Editing Ibuprofen

{{Short description|Nonsteroidal anti-inflammatory drug}}
{{Use dmy dates|date=April 2025}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 464191340
| image = Ibuprofen.svg
| image_class = skin-invert-image
| width = 200
| caption = (''R/S'')-ibuprofen
| alt = 
| image2 = Ibuprofen-3D-balls.png
| image_class2 = bg-transparent
| width2 = 250
| caption2 = (''R'')-ibuprofen
| alt2 = (R)-ibuprofen
| chirality = [[Racemic mixture]]

<!-- Clinical data -->
| pronounce = {{IPAc-en|ˈ|aɪ|b|juː|p|r|oʊ|f|ɛ|n|audio=LL-Q1860 (eng)-Naomi Persephone Amethyst (NaomiAmethyst)-ibuprofen.wav}}, {{IPAc-en|aɪ|b|juː|ˈ|p|r|oʊ|f|ən}}, {{respell|EYE|bew|PROH|fən}}
| tradename = Brufen, [[List of ibuprofen brand names|others]]
| Drugs.com = {{drugs.com|monograph|ibuprofen}}
| MedlinePlus = a682159
| DailyMedID = Ibuprofen
| pregnancy_AU = C
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{drugs.com|pregnancy|ibuprofen}}</ref>
| pregnancy_category = 
| routes_of_administration = [[Oral administration|By mouth]], [[Rectal administration|rectal]], [[Topical administration|topical]], [[intravenous therapy|intravenous]]
| class = [[Nonsteroidal anti-inflammatory drug]] (NSAID)
| ATC_prefix = C01
| ATC_suffix = EB16
| ATC_supplemental = {{ATC|G02|CC01}} {{ATC|M01|AE01}} {{ATC|M02|AA13}} {{ATC|R02|AX02}}

<!-- Legal status -->
| legal_AU = OTC
| legal_AU_comment  = 
| legal_BR          = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C5, D1, D2, E, F1, F2, F3, F4 -->
| legal_BR_comment  = 
| legal_CA = OTC
| legal_CA_comment  = 
| legal_DE          = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment  = 
| legal_NZ          = <!-- Class A, B, C -->
| legal_NZ_comment  = 
| legal_UK = GSL
| legal_UK_comment  = 
| legal_US = OTC
| legal_US_comment = /&nbsp;Rx-only
| legal_EU = OTC
| legal_EU_comment  = 
| legal_UN          = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment  = 
| legal_status      = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability = 80–100% (oral),<ref name="Davanzo2014">{{cite journal | vauthors = Davanzo R, Bua J, Paloni G, Facchina G | title = Breastfeeding and migraine drugs | journal = European Journal of Clinical Pharmacology | volume = 70 | issue = 11 | pages = 1313–1324 | date = November 2014 | pmid = 25217187 | doi = 10.1007/s00228-014-1748-0 | type = Review | s2cid = 17144030 }}</ref> 87% (rectal)
| protein_bound = 98%<ref name = clinp>{{cite journal | vauthors = Davies NM | title = Clinical pharmacokinetics of ibuprofen. The first 30 years | journal = Clinical Pharmacokinetics | volume = 34 | issue = 2 | pages = 101–154 | date = February 1998 | pmid = 9515184 | doi = 10.2165/00003088-199834020-00002 | s2cid = 1186212 }}</ref>
| metabolism = Liver ([[CYP2C9]])<ref name = clinp/>
| metabolites = ibuprofen glucuronide, 2-hydroxyibuprofen, 3-hydroxyibuprofen, carboxy-ibuprofen, 1-hydroxyibuprofen
| onset = 30{{nbsp}}min<ref>{{cite web |title=ibuprofen |url=http://web.squ.edu.om/med-lib/med_cd/e_cds/Nursing%20Drug%20Guide/mg/ibuprofen.htm |access-date=31 January 2015 |url-status=dead |archive-url=https://web.archive.org/web/20150113042104/http://web.squ.edu.om/med-Lib/MED_CD/E_CDs/Nursing%20Drug%20Guide/mg/ibuprofen.htm |archive-date=13 January 2015 }}</ref>
| elimination_half-life = 2–4 h<ref name="Grosser2017">{{cite journal | vauthors = Grosser T, Ricciotti E, FitzGerald GA | title = The Cardiovascular Pharmacology of Nonsteroidal Anti-Inflammatory Drugs | journal = Trends in Pharmacological Sciences | volume = 38 | issue = 8 | pages = 733–748 | date = August 2017 | pmid = 28651847 | pmc = 5676556 | doi = 10.1016/j.tips.2017.05.008 | type = Review }}</ref>
| duration_of_action = 
| excretion = Urine (95%)<ref name = clinp/><ref name=TGA>{{cite web |title=Brufen Tablets And Syrup |publisher=Therapeutic Goods Administration |date=31 July 2012 |access-date=8 May 2014 |url=https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2009-PI-00035-3 |format=PDF |url-status=live |archive-url=https://web.archive.org/web/20160820064609/https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2009-PI-00035-3 |archive-date=20 August 2016 }}</ref>

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 15687-27-1
| PubChem = 3672
| IUPHAR_ligand = 2713
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01050
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3544
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = WK2XYI10QM
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00126
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 5855
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 521
| NIAID_ChemDB      = 
| PDB_ligand = IBP
| synonyms = isobutylphenylpropionic acid

<!-- Chemical and physical data -->
| IUPAC_name = (''RS'')-2-(4-(2-Methylpropyl)phenyl)propanoic acid
| C = 13
| H = 18
| O = 2
| SMILES = CC(C)Cc1ccc(cc1)[C@@H](C)C(=O)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HEFNNWSXXWATRW-UHFFFAOYSA-N
| density = 1.03
| density_notes     = 
| melting_point = 75
| melting_high = 78
| melting_notes     = 
| boiling_point = 157
| boiling_notes = at 4&nbsp;mmHg
| solubility = 0.021
| sol_units         = 
| specific_rotation = 
}}

<!-- Definition and medical uses -->
'''Ibuprofen''' is a [[nonsteroidal anti-inflammatory drug]] (NSAID) that is used to relieve [[pain]], [[fever]], and [[inflammation]].<ref name="AHFS2016" /> This includes [[dysmenorrhea|painful menstrual periods]], [[migraine]]s, and [[rheumatoid arthritis]].<ref name="AHFS2016" /> It can be taken [[oral administration|orally]] (by mouth) or [[Intravenous therapy|intravenously]].<ref name="AHFS2016" /> It typically begins working within an hour.<ref name="AHFS2016" />

<!-- Side effects and mechanism of action -->
Common [[side effect]]s include [[heartburn]], [[nausea]], [[indigestion]], and [[abdominal pain]].<ref name="AHFS2016" /> Potential side effects include [[gastrointestinal bleeding]].<ref name="BNF67">{{cite book |title=British National Formulary, March 2014–September 2014 |date=2014 |publisher=British Medical Association |location=London |isbn=978-0857110862 |pages=686–688 |edition=2014}}</ref> Long-term use has been associated with [[kidney failure]], and rarely [[liver failure]], and it can exacerbate the condition of people with [[heart failure]].<ref name="AHFS2016" /> At low doses, it does not appear to increase the risk of [[myocardial infarction]] (heart attack); however, at higher doses it may.<ref name="BNF67" /> Ibuprofen can also worsen [[asthma]].<ref name="BNF67" /> While its safety in early [[pregnancy]] is unclear,<ref name="AHFS2016" /> it appears to be harmful in later pregnancy, so it is not recommended during that period.<ref>{{cite web |title=Ibuprofen Pregnancy and Breastfeeding Warnings |url=https://www.drugs.com/pregnancy/ibuprofen.html |website=Drugs.com |access-date=22 May 2016 |url-status=live |archive-url=https://web.archive.org/web/20170909052509/https://www.drugs.com/pregnancy/ibuprofen.html |archive-date=9 September 2017 }}</ref> It works by inhibiting the production of [[prostaglandins]] by decreasing the activity of the enzyme [[cyclooxygenase]] (COX).<ref name="AHFS2016" /> Ibuprofen is a weaker anti-inflammatory agent than other NSAIDs.<ref name="BNF67" />

