CAS 15687-27-1|CAS 58560-75-1|Ibu-Tab 200|Tab-Profen|Ibuprin|Dolocyl|Nurofen|Lebrufen|Children's Advil|Fenbid Spansule|Pedia-Profen|Rafen|ibuprofen|Codral|Ibu|Paxofen|Lidifen|Napacetin|Ebufac|Trenda...

General Information

Structure

Molecular Formula

C₁₃H₁₈O₂

Molecular Mass

206.28082

Exact Mass

206.13067982

Charge

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

Canonic Smiles

CC(Cc1ccc(cc1)C(C(=O)O)C)C

Isomeric Smiles

OC(=O)C(c1ccc(CC(C)C)cc1)C

Calculated Properties

JChem

LogD (pH = 7.4)

1.34

LogD (pH = 5.5)

3.11

Log P

3.84

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

4.85

Polar Surface Area

37.30

Polarizability

23.82

Molar Refractivity

60.73

LOG S

-3.54

Data Source

Names and Identifiers

Brand Name

Ibu-Tab 200Tab-ProfenIbuprinDolocylNurofenLebrufenChildren's AdvilFenbid SpansulePedia-ProfenRafenCodralIbuPaxofenLidifenNapacetinEbufacTrendarCap-ProfenAdranRufenIbutidAdvilAmibufenSusprenIbuprocinPediaprofenNobgenJunior Strength MotrinBuburoneNovoprofenProfenIbufenMynosedinAnflagenMidol 200InovenButyleninChildren's MotrinBrufortIbuprohmDolgiridSeclodinDolo-DolgitFemadonBrufenBrufanicAndranApo-IbuprofenChildren's IbuprofenHaltranIbu-SloDolginEpobronIbu-AttritinTabalonUremAmersolPantropNobfelonLamidonBlutonArtril 300Pediatric AdvilRebugenIbu-TabRoideninMidolChildren's ElixsureMediprenNobfenDolgitApsifen-FNuprinLiptanMotrinAncoIfenJunior Strength IbuprofenIbumetinNeoProfenInabrinJunior Strength AdvilActiprofenAdvil Liqui-GelsApsifenNovogent N

IUPAC Traditional name

ibuprofen 2-[4-(2-methylpropyl)phenyl]propanoic acid ibuprofen, (+-)-

Synonyms

P-Isobutylhydratropic AcidPara-Isobutylhydratropic AcidIbuprophenIbuprofen2-(4-Isobutylphenyl)propanoic acidIBUPROFEN USP GRADEα-Methyl-4-[2-methylpropyl] benzeneacetic AcidIbupIbrenBrufenMotrinGenprilNurofen(±)-2-(4-Isobutylphenyl)propanoic acidα-甲基-4-(异丁基)苯乙酸Ibuprofen布洛芬α-Methyl-4-(isobutyl)phenylacetic acid(±)-2-(4-异丁基苯基)丙酸2-(4-Isobutylphenyl)propionic Acidrac Ibuprofen2-[4-(2-methylpropyl)phenyl]propanoic acidLidifenCodafenPaxofenFemafen; ProflexLobufenApsifenEbufac4-异丁基-α-甲基苯基乙酸Ibuprofen4-Isobutyl-alpha-methylphenylacetic acid(+-)-p-isobutylhydratropic acid2-(4-isobutylphenyl)propanoic acid(+-)-alpha-methyl-4-(2-methylpropyl)benzeneacetic acid(4-isobutylphenyl)-alpha-methylacetic acidMotrinalpha-(4-isobutylphenyl)propionic acidalpha-(p-isobutylphenyl)propionic acid(RS)-ibuprofenIbuprofen(+-)-ibuprofen4-isobutylhydratropic acid(+-)-2-(p-isobutylphenyl)propionic acidibuprofen

IUPAC name

2-[4-(2-methylpropyl)phenyl]propanoic acid

API Name

Ibuprofen

Names and Identifiers

Registration numbers

CAS Number

15687-27-158560-75-1

PubChem SID

4650725516096438524277715248961308147017

EC Number

239-784-6

PubChem CID

3672

Registration numbers

Properties

Safety Information

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Pharmacology Properties

human ... ALB(213), ALOX5(240), CYP1A2(1544), CYP2C9(1559), IL8RA(3577), PTGS1(5742), PTGS2(5743)mouse ... Alox5(11689)rat ... Alox5(25290), Ptgs1(24693)

Cyclooxygenase (COX) inhibitor

Prostaglandin antagonist

Properties

Related Proteins

Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB01050

Drug Groups

approved

Description

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

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.

