Actiprofen;Adran;Advil;Advil Liqui-Gels;Amersol;Amibufen;Anco;Andran;Anflagen;Apo-Ibuprofen;Apsifen;Apsifen-F;Artril 300;Bluton;Brufanic;Brufen;Brufort;Buburone;Butylenin;Cap-Profen;Children's Advil;Children's Elixsure;Children's Ibuprofen;Children's Motrin;Codral;Dolgin;Dolgirid;Dolgit;Dolo-Dolgit;Dolocyl;Ebufac;Epobron;Femadon;Fenbid Spansule;Haltran;Ibu;Ibu-Attritin;Ibu-Slo;Ibu-Tab;Ibu-Tab 200;Ibufen;Ibumetin;Ibuprin;Ibuprocin;Ibuprohm;Ibutid;Ifen;Inabrin;Inoven;Junior Strength Advil;Junior Strength Ibuprofen;Junior Strength Motrin;Lamidon;Lebrufen;Lidifen;Liptan;Medipren;Midol;Midol 200;Motrin;Mynosedin;Napacetin;NeoProfen (Ovation);Nobfelon;Nobfen;Nobgen;Novogent N;Novoprofen;Nuprin;Nurofen;Pantrop;Paxofen;Pedia-Profen;Pediaprofen;Pediatric Advil;Profen;Rafen;Rebugen;Roidenin;Rufen;Seclodin;Suspren;Tab-Profen;Tabalon;Trendar;Urem;

Ibuprophen;P-Isobutylhydratropic Acid;Para-Isobutylhydratropic Acid;

Ibuprofen, a propionic acid derivative, is a prototypical nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties.

• Abbott laboratories pharmaceutical products div
• Actavis mid atlantic llc
• Advent pharmaceuticals inc
• Alra laboratories inc
• Alterna tchp llc
• Amneal pharmaceuticals ny llc
• Banner pharmacaps inc
• Basf corp
• Bayer healthcare llc
• Bristol myers products inc
• Contract pharmacal corp
• Cumberland pharmaceuticals inc
• Dr reddys laboratories inc
• Dr reddys laboratories louisiana llc
• Dr reddys laboratories ltd
• Halsey drug co inc
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• L perrigo co
• Lederle laboratories div american cyanamid co
• Leiner health products inc
• Lnk international inc
• Lundbeck inc
• Marksans pharma ltd
• Mcneil consumer healthcare
• Mcneil consumer healthcare div mcneil ppc inc
• Mcneil consumer products co div mcneilab inc
• Mcneil pediatrics
• Mutual pharmaceutical co inc
• Mylan laboratories inc
• Mylan pharmaceuticals inc
• Northstar healthcare holdings ltd
• Ohm corp
• Ohm laboratories inc
• Par pharmaceutical inc
• Perrigo co
• Perrigo r and d co
• Pliva inc
• Purepac pharmaceutical co
• Sandoz inc
• Shasun usa inc
• Superpharm corp
• Teva pharmaceuticals usa inc
• Tris pharma inc
• Vintage pharmaceuticals inc
• Watson laboratories inc
• Wyeth consumer healthcare

Synthesis Reference

Not Available

General Reference

Zawada ET Jr: Renal consequences of nonsteroidal antiinflammatory drugs. Postgrad Med. 1982 May;71(5):223-30. Pubmed Townsend KP, Pratico D: Novel therapeutic opportunities for Alzheimer’s disease: focus on nonsteroidal anti-inflammatory drugs. FASEB J. 2005 Oct;19(12):1592-601. Pubmed Chen H, Jacobs E, Schwarzschild MA, McCullough ML, Calle EE, Thun MJ, Ascherio A: Nonsteroidal antiinflammatory drug use and the risk for Parkinson’s disease. Ann Neurol. 2005 Dec;58(6):963-7. Pubmed Geisslinger G, Dietzel K, Bezler H, Nuernberg B, Brune K: Therapeutically relevant differences in the pharmacokinetical and pharmaceutical behavior of ibuprofen lysinate as compared to ibuprofen acid. Int J Clin Pharmacol Ther Toxicol. 1989 Jul;27(7):324-8. Pubmed Bergner T, Przybilla B: Photosensitization caused by ibuprofen. J Am Acad Dermatol. 1992 Jan;26(1):114-6. Pubmed

Form	Route	Strength
Capsule	Oral	200 mg
Concentrate	Intravenous	100 mg/ml
Suspension	Oral	100 mg/5 ml
Suspension	Oral	40 mg/ml
Tablet	Oral	200 mg
Tablet	Oral	400 mg
Tablet	Oral	600 mg
Tablet	Oral	800 mg
Tablet, chewable	Oral	100 mg
Tablet, chewable	Oral	50 mg
Tablet, film coated	Oral	100 mg
Tablet, film coated	Oral	200 mg
Tablet, film coated	Oral	400 mg
Tablet, film coated	Oral	600 mg
Tablet, film coated	Oral	800 mg