<!-- History, society and culture -->
Ibuprofen was discovered in 1961 by [[Stewart Adams (chemist)|Stewart Adams]] and John Nicholson<ref>{{cite web|vauthors=Kindy D|title=The Inventor of Ibuprofen Tested the Drug on His Own Hangover|url=https://www.smithsonianmag.com/innovation/inventor-ibuprofen-tested-drug-his-own-hangover-180975088/|access-date=3 July 2021|website=Smithsonian Magazine|quote=Stewart Adams and his associate John Nicholson invented a pharmaceutical drug known as 2-(4-isobutylphenyl) propionic acid.|archive-date=9 July 2021|archive-url=https://web.archive.org/web/20210709182932/https://www.smithsonianmag.com/innovation/inventor-ibuprofen-tested-drug-his-own-hangover-180975088/|url-status=live}}</ref> while working at [[Boots UK Limited]] and initially sold as Brufen.<ref name = plat12>{{cite journal | vauthors = Halford GM, Lordkipanidzé M, Watson SP | title = 50th anniversary of the discovery of ibuprofen: an interview with Dr Stewart Adams | journal = Platelets | volume = 23 | issue = 6 | pages = 415–422 | date = 2012 | pmid = 22098129 | doi = 10.3109/09537104.2011.632032 | s2cid = 26344532 }}</ref> It is available under a number of brand names including '''Advil''', '''Brufen''', '''Motrin''', and '''Nurofen'''.<ref name="AHFS2016">{{cite web |url=https://www.drugs.com/monograph/ibuprofen.html |title=Ibuprofen |publisher=The American Society of Health-System Pharmacists |access-date=12 October 2016 |url-status=live |archive-url=https://web.archive.org/web/20170909052204/https://www.drugs.com/monograph/ibuprofen.html |archive-date=9 September 2017 }}</ref><ref>{{cite web |url=http://www.rsc.org/learn-chemistry/resources/chemistry-in-your-cupboard/nurofen/4 |title=Chemistry in your cupboard: Nurofen |website=RSC Education |url-status=live |archive-url=https://web.archive.org/web/20140605052836/http://www.rsc.org/learn-chemistry/resources/chemistry-in-your-cupboard/nurofen/4 |archive-date=5 June 2014 }}</ref> Ibuprofen was first sold in 1969 in the United Kingdom and in 1974 in the United States.<ref name=AHFS2016/><ref name = plat12/> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> It is available as a [[generic medication]].<ref name=AHFS2016/> In 2022, it was the 33rd most commonly prescribed medication in the United States, with more than 17{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Ibuprofen Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Ibuprofen | access-date = 30 August 2024 | archive-date = 7 October 2024 | archive-url = https://web.archive.org/web/20241007125246/https://clincalc.com/DrugStats/Drugs/Ibuprofen | url-status = live }}</ref>
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==Medical uses==
[[File:200mg ibuprofen tablets.jpg|thumb|Example of some 200 mg ibuprofen tablets]]
[[File:Ibuprofen syrup.jpg|thumb|A 150 ml bottle (100 mg/5 ml dosage) of ibuprofen, sold in Greece]]
Ibuprofen is used primarily to treat [[fever]] (including post-vaccination fever), mild to moderate [[pain]] (including pain relief after [[surgery]]), [[dysmenorrhoea|painful menstruation]], [[osteoarthritis]], dental pain, [[headache]]s, and [[renal colic|pain from kidney stones]]. About 60% of people respond to any NSAID; those who do not respond well to a particular one may respond to another.<ref>{{cite web |url=https://www.evidence.nhs.uk/formulary/bnf/current/10-musculoskeletal-and-joint-diseases/101-drugs-used-in-rheumatic-diseases-and-gout/1011-non-steroidal-anti-inflammatory-drugs |title=10.1.1 Non-steroidal anti-inflammatory drugs |website=British National Formulary |author=<!-- not stated --> |access-date=13 April 2016 |url-status=dead |archive-url=https://web.archive.org/web/20161117090028/http://www.evidence.nhs.uk/formulary/bnf/current/10-musculoskeletal-and-joint-diseases/101-drugs-used-in-rheumatic-diseases-and-gout/1011-non-steroidal-anti-inflammatory-drugs |archive-date=17 November 2016 }}</ref> A Cochrane medical review of 51 trials of NSAIDs for the treatment of [[lower back pain]] found that "NSAIDs are effective for short-term symptomatic relief in patients with acute low back pain".<ref>{{cite journal | vauthors = Griffin G, Tudiver F, Grant WD | title = Do NSAIDs help in acute or chronic low back pain? | journal = American Family Physician | volume = 65 | issue = 7 | pages = 1319–1321 | date = April 2002 | pmid = 11996413 | url = https://www.aafp.org/pubs/afp/issues/2002/0401/p1319.html | access-date = 19 January 2023 | archive-date = 19 January 2023 | archive-url = https://web.archive.org/web/20230119180318/https://www.aafp.org/pubs/afp/issues/2002/0401/p1319.html | url-status = live }}</ref>

It is used for inflammatory diseases such as [[juvenile idiopathic arthritis]] and [[rheumatoid arthritis]].<ref name="BNF">{{cite book | isbn = 978-0-85711-084-8 | title = British National Formulary (BNF) | last1 = Joint Formulary Committee | year = 2013 | publisher = Pharmaceutical Press | location = London, UK | edition = 65 | pages = [https://archive.org/details/bnf65britishnati0000unse/page/665 665], 671 | url = https://archive.org/details/bnf65britishnati0000unse/page/665 }}</ref><ref name="AMH">{{cite book | veditors = Rossi S | isbn = 978-0-9805790-9-3 | title = Australian Medicines Handbook | place = Adelaide | publisher = The Australian Medicines Handbook Unit Trust | year = 2013 | edition = 2013 }}</ref> It is also used for [[pericarditis]] and to close a [[patent ductus arteriosus]] in a [[premature baby]].<ref name="Pedea EPAR">{{cite web | title=Pedea EPAR | website=[[European Medicines Agency]] (EMA) | date=29 July 2004 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/pedea | access-date=24 February 2024}}</ref><ref name="AHFS2016" /><ref name="Alabed2014">{{cite journal | vauthors = Alabed S, Cabello JB, Irving GJ, Qintar M, Burls A | title = Colchicine for pericarditis | journal = The Cochrane Database of Systematic Reviews | volume = 2014 | issue = 8 | pages = CD010652 | date = August 2014 | pmid = 25164988 | doi = 10.1002/14651858.CD010652.pub2 | pmc = 10645160 | url = http://openaccess.city.ac.uk/4043/5/Colchicine%20for%20pericarditis.pdf | type = Review | access-date = 26 January 2019 | archive-date = 22 September 2017 | archive-url = https://web.archive.org/web/20170922013941/http://openaccess.city.ac.uk/4043/5/Colchicine%20for%20pericarditis.pdf | url-status = live }}</ref><ref name="Rostas2016">{{cite journal | vauthors = Rostas SE, McPherson CC | title = Pharmacotherapy for Patent Ductus Arteriosus: Current Options and Outstanding Questions | journal = Current Pediatric Reviews | volume = 12 | issue = 2 | pages = 110–119 | date = 2016 | pmid = 27197952 | doi = 10.2174/157339631202160506002028 | type = Review }}</ref>

===Ibuprofen lysine===

In some countries, ibuprofen [[lysine]] (the lysine salt of ibuprofen, sometimes called "ibuprofen lysinate") is licensed for treatment of the same conditions as ibuprofen; the lysine salt is used because it is more water-soluble.<ref>{{cite journal | vauthors = Beaver WT | title = Review of the analgesic efficacy of ibuprofen | journal = International Journal of Clinical Practice. Supplement | issue = 135 | pages = 13–17 | date = April 2003 | pmid = 12723741 }}</ref> However, subsequent studies shown no statistical differences between the lysine salt and ibuprofen base.<ref>{{cite journal | vauthors = Kyselovič J, Koscova E, Lampert A, Weiser T | title = A Randomized, Double-Blind, Placebo-Controlled Trial of Ibuprofen Lysinate in Comparison to Ibuprofen Acid for Acute Postoperative Dental Pain | journal = Pain and Therapy | volume = 9 | issue = 1 | pages = 249–259 | date = June 2020 | pmid = 31912434 | pmc = 7203382 | doi = 10.1007/s40122-019-00148-1 }}</ref><ref>{{cite journal | vauthors = Moore AR, Derry S, Straube S, Ireson-Paine J, Wiffen PJ | title = Faster, higher, stronger? Evidence for formulation and efficacy for ibuprofen in acute pain | journal = Pain | volume = 155 | issue = 1 | pages = 14–21 | date = January 2014 | pmid = 23969325 | doi = 10.1016/j.pain.2013.08.013 }}</ref>

In 2006, ibuprofen lysine was approved in the United States by the [[Food and Drug Administration]] (FDA) for closure of patent ductus arteriosus in premature infants weighing between {{cvt|500|and|1500|g|lb|0|abbr=on}}, who are no more than 32 weeks gestational age when usual medical management (such as fluid restriction, diuretics, and respiratory support) is not effective.<ref>{{cite journal | vauthors = Fanos V, Antonucci R, Zaffanello M | title = Ibuprofen and acute kidney injury in the newborn | journal = The Turkish Journal of Pediatrics | volume = 52 | issue = 3 | pages = 231–238 | year = 2010 | pmid = 20718179 }}</ref>

