): 667–673.
4368:
4327:
4298:(1): 119–132.
4278:
4245:
4209:
4168:
4119:
4076:
4041:
4014:(2): 133–143.
3998:
3955:
3926:(2): 119–123.
3903:
3860:
3841:(6): 657–662.
3825:
3776:
3774:
3773:
3727:
3709:
3689:
3654:
3603:
3568:
3535:
3502:
3469:
3435:
3406:(7504): 1366.
3386:
3345:
3324:. 21 July 2017
3305:
3265:
3246:
3195:
3168:(8541): 1082.
3152:
3103:
3092:(3): 231–238.
3076:
3065:(135): 13–17.
3053:
3034:(2): 110–119.
3018:
2966:
2959:
2936:
2929:
2905:
2874:
2844:
2819:
2789:
2761:
2739:
2712:(6): 415–422.
2687:
2658:
2628:
2622:978-0857110862
2621:
2597:
2586:. 29 July 2004
2565:
2512:
2483:
2454:(8): 733–748.
2434:
2408:
2381:(2): 101–154.
2360:
2317:
2288:
2274:
2273:
2271:
2268:
2248:horse chestnut
2127:
2124:
2069:
2066:
2000:propionic acid
1980:
1977:
1933:for details).
1925:-isomers. The
1909:
1908:
1901:
1893:
1892:
1885:
1877:
1876:
1869:
1835:
1832:
1823:
1819:
1815:
1764:
1761:
1755:
1752:
1649:
1640:prostaglandins
1635:
1631:
1626:
1617:cyclooxygenase
1608:
1605:
1588:
1585:
1571:Gastric lavage
1536:cardiac arrest
1463:
1460:
1451:
1448:
1444:enteric-coated
1422:
1419:
1406:
1403:
1401:
1398:
1370:
1367:
1334:
1331:
1253:
1250:
1234:
1231:
1196:osteoarthritis
1159:
1156:
1109:cyclooxygenase
1105:prostaglandins
1085:kidney failure
1077:abdominal pain
1052:(by mouth) or
1046:premature baby
1005:
1004:
993:
992:
990:
989:
986:
984:
981:
973:
972:
971:
968:
967:
965:
964:
961:
953:
952:
951:
948:
947:
944:
938:
937:
934:
928:
927:
924:
918:
917:
916:1.03 g/cm
914:
908:
907:
902:
896:
895:
893:
892:
884:
882:
874:
873:
867:
861:
860:
857:
851:
845:
840:
834:
833:
829:
828:
818:
810:
809:
807:
806:
793:
791:
778:
777:
775:
774:
758:
756:
750:
749:
747:
746:
738:
736:
730:
729:
727:
726:
718:
716:
710:
709:
707:
706:
698:
696:
690:
689:
687:
686:
678:
676:
670:
669:
667:
666:
658:
656:
650:
649:
647:
646:
638:
636:
630:
629:
627:
626:
618:
616:
610:
609:
607:
606:
598:
596:
585:
584:
582:
581:
573:
571:
565:
564:
562:
561:
554:
546:
545:
544:
541:
540:
536:
535:
532:
526:
525:
522:
513:
512:
505:
499:
498:
495:
489:
488:
481:
475:
474:
471:
465:
464:
461:
455:
454:
447:
446:
444:
443:
434:
419:
406:
395:
385:
383:
377:
376:
372:
371:
369:
368:
315:
313:
307:
306:
300:
294:
293:
276:
274:administration
268:
267:
265:
264:
262:
252:
250:
242:
241:
239:
238:
220:
218:
212:
211:
204:
198:
197:
190:
180:
179:
176:
172:
171:
165:
159:
158:
64:
60:
59:
55:
54:
46:
45:
26:
9:
6:
4:
3:
2:
12665:
12654:
12651:
12649:
12646:
12644:
12641:
12639:
12636:
12634:
12631:
12629:
12626:
12624:
12621:
12619:
12616:
12614:
12611:
12609:
12606:
12604:
12601:
12600:
12598:
12588:
12578:
12577:
12574:
12561:
12560:
12556:
12553:
12552:
12549:
12543:
12540:
12538:
12537:Rivoglitazone
12535:
12533:
12530:
12528:
12527:Netoglitazone
12525:
12523:
12520:
12518:
12515:
12513:
12510:
12508:
12505:
12503:
12500:
12498:
12495:
12492:
12491:
12489:
12487:Non-selective
12485:
12479:
12476:
12473:
12472:
12469:
12466:
12464:
12461:
12459:
12456:
12454:
12451:
12448:
12447:
12444:
12441:
12439:
12436:
12434:
12431:
12429:
12426:
12424:
12421:
12416:
12410:
12409:
12406:
12403:
12401:
12398:
12396:
12393:
12391:
12390:Sodelglitazar
12388:
12386:
12383:
12381:
12378:
12376:
12373:
12371:
12370:Rosiglitazone
12368:
12366:
12365:Rivoglitazone
12363:
12361:
12358:
12356:
12353:
12351:
12345:
12343:
12340:
12338:
12335:
12333:
12330:
12328:
12325:
12323:
12320:
12318:
12317:Netoglitazone
12315:
12313:
12310:
12308:
12305:
12303:
12300:
12298:
12297:Lobeglitazone
12295:
12293:
12290:
12288:
12285:
12283:
12280:
12278:
12275:
12273:
12270:
12268:
12265:
12263:
12260:
12258:
12255:
12253:
12250:
12248:
12245:
12243:
12240:
12238:
12235:
12233:
12230:
12228:
12225:
12223:
12220:
12218:
12215:
12213:
12210:
12208:
12205:
12203:
12200:
12198:
12195:
12193:
12190:
12188:
12185:
12183:
12182:Balaglitazone
12180:
12178:
12175:
12173:
12170:
12168:
12165:
12163:
12160:
12158:
12152:
12150:
12147:
12145:
12142:
12139:
12138:
12136:
12131:
12125:
12119:
12116:
12114:
12111:
12109:
12106:
12103:
12102:
12099:
12096:
12094:
12093:Sodelglitazar
12091:
12089:
12086:
12084:
12081:
12079:
12076:
12074:
12071:
12069:
12066:
12064:
12061:
12059:
12056:
12054:
12051:
12049:
12046:
12044:
12041:
12039:
12036:
12034:
12031:
12029:
12026:
12024:
12021:
12018:
12017:
12015:
12010:
12004:
11998:
11995:
11993:
11990:
11987:
11986:
11983:
11980:
11978:
11975:
11973:
11970:
11968:
11965:
11963:
11962:Sodelglitazar
11960:
11958:
11955:
11953:
11950:
11948:
11945:
11943:
11940:
11938:
11935:
11933:
11930:
11928:
11925:
11923:
11920:
11918:
11917:Lobeglitazone
11915:
11913:
11910:
11908:
11905:
11903:
11899:Leukotriene B
11897:
11895:
11892:
11890:
11887:
11885:
11882:
11880:
11877:
11875:
11872:
11870:
11867:
11865:
11862:
11859:
11855:
11852:
11850:
11847:
11845:
11842:
11840:
11837:
11835:
11832:
11830:
11827:
11825:
11822:
11820:
11817:
11815:
11812:
11810:
11807:
11805:
11802:
11799:
11798:
11796:
11791:
11785:
11781:
11775:
11766:
11761:
11759:
11754:
11752:
11747:
11746:
11743:
11731:
11730:
11726:
11724:
11723:
11719:
11716:
11715:
11712:
11706:
11700:
11698:
11692:
11690:
11687:
11685:
11682:
11680:
11677:
11675:
11672:
11670:
11669:Linoleic acid
11667:
11664:
11663:
11661:
11657:
11647:
11644:
11642:
11639:
11637:
11634:
11632:
11629:
11627:
11624:
11622:
11619:
11617:
11614:
11612:
11609:
11607:
11604:
11602:
11599:
11597:
11594:
11592:
11589:
11587:
11584:
11582:
11579:
11577:
11574:
11572:
11569:
11568:
11566:
11561:
11555:
11551:
11547:
11542:
11532:
11528:
11524:
11519:
11513:
11509:
11505:
11500:
11494:
11487:
11483:
11479:
11475:
11472:
11470:
11467:
11466:
11464:
11459:
11449:
11443:
11440:
11438:
11435:
11433:
11430:
11428:
11425:
11423:
11420:
11418:
11415:
11413:
11410:
11408:
11405:
11403:
11400:
11398:
11395:
11393:
11390:
11388:
11385:
11383:
11380:
11378:
11375:
11373:
11370:
11368:
11365:
11363:
11360:
11358:
11351:
11349:
11346:
11344:
11341:
11339:
11336:
11334:
11331:
11329:
11326:
11324:
11321:
11319:
11316:
11314:
11311:
11309:
11306:
11304:
11301:
11299:
11296:
11294:
11291:
11289:
11286:
11282:
11279:
11277:
11274:
11272:
11269:
11267:
11264:
11262:
11259:
11257:
11254:
11252:
11249:
11247:
11244:
11242:
11239:
11237:
11234:
11232:
11229:
11227:
11224:
11222:
11219:
11217:
11214:
11210:
11207:
11205:
11202:
11200:
11197:
11195:
11192:
11190:
11187:
11185:
11182:
11180:
11177:
11173:
11170:
11168:
11165:
11161:
11158:
11156:
11153:
11151:
11148:
11144:
11141:
11139:
11138:Fluproquazone
11136:
11135:Quinazolines:
11132:
11129:
11127:
11124:
11122:
11119:
11115:
11112:
11110:
11107:
11105:
11102:
11100:
11097:
11095:
11092:
11090:
11087:
11085:
11082:
11080:
11077:
11073:
11070:
11068:
11065:
11063:
11060:
11058:
11055:
11053:
11050:
11046:
11043:
11041:
11038:
11036:
11033:
11031:
11028:
11026:
11023:
11021:
11018:
11016:
11013:
11011:
11008:
11006:
11003:
10999:
10996:
10994:
10991:
10989:
10986:
10984:
10981:
10979:
10976:
10974:
10971:
10969:
10966:
10964:
10961:
10959:
10956:
10954:
10951:
10949:
10946:
10944:
10941:
10939:
10936:
10934:
10931:
10929:
10926:
10924:
10921:
10919:
10916:
10914:
10913:Flunoxaprofen
10911:
10909:
10906:
10904:
10901:
10899:
10898:Dexketoprofen
10896:
10894:
10893:Dexindoprofen
10891:
10889:
10886:
10884:
10881:
10879:
10876:
10874:
10871:
10869:
10866:
10864:
10861:
10857:
10854:
10852:
10849:
10847:
10844:
10842:
10839:
10837:
10834:
10832:
10831:Proglumetacin
10829:
10827:
10824:
10822:
10819:
10817:
10814:
10812:
10809:
10807:
10804:
10802:
10799:
10797:
10794:
10792:
10789:
10787:
10784:
10782:
10779:
10777:
10774:
10772:
10769:
10767:
10764:
10762:
10761:Difenpiramide
10759:
10757:
10754:
10752:
10749:
10747:
10744:
10742:
10739:
10737:
10734:
10732:
10729:
10727:
10724:
10722:
10719:
10717:
10714:
10712:
10709:
10707:
10704:
10702:
10699:
10698:Acetic acids:
10695:
10692:
10690:
10687:
10685:
10682:
10680:
10677:
10675:
10672:
10670:
10667:
10665:
10662:
10660:
10657:
10655:
10652:
10650:
10647:
10645:
10642:
10640:
10637:
10635:
10632:
10630:
10627:
10625:
10622:
10620:
10617:
10615:
10612:
10610:
10607:
10604:
10603:
10601:
10599:
10587:
10584:
10580:
10574:
10570:
10560:
10557:
10555:
10552:
10550:
10547:
10545:
10542:
10540:
10537:
10535:
10532:
10530:
10527:
10525:
10522:
10520:
10517:
10515:
10512:
10510:
10507:
10505:
10502:
10500:
10497:
10495:
10492:
10490:
10487:
10485:
10482:
10480:
10477:
10475:
10472:
10470:
10467:
10465:
10462:
10460:
10457:
10455:
10452:
10450:
10447:
10445:
10442:
10440:
10437:
10435:
10432:
10430:
10429:Fenprostalene
10427:
10425:
10422:
10420:
10417:
10415:
10412:
10410:
10407:
10405:
10402:
10400:
10397:
10395:
10392:
10390:
10387:
10385:
10382:
10380:
10379:Delprostenate
10377:
10375:
10372:
10370:
10367:
10365:
10362:
10360:
10357:
10355:
10352:
10351:
10349:
10345:
10339:
10336:
10334:
10331:
10329:
10326:
10324:
10321:
10319:
10316:
10314:
10311:
10309:
10306:
10304:
10301:
10299:
10296:
10294:
10291:
10289:
10286:
10284:
10278:
10276:
10273:
10271:
10268:
10266:
10263:
10261:
10258:
10256:
10253:
10251:
10248:
10246:
10243:
10241:
10238:
10236:
10233:
10231:
10228:
10226:
10223:
10221:
10218:
10216:
10213:
10211:
10208:
10206:
10203:
10201:
10198:
10196:
10193:
10191:
10188:
10186:
10183:
10181:
10178:
10176:
10173:
10170:
10169:
10166:
10163:
10161:
10158:
10156:
10152:Thromboxane A
10150:
10148:
10145:
10143:
10137:
10134:
10133:
10131:
10126:
10116:
10110:
10107:
10104:
10103:
10100:
10097:
10095:
10092:
10090:
10087:
10085:
10082:
10080:
10077:
10075:
10074:(alprostadil)
10068:
10066:
10059:
10057:
10054:
10052:
10049:
10047:
10044:
10042:
10039:
10037:
10034:
10032:
10029:
10027:
10024:
10022:
10019:
10017:
10014:
10012:
10009:
10006:
10005:
10003:
9998:
9988:
9982:
9979:
9977:
9974:
9972:
9969:
9967:
9964:
9962:
9955:
9953:
9947:
9945:
9942:
9940:
9937:
9935:
9932:
9930:
9927:
9925:
9922:
9920:
9917:
9915:
9912:
9909:
9908:
9906:
9901:
9891:
9881:
9878:
9876:
9873:
9871:
9864:
9862:
9859:
9857:
9854:
9852:
9849:
9847:
9844:
9842:
9839:
9837:
9834:
9832:
9826:
9823:
9822:
9820:
9816:
9810:
9807:
9805:
9802:
9800:
9797:
9795:
9792:
9789:
9788:
9785:
9782:
9780:
9773:
9771:
9770:(alprostadil)
9764:
9762:
9759:
9757:
9754:
9751:
9750:
9748:
9743:
9734:
9728:
9725:
9722:
9721:
9718:
9715:
9713:
9710:
9708:
9705:
9703:
9696:
9694:
9693:(alprostadil)
9687:
9685:
9679:
9677:
9674:
9672:
9669:
9667:
9664:
9662:
9659:
9657:
9654:
9652:
9649:
9647:
9644:
9642:
9639:
9636:
9635:
9633:
9628:
9619:
9613:
9610:
9608:
9605:
9603:
9600:
9597:
9596:
9593:
9590:
9588:
9581:
9579:
9578:(alprostadil)
9572:
9570:
9567:
9565:
9562:
9559:
9558:
9556:
9551:
9542:
9536:
9533:
9531:
9528:
9526:
9523:
9521:
9518:
9516:
9513:
9510:
9509:
9506:
9503:
9501:
9494:
9492:
9491:(alprostadil)
9485:
9483:
9480:
9478:
9475:
9473:
9470:
9468:
9465:
9463:
9460:
9458:
9455:
9452:
9451:
9449:
9444:
9435:
9432:
9427:
9417:
9407:
9404:
9402:
9399:
9397:
9394:
9392:
9389:
9387:
9384:
9382:
9379:
9377:
9374:
9372:
9369:
9367:
9364:
9362:
9359:
9357:
9354:
9352:
9349:
9346:
9345:
9342:
9336:
9334:
9331:
9328:
9327:
9325:
9320:
9311:
9305:
9302:
9300:
9297:
9295:
9292:
9289:
9288:
9285:
9282:
9280:
9274:
9271:
9270:
9268:
9263:
9254:
9251:
9246:
9236:
9233:
9229:
9223:
9219:
9215:
9212:
9209:
9202:
9197:
9195:
9190:
9188:
9183:
9182:
9179:
9167:
9164:
9162:
9161:Flunoxaprofen
9159:
9157:
9154:
9152:
9149:
9148:
9146:
9143:
9137:
9133:
9127:
9124:
9122:
9119:
9117:
9114:
9112:
9109:
9107:
9104:
9102:
9099:
9097:
9094:
9092:
9091:Bromocriptine
9089:
9088:
9086:
9084:
9080:
9075:
9071:
9067:
9063:
9056:
9051:
9049:
9044:
9042:
9037:
9036:
9033:
9017:
9015:
9012:
9011:
9009:
9006:
9003:
9000:
8998:
8995:
8994:
8990:
8984:
8981:
8979:
8976:
8974:
8971:
8969:
8966:
8964:
8961:
8959:
8956:
8954:
8951:
8949:
8946:
8945:
8943:
8939:
8933:
8930:
8928:
8925:
8923:
8920:
8918:
8915:
8913:
8910:
8909:
8907:
8903:
8897:
8894:
8892:
8889:
8887:
8884:
8882:
8879:
8877:
8874:
8872:
8869:
8868:
8866:
8864:
8860:
8852:
8849:
8847:
8844:
8843:
8842:
8839:
8834:
8831:
8829:
8826:
8824:
8821:
8819:
8816:
8814:
8811:
8810:
8809:
8808:Antiandrogens
8806:
8805:
8803:
8801:
8797:
8790:
8787:
8785:
8782:
8780:
8776:
8775:Tetracyclines
8773:
8771:
8770:Sulfacetamide
8768:
8766:
8763:
8761:
8758:
8756:
8753:
8752:
8750:
8748:
8744:
8738:
8735:
8733:
8730:
8728:
8725:
8723:
8720:
8719:
8717:
8715:
8711:
8705:
8702:
8700:
8697:
8695:
8692:
8690:
8689:Glycolic acid
8687:
8686:
8684:
8682:
8678:
8672:
8669:
8667:
8664:
8662:
8659:
8657:
8654:
8652:
8649:
8648:
8646:
8644:
8643:Antibacterial
8640:
8635:
8631:
8624:
8619:
8617:
8612:
8610:
8605:
8604:
8601:
8585:
8583:
8580:
8579:
8577:
8574:
8571:
8568:
8566:
8563:
8562:
8558:
8552:
8549:
8547:
8544:
8542:
8539:
8537:
8534:
8532:
8529:
8527:
8524:
8522:
8519:
8517:
8514:
8512:
8509:
8507:
8504:
8502:
8499:
8497:
8494:
8492:
8489:
8487:
8484:
8483:
8481:
8477:
8471:
8468:
8466:
8465:Methocarbamol
8463:
8461:
8460:Mephenoxalone
8458:
8456:
8453:
8451:
8450:Chlorzoxazone
8448:
8446:
8443:
8442:
8440:
8438:
8434:
8424:
8421:
8420:
8418:
8416:
8412:
8406:
8403:
8401:
8398:
8396:
8393:
8386:
8385:
8381:
8380:amitriptyline
8377:
8374:
8372:
8369:
8367:
8364:
8361:
8357:
8353:
8350:
8348:
8345:
8343:
8342:Carbamazepine
8340:
8339:
8337:
8335:
8331:
8325:
8322:
8320:
8317:
8315:
8312:
8310:
8307:
8305:
8302:
8300:
8297:
8295:
8292:
8291:
8289:
8287:
8283:
8280:
8278:
8272:
8266:
8263:
8261:
8258:
8256:
8253:
8251:
8248:
8246:
8243:
8242:
8240:
8238:
8234:
8224:
8221:
8219:
8216:
8214:
8211:
8209:
8206:
8204:
8201:
8199:
8196:
8195:
8193:
8189:
8182:
8175:
8172:
8170:
8167:
8165:
8162:
8160:
8157:
8155:
8152:
8150:
8147:
8146:
8144:
8142:
8138:
8131:
8124:
8121:
8119:
8116:
8114:
8111:
8109:
8106:
8104:
8101:
8099:
8096:
8094:
8091:
8089:
8086:
8084:
8081:
8079:
8076:
8074:
8071:
8069:
8066:
8064:
8061:
8059:
8056:
8054:
8051:
8049:
8046:
8044:
8041:
8038:
8034:
8031:
8030:
8028:
8026:
8022:
8016:
8013:
8011:
8008:
8006:
8003:
8001:
7998:
7997:
7995:
7993:
7989:
7983:
7980:
7978:
7975:
7973:
7970:
7968:
7965:
7963:
7960:
7957:
7950:
7947:
7946:
7944:
7942:
7938:
7932:
7929:
7927:
7924:
7922:
7919:
7917:
7914:
7911:
7904:
7901:
7899:
7896:
7894:
7891:
7889:
7886:
7884:
7881:
7880:
7878:
7874:
7868:
7865:
7863:
7860:
7858:
7855:
7853:
7850:
7848:
7845:
7844:
7842:
7838:
7832:
7829:
7827:
7824:
7822:
7819:
7817:
7814:
7812:
7809:
7807:
7804:
7801:
7800:Dexketoprofen
7794:
7791:
7788:
7780:
7773:
7770:
7768:
7765:
7763:
7760:
7758:
7755:
7754:
7752:
7748:
7745:
7743:
7739:
7733:
7730:
7728:
7725:
7723:
7720:
7716:
7713:
7711:
7708:
7706:
7703:
7701:
7698:
7696:
7693:
7691:
7688:
7686:
7683:
7681:
7678:
7677:
7676:
7673:
7671:
7668:
7666:
7663:
7661:
7658:
7657:
7655:
7652:
7648:
7638:
7635:
7632:
7628:
7621:
7618:
7616:
7613:
7611:
7608:
7606:
7603:
7601:
7598:
7596:
7593:
7591:
7588:
7586:
7583:
7581:
7578:
7576:
7575:Phenoperidine
7573:
7571:
7568:
7566:
7563:
7561:
7558:
7556:
7553:
7551:
7548:
7546:
7543:
7541:
7538:
7536:
7533:
7531:
7528:
7526:
7523:
7521:
7518:
7515:
7511:
7508:
7506:
7505:Ethoheptazine
7503:
7501:
7498:
7496:
7493:
7491:
7488:
7486:
7483:
7481:
7478:
7476:
7473:
7471:
7468:
7466:
7463:
7461:
7458:
7456:
7453:
7452:
7450:
7446:
7440:
7437:
7435:
7432:
7430:
7427:
7424:
7420:
7416:
7412:
7408:
7401:
7398:
7396:
7393:
7391:
7388:
7386:
7383:
7381:
7378:
7376:
7373:
7371:
7368:
7366:
7365:Hydromorphone
7363:
7361:
7358:
7355:
7351:
7347:
7340:
7337:
7335:
7334:Ethylmorphine
7332:
7330:
7327:
7325:
7322:
7319:
7312:
7309:
7307:
7304:
7302:
7299:
7297:
7294:
7291:
7284:
7283:Buprenorphine
7281:
7279:
7276:
7274:
7271:
7270:
7268:
7266:Semisynthetic
7264:
7258:
7255:
7253:
7250:
7248:
7245:
7242:
7238:
7235:
7231:
7228:
7226:
7223:
7222:
7221:
7218:
7217:
7215:
7213:
7209:
7205:
7202:
7200:
7196:
7191:
7187:
7183:
7176:
7171:
7169:
7164:
7162:
7157:
7156:
7153:
7141:
7138:
7136:
7133:
7131:
7128:
7127:
7125:
7121:
7115:
7112:
7111:
7109:
7106:
7102:
7092:
7089:
7087:
7084:
7082:
7079:
7077:
7076:Niflumic acid
7074:
7072:
7069:
7067:
7064:
7062:
7059:
7057:
7054:
7052:
7049:
7047:
7044:
7042:
7039:
7037:
7034:
7032:
7029:
7027:
7024:
7022:
7019:
7017:
7014:
7012:
7009:
7008:
7006:
7002:
6996:
6993:
6991:
6988:
6986:
6983:
6982:
6980:
6976:
6972:
6966:
6963:
6961:
6958:
6956:
6953:
6951:
6948:
6947:
6945:
6943:
6942:Pyrazolidines
6939:
6936:
6934:
6931:preparations,
6926:
6921:
6917:
6916:muscular pain
6913:
6910:products for
6909:
6902:
6897:
6895:
6890:
6888:
6883:
6882:
6879:
6867:
6863:
6859:
6857:
6849:
6847:
6839:
6838:
6835:
6830:
6826:
6822:
6818:
6812:
6806:
6803:
6801:
6798:
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6793:
6791:
6788:
6786:
6783:
6781:
6778:
6776:
6773:
6772:
6770:
6764:
6758:
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6753:
6750:
6748:
6745:
6743:
6740:
6738:
6735:
6733:
6730:
6728:
6725:
6723:
6720:
6718:
6715:
6713:
6712:Fluproquazone
6710:
6708:
6705:
6703:
6700:
6698:
6695:
6693:
6690:
6689:
6687:
6683:
6677:
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6672:
6669:
6667:
6664:
6662:
6659:
6657:
6654:
6652:
6649:
6647:
6644:
6642:
6639:
6637:
6634:
6632:
6629:
6626:
6622:
6621:
6617:
6615:
6612:
6611:
6609:
6605:
6601:
6595:
6592:
6590:
6589:Niflumic acid
6587:
6585:
6582:
6580:
6579:
6575:
6573:
6570:
6568:
6565:
6563:
6560:
6558:
6555:
6553:
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6545:
6543:
6540:
6538:
6535:
6533:
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6527:
6524:
6518:
6514:
6508:
6504:
6503:
6499:
6497:
6494:
6492:
6489:
6487:
6484:
6482:
6479:
6477:
6474:
6472:
6469:
6467:
6464:
6462:
6459:
6457:
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6452:
6449:
6447:
6446:
6442:
6440:
6437:
6435:
6432:
6430:
6427:
6425:
6422:
6420:
6417:
6415:
6414:
6410:
6408:
6405:
6403:
6402:Flunoxaprofen
6400:
6398:
6395:
6393:
6390:
6388:
6387:Dexketoprofen
6385:
6383:
6380:
6378:
6375:
6373:
6370:
6368:
6365:
6364:
6362:
6359:
6356:derivatives (
6354:
6350:
6344:
6341:
6339:
6336:
6334:
6333:
6329:
6327:
6324:
6322:
6319:
6317:
6314:
6312:
6309:
6307:
6304:
6303:
6301:
6299:
6295:
6289:
6286:
6284:
6281:
6279:
6276:
6274:
6271:
6269:
6268:Proglumetacin
6266:
6264:
6263:Prodolic acid
6261:
6259:
6256:
6254:
6251:
6249:
6246:
6244:
6241:
6239:
6236:
6234:
6231:
6229:
6226:
6224:
6221:
6219:
6216:
6214:
6211:
6209:
6206:
6204:
6203:Difenpiramide
6201:
6199:
6198:
6194:
6192:
6189:
6187:
6184:
6182:
6179:
6177:
6174:
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6103:
6101:
6098:
6096:
6093:
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6076:
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6036:
6033:
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6026:
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5989:
5986:
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5976:
5974:
5971:
5969:
5966:
5964:
5961:
5959:
5956:
5955:
5953:
5951:
5950:pyrazolidines
5946:
5942:
5937:
5933:
5929:
5925:
5918:
5913:
5911:
5906:
5904:
5899:
5898:
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5876:
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5812:
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5649:
5644:
5639:
5635:
5631:
5627:
5620:
5612:
5608:
5603:
5598:
5594:
5590:
5587:(10): 863–9.