Unit description	Cost	Unit
Neoprofen 20 mg/2 ml vial	304.5 USD	ml
Caldolor 400 mg/4 ml vial	2.21 USD	ml
Caldolor 800 mg/8 ml vial	1.58 USD	ml
Nuprin arthritis patch	1.11 USD	patch
Ibuprofen powder	1.04 USD	g
Nuprin muscle & joint patch	1.03 USD	patch
Profen II 45-800 mg 12 Hour tablet	0.69 USD	tablet
Motrin 800 mg tablet	0.59 USD	tablet
Advil allergy sinus caplet	0.5 USD	caplet
Ibu-drops 40 mg/ml suspension drops	0.42 USD	ml
Motrin 600 mg tablet	0.4 USD	tablet
Ibuprofen 800 mg tablet	0.36 USD	tablet
Ibuprofen 400 mg tablet	0.35 USD	tablet
Infant's motrin 50 mg/1.25 ml	0.34 USD	ml
Childs ibuprofen susp drp	0.33 USD	ml
Ibuprofen 600 mg tablet	0.33 USD	tablet
Wal-profen cold & sinus cplt	0.3 USD	caplet
Infant ibuprofen susp drop	0.29 USD	ml
Motrin 400 mg tablet	0.29 USD	tablet
CVS Pharmacy infant ibuprofen susp drop	0.25 USD	ml
Infants medi-profen susp	0.23 USD	ml
Advil cold & sinus caplet	0.22 USD	caplet
Advil pm caplet	0.22 USD	caplet
Soba profen cold-sinus tablet	0.22 USD	tablet
Midol caplet	0.21 USD	caplet
Advil migraine 200 mg capsule	0.2 USD	capsule
Ibuprofen cold-sinus caplet	0.2 USD	caplet
Motrin 100 mg caplet	0.2 USD	caplet
Motrin pm caplet	0.2 USD	caplet
Advil 200 mg liqui-gel capsule	0.19 USD	capsule
Soba profen ib caplet	0.19 USD	caplet
Motrin 100 mg tablet chew	0.18 USD	tablet
Pub infants profenib drops	0.18 USD	ml
Sm ibuprofen ib 100 mg tablet	0.18 USD	tablet
Eck ibuprofen jr caplet	0.17 USD	caplet
Ibuprofen pm caplet	0.17 USD	caplet
Advil 200 mg caplet	0.15 USD	capsule
Advil 200 mg gel caplet	0.15 USD	caplet
Advil 200 mg tablet	0.15 USD	tablet
Ibuprofen 100 mg tablet chew	0.15 USD	tablet
Motrin ib 200 mg caplet	0.15 USD	caplet
Apo-Ibuprofen 600 mg Tablet	0.14 USD	tablet
CVS Pharmacy ibuprofen jr str 100 mg tablet	0.14 USD	tablet
Nu-Ibuprofen 600 mg Tablet	0.14 USD	tablet
Motrin ib 200 mg tablet	0.13 USD	tablet
Motrin ib 200 mg gelcap	0.12 USD	capsule
Nuprin 200 mg caplet	0.12 USD	caplet
Wal-profen 200 mg caplet	0.12 USD	caplet
Wal-profen 200 mg tablet	0.12 USD	tablet
Eql ibuprofen 200 mg tablet	0.1 USD	tablet
Nuprin 200 mg tablet	0.1 USD	tablet
Apo-Ibuprofen 400 mg Tablet	0.08 USD	tablet
Ibuprofen ib 200 mg tablet	0.08 USD	tablet
Novo-Profen 400 mg Tablet	0.08 USD	tablet
Apo-Ibuprofen 300 mg Tablet	0.07 USD	tablet
Medi-profen 200 mg tablet	0.07 USD	tablet
Ibuprofen 100 mg/5ml Suspension	0.06 USD	ml
Ibuprofen 200 mg caplet	0.06 USD	caplet
Child ibuprofen susp	0.05 USD	ml
Children's medi-profen susp	0.05 USD	ml
Children's motrin cold suspension	0.05 USD	ml
CVS Pharmacy ibuprofen 200 mg tablet	0.05 USD	tablet
Ibuprofen cold suspension	0.05 USD	ml
I-prin 200 mg tablet	0.05 USD	tablet
Novo-Profen 600 mg Tablet	0.05 USD	tablet
Children's motrin cold	0.04 USD	ml
Pv ibuprofen 200 mg caplet	0.04 USD	caplet
Soba children's profenib susp	0.04 USD	ml
Ibuprofen 200 mg tablet	0.03 USD	tablet
CVS Pharmacy ibuprofen 200 mg caplet	0.02 USD	caplet
Pv ibuprofen 200 mg tablet	0.02 USD	tablet

Type	small molecule

Classes

Phenylacetates

Substructures

Hydroxy Compounds Acetates Carboxylic Acids and Derivatives Phenylacetates Benzene and Derivatives Aromatic compounds