==Adverse effects==

Adverse effects include [[nausea]], [[heartburn]], [[indigestion]], [[diarrhea]], [[constipation]], [[gastrointestinal ulceration]], [[headache]], [[dizziness]], rash, salt and fluid retention, and [[hypertension|high blood pressure]].<ref name="AHFS2016" /><ref name="AMH"/><ref>{{cite journal | vauthors = Castellsague J, Riera-Guardia N, Calingaert B, Varas-Lorenzo C, Fourrier-Reglat A, Nicotra F, Sturkenboom M, Perez-Gutthann S | title = Individual NSAIDs and upper gastrointestinal complications: a systematic review and meta-analysis of observational studies (the SOS project) | journal = Drug Safety | volume = 35 | issue = 12 | pages = 1127–46 | date = December 2012 | pmid = 23137151 | pmc = 3714137 | doi = 10.1007/BF03261999 }}</ref>

Infrequent adverse effects include esophageal ulceration, [[Congestive heart failure|heart failure]], [[hyperkalemia|high blood levels of potassium]], [[Renal failure|kidney impairment]], confusion, and [[bronchospasm]].<ref name="AMH"/> Ibuprofen can exacerbate asthma, sometimes fatally.<ref name="Lancet1987-Ayres">{{cite journal | vauthors = Ayres JG, Fleming DM, Whittington RM | title = Asthma death due to ibuprofen | journal = Lancet | volume = 1 | issue = 8541 | pages = 1082 | date = May 1987 | pmid = 2883408 | doi = 10.1016/S0140-6736(87)90499-5 | s2cid = 38589434 }}</ref>

Allergic reactions, including [[anaphylaxis]], may occur.<ref>{{cite journal | vauthors = Shaikhain TA, Al-Husayni F, Elder K | title = Ibuprofen-induced Anaphylactic Shock in Adult Saudi Patient | journal = Cureus | volume = 11 | issue = 12 | pages = e6425 | date = December 2019 | pmid = 31993263 | pmc = 6970456 | doi = 10.7759/cureus.6425 | doi-access = free }}</ref> 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 [[monograph]] relating ibuprofen plasma concentration, time since ingestion, and risk of developing renal toxicity in people who have overdosed has been published.<ref name=Baselt>{{cite book| vauthors = Baselt R |title=Disposition of Toxic Drugs and Chemicals in Man|edition=8th|publisher=Biomedical Publications|location=[[Foster City]], USA|year=2008|pages=758–761}}</ref>

In October 2020, the U.S. FDA required the [[Drug labelling|drug label]] to be updated for all NSAID medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid.<ref name="FDA PR 20201015">{{cite press release | title=FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications | website=U.S. [[Food and Drug Administration]] (FDA) | date=15 October 2020 | url=https://www.fda.gov/news-events/press-announcements/fda-warns-using-type-pain-and-fever-medication-second-half-pregnancy-could-lead-complications | access-date=15 October 2020 | archive-date=16 October 2020 | archive-url=https://web.archive.org/web/20201016180003/https://www.fda.gov/news-events/press-announcements/fda-warns-using-type-pain-and-fever-medication-second-half-pregnancy-could-lead-complications | url-status=live }} {{PD-notice}}</ref><ref name="FDA safety 20201015">{{cite web | title=NSAIDs may cause rare kidney problems in unborn babies | website=U.S. [[Food and Drug Administration]] (FDA) | date=21 July 2017 | url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-recommends-avoiding-use-nsaids-pregnancy-20-weeks-or-later-because-they-can-result-low-amniotic | access-date=15 October 2020 | archive-date=17 October 2020 | archive-url=https://web.archive.org/web/20201017014419/https://www.fda.gov/drugs/drug-safety-and-availability/fda-recommends-avoiding-use-nsaids-pregnancy-20-weeks-or-later-because-they-can-result-low-amniotic | url-status=live }} {{PD-notice}}</ref>

===Cardiovascular risk===
Along with several other NSAIDs, chronic ibuprofen use is correlated with the risk of progression to [[hypertension]] in women, though less than for [[paracetamol]] (acetaminophen),<ref>{{cite journal | vauthors = Forman JP, Stampfer MJ, Curhan GC | title = Non-narcotic analgesic dose and risk of incident hypertension in US women | journal = Hypertension | volume = 46 | issue = 3 | pages = 500–7 | date = September 2005 | pmid = 16103274 | doi = 10.1161/01.HYP.0000177437.07240.70 | doi-access = free | title-link = doi }}</ref> and [[myocardial infarction]] (heart attack),<ref>{{cite journal | vauthors = Hippisley-Cox J, Coupland C | title = Risk of myocardial infarction in patients taking cyclo-oxygenase-2 inhibitors or conventional non-steroidal anti-inflammatory drugs: population based nested case-control analysis | journal = BMJ | volume = 330 | issue = 7504 | pages = 1366 | date = June 2005 | pmid = 15947398 | pmc = 558288 | doi = 10.1136/bmj.330.7504.1366 }}</ref> particularly among those chronically using higher doses. On 9 July 2015, the U.S. FDA toughened warnings of increased [[heart attack]] and [[stroke]] risk associated with ibuprofen and related NSAIDs; the NSAID [[aspirin]] is not included in this warning.<ref name="FDA-20150709">{{cite web|title=FDA Drug Safety Communication: FDA strengthens warning that non-aspirin nonsteroidal anti-inflammatory drugs (NSAIDs) can cause heart attacks or strokes |url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-fda-strengthens-warning-non-aspirin-nonsteroidal-anti-inflammatory |date=9 July 2015 |work=U.S. [[Food and Drug Administration]] (FDA) |access-date=9 July 2015 |url-status=live |archive-url=https://web.archive.org/web/20191028180713/https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-fda-strengthens-warning-non-aspirin-nonsteroidal-anti-inflammatory |archive-date=28 October 2019 }}</ref> The [[European Medicines Agency]] (EMA) issued similar warnings in 2015.<ref>{{cite web | title=Ibuprofen- and dexibuprofen-containing medicines | website=[[European Medicines Agency]] (EMA) | date=22 May 2015 | url=https://www.ema.europa.eu/en/medicines/human/referrals/ibuprofen-dexibuprofen-containing-medicines | archive-url=https://web.archive.org/web/20191028181523/https://www.ema.europa.eu/en/medicines/human/referrals/ibuprofen-dexibuprofen-containing-medicines | archive-date=28 October 2019 | url-status=live | access-date=28 October 2019 | id=EMA/325007/2015 }}</ref><ref>{{cite web | title=High-dose ibuprofen (≥2400mg/day): small increase in cardiovascular risk | website=[[Medicines and Healthcare products Regulatory Agency]] (MHRA) | date=26 June 2015 | url=https://www.gov.uk/drug-safety-update/high-dose-ibuprofen-2400mg-day-small-increase-in-cardiovascular-risk | archive-url=https://web.archive.org/web/20191028182113/https://www.gov.uk/drug-safety-update/high-dose-ibuprofen-2400mg-day-small-increase-in-cardiovascular-risk | archive-date=28 October 2019 | url-status=live | access-date=28 October 2019}}</ref>

=== Skin ===
Along with other NSAIDs, ibuprofen has been associated with the onset of [[bullous pemphigoid]] or pemphigoid-like blistering.<ref name="Chan">{{cite web| vauthors = Chan LS |title=Bullous Pemphigoid Clinical Presentation|work=[[eMedicine|Medscape Reference]]|publisher=[[WebMD]]|location=[[United States]]| veditors = Hall R, Vinson RP, Nunley JR, Gelfand JM, Elston DM |date=12 June 2014|url=http://emedicine.medscape.com/article/1062391-clinical#showall|url-status=live|archive-url=https://web.archive.org/web/20111110071913/http://emedicine.medscape.com/article/1062391-clinical#showall|archive-date=10 November 2011}}</ref> As with other NSAIDs, ibuprofen has been reported to be a [[photosensitivity|photosensitizing]] agent,<ref>{{cite journal | vauthors = Bergner T, Przybilla B | title = Photosensitization caused by ibuprofen | journal = Journal of the American Academy of Dermatology | volume = 26 | issue = 1 | pages = 114–6 | date = January 1992 | pmid = 1531054 | doi = 10.1016/0190-9622(92)70018-b }}</ref> but it is considered a weak photosensitizing agent compared to other members of the [[2-arylpropionic acid]] class. Like other NSAIDs, ibuprofen is an extremely rare cause of the [[autoimmune disease|autoimmune diseases]] [[Stevens–Johnson syndrome]] (SJS) and [[toxic epidermal necrolysis]].<ref>{{cite journal |vauthors=Raksha MP, Marfatia YS |year=2008 |title=Clinical study of cutaneous drug eruptions in 200 patients |journal=Indian Journal of Dermatology, Venereology and Leprology |volume=74 |issue=1 |pages=80 |doi=10.4103/0378-6323.38431 |pmid=18193504 |doi-access=free |hdl-access=free |title-link=doi |hdl=1807/48058}}</ref><ref>{{cite journal |vauthors=Ward KE, Archambault R, Mersfelder TL |date=February 2010 |title=Severe adverse skin reactions to nonsteroidal antiinflammatory drugs: A review of the literature |journal=American Journal of Health-System Pharmacy |volume=67 |issue=3 |pages=206–13 |doi=10.2146/ajhp080603 |pmid=20101062}}</ref><ref name="Rainsford" />