5586:
5582:
5578:
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5133:
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5119:
5111:
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5103:
5086:
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5054:
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5018:
5010:
5006:
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4993:
4977:. 14 May 2018
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3723:
3720:. Drugs.com.
3719:
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3705:
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3677:
3673:
3670:(3): 206–13.
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3555:United States
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3397:
3390:
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3378:
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3368:
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3356:
3349:
3342:
3341:public domain
3323:
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3315:
3309:
3302:
3301:public domain
3283:
3281:
3275:
3269:
3261:
3257:
3250:
3242:
3238:
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3228:
3223:
3218:
3215:(12): e6425.
3214:
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3206:
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2752:RSC Education
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2197:
2193:
2189:
2185:
2180:
2178:
2174:
2170:
2169:
2165:announced in
2164:
2160:
2156:
2152:
2147:
2145:
2141:
2137:
2133:
2123:
2121:
2120:intravenously
2117:
2112:
2109:
2107:
2103:
2099:
2095:
2091:
2087:
2080:
2075:
2064:
2059:
2057:
2051:
2046:
2044:
2039:
2037:
2033:
2029:
2024:
2022:
2018:
2017:Stewart Adams
2014:
2009:
2005:
2001:
1994:
1990:
1985:
1976:
1974:
1970:
1966:
1962:
1957:
1955:
1951:
1947:
1943:
1939:
1934:
1932:
1928:
1924:
1920:
1916:
1906:
1902:
1899:
1895:
1894:
1890:
1886:
1883:
1879:
1878:
1874:
1870:
1867:
1863:
1862:
1859:
1857:
1853:
1850:, contains a
1849:
1845:
1841:
1831:
1829:
1813:
1812:carbonylation
1809:
1804:
1802:
1798:
1794:
1778:
1769:
1760:
1751:
1749:
1744:
1742:
1738:
1734:
1730:
1726:
1722:
1718:
1714:
1710:
1706:
1702:
1698:
1694:
1689:
1687:
1683:
1679:
1675:
1671:
1667:
1662:
1660:
1656:
1652:
1648:thromboxane A
1645:
1641:
1629:
1622:
1618:
1614:
1604:
1602:
1598:
1594:
1584:
1581:
1577:
1572:
1568:
1564:
1559:
1557:
1540:
1537:
1533:
1529:
1525:
1521:
1517:
1513:
1509:
1505:
1501:
1497:
1493:
1489:
1485:
1481:
1477:
1473:
1469:
1459:
1457:
1447:
1445:
1440:
1436:
1432:
1428:
1418:
1416:
1412:
1397:
1395:
1391:
1388:
1384:
1380:
1376:
1366:
1364:
1360:
1356:
1352:
1348:
1344:
1340:
1330:
1328:
1323:
1321:
1317:
1312:
1310:
1306:
1302:
1298:
1297:heart failure
1293:
1291:
1287:
1283:
1279:
1275:
1271:
1267:
1263:
1259:
1249:
1247:
1242:
1240:
1230:
1228:
1224:
1220:
1216:
1211:
1209:
1205:
1201:
1197:
1193:
1189:
1185:
1181:
1172:
1164:
1155:
1149:
1145:
1141:
1137:
1136:
1131:
1130:
1125:
1121:
1117:
1116:Stewart Adams
1112:
1110:
1106:
1102:
1098:
1094:
1090:
1089:liver failure
1087:, and rarely
1086:
1082:
1078:
1074:
1070:
1066:
1062:
1057:
1055:
1054:intravenously
1051:
1047:
1043:
1039:
1035:
1031:
1027:
1023:
1019:
1015:
1011:
1001:
994:
985:
980:
979:
976:
969:
960:
959:
956:
949:
945:
943:
939:
935:
933:
932:Boiling point
929:
925:
923:
922:Melting point
919:
915:
913:
909:
906:
903:
901:
897:
890:
886:
885:
883:
880:
875:
868:
866:
862:
841:
839:
835:
830:
826:
822:
819:
817:
815:ECHA InfoCard
811:
803:
799:
798:DTXSID5020732
795:
794:
792:
783:
779:
771:
770:RCSB PDB
765:
760:
759:
757:
755:
751:
744:
740:
739:
737:
735:
731:
724:
720:
719:
717:
715:
711:
704:
700:
699:
697:
695:
691:
684:
680:
679:
677:
675:
671:
664:
660:
659:
657:
655:
651:
644:
640:
639:
637:
635:
631:
624:
620:
619:
617:
615:
611:
604:
600:
599:
597:
590:
586:
579:
575:
574:
572:
570:
566:
558:
553:
552:
549:
542:
537:
533:
531:
527:
523:
521:
514:
506:
504:
500:
496:
494:
490:
486:
482:
480:
476:
472:
470:
466:
462:
460:
456:
452:
448:
435:
432:
420:
417:
407:
405:
396:
387:
386:
384:
382:
378:
373:
365:
360:
355:
350:
345:
340:
335:
330:
325:
320:
317:
316:
314:
312:
308:
304:
301:
299:
295:
292:
288:
284:
280:
277:
275:
269:
263:
254:
253:
251:
249:
243:
236:
231:
222:
221:
219:
217:
213:
209:
205:
203:
199:
195:
191:
189:
185:
181:
177:
173:
170:
166:
164:
160:
156:
155:
141:
103:
65:
63:Pronunciation
61:
58:Clinical data
56:
52:
47:
43:
38:
30:
19:
12623:Nephrotoxins
12618:Hepatotoxins
12557:
12502:Clinofibrate
12497:Ciprofibrate
12493:
12474:
12450:Antagonists:
12449:
12411:
12405:Troglitazone
12400:Tesaglitazar
12385:Sipoglitazar
12380:Saroglitazar
12355:Ragaglitazar
12342:Pioglitazone
12332:Pemaglitazar
12327:Peliglitazar
12312:Naveglitazar
12277:Lanifibranor
12272:Indeglitazar
12261:
12227:Edaglitazone
12222:Darglitazone
12202:Cevoglitazar
12140:
12105:Antagonists:
12104:
12078:Lanifibranor
12019:
11989:Antagonists:
11988:
11977:Troglitazone
11967:Tesaglitazar
11957:Saroglitazar
11952:Pioglitazone
11922:Muraglitazar
11894:Lanifibranor
11800:
11727:
11720:
11665:
11284:
11212:
11209:Propacetamol
11199:Parapropamol
11175:
11163:
11146:
11134:
11126:Floctafenine
11117:
11075:
11052:Azapropazone
11049:Pyrazolones:
11048:
11001:
10983:Tarenflurbil
10922:
10918:Flurbiprofen
10888:Dexibuprofen
10868:Benoxaprofen
10863:Alminoprofen
10859:
10786:Glucametacin
10697:
10674:Salicylamide
10664:Salacetamide
10605:
10554:Trimoprostil
