Ibuprofen - Wikipedia Ibuprofen Ibuprofen Clinical data Pronunciation / ˈaɪbjuːproʊfɛn /, / aɪ bjuːˈproʊfən /, EYE - bew - PROH - fən Trade names Advil, Motrin, Nurofen, others Synonyms isobutylphenylpropionic acid AHFS / Drugs.com Monograph MedlinePlus a682159 License data EU EMA : by INN US FDA : Ibuprofen Pregnancy category AU : C US : C ( Risk not ruled out ) D ( US ) at ≥ 30 weeks of gestation, due to the potential for premature closure of the ductus arteriosus Routes of administration by mouth, rectal, topical, and intravenous ATC code C01EB16 ( WHO ) G02CC01 ( WHO ) M01AE01 ( WHO ) M02AA13 ( WHO ) R02AX02 ( WHO ) Legal status Legal status AU : S2 ( Pharmacy only ) to Prescription Only ( S4 ) CA : OTC UK : General sales list ( GSL, OTC ) US : OTC / R - only Pharmacokinetic data Bioavailability 87 -- 100 % ( oral ), 87 % ( rectal ) Protein binding 98 % Metabolism Liver ( CYP2C9 ) Onset of action 30 min Biological half - life 1.3 -- 3 h Excretion Urine ( 95 % ) Identifiers IUPAC name ( RS ) - 2 - ( 4 - ( 2 - Methylpropyl ) phenyl ) propanoic acid CAS Number 15687 - 27 - 1 PubChem CID 3672 IUPHAR / BPS 2713 DrugBank DB01050 ChemSpider 3544 UNII WK2XYI10QM KEGG D00126 ChEBI CHEBI : 5855 ChEMBL CHEMBL521 PDB ligand IBP ( PDBe, RCSB PDB ) ECHA InfoCard 100.036. 152 Chemical and physical data Formula Molar mass 206.29 g / mol 3D model ( JSmol ) Interactive image Chirality Racemic mixture Density 1.03 g / ml g / cm Melting point 75 to 78 ° C ( 167 to 172 ° F ) Boiling point 157 ° C ( 315 ° F ) Solubility in water 0.021 mg / mL ( 20 ° C ) SMILES CC ( C ) Cc1ccc ( cc1 ) ( C @ @ H ) ( C ) C ( = O ) O InChI 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 ) Key : HEFNNWSXXWATRW - UHFFFAOYSA - N ( verify ) Ibuprofen is a medication in the nonsteroidal anti-inflammatory drug ( NSAID ) class that is used for treating pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. About 60 % of people improve with any given NSAID, and it is recommended that if one does not work then another should be tried. It may also be used to close a patent ductus arteriosus in a premature baby. It can be used by mouth or intravenously. It typically begins working within an hour. Common side effects include heartburn and a rash. Compared to other NSAIDs it may have fewer side effects such as gastrointestinal bleeding. It increases the risk of heart failure, kidney failure, and liver failure. At low doses, it does not appear to increase the risk of heart attack ; however, at higher doses it may. Ibuprofen can also result in worsened asthma. While it is unclear if it is safe in early pregnancy, it appears to be harmful in later pregnancy and therefore is not recommended. Like other NSAIDs, it works by inhibiting the production of prostaglandins by decreasing the activity of the enzyme cyclooxygenase. Ibuprofen might be a weaker anti-inflammatory than other NSAIDs. Ibuprofen was discovered in 1961 by Stewart Adams and initially marketed as Brufen. It is available under a number of trade names, including Advil and Motrin. It was first marketed in 1969 in the United Kingdom and in the United States in 1974. It is on the World Health Organization 's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world is between 0.01 and 0.04 USD per dose. In the United States it costs about 0.05 USD per dose. Contents 1 Medical uses 1.1 Ibuprofen lysine 2 Adverse effects 2.1 Cardiovascular risk 2.2 Skin 2.3 Interactions 2.4 Overdose 2.5 Miscarriage 3 Pharmacology 4 Chemistry 4.1 Stereochemistry 5 History 6 Society and culture 6.1 Marketing 6.2 North America 7 Research 8 References 9 External links Medical uses 200 - mg ibuprofen tablets Ibuprofen is used primarily to treat fever ( including postimmunisation fever ), mild to moderate pain ( including pain relief after surgery ), painful menstruation, osteoarthritis, dental pain, headaches, and pain from kidney stones. About 60 % of people respond to any NSAID ; those who do not respond well to a particular one may respond to another. It is used for inflammatory diseases such as juvenile idiopathic arthritis and rheumatoid arthritis. It is also used for pericarditis and patent ductus arteriosus. 