=== Pregnancy ===
The [[National Health Service]] recommends against the use of ibuprofen for more than 3 days in pregnancy as it can affect the fetus' kidneys and circulatory system. Paracetamol is considered a safer alternative.<ref>{{cite web |title=Pregnancy, breastfeeding and fertility while taking or using ibuprofen |url=https://www.nhs.uk/medicines/ibuprofen-for-adults/pregnancy-breastfeeding-and-fertility-while-taking-ibuprofen/ |website=National Health Service |access-date=9 April 2025 |date=18 November 2021}}</ref>

A 2012 Canadian study of pregnant women suggested that those taking any type or amount of NSAIDs (including ibuprofen, [[diclofenac]], and [[naproxen]]) were 2.4 times more likely to [[miscarriage|miscarry]] than those not taking the medications.<ref>{{cite journal | vauthors = Verma P, Clark CA, Spitzer KA, Laskin CA, Ray J, Koren G | title = Use of non-aspirin NSAIDs during pregnancy may increase the risk of spontaneous abortion | journal = Evidence-Based Nursing | volume = 15 | issue = 3 | pages = 76–77 | date = July 2012 | pmid = 22411163 | doi = 10.1136/ebnurs-2011-100439 | s2cid = 28521248 }}</ref> However, a 2014 Israeli study found no increased risk of miscarriage in the group of mothers using NSAIDs and noted that two previous studies, including the 2012 Canadian study, "did not adjust for important known risk factors" which may have exposed those results to residual [[confounding]].<ref>{{cite journal | vauthors = Daniel S, Koren G, Lunenfeld E, Bilenko N, Ratzon R, Levy A | title = Fetal exposure to nonsteroidal anti-inflammatory drugs and spontaneous abortions | journal = CMAJ | volume = 186 | issue = 5 | pages = E177–E182 | date = March 2014 | pmid = 24491470 | pmc = 3956584 | doi = 10.1503/cmaj.130605 }}</ref>

=== Interactions ===

==== Alcohol ====
Drinking [[alcohol (drug)|alcohol]] when taking ibuprofen may increase the risk of [[stomach bleeding]].<ref name="drugs">{{cite web|url=https://www.drugs.com/ibuprofen.html|title=Ibuprofen|publisher=Drugs.com|url-status=live|archive-url=https://web.archive.org/web/20110806064653/http://www.drugs.com/ibuprofen.html|archive-date=6 August 2011}}</ref>

==== Aspirin ====
According to the FDA, "ibuprofen can interfere with the [[antiplatelet]] effect of low-dose [[aspirin]], potentially rendering aspirin less effective when used for [[cardioprotection]] and [[stroke]] prevention". Allowing sufficient time between doses of ibuprofen and immediate-release (IR) aspirin can avoid this problem. The recommended elapsed time between a dose of ibuprofen and a dose of aspirin depends on which is taken first. It would be 30&nbsp;minutes or more for ibuprofen taken after IR aspirin, and 8&nbsp;hours or more for ibuprofen taken before IR aspirin. However, this timing cannot be recommended for [[Enteric coating|enteric-coated]] 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.<ref name='FDA2006'>{{cite web |url=https://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm125222.htm |title=Information for Healthcare Professionals: Concomitant Use of Ibuprofen and Aspirin |access-date=22 November 2010 |date=September 2006 |publisher=U.S. [[Food and Drug Administration]] (FDA) |url-status=dead |archive-url=https://web.archive.org/web/20101113035657/https://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm125222.htm |archive-date=13 November 2010 }}
*{{lay source |template= cite web|url = https://www.fda.gov/drugs/postmarket-drug-safety-information-patients-and-providers/information-about-taking-ibuprofen-and-aspirin-together|title = Information about Taking Ibuprofen and Aspirin Together|date = 9 September 2019 |website = U.S. [[Food and Drug Administration]] (FDA) }}</ref>

==== Paracetamol (acetaminophen) ====
Ibuprofen combined with [[paracetamol]] is considered generally safe in children for short-term usage.<ref>{{cite journal | vauthors = Kanabar DJ | title = A clinical and safety review of paracetamol and ibuprofen in children | journal = Inflammopharmacology | volume = 25 | issue = 1 | pages = 1–9 | date = February 2017 | pmid = 28063133 | pmc = 5306275 | doi = 10.1007/s10787-016-0302-3 }}</ref>

===Overdose===
Ibuprofen overdose has become common since it was licensed for [[Over-the-counter drug|over-the-counter]] (OTC) use. Many overdose experiences are reported in the [[Medical journal|medical literature]], although the frequency of life-threatening complications from ibuprofen overdose is low.<ref>{{cite journal | vauthors = McElwee NE, Veltri JC, Bradford DC, Rollins DE | title = A prospective, population-based study of acute ibuprofen overdose: complications are rare and routine serum levels not warranted | journal = Annals of Emergency Medicine | volume = 19 | issue = 6 | pages = 657–662 | date = June 1990 | pmid = 2188537 | doi = 10.1016/S0196-0644(05)82471-0 }}</ref> 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, [[vomiting]], drowsiness, dizziness, headache, [[tinnitus|ear ringing]], and [[pathologic nystagmus|nystagmus]]. Rarely, more severe symptoms such as [[gastrointestinal bleeding]], [[seizures]], [[metabolic acidosis]], [[hyperkalemia]], [[hypotension|low blood pressure]], [[bradycardia|slow heart rate]], [[tachycardia|fast heart rate]], [[atrial fibrillation]], [[coma]], liver dysfunction, [[acute kidney failure]], [[cyanosis]], [[Hypoventilation|respiratory depression]], and [[cardiac arrest]] have been reported.<ref>{{cite journal | vauthors = Vale JA, Meredith TJ | title = Acute poisoning due to non-steroidal anti-inflammatory drugs. Clinical features and management | journal = Medical Toxicology | volume = 1 | issue = 1 | pages = 12–31 | date = January 1986 | pmid = 3537613 | doi = 10.1007/BF03259825 | s2cid = 25223555 }}</ref> 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.

The correlation between the severity of symptoms and measured ibuprofen plasma levels is weak. Toxic effects are unlikely at doses below 100{{nbsp}}mg/kg, but can be severe above 400{{nbsp}}mg/kg (around 150 tablets of 200{{nbsp}}mg units for an average adult male);<ref name = Clinicalmedicine2003-Volans>{{cite journal | vauthors = Volans G, Hartley V, McCrea S, Monaghan J | title = Non-opioid analgesic poisoning | journal = Clinical Medicine | volume = 3 | issue = 2 | pages = 119–123 | date = March–April 2003 | pmid = 12737366 | pmc = 4952728 | doi = 10.7861/clinmedicine.3-2-119 }}</ref> however, large doses do not indicate the clinical course is likely to be lethal.<ref>{{cite journal | vauthors = Seifert SA, Bronstein AC, McGuire T | title = Massive ibuprofen ingestion with survival | journal = Journal of Toxicology. Clinical Toxicology | volume = 38 | issue = 1 | pages = 55–57 | date = 2000 | pmid = 10696926 | doi = 10.1081/clt-100100917 | s2cid = 38588541 }}</ref> A precise [[lethal dose]] is difficult to determine, as it may vary with age, weight, and concomitant conditions of the person.

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 [[activated charcoal]]; charcoal absorbs the drug before it can enter the [[systemic circulation|bloodstream]]. [[Gastric lavage]] is now rarely used, but can be considered if the amount ingested is potentially life-threatening, and it can be performed within 60&nbsp;minutes of ingestion. Purposeful vomiting is not recommended.<ref>{{cite journal | title = Position paper: Ipecac syrup | journal = Journal of Toxicology. Clinical Toxicology | volume = 42 | issue = 2 | pages = 133–143 | date = 2004 | pmid = 15214617 | doi = 10.1081/CLT-120037421 | last1 = American Academy Of Clinical Toxico | s2cid = 218865551 }}</ref> Most ibuprofen ingestions produce only mild effects, and the management of overdose is straightforward. Standard measures to maintain normal urine output should be instituted and [[kidney function]] monitored.<ref name="Clinicalmedicine2003-Volans"/> Since ibuprofen has acidic properties and is also excreted in the urine, [[forced diuresis|forced alkaline diuresis]] 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.<ref>{{cite journal | vauthors = Hall AH, Smolinske SC, Conrad FL, Wruk KM, Kulig KW, Dwelle TL, Rumack BH | title = Ibuprofen overdose: 126 cases | journal = Annals of Emergency Medicine | volume = 15 | issue = 11 | pages = 1308–1313 | date = November 1986 | pmid = 3777588 | doi = 10.1016/S0196-0644(86)80617-5 }}</ref>

==Pharmacology==
Ibuprofen works by inhibiting [[cyclooxygenase]] (COX) enzymes, which convert [[arachidonic acid]] to [[prostaglandin H2]] (PGH<sub>2</sub>). PGH<sub>2</sub>, in turn, is converted by other enzymes into various [[Prostaglandin|prostaglandins]] (which mediate pain, [[inflammation]], and fever) and [[thromboxane A2]] (which stimulates [[platelet]] aggregation and promotes [[Thrombus|blood clot]] formation).