10549:Tiprostanide
10534:Spiriprostil
10469:Naxaprostene
10419:Esuberaprost
10374:Cobiprostone
10172:Antagonists:
10171:
10135:
10106:Antagonists:
10105:
10099:Treprostinil
10007:
9939:Fluprostenol
9929:Cloprostenol
9910:
9824:
9791:Antagonists:
9790:
9756:Lubiprostone
9752:
9724:Antagonists:
9723:
9637:
9599:Antagonists:
9598:
9592:Treprostinil
9560:
9512:Antagonists:
9511:
9477:Lubiprostone
9453:
9348:Antagonists:
9347:
9329:
9291:Antagonists:
9290:
9284:Treprostinil
9272:
9155:
8941:Combinations
8876:Isotretinoin
8823:Drospirenone
8813:Bicalutamide
8765:Erythromycin
8726:
8671:Tea tree oil
8651:Azelaic acid
8470:Orphenadrine
8445:Carisoprodol
8437:Myorelaxants
8387:
8237:Cannabinoids
8203:Floctafenine
8108:Salicylamide
7787:+paracetamol
7779:Dexibuprofen
7771:
7767:Flurbiprofen
7757:Benoxaprofen
7732:Propacetamol
7722:Parapropamol
7690:+hydrocodone
7631:+paracetamol
7600:Remifentanil
7590:Proheptazine
7520:Ketobemidone
7460:Alphaprodine
7407:+paracetamol
7395:Nicomorphine
7390:Nicodicodine
7346:+paracetamol
7318:+paracetamol
7301:Desomorphine
7230:+paracetamol
7135:Idrocilamide
7081:Piketoprofen
7045:
7041:Flurbiprofen
6955:Mofebutazone
6933:non-steroids
6816:
6768:combinations
6618:
6584:Morniflumate
6576:
6547:Floctafenine
6532:Azapropazone
6516:
6500:
6476:Tarenflurbil
6461:Piketoprofen
6456:Pelubiprofen
6443:
6412:
6411:
6407:Flurbiprofen
6382:Dexibuprofen
6372:Benoxaprofen
6367:Alminoprofen
6330:
6195:
6125:Salicylamide
6062:
6027:
6003:Mofebutazone
5983:Famprofazone
5978:Difenamizole
5968:Azapropazone
5883:
5810:
5806:
5796:
5763:
5759:
5752:
5717:
5713:
5703:
5678:
5674:
5668:
5633:
5629:
5619:
5584:
5580:
5570:
5537:
5533:
5527:
5494:
5490:
5484:
5459:
5455:
5449:
5416:
5412:
5405:
5380:
5376:
5370:
5337:
5333:
5327:
5302:
5298:
5292:
5284:the original
5270:
5248:
5216:
5204:. Retrieved
5191:
5182:
5170:. Retrieved
5157:
5148:
5136:. Retrieved
5132:the original
5118:
5089:. Retrieved
5079:
5067:. Retrieved
5062:
5053:
5038:. Retrieved
5027:
5017:
5003:(135): 3–8.
5000:
4979:. Retrieved
4972:
4963:
4930:
4926:
4920:
4887:
4883:
4877:
4844:
4840:
4834:
4809:
4805:
4799:
4788:the original
4759:
4755:
4742:
4717:
4713:
4703:
4686:
4682:
4676:
4649:
4639:
4620:
4595:
4591:
4578:
4543:
4539:
4529:
4517:. Retrieved
4507:
4495:. Retrieved
4485:
4473:. Retrieved
4468:
4420:
4416:
4406:
4381:
4377:
4371:
4344:
4340:
4330:
4295:
4291:
4281:
4269:. Retrieved
4260:
4223:
4219:
4212:
4185:
4181:
4171:
4136:
4132:
4122:
4092:(3): 76–77.
4089:
4085:
4079:
4054:
4050:
4044:
4011:
4007:
4001:
3971:(1): 55–57.
3968:
3964:
3958:
3923:
3919:
3876:(1): 12–31.
3873:
3869:
3863:
3838:
3834:
3828:
3793:
3789:
3779:
3764:
3748:. Retrieved
3744:the original
3730:
3712:
3703:
3667:
3663:
3657:
3620:
3616:
3606:
3584:(1): 114–6.
3581:
3577:
3571:
3548:
3538:
3526:. Retrieved
3514:
3505:
3493:. Retrieved
3481:
3472:
3460:. Retrieved
3447:
3438:
3403:
3399:
3389:
3365:(3): 500–7.
3362:
3359:Hypertension
3358:
3348:
3326:. Retrieved
3317:
3308:
3286:. Retrieved
3277:
3268:
3255:
3249:
3212:
3208:
3198:
3165:
3161:
3155:
3120:
3116:
3106:
3089:
3085:
3079:
3062:
3056:
3031:
3027:
3021:
2986:
2982:
2969:
2950:
2915:
2908:
2891:
2887:
2877:
2865:. Retrieved
2861:the original
2856:
2847:
2835:. Retrieved
2831:
2822:
2810:. Retrieved
2801:
2792:
2783:10665/371090
2773:
2764:
2751:
2742:
2709:
2705:
2682:
2675:. Retrieved
2671:
2661:
2649:. Retrieved
2640:
2631:
2612:
2588:. Retrieved
2580:
2577:"Pedea EPAR"
2556:. Retrieved
2503:. Retrieved
2486:
2451:
2447:
2437:
2425:. Retrieved
2421:the original
2411:
2378:
2374:
2330:
2326:
2320:
2308:. Retrieved
2300:
2291:
2278:
2264:
2242:, including
2235:
2227:
2190:, including
2181:
2166:
2148:
2129:
2113:
2110:
2089:
2088:
2085:
2061:
2053:
2048:
2040:
2025:
1997:
1972:
1958:
1949:
1945:
1944:, converts (
1935:
1931:dexibuprofen
1926:
1922:
1918:
1912:
1907:)-ibuprofen
1904:
1897:
1852:stereocenter
1844:flurbiprofen
1837:
1805:
1774:
1757:
1745:
1740:
1736:
1732:
1728:
1724:
1720:
1716:
1712:
1708:
1704:
1703:-enantiomer
1700:
1696:
1690:
1666:indomethacin
1663:
1644:inflammation
1610:
1607:Pharmacology
1590:
1560:
1541:
1500:hyperkalemia
1465:
1453:
1427:antiplatelet
1424:
1408:
1400:Interactions
1372:
1351:heart attack
1339:hypertension
1336:
1324:
1313:
1309:bronchospasm
1294:
1274:constipation
1255:
1243:
1236:
1223:pericarditis
1212:
1177:
1158:Medical uses
1139:
1133:
1127:
1123:
1113:
1093:heart attack
1061:side effects
1058:
1026:inflammation
1009:
1008:
997:
556:
517:Elimination
381:Legal status
375:Legal status
216:License data
29:
12608:Dermatoxins
12532:Ronifibrate
12522:Farglitazar
12512:Englitazone
12395:Telmisartan
12322:Oxeglitazar
12267:Imiglitazar
12247:Farglitazar
12237:Englitazone
12232:Efatutazone
12212:Ciglitazone
12207:Chiglitazar
12197:Cannabidiol
12192:Bezafibrate
12172:Aleglitazar
12048:Elafibranor
12038:Bezafibrate
11937:Pemafibrate
11884:Gemfibrozil
11874:Fenofibrate
11864:Elafibranor
11834:Chiglitazar
11829:Bezafibrate
11814:Aleglitazar
11666:Precursors:
11606:Nicogrelate
11586:Furegrelate
11527:Bimatoprost
11437:Trifenagrel
11427:Tiflamizole
11397:Rutecarpine
11382:Resveratrol
11323:Glimepiride
11288:Anitrazafen
11266:Robenacoxib
11246:Lumiracoxib
11179:Acetanilide
11121:Antrafenine
11079:Ampiroxicam
10973:Pranoprofen
10958:Naproxcinod
10851:Zidometacin
10776:Fenclofenac
10701:Aceclofenac
10639:Ethenzamide
10634:Dipyrocetyl
10529:Rosaprostol
10509:Posaraprost
10494:Penprostene
10484:Ornoprostil
