{"ATC Code":"C01EB16","Abbreviation":"","Aliases":["2-(4-Isobutylphenyl)propanoic acid","Motrin","Brufen","Advil","Nurofen","Dolgit","Liptan","Medipren","Nuprin","Anflagen"],"Biological Half-Life":"The serum half-life of ibuprofen is 1.2-2 hours. In patients with a compromised liver function, the half-life can be prolonged to 3.1-3.4 hours.","CAS":"15687-27-1","ChEBI":"CHEBI:5855","ChEMBL":"CHEMBL521","ChemicalClasses":[],"Chirality":"racemic","Color/Form":"Colorless, crystalline stable solid","Decomposition":"When heated to decomposition it emits acrid smoke and fumes.","Drug Classes":"Breast Feeding; Lactation; Milk, Human; Analgesic Agents; Anti-inflammatory Agents, Nonsteroidal","Drug Indication":"Ibuprofen is the most commonly used and prescribed NSAID. It is a very common over-the-counter medication widely used as an analgesic, anti-inflammatory and antipyretic.  The use of ibuprofen and its enantiomer [DB09213] in a racemic mix is common for the management of mild to moderate pain related to dysmenorrhea, headache, migraine, postoperative dental pain, spondylitis, osteoarthritis, rheumatoid arthritis, and soft tissue disorder.  Due to its activity against prostaglandin and thromboxane synthesis, ibuprofen has been attributed to alteration of platelet function and prolongation of gestation and labour.  As ibuprofen is a widely used medication, the main therapeutic indications are:  * Patent Ductus Arteriosus - it is a neonatal condition wherein the ductus arteriosus (blood vessel that connects the main pulmonary artery to the proximal descending aorta) fails to close after birth causing severe risk of heart failure. The prostaglandin inhibition of ibuprofen has been studied for the treatment of this condition as it is known that prostaglandin E2 is responsible for keeping the ductus arteriosus open.  * Rheumatoid- and osteo-arthritis - ibuprofen is very commonly used in the symptomatic treatment of inflammatory, musculoskeletal and rheumatic disorders.  * Cystic fibrosis - the use of high dosages of ibuprofen has been proven to decrease inflammation and decreasing polymorphonuclear cell influx in the lungs.  * Orthostatic hypotension - ibuprofen can induce sodium retention and antagonize the effect of diuretics which has been reported to be beneficial for patients with severe orthostatic hypotension.  * Dental pain - ibuprofen is used to manage acute and chronic orofacial pain.  * Pain - ibuprofen is widely used to reduce minor aches and pains as well as to reduce fever and manage dysmenorrhea. It is very commonly used for the relief of acute indications such as fever and tension headaches. It is also used to manage mild to moderate pain and moderate to severe pain as an adjunct to opioid analgesics.  * Investigational uses - efforts have been put into developing ibuprofen for the prophylaxis of Alzheimer's disease, Parkinson disease, and breast cancer.","Drug Warnings":"Ibuprofen should be used with caution in patients with peptic ulcer disease, GI perforation or bleeding, bleeding abnormalities (especially in patients who may be adversely affected by prolongation of bleeding time), impaired renal function, hypertension, or compromised cardiac function.","DrugClasses":["opioid","cannabinoid"],"EINECS":"239-784-6","European Community (EC) Number":"239-784-6","FDA Pharmacological Classification":"WK2XYI10QM","Human Drugs":"Breast Feeding; Lactation; Milk, Human; Analgesic Agents; Anti-inflammatory Agents, Nonsteroidal","IUPACName":"2-[4-(2-methylpropyl)phenyl]propanoic acid","Impurities":["2-(4-formylphenyl)propionic acid","7-(2-methylpropyl)-1-(4-(2-methylpropyl)phenyl)-1,2,3,4-tetrahydronaphthalene-1,4-dicarboxylic acid","4'-isobutylacetophenone","2-(4-ethylphenyl)propionic acid","2-(3-isobutylphenyl)propionic acid","1-(2-methylpropyl)-4-(3-(4-(2-methylpropyl)phenyl)butyl)benzene","2-(4-isobutyrylphenyl)propionic acid","1-(4-acetylphenyl)-2-methyl-1-propanone","1,3-bis(4-(2-methylpropyl)phenyl)butan-1-one","1,1-bis(p-isobutylphenyl)ethane","ibuprofen alcohol","2-(4'-(1-hydroxy-2-methylpropyl)phenyl)propionic acid","3-(4-isobutylphenyl)propanoic acid","2-(4-isobutylphenyl)-2-hydroxypropionic