Like aspirin and [[indomethacin]], ibuprofen is a nonselective COX inhibitor, in that it inhibits two [[isozyme|isoforms]] of cyclooxygenase, [[COX-1]] and [[COX-2]]. The [[analgesic]], [[antipyretic]], and anti-inflammatory activity of NSAIDs appears to operate mainly through inhibition of COX-2, which decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever, and swelling. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Inhibition of COX-1 instead would be responsible for unwanted effects on the gastrointestinal tract.<ref>{{cite journal | vauthors = Rao P, Knaus EE | title = Evolution of nonsteroidal anti-inflammatory drugs (NSAIDs): cyclooxygenase (COX) inhibition and beyond | journal = Journal of Pharmacy & Pharmaceutical Sciences | volume = 11 | issue = 2 | pages = 81s–110s | date = September 2008 | pmid = 19203472 | doi = 10.18433/J3T886 | doi-access = free | title-link = doi }}</ref> 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.<ref>{{cite journal | vauthors = Kakuta H, Zheng X, Oda H, Harada S, Sugimoto Y, Sasaki K, Tai A | title = Cyclooxygenase-1-selective inhibitors are attractive candidates for analgesics that do not cause gastric damage. design and in vitro/in vivo evaluation of a benzamide-type cyclooxygenase-1 selective inhibitor | journal = Journal of Medicinal Chemistry | volume = 51 | issue = 8 | pages = 2400–2411 | date = April 2008 | pmid = 18363350 | doi = 10.1021/jm701191z }}</ref>
{| class="wikitable"
|+IC<sub>50</sub> of ibuprofen<ref>{{cite journal | vauthors = Noreen Y, Ringbom T, Perera P, Danielson H, Bohlin L | title = Development of a radiochemical cyclooxygenase-1 and -2 in vitro assay for identification of natural products as inhibitors of prostaglandin biosynthesis | journal = Journal of Natural Products | volume = 61 | issue = 1 | pages = 2–7 | date = January 1998 | pmid = 9461646 | doi = 10.1021/np970343j }}</ref>
!Enzyme
!IC<sub>50</sub> [μM]
|-
|[[COX-1]]
|13
|-
|[[COX-2]]
|370
|}
Ibuprofen is administered as a [[racemic mixture]]. The ''R''-enantiomer undergoes extensive interconversion to the ''S''-enantiomer ''in vivo''. The ''S''-enantiomer is believed to be the more pharmacologically active enantiomer.<ref name="DrugBank">{{cite web |url=https://www.drugbank.ca/drugs/DB01050 |title=Ibuprofen |work=DrugBank |access-date=24 July 2014 |url-status=live |archive-url=https://web.archive.org/web/20140721050937/http://www.drugbank.ca/drugs/db01050 |archive-date=21 July 2014 }}</ref> The ''R''-enantiomer is converted through a series of three main enzymes. These enzymes include acyl-CoA-synthetase, which converts the ''R''-enantiomer to (&minus;)-''R''-ibuprofen I-CoA; 2-arylpropionyl-CoA epimerase, which converts (&minus;)-''R''-ibuprofen I-CoA to (+)-''S''-ibuprofen I-CoA; and hydrolase, which converts (+)-''S''-ibuprofen I-CoA to the ''S''-enantiomer.<ref name=Rainsford>{{cite book |title=Ibuprofen: Pharmacology, Therapeutics and Side Effects | vauthors = Rainsford KD |publisher=Springer |year=2012 |location=London}}</ref> In addition to the conversion of ibuprofen to the ''S''-enantiomer, the body can metabolize ibuprofen to several other compounds, including numerous hydroxyl, carboxyl and glucuronyl metabolites. Virtually all of these have no pharmacological effects.<ref name=Rainsford/>

Unlike most other NSAIDs, ibuprofen also acts as an inhibitor of [[Rho-associated protein kinase|Rho kinase]] and may be useful in recovery from spinal cord injury.<ref>{{cite journal | vauthors = Kopp MA, Liebscher T, Niedeggen A, Laufer S, Brommer B, Jungehulsing GJ, Strittmatter SM, Dirnagl U, Schwab JM | title = Small-molecule-induced Rho-inhibition: NSAIDs after spinal cord injury | journal = Cell and Tissue Research | volume = 349 | issue = 1 | pages = 119–132 | date = July 2012 | pmid = 22350947 | doi = 10.1007/s00441-012-1334-7 | pmc = 3744771 }}</ref><ref>{{cite journal | vauthors = Luo M, Li YQ, Lu YF, Wu Y, Liu R, Zheng YR, Yin M | title = Exploring the potential of RhoA inhibitors to improve exercise-recoverable spinal cord injury: A systematic review and meta-analysis | journal = Journal of Chemical Neuroanatomy | volume = 111 | pages = 101879 | date = November 2020 | pmid = 33197553 | doi = 10.1016/j.jchemneu.2020.101879 | doi-access = free | title-link = doi }}</ref> Another unusual activity is inhibition of the sweet taste receptor.<ref>{{cite journal | vauthors = Nakagita T, Taketani C, Narukawa M, Hirokawa T, Kobayashi T, Misaka T | title = Ibuprofen, a Nonsteroidal Anti-Inflammatory Drug, is a Potent Inhibitor of the Human Sweet Taste Receptor | journal = Chemical Senses | volume = 45 | issue = 8 | pages = 667–673 | date = November 2020 | pmid = 32832995 | doi = 10.1093/chemse/bjaa057 }}</ref>

===Pharmacokinetics===
After oral administration, [[Cmax (pharmacology)|peak serum concentration]] is reached after 1{{ndash}}2&nbsp;hours, and up to 99% of the drug is [[Plasma protein binding|bound to plasma proteins]].<ref>{{cite journal | vauthors = Bushra R, Aslam N | title = An overview of clinical pharmacology of Ibuprofen | journal = Oman Medical Journal | volume = 25 | issue = 3 | pages = 155–161 | date = July 2010 | pmid = 22043330 | pmc = 3191627 | doi = 10.5001/omj.2010.49 }}</ref> The majority of ibuprofen is metabolized and eliminated within 24&nbsp;hours in the urine; however, 1% of the unchanged drug is removed through [[Bile|biliary excretion]].<ref name="DrugBank" />

=== Metabolism ===
Ibuprofen mainly undergoes [[hepatic metabolism]]. The following table shows potential pathways of ibuprofen metabolism. Both hydroxymetabolites and carboxyl-ibuprofen are inactive.<ref>{{cite journal | vauthors = Xie G, Sun Y, Nie T, Mackenzie GG, Huang L, Kopelovich L, Komninou D, Rigas B | title = Phospho-ibuprofen (MDC-917) is a novel agent against colon cancer: efficacy, metabolism, and pharmacokinetics in mouse models | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 337 | issue = 3 | pages = 876–886 | date = June 2011 | pmid = 21422165 | pmc = 3101013 | doi = 10.1124/jpet.111.180224 }}</ref>
{| class="wikitable"
|+Hepatic metabolism of ibuprofen<ref name=":0">{{cite journal | vauthors = Frolkis A, Knox C, Lim E, Jewison T, Law V, Hau DD, Liu P, Gautam B, Ly S, Guo AC, Xia J, Liang Y, Shrivastava S, Wishart DS | title = SMPDB: The Small Molecule Pathway Database | journal = Nucleic Acids Research | volume = 38 | issue = Database issue | pages = D480–D487 | date = January 2010 | pmid = 19948758 | pmc = 2808928 | doi = 10.1093/nar/gkp1002 }}</ref><ref name=":1">{{cite journal | vauthors = Jewison T, Su Y, Disfany FM, Liang Y, Knox C, Maciejewski A, Poelzer J, Huynh J, Zhou Y, Arndt D, Djoumbou Y, Liu Y, Deng L, Guo AC, Han B, Pon A, Wilson M, Rafatnia S, Liu P, Wishart DS | title = SMPDB 2.0: big improvements to the Small Molecule Pathway Database | journal = Nucleic Acids Research | volume = 42 | issue = Database issue | pages = D478–D484 | date = January 2014 | pmid = 24203708 | pmc = 3965088 | doi = 10.1093/nar/gkt1067 }}</ref><ref name=":2">{{Cite web |title=Ibuprofen Metabolism Pathway |url=https://smpdb.ca/view/SMP0000590 |access-date=1 March 2025 |website=SMPDB}}</ref>
!Drug substrate
!Other substrates
!Enzymes
!Products
!Side products
|-
|ibuprofen
|n/d
|n/d
|1-hydroxyibuprofen
|
|-
|ibuprofen
|oxygen, protons, NADPH
|[[CYP3A4]], [[CYP2C19]], [[CYP2C8]], [[CYP2C9]]
|2-hydroxyibuprofen
|NADP, water
|-
|ibuprofen
|oxygen, protons, NADPH
|CYP2C8, CYP2C9, CYP2C19
|3-hydroxyibuprofen
|NADP, water
|-
|3-hydroxyibuprofen
|water, oxygen
|CYP2C9
|carboxyl-ibuprofen
|hydrogen peroxide
|-
|ibuprofen
|[[uridine diphosphate glucuronic acid]]
|[[UDP-glucuronosyltransferase]] (1-1, 1-3, 1-9, 1-10, 2B4, 2B7)
|ibuprofen glucuronide
|[[Uridine diphosphate|uridine 5'-diphosphate]]
|}

