Ibuprofen

• Catalog No.: DB01050
• CAS Number: 15687-27-1
• M. F.: C13H18O2
• M. W.: 206.28082

SYNONYMS

• IUPAC name: 2-[4-(2-methylpropyl)phenyl]propanoic acid
• IUPAC Traditional name: ibuprofen
• Brand Name: Ibuprin; Inabrin; Midol 200; Mynosedin; Roidenin; Amersol; Apo-Ibuprofen; Brufen; Dolocyl; Epobron; Ibutid; Junior Strength Advil; Lidifen; Liptan; Motrin; Nobfen; Pediaprofen; Adran; Advil; Advil Liqui-Gels; Anflagen; Artril 300; Brufanic; Children's Elixsure; Dolgirid; Dolo-Dolgit; Fenbid Spansule; Haltran; Ibu-Slo; Ibuprocin; Ifen; Napacetin; Paxofen; Pedia-Profen; Pediatric Advil; Rebugen; Seclodin; Trendar; Actiprofen; Amibufen; Anco; Andran; Apsifen; Apsifen-F; Bluton; Brufort; Buburone; Butylenin; Cap-Profen; Children's Advil; Children's Ibuprofen; Children's Motrin; Codral; Dolgin; Dolgit; Ebufac; Femadon; Ibu; Ibu-Attritin; Ibu-Tab; Ibu-Tab 200; Ibufen; Ibumetin; Ibuprohm; Inoven; Junior Strength Ibuprofen; Junior Strength Motrin; Lamidon; Lebrufen; Medipren; Midol; Nobfelon; Nobgen; Novogent N; Novoprofen; Nuprin; Nurofen; Pantrop; Rafen; Suspren; Tab-Profen; Tabalon; Urem; NeoProfen; Profen; Rufen
• Synonyms: P-Isobutylhydratropic Acid; Ibuprophen; Para-Isobutylhydratropic Acid

DATABASE IDS

• CAS Number: 15687-27-1
• PubChem SID: 46507255
• PubChem CID: 3672

PROPERTIES

• Hydrophobicity(logP): 3.6
• Solubility: 0.049 mg/ml

DETAILS

Description (English)

• 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

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