acid","2-(4-(2-methylpropyl)phenyl)ethanol","2-(4-(1-methylpropyl)phenyl)propanoic acid"],"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)","InChIKey":"HEFNNWSXXWATRW-UHFFFAOYSA-N","MeSH Pharmacological Classification":"A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)","Melting Point":"75-77.5 ºC","MolecularFormula":"C\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"206.28 g/mol","Odor":"Characteristic odor","Opticalactivity":"( + / - )","Pharmacodynamics":"Ibuprofen has multiple actions in different inflammatory pathways involved in acute and chronic inflammation. The main effects reported in ibuprofen are related to the control of pain, fever and acute inflammation by the inhibition of the synthesis of prostanoids by COX-1 and COX-2. Pain relief is attributed to peripheral affected regions and central nervous system effects in the pain transmission mediated by the dorsal horn and higher spinothalamic tract. Some reports have tried to link the pain regulation with a possible enhancement on the synthesis of endogenous cannabinoids and action on the NMDA receptors. The effect on pain has been shown to be related to the cortically evoked potentials.  The antipyretic effect is reported to be linked to the effect on the prostanoid synthesis due to the fact that the prostanoids are the main signaling mediator of pyresis in the hypothalamic-preoptic region.  The use of ibuprofen in dental procedures is attributed to the local inhibition of prostanoid production as well as to anti-oedemic activity and an increase of plasma beta-endorphins. Some reports have suggested a rapid local reduction of the expression of COX-2 in dental pulp derived by the administration of ibuprofen.  The administration of ibuprofen in patients with rheumatic diseases has shown to control joint symptoms.   Ibuprofen is largely used in OTC products such as an agent for the management of dysmenorrhea which has been proven to reduce the amount of menstrual prostanoids and to produce a reduction in the uterine hypercontractility. As well, it has been reported to reduce significantly the fever and the pain caused by migraines. This effect is thought to be related to the effect on platelet activation and thromboxane A2 production which produces local vascular effects in the affected regions. This effect is viable as ibuprofen can enter in the central nervous system.  In the investigational uses of ibuprofen, it has been reported to reduce neurodegeneration when given in low doses over a long time. On the other hand, its use in Parkinson disease is related to the importance of inflammation and oxidative stress in the pathology of this condition. The use of ibuprofen for breast cancer is related to a study that shows a decrease of 50% in the rate of breast cancer.","Physical Description":"Solid","PubChemId":3672,"Record Description":["Ibuprofen is a monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(2-methylpropyl)phenyl group. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, a cyclooxygenase 2 inhibitor, a cyclooxygenase 1 inhibitor, an antipyretic, a xenobiotic, an environmental contaminant, a radical scavenger, a drug allergen and a geroprotector. It is functionally related to a propionic acid. It is a conjugate acid of an ibuprofen(1-).","Ibuprofen is a non-steroidal anti-inflammatory drug (NSAID) derived from propionic acid and it is considered the first of the propionics. The formula of ibuprofen is 2-(4-isobutylphenyl) propionic acid and its initial development was in 1960 while researching for a safer alternative for aspirin. Ibuprofen was finally patented in 1961 and this drug was first launched against rheumatoid arthritis in the UK in 1969 and USA in 1974. It was the first available over-the-counter NSAID.  