10464:Mexiprostil
10459:Meteneprost
10414:Eptaloprost
10389:Dimoxaprost
10354:Arbaprostil
10308:Seratrodast
10200:BMS-180,291
10031:Carbacyclin
9981:Unoprostone
9961:(dinoprost)
9944:Latanoprost
9919:Bimatoprost
9914:Alfaprostol
9870:(dinoprost)
9809:ONO-AE3-208
9761:Misoprostol
9717:Sulprostone
9707:Remiprostol
9676:Misoprostol
9671:Latanoprost
9646:Carbacyclin
9607:PF-04418948
9569:Misoprostol
9505:Sulprostone
9482:Misoprostol
9472:Latanoprost
9406:Vidupiprant
9396:Timapiprant
9391:Setipiprant
9366:Fevipiprant
9333:Indometacin
9304:Vidupiprant
9299:Laropiprant
9151:Benzydamine
9121:Quinagolide
9111:Metergoline
9096:Cabergoline
9074:G02CB–G02CC
9004:from market
8912:Epristeride
8896:Trifarotene
8881:Motretinide
8789:Doxycycline
8784:Minocycline
8779:Lymecycline
8755:Clindamycin
8747:Antibiotics
8722:Niacinamide
8681:Keratolytic
8572:from market
8516:Frunevetmab
8496:Bedinvetmab
8405:PF-05089771
8314:Mirogabalin
8275:Ion channel
8245:Cannabidiol
8198:Benzydamine
8141:Pyrazolones
8123:Wintergreen
8073:Ethenzamide
8068:Dipyrocetyl
8025:Salicylates
7967:Lumiracoxib
7903:Indometacin
7831:Zaltoprofen
7750:Propionates
7660:Acetanilide
7651:Paracetamol
7585:Piritramide
7570:Phenazocine
7565:Phenadoxone
7555:Pentazocine
7550:Oliceridine
7545:Norpipanone
7514:+fluanisone
7495:Dimenoxadol
7475:Carfentanil
7470:Bezitramide
7465:Anileridine
7434:Papaveretum
7429:Oxymorphone
7423:+naltrexone
7385:Nicocodeine
7370:Levorphanol
7339:Hydrocodone
7296:Butorphanol
7241:+naltrexone
7114:Zucapsaicin
7107:derivatives
7051:Indometacin
7026:Etofenamate
7016:Benzydamine
6978:derivatives
6975:Acetic acid
6717:Glucosamine
6697:Benzydamine
6666:Robenacoxib
6651:Lumiracoxib
6542:Etofenamate
6507:Naproxcinod
6496:Zaltoprofen
6306:Ampiroxicam
6228:Indometacin
6156:Aceclofenac
6147:derivatives
6145:acetic acid
6095:Ethenzamide
6090:Dipyrocetyl
6055:salicylates
5945:pyrazolones
5222:"Ibuprofen"
5091:20 February
5069:20 February
4497:22 November
4465:"Ibuprofen"
4257:"Ibuprofen"
3750:22 November
3718:"Ibuprofen"
3260:Foster City
3117:Drug Safety
2590:24 February
2548:"Ibuprofen"
2417:"ibuprofen"
2224:meadowsweet
2159:paracetamol
2008:Boots Group
1900:)-ibuprofen
1759:excretion.
1686:antipyretic
1659:blood clots
1587:Miscarriage
1567:bloodstream
1556:lethal dose
1480:ear ringing
1456:paracetamol
1343:paracetamol
1316:anaphylaxis
1266:indigestion
1073:indigestion
872: g·mol
821:100.036.152
539:Identifiers
534:Urine (95%)
493:Metabolites
291:intravenous
202:MedlinePlus
175:Other names
163:Trade names
12597:Categories
12542:Simfibrate
12517:Etofibrate
12507:Clofibride
12360:Reglitazar
12088:Seladelpar
12053:Fonadelpar
11858:prasterone
11839:Clofibrate
11780:modulators
11636:Samixogrel
11631:Rolafagrel
11616:Picotamide
11596:Midazogrel
11571:Camonagrel
11432:Timegadine
11377:Pamicogrel
11348:Licofelone
11328:Hyperforin
11293:Clobuzarit
11281:Valdecoxib
11276:Tilmacoxib
11261:Polmacoxib
11236:Etoricoxib
11204:Phenacetin
11172:Nimesulide
11150:Clonixeril
11143:Proquazone
11099:Lornoxicam
10998:Vedaprofen
10948:Miroprofen
10943:Loxoprofen
10938:Ketoprofen
10933:Indoprofen
10908:Fenoprofen
10821:Oxametacin
10816:Nabumetone
10756:Diclofenac
10751:Clometacin
10746:Cinmetacin
10741:Bumadizone
10721:Alclofenac
10706:Acemetacin
10644:Guacetisal
10629:Diflunisal
10579:inhibitors
10544:Tilsuprost
10524:Rivenprost
10519:Rioprostil
10514:Prostalene
10499:Pimilprost
10489:Oxoprostol
10479:Nocloprost
10454:Luprostiol
10444:Lanproston
10439:Froxiprost
10434:Flunoprost
10424:Etiproston
10409:Enisoprost
10404:Eganoprost
10364:Ciprostene
10333:Terutroban
10323:Sulotroban
10303:Samixogrel
10288:Ramatroban
10275:Picotamide
10260:Mipitroban
10255:Linotroban
10240:Imitrodast
10230:ICI-192605
10225:ICI-185282
10210:Domitroban
10190:Argatroban
10089:Taprostene
10011:ACT-333679
9976:Travoprost
9971:Tafluprost
9966:Sulotroban
9924:Carboprost
9880:Taprenepag
9861:Omidenepag
9856:Nocloprost
9846:Evatanepag
9841:Carboprost
9794:Grapiprant
9386:Ramatroban
9294:Asapiprant
9214:modulators
9208:Prostanoid
8886:Tazarotene
8546:Rimazolium
8541:Proglumide
8486:Analgecine
8423:Flupirtine
8366:Mexiletine
8347:Lacosamide
8324:Ziconotide
8319:Pregabalin
8309:Leconotide
8299:Gabapentin
8277:modulators
8260:Nabiximols
8223:Proquazone
8218:Nimesulide
8213:Nabumetone
8164:Nifenazone
8078:Guacetisal
8063:Diflunisal
8048:Benorylate
7982:Valdecoxib
7962:Etoricoxib
7893:Diclofenac
7883:Acemetacin
7852:Lornoxicam
7806:Loxoprofen
7793:Ketoprofen
7762:Fenoprofen
7727:Phenacetin
7705:+oxycodone
7695:+ibuprofen
7627:+celecoxib
7610:Tapentadol
7605:Sufentanil
7580:Piminodine
7530:Meptazinol
7525:Lofentanil
7500:Dipipanone
7455:Alfentanil
7415:+ibuprofen
7380:Nalbuphine
7350:+ibuprofen
7182:Analgesics
7140:Tolazoline
7091:Suxibuzone
7071:Nifenazone
7056:Ketoprofen
6985:Diclofenac
6747:Proquazone
6737:Nimesulide
6732:Nabumetone
6727:Hyperforin
6676:Valdecoxib
6641:Etoricoxib
6491:Vedaprofen
6439:Miroprofen
6434:Loxoprofen
6429:Ketoprofen
6424:Indoprofen
6397:Fenoprofen
6321:Lornoxicam
6258:Oxametacin
6197:Diclofenac
6191:Bumadizone
6166:Alclofenac
6161:Acemetacin
6100:Guacetisal
6085:Diflunisal
6075:Benorylate
6045:Suxibuzone
6013:Nifenazone
5998:Metamizole
5636:(5): 244.
5206:28 October
5172:28 October
5040:23 October
4667:1808/18897
4626:US4981995A
4347:: 101879.
3796:(1): 1–9.
3640:1807/48058
3528:28 October
3495:28 October
3328:15 October
3288:15 October
3030:(Review).
2985:(Review).
2558:12 October
2450:(Review).
2427:31 January
2329:(Review).
