QuickView for ibuprofen (compound)

Summary
General Info

PubChem

PubChem Compound 3672

Name:	Ibuprofen
PubChem Compound ID:	3672
Description:	A nonsteroidal anti-inflammatory agent with analgesic properties used in the therapy of rheumatism and arthritis.
Molecular formula:	C₁₃H₁₈O₂
Molecular weight:	206.281 g/mol
Synonyms:	DivK1c_000887; Apo-Ibuprofen; Ibumetin; Togal N; Urem; Sine-Aid IB Caplets; Librofem; Unipron; Schmerz-Dolgit; Upfen. show more » DivK1c_000887; Apo-Ibuprofen; Ibumetin; Togal N; Urem; Sine-Aid IB Caplets; Librofem; Unipron; Schmerz-Dolgit; Upfen; Artofen; Balkaprofen; AIDS-025464; Fenbid; Kontagripp Mono; Sadefen; Motrin IB Gelcaps; Rebugen; Seklodin; R.D. 13621; Neo-Mindol; Andran; Relcofen; Brofen; Nobfen; PediaProfen; Ibusal; Spectrum3_000465; Dignoflex; 4-Isobutyl-.alpha.-methylphenylacetic acid; SPBio_000178; CBMicro_005634; Acide (isobutyl-4-phenyl)-2 propionique [French]; CHEBI:5855; Bloom; Motrin IB; .alpha.-(4-Isobutylphenyl)propionic acid; Dolocyl; Panafen; Jenaprofen; Nerofen; Solpaflex; Epobron; Fendol; NCI60_002065; (+-)-Ibuprofen; (+-)-p-Isobutylhydratropic acid; U-18,573; Ibuprofen [USAN:BAN:INN:JAN]; Codral Period Pain; Ibuprofen [USAN]; Mensoton; Tonal; Ibulagic; Burana; Ostofen; Rafen; Mynosedin; Lidifen; Esprenit; Acide (isobutyl-4 phenyl)-2 propionique; p-Isobutylhydratropic acid; Act-3; Midol 200; Ibu; Solufen; Uprofen; Am-Fam 400; Alaxan; Children's Advil; Norton; Novogent; Nobgen; 4-Isobutylhydratropic acid; ( -)-Ibuprofen; Haltran; Ibuprofeno [INN-Spanish]; Rufin; Bruflam; Drin; Kesan; Nagifen-D; Brufen; Children's Motrin; (+-)-Ibuprophen; MLS000069733; Siyafen; Melfen; Anafen; Ibuprin; Ifen; Dolven; Femafen; RD 13621; Ibugesic; 79261-49-7; Brufanic; Syntofene; KBioSS_001329; Faspic; Apsifen; Artril; Narfen; Buracaps; Dysdolen; Tabalon; Buburone; Artril 300; 2-(4-Isobutylphenyl)propanoic acid; Algofen; Rofen; Novo Dioxadol; Fenspan; (+-)-2-(p-Isobutylphenyl)propionic acid; Antagil; Nuprin; DOLO PUREN; D00126; Dansida; Dorival; Ranofen; Ibudolor; (.+ -.)-2-(p-Isobutylphenyl)propionic acid; Butylenin; Tatanal; Ibulgan; Proflex; Benzeneacetic acid, .alpha.