On the available products, ibuprofen is administered as a racemic mixture. Once administered, the R-enantiomer undergoes extensive interconversion to the S-enantiomer in vivo by the activity of the alpha-methylacyl-CoA racemase. In particular, it is generally proposed that the S-enantiomer is capable of eliciting stronger pharmacological activity than the R-enantiomer.","Ibuprofen is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of ibuprofen is as a Cyclooxygenase Inhibitor.","Ibuprofen is a commonly used nonsteroidal antiinflammatory (NSAID) drug which is available both by prescription and over-the-counter. Ibuprofen is considered to be among the safest NSAIDs and is generally well tolerated but can, nevertheless, rarely cause clinically apparent and serious acute liver injury.","Ibuprofen has been reported in Plantago major, Syzygium aromaticum, and Artemisia argyi with data available.","Ibuprofen is a propionic acid derivate and nonsteroidal anti-inflammatory drug (NSAID) with anti-inflammatory, analgesic, and antipyretic effects. Ibuprofen inhibits the activity of cyclo-oxygenase I and II, resulting in a decreased formation of precursors of prostaglandins and thromboxanes. This leads to decreased prostaglandin synthesis, by prostaglandin synthase, the main physiologic effect of ibuprofen. Ibuprofen also causes a decrease in the formation of thromboxane A2 synthesis, by thromboxane synthase, thereby inhibiting platelet aggregation. (NCI05)","IBUPROFEN is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1974 and has 21 approved and 61 investigational indications. This drug has a black box warning from the FDA.","Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) widely marketed under various trademarks including Act-3, Advil, Brufen, Motrin, Nuprin, and Nurofen. It is used for relief of symptoms of arthritis, primary dysmenorrhoea, and fever; Ibuprofen is an NSAID which is believed to work through inhibition of cyclooxygenase (COX), thus inhibiting prostaglandin synthesis. There are at least 2 variations of cyclooxygenase (COX-1 and COX-2), ibuprofen inhibits both COX-1 and COX-2. It appears that its analgesic, antipyretic, and anti-inflammatory activity are achieved principally through COX-2 inhibition; whereas COX-1 inhibition is responsible for its unwanted effects on platelet aggregation and the GI mucosa. As with other NSAIDs, ibuprofen inhibits platelet aggregation, but is not used therapeutically for this action since it is a minor and reversible effect. -- Wikipedia.","A non-steroidal anti-inflammatory agent with analgesic, antipyretic, and anti-inflammatory properties","See also: Ibuprofen Sodium (active moiety of); Ibuprofen Lysine (active moiety of); Ibuprofen; pseudoephedrine hydrochloride (component of) ... View More ...","Ibuprofen is a monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(2-methylpropyl)phenyl group. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, a cyclooxygenase 2 inhibitor, a cyclooxygenase 1 inhibitor, an antipyretic, a xenobiotic, an environmental contaminant, a radical scavenger, a drug allergen and a geroprotector. It is functionally related to a propionic acid. It is a conjugate acid of an ibuprofen(1-).","LiverTox|Analgesic|Mild-Moderate Pain|NSAID"],"References":[{"name":"Wikipedia","url":"https://en.wikipedia.org/wiki/Ibuprofen"},{"name":"Wikidata","url":"https://www.wikidata.org/wiki/Q186969"},{"name":"DrugBank","url":"https://go.drugbank.com/drugs/DB01050"},{"name":"PubChem","url":"https://pubchem.ncbi.nlm.nih.gov/compound/3672"},{"name":"ChemSpider","url":"https://www.chemspider.com/Chemical-Structure.102822.html"},{"name":"ChEMBL","url":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL521"},{"name":"ChEBI","url":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5855"},{"name":"Common Chemistry","url":"https://commonchemistry.cas.org/detail?cas_rn=15687-27-1"},{"name":"HMDB","url":"https://hmdb.ca/metabolites/HMDB0001925"},{"name":"KEGG","url":"https://www.kegg.jp/entry/C01588"},{"name":"UNII","url":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/WK2XYI10QM"},{"name":"EPA DSSTox","url":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID5020732"}],"SMILES":"CC(C)CC1=CC=C(C=C1)C(C)C(=O)O","Salts":null,"Solubility":"Readily sol in most org solvents","Stability/Shelf Life":"STABLE","Stereoisomers":["(+)-Ibuprofen","(-)-Ibuprofen"],"StructureBase64":"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Uses":"Analgesics, Non-Narcotic; Anti-Inflammatory Agents, Non-Steroidal; Cyclooxygenase Inhibitors","Title":"Ibuprofen","UNII":"WK2XYI10QM","Wikidata":"Q186969","XLogP":3.5}