ANTIINFLAMMATORY AND ANTIRHEUMATIC 消炎抗风湿;

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.
Pharmacodynamics	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 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.
Absorption	~ 80% absorbed from GI tract Time to reach peak plasma concentration = 47 minutes (suspension), 62 minutes (chewable tablets), 120 minutes (conventional tablets)
Volume of distribution	Not Available
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.
Metabolism	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. Enzyme Metabolite Reaction Km Vmax Cytochrome P450 2C9 2-Hydroxyibuprofen 2-hydroxylation Cytochrome P450 2C9 3-Hydroxyibuprofen 3-hydroxylation 53 0.58 Cytochrome P450 2C8 2-Hydroxyibuprofen 2-hydroxylation Cytochrome P450 2C8 3-Hydroxyibuprofen 3-hydroxylation UDP-glucuronosyltransferase 1-9 Ibuprofen glucuronide glucuronidation UDP-glucuronosyltransferase 1-1 Ibuprofen glucuronide glucuronidation UDP-glucuronosyltransferase 1-3 Ibuprofen glucuronide glucuronidation UDP-glucuronosyltransferase 2B7 Ibuprofen glucuronide glucuronidation UDP-glucuronosyltransferase 2B4 Ibuprofen glucuronide glucuronidation
Route of elimination	Ibuprofen is rapidly metabolized and eliminated in the urine.
Half life	2-4 hours
Clearance	Not Available
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
Pathways	Pathway Name SMPDB ID Ibuprofen Pathway SMP00086

Properties
State	solid
Melting point	75 - 77 oC
Experimental Properties	Property Value Source water solubility 0.049 mg/ml PhysProp logP 3.6 PhysProp logS -3.99 [ADME Research, USCD] PhysProp Caco2 permeability -4.28 [ADME Research, USCD] BiGG pKa 4.91 Various sources
Predicted Properties	Property Value Source water solubility 6.84e-02 g/l ALOGPS logP 3.50 ALOGPS logP 3.84 ChemAxon Molconvert logS -3.48 ALOGPS pKa ChemAxon Molconvert hydrogen acceptor count 2 ChemAxon Molconvert hydrogen donor count 1 ChemAxon Molconvert polar surface area 37.30 ChemAxon Molconvert rotatable bond count 4 ChemAxon Molconvert refractivity 60.73 ChemAxon Molconvert polarizability 23.76 ChemAxon Molconvert

Drug	Interaction
Acebutolol	Risk of inhibition of renal prostaglandins
Acenocoumarol	The NSAID, ibuprofen, may increase the anticoagulant effect of acenocoumarol.
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.
Alendronate	Increased risk of gastric toxicity
Anisindione	The NSAID, ibuprofen, may increase the anticoagulant effect of anisindione.
Atenolol	Risk of inhibition of renal prostaglandins
Betaxolol	Risk of inhibition of renal prostaglandins
Bevantolol	Risk of inhibition of renal prostaglandins
Bisoprolol	Risk of inhibition of renal prostaglandins
Bumetanide	The NSAID, ibuprofen, may antagonize the diuretic and antihypertensive effects of the loop diuretic, bumetanide.
Carteolol	Risk of inhibition of renal prostaglandins
Carvedilol	Risk of inhibition of renal prostaglandins
Cyclosporine	Monitor for nephrotoxicity
Dicumarol	The NSAID, ibuprofen, may increase the anticoagulant effect of dicumarol.
Esmolol	Risk of inhibition of renal prostaglandins
Ethacrynic acid	The NSAID, ibuprofen, may antagonize the diuretic and antihypertensive effects of the loop diuretic, ethacrynic acid.
Furosemide	The NSAID, ibuprofen, may antagonize the diuretic and antihypertensive effects of the loop diuretic, furosemide.
Ginkgo biloba	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Labetalol	Risk of inhibition of renal prostaglandins
Lithium	The NSAID, ibuprofen, may decrease the renal excretion of lithium. Increased risk of lithium toxicity.
Methotrexate	The NSAID, ibuprofen, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
Metoprolol	Risk of inhibition of renal prostaglandins
Nadolol	Risk of inhibition of renal prostaglandins
Oxprenolol	Risk of inhibition of renal prostaglandins
Penbutolol	Risk of inhibition of renal prostaglandins
Pindolol	Risk of inhibition of renal prostaglandins
Practolol	Risk of inhibition of renal prostaglandins
Propranolol	Risk of inhibition of renal prostaglandins
Sotalol	Risk of inhibition of renal prostaglandins
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.
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.
Torasemide	The NSAID, ibuprofen, may decrease the diuretic and antihypertensive effect of the loop diuretic, torasemide.
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.
Treprostinil	The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Ibuprofen. Monitor for increased bleeding during concomitant thearpy.
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.
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.
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.

• Avoid alcohol.
• 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.
• Take with food to reduce gastric irritation.