==Chemistry==
Ibuprofen is practically insoluble in water, but very soluble in most organic solvents like [[ethanol]] (66.18{{nbsp}}g/100{{nbsp}}mL at 40{{nbsp}}°C for 90% EtOH), [[methanol]], [[acetone]] and [[dichloromethane]].<ref name="MD">{{cite web|title=Ibuprofen|work=Martindale: The Complete Drug Reference|publisher=Pharmaceutical Press|location=London, UK|date=14 January 2014|access-date=26 June 2014|url=http://www.medicinescomplete.com/mc/martindale/current/ms-2657-h.htm|veditors=Brayfield A|archive-date=28 August 2021|archive-url=https://web.archive.org/web/20210828122132/https://about.medicinescomplete.com/wp-content/themes/mc-marketing/assets/images/favicons-tiles/favicon.ico|url-status=live}}</ref>

The original synthesis of ibuprofen by the [[Boots Group]] started with the compound [[isobutylbenzene]]. The synthesis took six steps. Firstly, isobutylbenzene undergoes [[Friedel-Crafts acylation]] with [[acetic anhydride]], yielding ''p''-isobuthylphenyl methyl [[ketone]]. Then, through [[Darzens reaction]] with [[ethyl chloroacetate]], a α,β-epoxyester is obtained. Then, in acidic environment, it undergoes [[decarboxylation]] and [[hydrolysis]], yielding an [[aldehyde]] bearing one more carbon atom than the initial ketone. Then, it goes through a reaction with [[hydroxylamine]], yielding a corresponding [[oxime]]. Later, it is converted into a [[nitrile]] and hydrolyzed into ibuprofen.<ref>{{Cite journal | vauthors = Hu X, Song Y, Li J, Huang Y |date=26 July 2024 |title=Modification of ibuprofen synthesis through the mechanism analysis |url=https://www.ewadirect.com/proceedings/tns/article/view/14366 |journal=Theoretical and Natural Science |volume=45 |issue=1 |pages=168–178 |doi=10.54254/2753-8818/45/20240519 |issn=2753-8818|doi-access=free }}</ref>
[[File:Boots synthesis of ibuprofen.png|center|thumb|656x656px|Boots synthesis of ibuprofen]]


A modern, [[Green chemistry|greener technique]] with fewer waste byproducts (23% of total product mass vs. 60% theoretical value) for the synthesis involves only three steps and was developed in the 1980s by the [[Celanese|Celanese Chemical Company]].<ref>{{cite web|url=http://www.rsc.org/learn-chemistry/resource/download/res00000012/cmp00000014/pdf|title=The Synthesis of Ibuprofen|publisher=Royal Society of Chemistry|access-date=22 November 2018|archive-date=22 November 2018|archive-url=https://web.archive.org/web/20181122215409/http://www.rsc.org/learn-chemistry/resource/download/res00000012/cmp00000014/pdf|url-status=live}}</ref><ref>{{cite web|url=https://www.science.org/content/blog-post/ibuprofen-revolution|title=The Ibuprofen Revolution|publisher=Science|access-date=17 March 2023}}</ref> The synthesis is initiated with the acylation of isobutylbenzene using the recyclable [[Lewis acid]] catalyst [[hydrogen fluoride]].<ref>{{cite journal | vauthors = Murphy MA |date=1 July 2018 |title=Early Industrial Roots of Green Chemistry and the history of the BHC Ibuprofen process invention and its Quality connection |journal=Foundations of Chemistry |volume=20 |issue=2 |pages=121–165 |doi=10.1007/s10698-017-9300-9 |s2cid=254510261 |issn=1572-8463|doi-access=free }}</ref><ref>{{cite journal | vauthors = Grimaldi F, Tran NN, Sarafraz MM, Lettieri P, Morales-Gonzalez OM, Hessel V |date=4 October 2021 |title=Life Cycle Assessment of an Enzymatic Ibuprofen Production Process with Automatic Recycling and Purification |journal=ACS Sustainable Chemistry & Engineering |volume=9 |issue=39 |pages=13135–13150 |doi=10.1021/acssuschemeng.1c02309 |issn=2168-0485|url=https://wrap.warwick.ac.uk/158477/1/WRAP-Life-cycle-assessment-enzymatic-ibuprofen-automatic-recycling-purification-2021.pdf }}</ref> The following [[catalytic hydrogenation]] of isobutylacetophenone is performed with either [[Raney nickel]] or [[palladium on carbon]] to lead into the key-step, the [[carbonylation]] of 1-(4-isobutylphenyl)ethanol. This is achieved by a [[Bis(triphenylphosphine)palladium chloride|PdCl<sub>2</sub>(PPh<sub>3</sub>)<sub>2</sub>]] catalyst, at around 50 bar of CO pressure, in the presence of HCl (10%).<ref>{{cite patent|number=US4981995A|title=Method for producing ibuprofen|gdate=1991-01-01|inventor=Elango V, Murphy MA, Smith BL, Davenport KG|url=https://patents.google.com/patent/US4981995A/en}} {{Webarchive|url=https://web.archive.org/web/20231028101201/https://patents.google.com/patent/US4981995A/en |date=28 October 2023 }}</ref> The reaction presumably proceeds through the intermediacy of the [[styrene]] derivative (acidic elimination of the alcohol) and (1-chloroethyl)benzene derivative ([[Markovnikov's rule|Markovnikow addition]] of HCl to the double bond).<ref>{{cite journal | vauthors = Jayasree S, Seayad A, Chaudhari RV |date=1999 |title=Highly active supported palladium catalyst for the regioselective synthesis of 2-arylpropionic acids by carbonylation |url=http://xlink.rsc.org/?DOI=a902541c |journal=Chemical Communications |issue=12 |pages=1067–1068 |doi=10.1039/a902541c|hdl=1808/18897 |hdl-access=free }}</ref>[[File:Synthesis of ibuprofen.jpg|class=skin-invert-image|alt=Modern synthesis of ibuprofen|thumb|462x462px|Modern synthesis of ibuprofen|center]]
===Stereochemistry===
{| class="wikitable" style="float:right;text-align:center;"
| colspan = 2 | [[File:Ibuprofen_enantiomers_labelled_from_xtal.svg|400px]]
|-
|[[File:Ibuprofen-3D-balls.png|200px]]||[[File:(S)-ibuprofen-3D-balls.png|200px]]
|-
|(''R'')-ibuprofen||(''S'')-ibuprofen
|}

Ibuprofen, like other [[Profen (drug class)|2-arylpropionate derivatives]] such as [[ketoprofen]], [[flurbiprofen]] and [[naproxen]], contains a [[stereocenter]] in the α-position of the [[Propionic acid|propionate]] moiety. The product sold in pharmacies is a [[racemic mixture]] of the ''S'' and ''R''-isomers. The ''S'' (dextrorotatory) isomer is the more biologically active; this isomer has been isolated and used medically (see [[dexibuprofen]] for details).<ref name = MD/>