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. In 2006, ibuprofen lysine was approved in the US by the Food and Drug Administration ( FDA ) for closure of patent ductus arteriosus in premature infants weighing between 500 and 1,500 grams ( 1 and 3 lb ), who are no more than 32 weeks gestational age when usual medical management ( such as fluid restriction, diuretics, and respiratory support ) is not effective. Adverse effects Adverse effects include nausea, dyspepsia, diarrhea, constipation, gastrointestinal ulceration / bleeding, headache, dizziness, rash, salt and fluid retention, and hypertension. Infrequent adverse effects include esophageal ulceration, heart failure, hyperkalemia, renal impairment, confusion, and bronchospasm. Ibuprofen can exacerbate asthma, sometimes fatally. Ibuprofen may be quantified in blood, plasma, or serum to demonstrate the presence of the drug in a person having experienced an anaphylactic reaction, confirm a diagnosis of poisoning in hospitalized patients, or assist in a medicolegal death investigation. A monograph relating ibuprofen plasma concentration, time since ingestion, and risk of developing renal toxicity in overdose patients has been published. Cardiovascular risk Along with several other NSAIDs, chronic ibuprofen use has been found correlated with risk of hypertension and myocardial infarction ( heart attack ), particularly among those treated chronically using high doses. In older hypertensive patients treated with hydrochlorothiazide, ibuprofen at a high daily dose was found to significantly increase systolic blood pressure. On 9 July 2015, the US FDA toughened warnings of increased heart attack and stroke risk associated with ibuprofen and related NSAIDs ; the NSAID aspirin is not included in this warning. Skin Along with other NSAIDs, ibuprofen has been associated with the onset of bullous pemphigoid or pemphigoid - like blistering. As with other NSAIDs, ibuprofen has been reported to be a photosensitising agent, but it is considered a weak photosensitising agent compared to other members of the 2 - arylpropionic acid class. Like other NSAIDs, ibuprofen is an extremely rare cause of the autoimmune disease Stevens -- Johnson syndrome ( SJS ). Ibuprofen is also an extremely rare cause of Lyell 's Syndrome ( toxic epidermal necrolysis ). Interactions Drinking alcohol when taking ibuprofen may increase the risk of stomach bleeding. According to the US Food and Drug Administration ( FDA ), `` ibuprofen can interfere with the antiplatelet effect of low - dose aspirin, potentially rendering aspirin less effective when used for cardioprotection and stroke prevention. '' Allowing sufficient time between doses of ibuprofen and immediate - release ( IR ) aspirin can avoid this problem. The recommended elapsed time between a dose of ibuprofen and a dose of aspirin depends on which is taken first. It would be 30 minutes or more for ibuprofen taken after IR aspirin, and eight hours or more for ibuprofen taken before IR aspirin. However, this timing can not be recommended for enteric - coated aspirin. But, if ibuprofen is taken only occasionally without the recommended timing, the reduction of the cardioprotection and stroke prevention of a daily aspirin regimen is minimal. Overdose Ibuprofen overdose has become common since it was licensed for OTC use. Many overdose experiences are reported in the medical literature, although the frequency of life - threatening complications from ibuprofen overdose is low. Human response in cases of overdose ranges from absence of symptoms to fatal outcome despite intensive - care treatment. Most symptoms are an excess of the pharmacological action of ibuprofen, and include abdominal pain, nausea, vomiting, drowsiness, dizziness, headache, tinnitus, and nystagmus. Rarely, more