2310:22 October
2270:References
2256:red clover
2136:adult acne
2104:(AAN) and
2072:See also:
1954:enantiomer
1856:propionate
1840:ketoprofen
1748:Rho kinase
1613:inhibiting
1593:diclofenac
1392:(SJS) and
1327:drug label
877:3D model (
865:Molar mass
754:PDB ligand
723:CHEBI:5855
683:WK2XYI10QM
654:ChemSpider
614:IUPHAR/BPS
578:15687-27-1
569:CAS Number
548:IUPAC name
479:Metabolism
418:(GSL, OTC)
298:Drug class
12494:Agonists:
12468:T-0070907
12292:LG-101506
12287:LG-100754
12282:LG-100268
12262:Ibuprofen
12252:Genistein
12187:Berberine
12144:5-Oxo-ETE
12141:Agonists:
12083:LG-101506
12073:L-165,041
12068:GW-501516
12058:Genistein
12020:Agonists:
11912:LG-100754
11907:LG-101506
11879:Genistein
11844:CP-775146
11801:Agonists:
11641:Terbogrel
11621:Pirmagrel
11581:Dazoxiben
11576:Dazmegrel
11469:Retinoids
11387:Romazarit
11333:Itazigrel
11318:FR-122047
11313:Flumizole
11271:Rofecoxib
11256:Parecoxib
11251:Mavacoxib
11241:Firocoxib
11231:Deracoxib
11226:Cimicoxib
11221:Celecoxib
11216:Apricoxib
11167:Flosulide
11131:Glafenine
11114:Tenoxicam
11109:Piroxicam
11104:Meloxicam
10988:Tepoxalin
10968:Pirprofen
10963:Oxaprozin
10928:Ibuproxam
10923:Ibuprofen
10883:Carprofen
10878:Butibufen
10856:Zomepirac
10826:Oxindanac
10811:Mofezolac
10806:Lonazolac
10801:Ketorolac
10781:Fentiazac
10736:Bufexamac
10731:Bromfenac
10711:Aclofenac
10694:Triflusal
10684:Salsalate
10609:Aloxiprin
10559:Viprostol
10504:Piriprost
10474:Nileprost
10449:Limaprost
10399:Ecraprost
10394:Doxaprost
10384:Deprostil
10369:Clinprost
10328:Terbogrel
10318:SQ-29,548
10313:SQ-28,668
10270:ONO-11120
10235:Ifetroban
10205:Daltroban
10195:Bay U3405
10165:Vapiprost
10136:Agonists:
10109:RO1138452
10084:Selexipag
10079:Ralinepag
10036:Cicaprost
10026:BMY-45778
10021:Beraprost
10008:Agonists:
9934:Enprostil
9911:Agonists:
9875:Simenepag
9851:Gemeprost
9825:Agonists:
9799:GW-627368
9753:Agonists:
9656:Enprostil
9651:Cicaprost
9641:Beraprost
9638:Agonists:
9564:Butaprost
9561:Agonists:
9462:Enprostil
9457:Beraprost
9454:Agonists:
9361:Bay U3405
9330:Agonists:
9273:Agonists:
9211:signaling
9156:Ibuprofen
9126:Terguride
9116:Pergolide
9014:Phase III
9002:Withdrawn
8932:Tioxolone
8891:Tretinoin
8871:Adapalene
8863:Retinoids
8846:Estradiol
8841:Estrogens
8828:Flutamide
8727:Ibuprofen
8582:Phase III
8570:Withdrawn
8551:Tanezumab
8511:Clonidine
8506:Capsaicin
8360:lidocaine
8208:Glafenine
8169:Phenazone
8113:Salsalate
8043:Aloxiprin
7992:Fenamates
7977:Rofecoxib
7972:Parecoxib
7956:+tramadol
7949:Celecoxib
7931:Zomepirac
7916:Ketorolac
7888:Bromfenac
7867:Tenoxicam
7862:Piroxicam
7857:Meloxicam
7816:Oxaprozin
7772:Ibuprofen
7715:+tramadol
7670:Butacetin
7535:Methadone
7448:Synthetic
7419:+naloxone
7400:Oxycodone
7329:Etorphine
7290:+naloxone
7257:Paregoric
7105:Capsaicin
7086:Piroxicam
7046:Ibuprofen
7036:Feprazone
7021:Bufexamac
6990:Fentiazac
6950:Clofezone
6817:underline
6742:Oxaceprol
6707:Diacerein
6671:Rofecoxib
6661:Parecoxib
6656:Mavacoxib
6646:Firocoxib
6636:Deracoxib
6631:Cimicoxib
6625:+tramadol
6620:Celecoxib
6614:Apricoxib
6567:Glafenine
6562:Flutiazin
6523:fenamates
6481:Tepoxalin
6466:Pirprofen
6451:Oxaprozin
6419:Ibuproxam
6413:Ibuprofen
6377:Carprofen
6343:Tenoxicam
6338:Pivoxicam
6332:Piroxicam
6326:Meloxicam
6288:Zomepirac
6253:Mofezolac
6248:Lonazolac
6243:Ketorolac
6223:Fentiazac
6186:Bufexamac
6181:Bromfenac
6115:Salsalate
6070:Aloxiprin
6023:Phenazone
5988:Feprazone
5973:Clofezone
5581:Neurology
5534:Neurology
5362:195105870
5354:1173-8324
4612:2168-0485
4570:254510261
4562:1572-8463
4515:. Science
4036:218865551
3623:(1): 80.
2837:30 August
2812:30 August
2706:Platelets
2666:Kindy D.
2641:Drugs.com
2252:fenugreek
2244:chamomile
2208:dong quai
2168:Neurology
2090:Ibuprofen
2050:worldwide
1938:isomerase
1763:Chemistry
1682:analgesic
1484:nystagmus
1409:Drinking
1320:monograph
1286:dizziness
1262:heartburn
1200:headaches
1101:pregnancy
1065:heartburn
1034:migraines
1010:Ibuprofen
900:Chirality
743:ChEMBL521
530:Excretion
519:half-life
442: OTC
394: OTC
272:Routes of
246:Pregnancy
235:Ibuprofen
194:Monograph
188:Drugs.com
34:Ibuprofen
12587:Medicine
12554:See also
12475:Unknown:
12242:Etalocib
12217:Daidzein
12167:15-HpETE
12118:GSK-3787
12113:GSK-0660
12043:Daidzein
12028:15-HpETE
11982:WY-14643
11869:Etomoxir
11849:Daidzein
11809:15-HpETE
11717:See also
11626:Ridogrel
11601:Nafagrel
11591:Isbogrel
11474:Selenium
11442:Tropesin
11417:SC-58125
11402:Satigrel
11367:NCX-4040
11343:L-670596
11338:L-655240
11298:Curcumin
11160:Flunixin
11155:Clonixin
11094:Isoxicam
11089:Enolicam
11084:Droxicam
11062:Isopyrin
11057:Dipyrone
10978:Suprofen
10953:Naproxen
10903:Fenbufen
10846:Tolmetin
10836:Sulindac
10771:Felbinac
10766:Etodolac
10726:Bendazac
10539:Tiaprost
10359:Ataprost
10347:Unsorted
10293:Ridogrel
10265:ONO-3708
10250:L-670596
10245:L-655240
10220:GR-32191
9836:Aganepag
9818:Unsorted
9804:L-161982
9784:TCS-2510
9727:L-798106
9612:TG 4-155
9535:SC-51322
9530:SC-51089
9525:SC-19220
9520:ONO-8130
9356:AZD-1981
9351:ADC-3680
9222:Receptor
9166:Naproxen
9138:products
9106:Lisuride
9101:Ergoloid
8922:Pelretin
8917:Mesulfen
8800:Hormonal
8521:Ketamine
8400:Funapide
8395:DSP-2230
8255:Nabilone
8250:Cannabis
8154:Ampyrone
7926:Tolmetin
7921:Sulindac
7898:Etodolac
7876:Acetates
7847:Isoxicam
7821:Suprofen
7811:Naproxen
7685:+codeine
7620:Tramadol
7615:Tilidine
7595:Propiram
7510:Fentanyl
7490:Dezocine
7439:Thebacon
7411:+aspirin
7354:+aspirin
7252:Laudanum
7237:Morphine
7225:+aspirin
7066:Naproxen
7031:Felbinac
7011:Bendazac
6995:Tolmetin
6846:category
6607:(coxibs)
6557:Flunixin
6537:Clonixin
6471:Suprofen
6445:Naproxen
6392:Fenbufen
6316:Isoxicam
6311:Droxicam
6283:Tolmetin
6278:Tiopinac
6273:Sulindac
6238:Isoxepac
6213:Felbinac
6208:Etodolac
6176:Bendazac
6008:Morazone
5993:Kebuzone
5963:Ampyrone
5878:Lowe D.