-methyl-4-(2-methylpropyl)-; Eputex; Ibucasen; Ibuprohm; EU-0100691; Amersol; 4-Isobutyl-alpha-methylphenylacetic acid; Gynofug; Brufort; Duobrus; Doloren; 58560-75-1; Ibuprocin; Bluton; C01588; 31121-93-4; Anflagen; alpha-p-Isobutylphenylpropionic acid; Dristan Sinus; Nurofen; (+-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid; Ibren; Bufeno; Hemagene Tailleur; Ibol; Rhinadvil; alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid; Deep Relief; Rufen; Antiflam; KBioGR_000389; Inflam; Dentigoa; Brufen 400; Emflam-200; Neobrufen; Dolofort; Citalgan; Fibraflex; BRN 2049713; Gelufene; Suspren; Advil (TN); Advil Cold & Sinus; Grefen; Kratalgin; Tempil; Bupron; Sugafen; Roidenin; Duafen; Junifen; Profen; Betaprofen; Combiflam; Dibufen; Optifen; Spectrum2_000129; Ibu-slo; Stelar; duralbuprofen; Neo-Helvagit; Zofen; Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-; Ibuprofen (+-) mixture; Advil; Hydratropic acid, p-isobutyl-; NSC256857; (RS)-Ibuprofen; Antarene; SMR000058184; Ozonol; Adran; Ibuhexal; UCB 79171; Ibuprofen (JP15/USP); Ibudol; Dolgit; IP-82; Novadol; Benzeneacetic acid, .alpha.-methyl-4- (2-methylpropyl)-; Exneural; Carol; Dolormin; Brufen Retard; Motrin; Dura-Ibu; Nuprilan; Dolgin; Ibugen; Paduden; Nobfelon; Ibuprofenum [INN-Latin]; Ibugel; Suprafen; Pantrop; Ibuflamar; Anco; U 18573; 15687-27-1; Noalgil; Quadrax; KBio1_000887; Dolofin; Easifon; Doltibil; (2RS)-2-[4-(2-methylpropyl)phenyl]propanoic acid; KBio2_003897; IB-100; NSC 256857; p-Isobutyl-2-phenylpropionic acid; AIDS025464; Bukrefen; Ibu-slow; Napacetin; Paxofen; Dolomax; CCRIS 3223; Ak+C2278tren; Children's Elixsure IB; KBio2_001329; Lopane; alpha-(4-Isobutylphenyl)propionic acid; Salivia; Oralfene; Butacortelone; EINECS 239-784-6; Dolmaral; Moment; VUFB 9649; Malafene; Midol IB Cramp Relief; Ibuprofen; Dologel; Gofen; Irfen; Ibufen; Novo-Profen; Lamidon; Manypren; Isodol; Proartinal; Ibufug; Donjust B; Trendar; KBio2_006465; 2-(p-Isobutylphenyl)propionic acid; Spectrum_000849; Daiprophen; Combunox; Sednafen; KBio3_001390; Ibubest; Ibuleve; Noritis; (S)-4-Isobutyl-alpha-methylphenylacetic acid; Ibupirac; Bayer Select Pain Relief; Nobafon; Tofen; (4-Isobutylphenyl)-alpha-methylacetic acid; Ibumerck; Zafen; Bufigen; Ibubeta; Advil, Children's; Ipren; DRG-0069; Inabrin; Spectrum4_000015; Emflam; Dolofen; Provon; Adex 200; HSDB 3099; .alpha.-Methyl-4-(2-methylpropyl)benzeneacetic acid; Cunil; Femidol; Medipren; Novoprofen; Tabalon 400; .alpha.-(p-isobutylphenyl)propionic acid; (.+ -.)-p-Isobutylhydratropic acid; Opturem; Ostarin; Femapirin; Ibumed; NINDS_000887; Rupan; Ibuprofene [INN-French]; Liptan; Dolibu; Ergix; Ibulav; Ebufac; Ibu-Tab; Ibular; Dularbuprofen; Antalfene; Cobo; Perofen; Dolofen-F; Seskafen; Dalsy; Cesra show less «