The [[isomerase]] enzyme, [[alpha-methylacyl-CoA racemase]], converts (''R'')-ibuprofen into the (''S'')-[[enantiomer]].<ref>{{cite journal | vauthors = Tracy TS, Hall SD | title = Metabolic inversion of (R)-ibuprofen. Epimerization and hydrolysis of ibuprofenyl-coenzyme A | journal = Drug Metabolism and Disposition | volume = 20 | issue = 2 | pages = 322–327 | date = March–April 1992 | doi = 10.1016/S0090-9556(25)08607-6 | pmid = 1352228 }}</ref><ref>{{cite journal | vauthors = Chen CS, Shieh WR, Lu PH, Harriman S, Chen CY | title = Metabolic stereoisomeric inversion of ibuprofen in mammals | journal = Biochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology | volume = 1078 | issue = 3 | pages = 411–417 | date = July 1991 | pmid = 1859831 | doi = 10.1016/0167-4838(91)90164-U | url = http://ntur.lib.ntu.edu.tw//handle/246246/173009 | access-date = 21 February 2022 | archive-date = 12 April 2023 | archive-url = https://web.archive.org/web/20230412060537/http://ntur.lib.ntu.edu.tw//handle/246246/173009 | url-status = dead }}</ref><ref>{{cite journal | vauthors = Reichel C, Brugger R, Bang H, Geisslinger G, Brune K | title = Molecular cloning and expression of a 2-arylpropionyl-coenzyme A epimerase: a key enzyme in the inversion metabolism of ibuprofen | journal = Molecular Pharmacology | volume = 51 | issue = 4 | pages = 576–582 | date = April 1997 | pmid = 9106621 | doi = 10.1124/mol.51.4.576 | url = http://pdfs.semanticscholar.org/a21e/78f2ae338b18b086911c23ccbbef4fd51275.pdf | archive-url = https://web.archive.org/web/20190302210440/http://pdfs.semanticscholar.org/a21e/78f2ae338b18b086911c23ccbbef4fd51275.pdf | url-status = dead | archive-date = 2 March 2019 | s2cid = 835701 }}</ref>

(S)-ibuprofen, the [[Eudysmic ratio|eutomer]], harbors the desired therapeutic activity. The inactive (R)-enantiomer, the [[distomer]], undergoes a unidirectional [[chiral inversion]] to offer the active (S)-enantiomer. That is, when the ibuprofen is administered as a racemate the distomer is converted ''in vivo'' into the eutomer while the latter is unaffected.<ref>{{cite journal | vauthors = Caldwell J, Hutt AJ, Fournel-Gigleux S | title = The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences | journal = Biochemical Pharmacology | volume = 37 | issue = 1 | pages = 105–114 | date = January 1988 | pmid = 3276314 | doi = 10.1016/0006-2952(88)90762-9 }}</ref><ref>{{cite journal | vauthors = Simonyi M | title = On chiral drug action | journal = Medicinal Research Reviews | volume = 4 | issue = 3 | pages = 359–413 | date = 1984 | pmid = 6087043 | doi = 10.1002/med.2610040304 | s2cid = 38829275 }}</ref><ref>{{cite journal | vauthors = Hutt AJ, Caldwell J | title = The metabolic chiral inversion of 2-arylpropionic acids--a novel route with pharmacological consequences | journal = The Journal of Pharmacy and Pharmacology | volume = 35 | issue = 11 | pages = 693–704 | date = November 1983 | pmid = 6139449 | doi = 10.1111/j.2042-7158.1983.tb02874.x | s2cid = 40669413 | doi-access = }}</ref>

==History==
[[File:Ibuprofen Blue Plaque, BioCity, Nottingham 01.jpg|thumb|upright|The [[List of blue plaques erected by the Royal Society of Chemistry|Royal Society of Chemistry blue plaque]] at [[BioCity Nottingham]] ]]

Ibuprofen was derived from [[propionic acid]] by the [[research]] arm of [[Boots Group]] during the 1960s.<ref name = pmid1569234>{{cite journal | vauthors = Adams SS | title = The propionic acids: a personal perspective | journal = Journal of Clinical Pharmacology | volume = 32 | issue = 4 | pages = 317–323 | date = April 1992 | pmid = 1569234 | doi = 10.1002/j.1552-4604.1992.tb03842.x | s2cid = 22857259 }}</ref> The name is derived from the 3 functional groups: isobutyl (ibu) propionic acid (pro) phenyl (fen).<ref>{{cite web |title=Molecule of the Week Archive: Ibuprofen |url=https://www.acs.org/molecule-of-the-week/archive/i/ibuprofen.html |website=[[American Chemical Society]] |access-date=21 March 2024 |date=14 May 2018}}</ref> Its discovery was the result of research during the 1950s and 1960s to find a safer alternative to [[aspirin]].<ref name = plat12/><ref name=IJCP03/> The molecule was discovered and synthesized by a team led by [[Stewart Adams (chemist)|Stewart Adams]], with a patent application filed in 1961.<ref name=plat12/> Adams initially tested the drug as treatment for his [[hangover]].<ref>{{cite news | vauthors = Lambert V |title=Dr Stewart Adams: 'I tested ibuprofen on my hangover' |url=https://www.telegraph.co.uk/news/health/3351540/Dr-Stewart-Adams-I-tested-ibuprofen-on-my-hangover.html |newspaper=[[The Daily Telegraph]] |location=UK |date=8 October 2007 |access-date=23 October 2015 |url-status=live |archive-url=https://web.archive.org/web/20151118030006/http://www.telegraph.co.uk/news/health/3351540/Dr-Stewart-Adams-I-tested-ibuprofen-on-my-hangover.html |archive-date=18 November 2015 }}{{subscription required|s}}</ref> In 1985, Boots's worldwide patent for ibuprofen expired and generic products were launched.<ref>{{cite web |title=A brief History of Ibuprofen |url=https://pharmaceutical-journal.com/article/infographics/a-brief-history-of-ibuprofen |website=Pharmaceutical Journal |date=27 July 2017 |access-date=20 February 2022 |archive-date=20 February 2022 |archive-url=https://web.archive.org/web/20220220172346/https://pharmaceutical-journal.com/article/infographics/a-brief-history-of-ibuprofen |url-status=live }}</ref>

The medication was launched as a treatment for [[rheumatoid arthritis]] in the United Kingdom in 1969, and in the United States in 1974. Later, in 1983 and 1984, it became the first NSAID (other than aspirin) to be available [[Over-the-counter drug|over-the-counter]] (OTC) in these two countries.<ref name = plat12/><ref name = IJCP03>{{cite journal | vauthors = Rainsford KD | title = Discovery, mechanisms of action and safety of ibuprofen | journal = International Journal of Clinical Practice. Supplement | issue = 135 | pages = 3–8 | date = April 2003 | pmid = 12723739 }}</ref> Boots was awarded the [[Queen's Awards for Enterprise|Queen's Award for Technical Achievement]] in 1985 for the development of the drug.<ref>{{cite press release |title=Boots Hidden Heroes - Honoring Dr Stewart Adams |url=https://www.boots-uk.com/newsroom/features/boots-hidden-heroes-honouring-dr-stewart-adams/ |publisher=Boots |access-date=20 February 2022}}</ref>

In November 2013, work on ibuprofen was recognized by the erection of a [[List of blue plaques erected by the Royal Society of Chemistry|Royal Society of Chemistry blue plaque]] at Boots' Beeston Factory site in Nottingham,<ref name="rsc.org">{{cite press release|title=Chemical landmark plaque honours scientific discovery past and future|url=http://www.rsc.org/AboutUs/News/PressReleases/2013/ibuprofen-chemical-landmark.asp|publisher=Royal Society of Chemistry (RSC)|date=21 November 2013|access-date=31 January 2019|archive-date=27 September 2018|archive-url=https://web.archive.org/web/20180927004543/http://www.rsc.org/AboutUs/News/PressReleases/2013/ibuprofen-chemical-landmark.asp|url-status=live}}</ref> which reads:

{{Blockquote|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 worldwide}}

and another at [[BioCity Nottingham]], the site of the original laboratory,<ref name="rsc.org" /> which reads:

{{blockquote|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 pain.}}

==Availability and administration==
{{See also|Ibuprofen brand names}}
[[File:Bottle of Ibuprofen tablets with cap removed and tablets in front.jpg|thumb|upright|A bottle of generic ibuprofen]]

Ibuprofen was made available by prescription in the United Kingdom in 1969 and in the United States in 1974.<ref>{{cite web | url=https://www.fda.gov/ohrms/dockets/ac/02/briefing/3882b2_06_international%20ibuprofen%20foundation.htm | title=Written submission to the NDAC meeting on risks of NSAIDs presented by the International Ibuprofen Foundation | publisher=U.S. [[Food and Drug Administration]] (FDA) | date=August 2002 | access-date=20 March 2014 | url-status=dead | archive-url=https://web.archive.org/web/20130815040113/https://www.fda.gov/ohrms/dockets/ac/02/briefing/3882b2_06_international%20ibuprofen%20foundation.htm | archive-date=15 August 2013 }}</ref>

Ibuprofen is the [[international nonproprietary name]] (INN), [[British Approved Name]] (BAN), [[Australian Approved Name]] (AAN) and [[United States Adopted Name]] (USAN). In the United States, it has been sold under the brand-names Motrin and Advil since 1974<ref>{{cite web | title=New Drug Application (NDA): 017463 | website=U.S. [[Food and Drug Administration]] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=017463 | archive-url=https://web.archive.org/web/20191028235657/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=017463 | archive-date=28 October 2019 | url-status=live | access-date=28 October 2019}}</ref> and 1984,<ref>{{cite web | title=New Drug Application (NDA): 018989 | website=U.S. [[Food and Drug Administration]] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=018989 | archive-url=https://web.archive.org/web/20191028235917/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=018989 | archive-date=28 October 2019 | url-status=live | access-date=28 October 2019}}</ref> respectively.