severe symptoms, such as gastrointestinal bleeding, seizures, metabolic acidosis, hyperkalaemia, hypotension, bradycardia, tachycardia, atrial fibrillation, coma, liver dysfunction, acute renal failure, cyanosis, respiratory depression, and cardiac arrest have been reported. The severity of symptoms varies with the ingested dose and the time elapsed ; however, individual sensitivity also plays an important role. Generally, the symptoms observed with an overdose of ibuprofen are similar to the symptoms caused by overdoses of other NSAIDs. Correlation between severity of symptoms and measured ibuprofen plasma levels is weak. Toxic effects are unlikely at doses below 100 mg / kg, but can be severe above 400 mg / kg ( around 150 tablets of 200 mg units for an average man ) ; however, large doses do not indicate the clinical course is likely to be lethal. A precise lethal dose is difficult to determine, as it may vary with age, weight, and concomitant conditions of the individual person. Therapy is largely symptomatic. In cases presenting early, gastric decontamination is recommended. This is achieved using activated charcoal ; charcoal adsorbs the drug before it can enter the systemic circulation. Gastric lavage is now rarely used, but can be considered if the amount ingested is potentially life - threatening, and it can be performed within 60 minutes of ingestion. Emesis is not recommended. The majority of ibuprofen ingestions produce only mild effects and the management of overdose is straightforward. Standard measures to maintain normal urine output should be instituted and renal function monitored. Since ibuprofen has acidic properties and is also excreted in the urine, forced alkaline diuresis is theoretically beneficial. However, because ibuprofen is highly protein - bound in the blood, renal excretion of unchanged drug is minimal. Forced alkaline diuresis is, therefore, of limited benefit. Symptomatic therapy for hypotension, gastrointestinal bleeding, acidosis, and renal toxicity may be indicated. On occasion, close monitoring in an intensive - care unit for several days is necessary. A patient who survives the acute intoxication usually experiences no late sequelae. Miscarriage A study of pregnant women suggests those taking any type or amount of NSAIDs ( including ibuprofen, diclofenac and naproxen ) were 2.4 times more likely to miscarry than those not taking the drugs. However, an Israeli study found no increased risk of miscarriage in the group of mothers using NSAIDs. Pharmacology NSAIDs such as ibuprofen work by inhibiting the cyclooxygenase ( COX ) enzymes, which convert arachidonic acid to prostaglandin H ( PGH ). PGH, in turn, is converted by other enzymes to several other prostaglandins ( which are mediators of pain, inflammation, and fever ) and to thromboxane A ( which stimulates platelet aggregation, leading to the formation of blood clots ). Like aspirin and indomethacin, ibuprofen is a nonselective COX inhibitor, in that it inhibits two isoforms of cyclooxygenase, COX - 1 and COX - 2. The analgesic, antipyretic, and anti-inflammatory activity of NSAIDs appears to operate mainly through inhibition of COX - 2, which decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever, and swelling. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Inhibition of COX - 1 instead would be responsible for unwanted effects on the gastrointestinal tract. 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. 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. The R - enantiomer is converted through a series of three main enzymes. These enzymes include acyl - CoA - synthetase, which converts the R - enantiomer to ( - ) - R - ibuprofen I - CoA ; 2 - arylpropionyl - CoA epimerase, which converts ( - ) - R - ibuprofen I - CoA to ( + ) - S - Ibuprofen I - CoA ; and hydrolase, which converts ( + ) - S - ibuprofen I - CoA to the S - enantiomer. 