DrugBank

Identification

Name:	Ibuprofen
Name (isomeric):	DB01050
Drug Type:	small molecule
Description:	A nonsteroidal anti-inflammatory agent with analgesic properties used in the therapy of rheumatism and arthritis.
Synonyms:	Para-Isobutylhydratropic Acid; Ibuprophen; P-Isobutylhydratropic Acid
Brand:	Children's Advil, Inabrin, Rebugen, Apo-Ibuprofen, Cap-Profen, Dolo-Dolgit, Seclodin, Ibumetin, Bluton, Pedia-Profen, Children's Motrin, Epobron, NeoProfen, Ibutid, Ebufac, Amersol, Amibufen, Ibu, Nobfelon, Napacetin, Anflagen, Advil Liqui-Gels, Lebrufen, Profen, Midol 200, Apsifen-F, Medipren, Roidenin, Dolgit, Pediaprofen, Nobgen, Nobfen, Rufen, Anco, Junior Strength Advil, Tab-Profen, Haltran, Brufort, Ibuprin, Junior Strength Ibuprofen, Dolgin, Ibufen, Buburone, Ibu-Tab, Children's Elixsure, Dolocyl, Nuprin, Lamidon, Novoprofen, Midol, Ibuprohm, Motrin, Adran, Nurofen, Liptan, Suspren, Artril 300, Lidifen, Andran, Actiprofen, Junior Strength Motrin, Apsifen, Paxofen, Rafen, Dolgirid, Ibu-Tab 200, Pediatric Advil, Mynosedin, Femadon, Tabalon, Advil, Children's Ibuprofen, Pantrop, Ibuprocin, Inoven, Brufen, Novogent N, Brufanic, Codral, Trendar, Butylenin, Urem, Fenbid Spansule, Ifen, Ibu-Attritin, Ibu-Slo
Brand name mixture:	Advil® Cold and Sinus Plus(ibuprofen + pseudoephedrine HCl + chlorpheniramine maleate), Advil® Flu & Body Ache(ibuprofen + pseudoephedrine HCl), Advil® Cold & Sinus(ibuprofen + pseudoephedrine HCl), Robax Platinum®(methocarbamol + ibuprofen), Motrin® Sinus Headache(ibuprofen + pseudoephedrine HCl), Advil® Cold & Sinus Daytime(ibuprofen + pseudoe... show more » Advil® Cold and Sinus Plus(ibuprofen + pseudoephedrine HCl + chlorpheniramine maleate), Advil® Flu & Body Ache(ibuprofen + pseudoephedrine HCl), Advil® Cold & Sinus(ibuprofen + pseudoephedrine HCl), Robax Platinum®(methocarbamol + ibuprofen), Motrin® Sinus Headache(ibuprofen + pseudoephedrine HCl), Advil® Cold & Sinus Daytime(ibuprofen + pseudoephedrine HCl), Vicoprofen®(ibuprofen + hydrocodone bitartrate), Children's Advil® Cold(ibuprofen + pseudoephedrine HCl), Sudafed® Sinus Advance(ibuprofen + pseudoephedrine HCl), Advil® Cold and Sinus Nighttime(ibuprofen + pseudoephedrine HCll + chlorpheniramine maleate), Dristan® Sinus Caplets®(ibuprofen + pseudoephedrine HCl), Motrin® Children's Cold(ibuprofen + pseudoephedrine HCl) show less «
Category:	Analgesics, Non-Narcotic, Antipyretics, Cyclooxygenase Inhibitors, Analgesics, Anti-inflammatory Agents, Nonsteroidal Anti-inflammatory Agents (NSAIAs)
CAS number:	15687-27-1