5837:31912434
5780:15460211
5736:12472978
5695:21334642
5660:35880887
5652:21555992
5611:21368281
5562:46104705
5554:21368280
5519:30843070
5511:16240369
5476:25227314
5441:35357112
5433:25644018
5262:Archived
5234:cite web
5200:Archived
5166:Archived
5138:20 March
5034:Archived
5009:12723739
4981:21 March
4955:22857259
4912:40669413
4869:38829275
4519:17 March
4447:22043330
4398:32832995
4363:33197553
4322:22350947
4265:Archived
4261:DrugBank
4240:18363350
4204:19203472
4163:24491470
4114:28521248
4106:22411163
4028:15214617
3993:38588541
3985:10696926
3950:12737366
3898:25223555
3820:28063133
3722:Archived
3684:20101062
3649:18193504
3563:Archived
3522:Archived
3489:Archived
3456:Archived
3430:15947398
3381:16103274
3241:31993263
3190:38589434
3147:23137151
3098:20718179
3071:12723741
3048:27197952
3013:25164988
3004:10645160
2900:11996413
2867:13 April
2832:ClinCalc
2806:Archived
2802:ClinCalc
2772:(2023).
2756:Archived
2734:26344532
2726:22098129
2645:Archived
2552:Archived
2499:Archived
2478:28651847
2355:17144030
2347:25217187
2260:tamarind
2240:coumarin
2220:turmeric
2212:feverfew
2204:bilberry
2126:Research
2021:hangover
2004:research
1965:distomer
1940:enzyme,
1858:moiety.
1848:naproxen
1793:methanol
1787:mL at 40
1670:isoforms
1655:platelet
1601:miscarry
1597:naproxen
1528:cyanosis
1492:seizures
1476:vomiting
1462:Overdose
1282:headache
1270:diarrhea
1063:include
1000:(verify)
634:DrugBank
311:ATC code
279:By mouth
248:category
230:DailyMed
12478:SR-1664
12458:GW-9662
12438:MK-0533
12433:INT-131
12428:EPI-001
12414:SPPARMs
12257:GW-1929
12162:15-HETE
12063:GW-0742
12023:15-HETE
11992:GW-6471
11889:GW-7647
11804:15-HETE
11646:U63557A
11611:Ozagrel
11422:Tenidap
11362:NCX-466
11308:FK-3311
11303:DuP-697
11189:Bucetin
10716:Amfenac
10669:Salicin
10338:TRA-418
10185:AA-2414
10175:12-HETE
10160:U-46619
10094:TRA-418
10051:MRE-269
9602:AH-6809
9515:AH-6809
9401:TM30089
9381:QAV-680
9376:MK-7246
9371:MK-1029
9228:ligands
9142:vaginal
8927:Stridex
8760:Dapsone
8732:Aspirin
8526:Menthol
8501:Camphor
8378:(e.g.,
8371:Nefopam
8356:cocaine
8354:(e.g.,
8103:Salicin
7840:Oxicams
7665:Bucetin
7637:Viminol
7375:Metopon
7220:Codeine
7208:Opiates
7199:Opioids
6908:Topical
6856:commons
6757:Tenidap
6521:acids (
6358:profens
6298:oxicams
6171:Amfenac
6120:Salicin
5934:, also
5885:Science
5828:7203382
5744:1828900
5602:3059148
5397:7041104
5319:6239884
5256:. U.S.
5224:. U.S.
5126:. U.S.
4947:1569234
4904:6139449
4861:6087043
4826:3276314
4776:9106621
4734:1859831
4695:1352228
4475:26 June
4438:3191627
4313:3744771
4271:24 July
4154:3956584
4071:3777588
3941:4952728
3890:3537613
3855:2188537
3811:5306275
3738:. U.S.
3598:1531054
3232:6970456
3182:2883408
3138:3714137
2923:, 671.
2469:5676556
2403:1186212
2395:9515184
2230:), and
2216:ginseng
2155:Aspirin
2100:(BAN),
2096:(INN),
2092:is the
2013:aspirin
2006:arm of
2002:by the
1979:History
1973:in vivo
1961:eutomer
1917:of the
1828:styrene
1797:acetone
1777:ethanol
1705:in vivo
1431:aspirin
1421:Aspirin
1411:alcohol
1405:Alcohol
1359:aspirin
1188:surgery
1129:Nurofen
1059:Common
912:Density
870:206.285
838:Formula
643:DB01050
589:PubChem
483:Liver (
430:WARNING
402::
361: (
359:R02AX02
351: (
349:M02AA13
341: (
339:M01AE01
331: (
329:G02CC01
327:)
321: (
319:C01EB16
305:(NSAID)
287:topical
261: C
232::
208:a682159
12613:Haleon
12573:Portal
12463:SR-202
12453:FH-535
12443:S26948
12375:RS5444
12307:nTZDpa
12108:FH-535
11997:MK-886
11659:Others
11508:HQL-79
11412:SC-560
11407:SC-236
11372:NS-398
10573:Enzyme
10215:EP-045
10180:13-APA
10120:TP (TX
10056:NS-304
10016:AFP-07
8997:WHO-EM
8699:Sulfur
8565:WHO-EM
8479:Others
8191:Others
8177:
8126:
7952:
7906:
7796:
7783:
7775:
7742:NSAIDs
7623:
7403:
7342:
7314:
7286:
6866:portal
5861:
5835:
5825:
5788:592438
5786:
5778:
5742:
5734:
5693:
5658:
5650:
5609:
5599:
5560:
5552:
5517:
5509:
5474:
5439:
5431:
5395:
5360:
5352:
5317:
5032:. UK.
5007:
4953:
4945:
4910:
4902:
4867:
4859:
4824:
4784:835701
4782:
4774:
4732:
4693:
4632:
4610:
4568:
4560:
4445:
4435:
4396:
4361:
4320:
4310:
4238:
4202:
4161:
4151:
4112:
4104:
4069:
4034:
4026:
3991:
3983:
3948:
3938:
3896:
3888:
3853:
3818:
3808:
3682:
3647:
3596:
3518:(MHRA)
3462:9 July
3428:
3421:558288
3418:
3379:
3239:
3229:
3209:Cureus
3188:
3180:
3162:Lancet
3145:
3135:
3096:
3069:
3046:
3011:
3001:
2957:
2927:
2898:
2732:
2724:
2677:3 July
2651:22 May
2619:
2476:
2466:
2401:
2393:
2353:
2345:
2232:willow
2200:ginger
2196:garlic
2192:ginkgo
2116:orally
1789:
1785:
1781:
1779:(66.18
1707:. The
1695:. The
1680:. The
1634:). PGH
1595:, and
1552:
1548:
1544:
1534:, and
1482:, and
1439:stroke
1355:stroke
1258:nausea
1239:lysine
1202:, and
1152:
1140:Motrin
1138:, and
1124:Brufen
1097:asthma
1075:, and
1069:nausea
1050:orally
1036:, and
1024:, and
955:SMILES
734:ChEMBL
703:D00126
509:
485:CYP2C9
427:
414:
283:rectal
228:
169:others
157:
18:Motrin
12423:BADGE
12129:PPARγ
12008:PPARδ
11789:PPARα
10298:S-145
10147:I-BOP
9992:IP (I
9895:FP (F
9421:EP (E
9240:DP (D
8905:Other
7653:-type
7540:NFEPP
7247:Opium
7212:opium
7123:Other
7004:Other
6912:joint
6815:Key:
6766:NSAID
6685:other
5936:N02BA
5871:(PDF)
5784:S2CID
5740:S2CID
5656:S2CID
5558:S2CID
5515:S2CID
5437:S2CID
5358:S2CID
5196:(FDA)
5192:U.S.
5162:(FDA)
5158:U.S.
4951:S2CID
4908:S2CID
4865:S2CID
4791:(PDF)
4780:S2CID
4752:(PDF)
4588:(PDF)
4566:S2CID
4110:S2CID
4032:S2CID
3989:S2CID
3894:S2CID
3769:(FDA)
3765:U.S.
3559:WebMD
3485:(EMA)
3452:(FDA)
3448:U.S.
3322:(FDA)
3318:U.S.
3282:(FDA)
3278:U.S.
3186:S2CID
2979:(PDF)
2730:S2CID
2584:(EMA)
2505:8 May
2495:(PDF)
2399:S2CID
2351:S2CID
2236:Salix
2182:Some
2063:pain.
1783:g/100
1678:COX-2
1674:COX-1
1180:fever
1135:Advil
1044:in a
1022:fever
1012:is a
975:InChI
879:JSmol
761:IBP (
714:ChEBI
524:2–4 h
150:-bew-
11854:DHEA
11773:PPAR
11559:TXAS
11517:PGFS
11498:PGES
10596:PTGS
9140:for
9068:for
9064:and
8630:Acne
7190:N02B
7186:N02A
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