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. Chemistry Ibuprofen is practically insoluble in water, but very soluble in most organic solvents like ethanol ( 66.18 g / 100mL at 40 ° C for 90 % EtOH ), methanol, acetone and dichloromethane. The original synthesis of ibuprofen by the Boots Group started with the compound 2 - methylpropylbenzene. The synthesis took six steps. A modern, greener technique for the synthesis involves only three steps. Stereochemistry ( R ) - ibuprofen ( S ) - ibuprofen It is an optically active compound with both S and R - isomers, of which the S ( dextrorotatory ) isomer is the more biologically active ; this isomer has also been isolated and used medically ( see dexibuprofen for details ). Ibuprofen is produced industrially as a racemate. The compound, like other 2 - arylpropionate derivatives ( including ketoprofen, flurbiprofen, naproxen, etc. ), does contain a stereocenter in the α - position of the propionate moiety. So two enantiomers of ibuprofen occur, with the potential for different biological effects and metabolism for each enantiomer. Indeed, the ( S ) - ( + ) - ibuprofen ( dexibuprofen ) was found to be the active form both in vitro and in vivo. An isomerase ( alpha - methylacyl - CoA racemase ) converts ( R ) - ibuprofen to the active ( S ) - enantiomer. History Ibuprofen was derived from propionic acid by the research arm of Boots Group during the 1960s. Its discovery was the result of research during the 1950s and 1960s to find a safer alternative to aspirin. It was discovered by a team led by Stewart Adams and the patent application was filed in 1961. Adams initially tested the drug as treatment for his hangover. The drug was launched as a treatment for rheumatoid arthritis in the United Kingdom in 1969, and in the United States in 1974. Later, in 1983 and 1984, it became the first NSAID ( other than aspirin ) to be available over the counter ( OTC ) in these two countries. Dr. Adams was subsequently awarded an OBE in 1987. Boots was awarded the Queen 's Award for Technical Achievement for the development of the drug in 1987. Society and culture Marketing See also : Ibuprofen brand names A bottle of generic ibuprofen Ibuprofen was made available under prescription in the United Kingdom in 1969, and in the United States in 1974. In the years since, the good tolerability profile, along with extensive experience in the population, as well as in so - called phase - IV trials ( postapproval studies ), have resulted in the availability of ibuprofen OTC in pharmacies worldwide, as well as in supermarkets and other general retailers. Ibuprofen is its INN, BAN, AAN and USAN approved name. Advil is manufactured by Pfizer and has been on the market since 1984. North america Ibuprofen is commonly available in the United States up to the FDA 's 1984 dose limit OTC, rarely used higher by prescription. In 2009, the first injectable formulation of ibuprofen was approved in the United States, under the trade name Caldolor. Research This section needs to be updated. Please update this article to reflect recent events or newly available information. Last update : PMID 25227314, PMID 25644018 ( November 2017 ) Ibuprofen is sometimes used for the treatment of acne because of its anti-inflammatory properties, and has been sold in Japan in topical form for adult acne. As with other NSAIDs, ibuprofen may be useful in the treatment of severe orthostatic hypotension ( low blood pressure when standing up ). In some studies, ibuprofen showed superior results compared with a placebo in the prevention of Alzheimer 's disease, when given in low doses over a long time. 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. In March 2011, researchers at Harvard Medical School announced in Neurology that ibuprofen had a neuroprotective effect against the risk of developing Parkinson 's disease. 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. Some dietary supplements might be dangerous to take along with ibuprofen and other NSAIDs, but as of 2016 more research needs to be conducted to be certain. 