Pharmacology

Indication:	For symptomatic treatment of rheumatoid arthritis, juvenile rheumatoid arthritis and osteoarthritis. May be used to treat mild to moderate pain and for the management of dysmenorrhea. May be used to reduce fever. Has been used with some success for treating ankylosing spondylitis, gout and psoriatic arthritis. May reduce pain, fever and inflammation of pericarditis. May be used IV with opiates to relieve moderate to severe pain. Ibuprofen lysine may be used IV to treat patent ductus arteriosus (PDA) in premature neonates.
Pharmacology:	Ibuprofen is a nonsteroidal anti-inflammatory agent (NSAIA) or nonsteroidal anti-inflammatory drug (NSAID), with analgesic and antipyretic properties. Ibuprofen has pharmacologic actions similar to those of other prototypical NSAIAs, which are thought to act through inhibition of prostaglandin synthesis.
Mechanism of Action:	The exact mechanism of action of ibuprofen is unknown. Ibuprofen is a non-selective inhibitor of cyclooxygenase, an enzyme invovled in prostaglandin synthesis via the arachidonic acid pathway. Its pharmacological effects are believed to be due to inhibition cylooxygenase-2 (COX-2) which decreases the synthesis of prostaglandins involved in mediati... show more » The exact mechanism of action of ibuprofen is unknown. Ibuprofen is a non-selective inhibitor of cyclooxygenase, an enzyme invovled in prostaglandin synthesis via the arachidonic acid pathway. Its pharmacological effects are believed to be due to inhibition cylooxygenase-2 (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 is thought to cause some of the side effects of ibuprofen including GI ulceration. 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. show less «
Absorption:	~ 80% absorbed from GI tract Time to reach peak plasma concentration = 47 minutes (suspension), 62 minutes (chewable tablets), 120 minutes (conventional tablets)
Protein binding:	90-99% to whole human plasma and site II of purified albumin, binding appears to be saturable and becomes non-linear at concentrations exceeding 20 mcg/ml.
Biotransformation:	R-enanatiomer undergoes extensive enantiomeric conversion (53-65%) to the more active S-enantiomer in vivo. Metablized by oxidation to 2 inactive metabolites: (+)-2[4´-(2-hydroxy-2-methylpropyl)phenyl]propionic acid and (+)-2-[4´-(2-carboxypropyl)phenyl]propionic acid. Very small amounts of 1-hydroxyibuprofen and 3-hydroxyibuprofen have been recovered from urine. Cytochrome P450 2C9 is the major catalyst in the formation of oxidative metabolites. Oxidative metabolites may be conjugated to glucuronide prior to excretion.
Route of elimination:	Ibuprofen is rapidly metabolized and eliminated in the urine.
Half Life:	2-4 hours
Toxicity:	Side effects: May cause peripheral edema and fluid retention. Use caution in patients with congestive heart failure or severe uncontrolled hypertension. May cause dyspepsia, heartburn, nausea, vomiting, anorexia, diarrhea, constipation, stomatitis, flatulence, bloating, epigastric pain, and abdominal pain. Peptic ulcer and GI bleeding have been reported. May also cause dizziness, headache and nervousness. Acute renal failure accompanied by acute tubular necrosis has been reported. Most common symptoms of overdose are abdominal pain, nausea, vomiting, lethargy, vertigo, drowsiness (somnolence), dizziness and insomnia. Other symptoms of overdose include headache, loss of consciousness, tinnitus, CNS depression, convulsions and seizures. May rarely cause metabolic acidosis, abnormal hepatic function, hyperkalemia, renal failure, dyspnea, respiratory depression, coma, acute renal failure, and apnea (primarily in very young pediatric patients). LD₅₀=1255mg/kg(orally in mice)
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Avoid alcohol.

Take with food to reduce gastric irritation.

Food delays the time to reach peak plasma concentrations by 30-60 minutes and reduces peak plasma concentrations by 30-50%. Extent of absorption is unaffected.

Drug interaction:

Torasemide	The NSAID, ibuprofen, may decrease the diuretic and antihypertensive effect of the loop diuretic, torasemide.
Carteolol	Risk of inhibition of renal prostaglandins
Bumetanide	The NSAID, ibuprofen, may antagonize the diuretic and antihypertensive effects of the loop diuretic, bumetanide.
Atenolol	Risk of inhibition of renal prostaglandins
Trandolapril	The NSAID, Ibuprofen, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Ibuprofen is initiated, discontinued or dose changed.