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

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.

Absorption

~ 80% absorbed from GI tract

Time to reach peak plasma concentration = 47 minutes (suspension), 62 minutes (chewable tablets), 120 minutes (conventional tablets)

Half Life

2-4 hours

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.

Elimination

Ibuprofen is rapidly metabolized and eliminated in the urine.

References

• 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]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Molecule Details

References

PubChem Literature

From Data Sources

• Zawada ET Jr: Renal consequences of nonsteroidal antiinflammatory drugs. Postgrad Med. 1982 May;71(5):223-30. Pubmed

• Bergner T, Przybilla B: Photosensitization caused by ibuprofen. J Am Acad Dermatol. 1992 Jan;26(1):114-6. 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

• Noreen Y, et al. J Nat Prod, 1998, 61(1), 2-7.

• Driban JB, et al. J Biomed Biotechnol, 2011, 2011, 691412-691428.

• Palayoor ST, et al. Oncogene, 1999, 18(51), 7389-7394.

• Khwaja F, et al. Cancer Res, 2004, 64(17), 6207-6213.

• Rao GH, et al. Arteriosclerosis, 1983, 3(4), 383-388.

• Davies, N.M., et al.: Clin. Pharmacokinet., 34, 101 (1986)

• Busson, M., et al.: J. Int. Med Res., 14, 53 (1986)

• Meade, E.A., et al.: J. Biol. Chem., 268, 6610 (1986)

• Hiyama, T. et al., Synthesis, 1986, 645, (synth)

• Kaiser, D.G. et al., J. Pharm. Sci., 1976, 65, 269, (resoln, glc, bibl)

• Nicoll-Griffith, D.A., J. Chromatogr., 1987, 402, 179, (resoln)

• Eur. Pat., 1988, Gist-Brocades; Shell Int. Res., 274 146; CA, 110, 113203, (dexibuprofen lysine)

• Shankland, N. et al., Acta Cryst. C, 1997, 53, 951-954, (cryst struct)

• McConnell, J.F., Cryst. Struct. Commun., 1974, 3, 73, (cryst struct)

• Davies, N.M. et al., Clin. Pharmacokinet., 1998, 34, 101-154, (rev)

• U.K. Pat., 1964, 971 700; CA, 61, 14591, (synth, pharmacol)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1011B, (nmr)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 2867, (synonyms)

• Gonzalez, A., Synth. Commun., 1991, 21, 1353, (synth)

• Nicholson, J.S., Chron. Drug Discovery, 1982, 1, 149, (rev)

• Freer, A.A., Acta Cryst. C, 1993, 49, 1378, (cryst struct)

• Lalonde, J.J. et al., J.A.C.S., 1995, 117, 6845, (resoln)

• Higgins, J.D. et al., Anal. Profiles Drug Subst., 2001, 27, 265-300, (rev)

• Ghislandi, V. et al., Farmaco, Ed. Sci., 1982, 37, 81, (abs config)

• Gruber, K. et al., Arzneim.-Forsch., 1983, 33, 1176, (pharmacol, tox)

• Sonawane, H.R. et al., Tetrahedron, 1994, 50, 1243, (synth)

• Adams, S.S. et al., Arch. Int. Pharmacodyn. Ther., 1969, 178, 115

• Adams, S.S. et al., Toxicol. Appl. Pharmacol., 1969, 15, 310, (metab, tox)

• Ger. Pat., 1975, 2 508 895; CA, 84, 5394, (lysine, salt)

• Yamauchi, T. et al., Synthesis, 1986, 1044, (synth)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 50

• Shiori, T. et al., J.O.C., 1978, 43, 2936, (synth)

• Wolber, E.K.A. et al., Chem. Ber., 1991, 124, 1667, (synth, pmr)

References

Bioactivity

PubChem BioAssay

Bioactivity