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Neurology. 76 ( 10 ) : 854 -- 5. doi : 10.1212 / WNL. 0b013e31820f2e7a. PMID 21368280. Jump up ^ Gao, X ; Chen, H ; Schwarzschild, MA ; Ascherio, A ( 8 March 2011 ). `` Use of ibuprofen and risk of Parkinson disease ''. Neurology. 76 ( 10 ) : 863 -- 9. doi : 10.1212 / WNL. 0b013e31820f2d79. PMC 3059148. PMID 21368281. Jump up ^ McSharry, C ( May 2011 ). `` Parkinson disease : Could over-the - counter treatment protect against Parkinson disease ? ''. Nature Reviews. Neurology. 7 ( 5 ) : 244. doi : 10.1038 / nrneurol. 2011.49. PMID 21555992. Jump up ^ Gleason, JM ; Slezak, JM ; Jung, H ; Reynolds, K ; Van den Eeden, SK ; Haque, R ; Quinn, VP ; Loo, RK ; Jacobsen, SJ ( April 2011 ). `` Regular nonsteroidal anti-inflammatory drug use and erectile dysfunction ''. The Journal of Urology. 185 ( 4 ) : 1388 -- 93. doi : 10.1016 / j. juro. 2010.11. 092. PMID 21334642. Jump up ^ Abebe, W. ( 2002 - 12 - 01 ). `` Herbal medication : potential for adverse interactions with analgesic drugs ''. Journal of Clinical Pharmacy and Therapeutics. 27 ( 6 ) : 391 -- 401. doi : 10.1046 / j. 1365 - 2710.2002. 00444. x. ISSN 0269 - 4727. PMID 12472978. External links Wikimedia Commons has media related to Ibuprofen. U.S. National Library of Medicine : MedlinePlus Drug Information : Ibuprofen University of Bristol chemistry department page on Ibuprofen U.S. National Library of Medicine : Drug Information Portal -- Ibuprofen Nonsteroidal anti-inflammatory drugs ( NSAIDs ) ( primarily M01A and M02A, also N02BA ) Pyrazolones / Pyrazolidines Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone Salicylates Aspirin ( acetylsalicylic acid ) Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid ( salicylate ) Sodium salicylate Acetic acid derivatives and related substances Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bumadizone Bufexamac Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac Oxicams Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam Propionic acid derivatives ( profens ) Alminoprofen Benoxaprofen Carprofen Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pirprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid Vedaprofen COX - inhibiting nitric oxide donator : Naproxcinod N - Arylanthranilic acids ( fenamates ) Azapropazone Clonixin Etofenamate Flufenamic acid Flunixin Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid Flutiazin Coxibs Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Robenacoxib Rofecoxib Valdecoxib Other Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / Orgotein Tenidap Items listed in bold indicate initially developed compounds of specific groups. WHO - EM Withdrawn drugs. Veterinary use medications. Topical products for joint and muscular pain ( M02 ) Anti-inflammatory preparations, non-steroids Pyrazolidines Clofezone Mofebutazone Oxyphenbutazone Phenylbutazone Acetic acid derivatives Diclofenac Fentiazac Tolmetin Other Bendazac Benzydamine Bufexamac Etofenamate Felbinac Feprazone Flurbiprofen Ibuprofen Indometacin Ketoprofen Meclofenamic acid Naproxen Nifenazone Niflumic acid Piketoprofen Piroxicam Suxibuzone Capsaicin derivatives Zucapsaicin Other Dimethyl sulfoxide Idrocilamide Tolazoline Analgesics ( N02A, N02B ) Opioids Opiates / opium Codeine ( + paracetamol, + aspirin ) Morphine ( + naltrexone ) Opium Laudanum Paregoric Semisynthetic Acetyldihydrocodeine Benzylmorphine Buprenorphine ( + naloxone ) Desomorphine Diamorphine ( heroin ) Dihydrocodeine ( + paracetamol ) Dihydromorphine Ethylmorphine Hydrocodone ( + paracetamol, + ibuprofen, + aspirin ) Hydromorphinol Hydromorphone Nicocodeine Nicodicodeine Nicomorphine Oxycodone ( + paracetamol, + aspirin, + ibuprofen, + naloxone, + naltrexone ) Oxymorphone Thebacon Synthetic Alfentanil Alphaprodine Anileridine Butorphanol Carfentanil Dextromoramide Dextropropoxyphene Dezocine Fentanyl ( + fluanisone ) Ketobemidone Levorphanol Lofentanil Meptazinol