Torasemide	The NSAID, ibuprofen, may decrease the diuretic and antihypertensive effect of the loop diuretic, torasemide.
Carteolol	Risk of inhibition of renal prostaglandins
Bumetanide	The NSAID, ibuprofen, may antagonize the diuretic and antihypertensive effects of the loop diuretic, bumetanide.
Atenolol	Risk of inhibition of renal prostaglandins
Trandolapril	The NSAID, Ibuprofen, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Ibuprofen is initiated, discontinued or dose changed.
Penbutolol	Risk of inhibition of renal prostaglandins
Bisoprolol	Risk of inhibition of renal prostaglandins
Metoprolol	Risk of inhibition of renal prostaglandins
Warfarin	Ibuprofen, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. The antiplatelet effect of ibuprofen may also increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if ibuprofen is initiated, discontinued or dose changed.
Tamoxifen	Ibuprofen may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Ibuprofen is initiated, discontinued or dose changed.
Bevantolol	Risk of inhibition of renal prostaglandins
Treprostinil	The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Ibuprofen. Monitor for increased bleeding during concomitant thearpy.
Colesevelam	Bile acid sequestrants may decrease the absorption of Nonsteroidal Anti-Inflammatory Agents. Monitor for decreased serum concentrations/therapeutic effects of nonsteroidal anti-inflammatory agents (NSAID) if coadministered with bile acid sequestrants. Separating the administration of doses by 2 or more hours may reduce (but not eliminate) the risk of interaction. The manufacturer of colesevelam recommends that drugs should be administered at least 1 hour before or 4 hours after colesevelam.
Betaxolol	Nonsteroidal Anti-Inflammatory Agents such as ibuprofen may diminish the antihypertensive effect of Beta-Blockers such as betaxolol. Monitor for increases in blood pressure if a nonsteroidal anti-inflammatory agent (NSAID) is initiated/dose increased, or decreases in blood pressure if a NSAID is discontinued/dose decreased; this is particularly important if NSAID treatment is for extended periods of time. Ophthalmic beta-blockers are likely of little concern.
Acebutolol	Risk of inhibition of renal prostaglandins
Triflusal	The metabolite of triflusal, 2-hydroxy-4-trifluoro-methyl-benzoic acid (HTB), impairs the serum protein binding of ibuprofen to the same extent as acetylsalisylic acid. Thus, the free fraction of glisentide may be increased. A dosage reduction may be required if used in combination.
Lithium	The NSAID, ibuprofen, may decrease the renal excretion of lithium. Increased risk of lithium toxicity.
Anisindione	The NSAID, ibuprofen, may increase the anticoagulant effect of anisindione.
Carvedilol	Risk of inhibition of renal prostaglandins
Labetalol	Risk of inhibition of renal prostaglandins
Cyclosporine	Monitor for nephrotoxicity
Methotrexate	The NSAID, ibuprofen, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
Nadolol	Risk of inhibition of renal prostaglandins
Tolbutamide	Ibuprofen, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Ibuprofen is initiated, discontinued or dose changed.
Sotalol	Risk of inhibition of renal prostaglandins
Oxprenolol	Risk of inhibition of renal prostaglandins
Voriconazole	Ibuprofen, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of voriconazole if ibuprofen is initiated, discontinued or dose changed.
Practolol	Risk of inhibition of renal prostaglandins
Trimethoprim	The strong CYP2C9 inhibitor, Ibuprofen, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Ibuprofen is initiated, discontinued or dose changed.
Pindolol	Risk of inhibition of renal prostaglandins
Ethacrynic acid	The NSAID, ibuprofen, may antagonize the diuretic and antihypertensive effects of the loop diuretic, ethacrynic acid.
Ginkgo biloba	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Furosemide	The NSAID, ibuprofen, may antagonize the diuretic and antihypertensive effects of the loop diuretic, furosemide.
Alendronate	Increased risk of gastric toxicity
Acetylsalicylic acid	Concomitant therapy of the NSAID, ketoprofen, and acetylsalicylic acid may result in additive adverse/toxic effects (e.g. GI bleeding). The NSAID may also limit the cardioprotective effect of acetylsalicylic acid. Occasional concomitant use may not cause clinically significant problems, but regular, frequent concomitant therapy is not recommended.
Esmolol	Risk of inhibition of renal prostaglandins
Acenocoumarol	The NSAID, ibuprofen, may increase the anticoagulant effect of acenocoumarol.
Vilazodone	Increased risk of bleeding with concomitant use of non-steroidal anti-inflammatory drugs with vilazodone.
Propranolol	Risk of inhibition of renal prostaglandins
Dicumarol	The NSAID, ibuprofen, may increase the anticoagulant effect of dicumarol.