In 2009, the first injectable formulation of ibuprofen was approved in the United States, under the brand name Caldolor.<ref>{{cite web|url=http://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022348_caldolor_toc.cfm|title=Drug Approval Package: Caldolor (Ibuprofen) NDA #022348|publisher=U.S. [[Food and Drug Administration]] (FDA)|date=11 March 2010|url-status=live|archive-url=https://web.archive.org/web/20121019090729/http://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022348_caldolor_toc.cfm|archive-date=19 October 2012}}</ref><ref>{{cite press release|url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm165971.htm|date=11 June 2009|title=FDA Approves Injectable Form of Ibuprofen|publisher=U.S. [[Food and Drug Administration]] (FDA)|url-status=dead|archive-url=https://web.archive.org/web/20121018201824/https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm165971.htm|archive-date=18 October 2012}}</ref>

Ibuprofen can be taken [[oral administration|orally]] (by mouth) and [[Intravenous therapy|intravenously]].<ref name=AHFS2016/>

==Research==
Ibuprofen is sometimes used for the treatment of [[acne]] because of its [[anti-inflammatory]] properties, and has been sold in Japan in topical form for adult acne.<ref>{{cite journal | vauthors = Wong RC, Kang S, Heezen JL, Voorhees JJ, Ellis CN | title = Oral ibuprofen and tetracycline for the treatment of acne vulgaris | journal = Journal of the American Academy of Dermatology | volume = 11 | issue = 6 | pages = 1076–1081 | date = December 1984 | pmid = 6239884 | doi = 10.1016/S0190-9622(84)80192-9 }}</ref><ref name=inpharma>{{cite journal|title=In Japan, an OTC ibuprofen ointment (Fukidia) for alleviating adult acne has been launched| journal=Inpharma Weekly| volume=1|issue=1530|date=25 March 2006| page=18| issn=1173-8324| doi=10.2165/00128413-200615300-00043| s2cid=195105870}}</ref> As with other NSAIDs, ibuprofen may be useful in the treatment of severe [[orthostatic hypotension]] (low blood pressure when standing up).<ref>{{cite journal | vauthors = Zawada ET | title = Renal consequences of nonsteroidal antiinflammatory drugs | journal = Postgraduate Medicine | volume = 71 | issue = 5 | pages = 223–230 | date = May 1982 | pmid = 7041104 | doi = 10.1080/00325481.1982.11716077 }}</ref> NSAIDs are of unclear utility in the prevention and treatment of [[Alzheimer's disease]].<ref>{{cite journal | vauthors = Miguel-Álvarez M, Santos-Lozano A, Sanchis-Gomar F, Fiuza-Luces C, Pareja-Galeano H, Garatachea N, Lucia A | title = Non-steroidal anti-inflammatory drugs as a treatment for Alzheimer's disease: a systematic review and meta-analysis of treatment effect | journal = Drugs & Aging | volume = 32 | issue = 2 | pages = 139–147 | date = February 2015 | pmid = 25644018 | doi = 10.1007/s40266-015-0239-z | s2cid = 35357112 }}</ref><ref>{{cite journal | vauthors = Wang J, Tan L, Wang HF, Tan CC, Meng XF, Wang C, Tang SW, Yu JT | title = Anti-inflammatory drugs and risk of Alzheimer's disease: an updated systematic review and meta-analysis | journal = Journal of Alzheimer's Disease | volume = 44 | issue = 2 | pages = 385–396 | date = 2015 | pmid = 25227314 | doi = 10.3233/JAD-141506 }}</ref>

Ibuprofen has been associated with a lower risk of [[Parkinson's disease]] and may delay or prevent it. [[Aspirin]], other NSAIDs, and [[paracetamol]] (acetaminophen) had no effect on the risk for Parkinson's.<ref>{{cite journal | vauthors = Chen H, Jacobs E, Schwarzschild MA, McCullough ML, Calle EE, Thun MJ, Ascherio A | title = Nonsteroidal antiinflammatory drug use and the risk for Parkinson's disease | journal = Annals of Neurology | volume = 58 | issue = 6 | pages = 963–967 | date = December 2005 | pmid = 16240369 | doi = 10.1002/ana.20682 | s2cid = 30843070 }}</ref> In March 2011, researchers at [[Harvard Medical School]] announced that ibuprofen had a [[Neuroprotection|neuroprotective]] effect against the risk of developing [[Parkinson's disease]].<ref>{{cite journal | vauthors = Bower JH, Ritz B | title = Is the answer for Parkinson disease already in the medicine cabinet?: Unfortunately not | journal = Neurology | volume = 76 | issue = 10 | pages = 854–855 | date = March 2011 | pmid = 21368280 | doi = 10.1212/WNL.0b013e31820f2e7a | s2cid = 46104705 }}</ref><ref>{{cite journal | vauthors = Gao X, Chen H, Schwarzschild MA, Ascherio A | title = Use of ibuprofen and risk of Parkinson disease | journal = Neurology | volume = 76 | issue = 10 | pages = 863–9 | date = March 2011 | pmid = 21368281 | pmc = 3059148 | doi = 10.1212/WNL.0b013e31820f2d79 }}</ref><ref>{{cite journal | vauthors = McSharry C | title = Parkinson disease: Could over-the-counter treatment protect against Parkinson disease? | journal = Nature Reviews. Neurology | volume = 7 | issue = 5 | pages = 244 | date = May 2011 | pmid = 21555992 | doi = 10.1038/nrneurol.2011.49 | s2cid = 35880887 | doi-access = free | title-link = doi }}</ref> 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.<ref name=urj2011>{{cite journal | vauthors = Gleason JM, Slezak JM, Jung H, Reynolds K, Van den Eeden SK, Haque R, Quinn VP, Loo RK, Jacobsen SJ | title = Regular nonsteroidal anti-inflammatory drug use and erectile dysfunction | journal = The Journal of Urology | volume = 185 | issue = 4 | pages = 1388–1393 | date = April 2011 | pmid = 21334642 | doi = 10.1016/j.juro.2010.11.092 }}</ref>

Some [[dietary supplements]] might be dangerous to take along with ibuprofen and other NSAIDs, but {{as of|2016|lc=y}}, more research needs to be conducted to be certain. These supplements include those that can [[Platelet#Aggregation|prevent platelet aggregation]], including [[ginkgo]], [[garlic]], [[ginger]], [[bilberry]], [[dong quai]], [[feverfew]], [[ginseng]], [[turmeric]], [[Filipendula ulmaria|meadowsweet]] (''Filipendula ulmaria''), and [[willow]] (''Salix'' spp.); those that contain [[coumarin]], including [[chamomile]], [[horse chestnut]], [[fenugreek]] and [[red clover]]; and those that increase the risk of bleeding, like [[tamarind]].<ref>{{cite journal | vauthors = Abebe W | title = Herbal medication: potential for adverse interactions with analgesic drugs | journal = Journal of Clinical Pharmacy and Therapeutics | volume = 27 | issue = 6 | pages = 391–401 | date = December 2002 | pmid = 12472978 | doi = 10.1046/j.1365-2710.2002.00444.x | s2cid = 1828900 | doi-access = free | title-link = doi }}</ref>

== References ==
{{Reflist}}

== External links ==
{{Commons category}}
* {{cite patent |country=GB |number=971700 |status=patent |title=Anti-Inflammatory Agents |pubdate=1964-09-30 |fdate=1961-02-02
 |pridate=1961-02-02 |invent1=Stewart Sanders Adams |invent2=John Stuart Nicholson |assign1=Boots Pure Drug Co Ltd |url=https://worldwide.espacenet.com/publicationDetails/biblio?II=7&ND=3&adjacent=true&locale=en_EP&FT=D&date=19640930&CC=GB&NR=971700A&KC=A}}
* {{cite web | title=Evidence for the efficacy of pain medications | publisher = National Safety Council (NSC) | date=26 August 2020 | url=https://www.nsc.org/Portals/0/Documents/RxDrugOverdoseDocuments/Evidence-Efficacy-Pain-Medications.pdf }}
* {{cite web| vauthors = Lowe D |title=The Ibuprofen Revolution |url=https://www.science.org/content/blog-post/ibuprofen-revolution |website=[[Science (journal)|Science]]}}

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