Methadone Nalbuphine NFEPP Pentazocine Pethidine ( meperidine ) Phenadoxone Phenazocine Piminodine Piritramide Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol Paracetamol - type Acetanilide Bucetin Butacetin Paracetamol ( acetaminophen ) Parapropamol Phenacetin Propacetamol NSAIDs Propionates Fenoprofen Flurbiprofen Ibuprofen Ketoprofen Naproxen Oxaprozin Oxicams Meloxicam Piroxicam Acetates Diclofenac Indometacin Ketorolac Nabumetone Sulindac Tolmetin COX - 2 inhibitors Celecoxib Etoricoxib Lumiracoxib Parecoxib Rofecoxib Valdecoxib Fenamates Meclofenamic acid Mefenamic acid Salicylates Aspirin ( acetylsalicylic acid ) ( + paracetamol / caffeine ) Benorylate Diflunisal Ethenzamide Magnesium salicylate Salicin Salicylamide Salsalate Wintergreen ( methyl salicylate ) Pyrazolones Aminophenazone Ampyrone Metamizole ( dipyrone ) Nifenazone Phenazone Propyphenazone ( + paracetamol / caffeine ) Others Glafenine Cannabinoids Cannabidiol Cannabis Nabilone Nabiximols Tetrahydrocannabinol ( dronabinol ) Ion channel modulators Calcium blockers Gabapentin Gabapentin enacarbil Pregabalin Ziconotide Sodium blockers Carbamazepine Lacosamide Local anesthetics ( e.g., cocaine, lidocaine ) Mexiletine Nefopam Tricyclic antidepressants ( e.g., amitriptyline ) Na 1.7 / 1.8 - selective : DSP - 2230 Funapide PF - 05089771 Raxatrigine Potassium openers Flupirtine Myorelaxants Carisoprodol Chlorzoxazone Cyclobenzaprine Mephenoxalone Methocarbamol Orphenadrine Others Analgesic adjuvant Analgecine Camphor Capsaicin Clonidine Ketamine Menthol Methoxyflurane Nefopam Proglumide Tricyclic antidepressants ( e.g., amitriptyline ) WHO - EM Withdrawn from market Clinical trials : Phase III Never to phase III Acne - treating agents ( D10 ) Antibacterial Azelaic acid Benzoyl peroxide 8 - Hydroxyquinoline Blue light therapy Tea tree oil Keratolytic Glycolic acid Salicylic acid Sulfur Benzoyl peroxide Anti-inflammatory Nicotinamide Ibuprofen Aspirin Red light therapy Antibiotics Clindamycin Dapsone Erythromycin Sulfacetamide Tetracyclines ( Lymecycline Minocycline Doxycycline ) Hormonal Antiandrogens Bicalutamide Cyproterone acetate Drospirenone Flutamide Spironolactone ) Estrogens Estradiol Ethinylestradiol Retinoids Adapalene Isotretinoin Motretinide Tazarotene Tretinoin Other Benzamycin Epristeride Mesulfen Pelretin Stridex Tioxolone Combinations Adapalene / benzoyl peroxide Benzoyl peroxide / clindamycin Clindamycin / tretinoin Erythromycin / isotretinoin Sulfacetamide / sulfur WHO - EM Withdrawn from market Clinical trials : Phase III Never to phase III Prolactin inhibitors and anti-inflammatory products for vaginal administration ( G02CB -- G02CC ) Prolactin inhibitors Bromocriptine Cabergoline Lisuride Metergoline Quinagolide Terguride Anti-inflammatory products for vaginal administration Benzydamine Ibuprofen Flunoxaprofen Naproxen Prostanoid signaling modulators Receptor ( ligands ) DP ( D ) DP Agonists : Prostaglandin D Treprostinil Antagonists : Asapiprant Laropiprant Vidupiprant DP Agonists : Indometacin Prostaglandin D Antagonists : ADC - 3680 AZD - 1981 Bay U3405 Fevipiprant MK - 1029 MK - 7246 QAV - 680 Ramatroban Setipiprant Timapiprant TM30089 Vidupiprant EP ( E ) EP Agonists : Beraprost Enprostil Iloprost ( ciloprost ) Latanoprost Lubiprostone Misoprostol Prostaglandin E ( alprostadil ) Prostaglandin E ( dinoprostone ) Sulprostone Antagonists : AH - 6809 ONO - 8130 SC - 19220 SC - 51089 SC - 51322 EP Agonists : Butaprost Misoprostol Prostaglandin E ( alprostadil ) Prostaglandin E ( dinoprostone ) Treprostinil Antagonists : AH - 6809 PF - 04418948 TG 4 - 155 EP Agonists : Beraprost Carbacyclin Cicaprost Enprostil Iloprost ( ciloprost ) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D Prostaglandin E ( alprostadil ) Prostaglandin E ( dinoprostone ) Remiprostol Sulprostone Antagonists : L - 798106 EP Agonists : Lubiprostone Misoprostol Prostaglandin E ( alprostadil ) Prostaglandin E ( dinoprostone ) TCS - 2510 Antagonists : Grapiprant GW - 627368 L - 161982 ONO - AE3 - 208 Unsorted Agonists : 16, 16 - Dimethyl Prostaglandin E Aganepag Carboprost Evatanepag Gemeprost Nocloprost Omidenepag Prostaglandin F ( dinoprost ) Simenepag Taprenepag FP ( F ) Agonists : Alfaprostol Bimatoprost Carboprost Cloprostenol Enprostil Fluprostenol Latanoprost Prostaglandin D Prostaglandin F ( dinoprost ) Sulotroban Tafluprost Travoprost Unoprostone IP ( I ) Agonists : ACT - 333679 AFP - 07 Beraprost BMY - 45778 Carbacyclin Cicaprost Iloprost ( ciloprost ) Isocarbacyclin MRE - 269 NS - 304 Prostacyclin ( prostaglandin I, epoprostenol ) Prostaglandin E ( alprostadil ) Ralinepag Selexipag Taprostene TRA - 418 Treprostinil Antagonists : RO1138452 TP ( TX ) Agonists : Carbocyclic thromboxane A I - BOP Thromboxane A U-46619 Vapiprost Antagonists : 12 - HETE 13 - APA AA - 2414 Argatroban Bay U3405 BMS - 180,291 Daltroban Domitroban EP - 045 GR - 32191 ICI - 185282 ICI - 192605 Ifetroban Imitrodast L - 655240 L - 670596 Linotroban Mipitroban ONO - 3708 ONO - 11120 Picotamide Pinane thromboxane A Ramatroban Ridogrel S - 145 Samixogrel Seratrodast SQ - 28,668 SQ - 29,548 Sulotroban Terbogrel Terutroban TRA - 418 Unsorted Arbaprostil Ataprost Ciprostene Clinprost Cobiprostone Delprostenate Deprostil Dimoxaprost Doxaprost Ecraprost Eganoprost Enisoprost Eptaloprost Esuberaprost Etiproston Fenprostalene Flunoprost Froxiprost Lanproston Limaprost Luprostiol Meteneprost Mexiprostil Naxaprostene Nileprost Nocloprost Ornoprostil Oxoprostol Penprostene Pimilprost Piriprost Posaraprost Prostalene Rioprostil Rivenprost Rosaprostol Spiriprostil Tiaprost Tilsuprost Tiprostanide Trimoprostil Viprostol Enzyme ( inhibitors ) COX ( PTGS ) Salicylic acids : Aloxiprin Aspirin ( acetylsalicylic acid ) Benorilate ( benorylate ) Carbasalate calcium Diflusinal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Mesalazine ( 5 - aminosalicylic acid ) Methyl salicylate Salacetamide Salicin Salicylamide Salicylate ( salicylic acid ) Salsalate Sodium salicylate Triflusal ; Acetic acids : Aceclofenac Acemetacin Aclofenac Amfenac Alclofenac Bendazac Bromfenac Bufexamac Bumadizone Cinmetacin Clometacin Diclofenac Difenpiramide Etodolac Felbinac Fenclofenac Fentiazac Glucametacin Indometacin ( indomethacin ) Indometacin farnesil Ketorolac Lonazolac Mofezolac Nabumetone Oxametacin Oxindanac Proglumetacin Sulindac Sulindac sulfide Tolmetin Zidometacin Zomepirac ; Propionic acids : Alminoprofen Benoxaprofen Bucloxic acid ( blucloxate ) Butibufen Carprofen Dexibuprofen Dexindoprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Naproxcinod Oxaprozin Pirprofen Pranoprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid ( tiaprofenate ) Vedaprofen ; Anthranilic acids ( fenamic acids ) : Etofenamic acid ( etofenamate ) Floctafenic acid ( floctafenate ) Flufenamic acid ( flufenamate ) Meclofenamic acid ( meclofenamate ) Mefenamic acid ( mefenamate ) Morniflumic acid ( morniflumate ) Niflumic acid ( niflumate ) Talinflumic acid ( talinflumate ) Tolfenamic acid ( tolfenamate ) ; Pyrazolones : Azapropazone Dipyrone Isopyrin Oxyphenbutazone Phenylbutazone ; Enolic acids ( oxicams ) : Ampiroxicam Droxicam Enolicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam ; 4 - Aminoquinolines : Antrafenine Floctafenine Glafenine ; Quinazolines : Fluproquazone Proquazone ; Aminonicotinic acids : Clonixeril Clonixin Flunixin ; Sulfonanilides : Flosulide Nimesulide ; Aminophenols ( anilines ) : Acetanilide AM - 404 ( N - arachidonoylaminophenol ) Bucetin Paracetamol ( acetaminophen ) Parapropamol Phenacetin Propacetamol ; Selective COX - 2 inhibitors ( coxibs ) : Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Polmacoxib Robenacoxib Rofecoxib Tilmacoxib Valdecoxib ; Others / unsorted : Anitrazafen Clobuzarit Curcumin DuP - 697 FK - 3311 Flumizole FR - 122047 Glimepiride Hyperforin Itazigrel L - 655240 L - 670596 Licofelone Menatetrenone ( vitamin K ) NCX - 466 NCX - 4040 NS - 398 Pamicogrel Resveratrol Romazarit Rosmarinic acid Rutecarpine Satigrel SC - 236 SC - 560 SC - 58125 Tenidap Tiflamizole Timegadine Trifenagrel Tropesin PGD S Retinoids Selenium ( selenium tetrachloride, sodium selenite, selenium disulfide ) PGES HQL - 79 PGFS Bimatoprost PGI S Tranylcypromine TXAS Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A Others Precursors : Linoleic acid γ - Linolenic acid ( gamolenic acid ) Dihomo - γ - linolenic acid Diacylglycerol Arachidonic acid Prostaglandin G Prostaglandin H See also Receptor / signaling modulators Leukotriene signaling modulators Nuclear receptor modulators PPAR modulators PPARα Agonists : 15 - HETE 15 - HpETE Aleglitazar Aluminium clofibrate Arachidonic acid Bezafibrate Clofibrate CP - 775146 Daidzein DHEA ( prasterone ) ( in rodents ) Elafibranor Etomoxir Fenofibrate Genistein Gemfibrozil GW - 7647 Leukotriene B LG - 101506 LG - 100754 Lobeglitazone Muraglitazar Oleylethanolamide Palmitoylethanolamide Pemafibrate Perfluorononanoic acid Perfluorooctanoic acid Pioglitazone Saroglitazar Sodelglitazar Tesaglitazar Tetradecylthioacetic acid Troglitazone WY - 14643 Antagonists : GW - 6471 MK - 886 PPARδ Agonists : 15 - HETE 15 - HpETE Arachidonic acid Bezafibrate Daidzein Elafibranor Fonadelpar Genistein GW - 0742 GW - 501516 L - 165,041 LG - 101506 MBX - 8025 Sodelglitazar Tetradecylthioacetic acid Antagonists : FH - 535 GSK - 0660 GSK - 3787 PPARγ Agonists : 5 - Oxo - ETE 5 - Oxo - 15 - hydroxy - ETE 15 - Deoxy - Δ - prostaglandin J 15 - HETE 15 - HpETE Aleglitazar Arachidonic acid Balaglitazone Berberine Bezafibrate Cevoglitazar Ciglitazone Daidzein Darglitazone Edaglitazone Efatutazone Englitazone Etalocib Farglitazar Genistein GW - 1929 Ibuprofen Imiglitazar Indeglitazar LG - 100268 LG - 100754 LG - 101506 Lobeglitazone Muraglitazar ( muroglitazar ) nTZDpa Naveglitazar Netoglitazone Oxeglitazar Peliglitazar Pemaglitazar Perfluorononanoic acid Pioglitazone Prostaglandin J Ragaglitazar Reglitazar Rivoglitazone Rosiglitazone RS5444 Saroglitazar Sipoglitazar Sodelglitazar Telmisartan Tesaglitazar Troglitazone SPPARMs : BADGE EPI - 001 INT - 131 MK - 0533 S26948 Antagonists : FH - 535 GW - 9662 SR - 202 T - 0070907 Unknown : SR - 1664 Non-selective Agonists : Ciprofibrate Clinofibrate Clofibride Englitazone Etofibrate Farglitazar Netoglitazone Ronifibrate Rivoglitazone Simfibrate Unsorted Agonists : Lanifibranor Seladelpar See also Receptor / signaling modulators Nuclear receptor modulators LCCN : sh97005926 GND : 4123405 - 4 Retrieved from `` https://en.wikipedia.org/w/index.php?title=Ibuprofen&oldid=822005769 '' Categories : British inventions Hepatotoxins Nonsteroidal anti-inflammatory drugs Pfizer products Propionic acids World Health Organization essential medicines Analgesics Hidden categories : Use dmy dates from November 2014 Template : drugs.com link with non-standard subpage ECHA InfoCard ID from Wikidata Drug has EMA link Drugboxes which contain changes to watched fields All articles with unsourced statements Articles with unsourced statements from February 2017 Articles with unsourced statements from March 2011 Wikipedia articles in need of updating from November 2017 All Wikipedia articles in need of updating Wikipedia articles with LCCN identifiers Wikipedia articles with GND identifiers RTT Pages using PMID magic links Talk Contents About Wikipedia Afrikaans تۆرکجه Български Bosanski Català Čeština Cymraeg Dansk Deutsch Eesti Ελληνικά Español Euskara فارسی Français 한국어 Հայերեն Hrvatski Bahasa Indonesia Íslenska Italiano עברית Latviešu Lietuvių Magyar Bahasa Melayu Nederlands 日本 語 Norsk Occitan ଓଡ଼ିଆ ਪੰਜਾਬੀ پښتو Polski Português Română Русский Scots Simple English Slovenščina کوردی Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska தமிழ் తెలుగు ไทย Türkçe Українська اردو Tiếng Việt 中文 Edit links This page was last edited on 23 January 2018, at 21 : 52. 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Question: when did ibuprofen become available over the counter
Answer: 1983; 1984; 1984; 1984