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Statements

Subject Item
n2:DB01050
rdf:type
n3:Drug
n3:description
Ibuprofen, a propionic acid derivative, is a prototypical nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties.
n3:dosage
n26:271B5B04-363D-11E5-9242-09173F13E4C5 n26:271B5B05-363D-11E5-9242-09173F13E4C5 n26:271B5B06-363D-11E5-9242-09173F13E4C5 n26:271B5B0F-363D-11E5-9242-09173F13E4C5 n26:271B5B10-363D-11E5-9242-09173F13E4C5 n26:271B5B11-363D-11E5-9242-09173F13E4C5 n26:271B5B12-363D-11E5-9242-09173F13E4C5 n26:271B5B13-363D-11E5-9242-09173F13E4C5 n26:271B5B14-363D-11E5-9242-09173F13E4C5 n26:271B5B15-363D-11E5-9242-09173F13E4C5 n26:271B5B16-363D-11E5-9242-09173F13E4C5 n26:271B5B07-363D-11E5-9242-09173F13E4C5 n26:271B5B08-363D-11E5-9242-09173F13E4C5 n26:271B5B09-363D-11E5-9242-09173F13E4C5 n26:271B5B0A-363D-11E5-9242-09173F13E4C5 n26:271B5B0B-363D-11E5-9242-09173F13E4C5 n26:271B5B0C-363D-11E5-9242-09173F13E4C5 n26:271B5B0D-363D-11E5-9242-09173F13E4C5 n26:271B5B0E-363D-11E5-9242-09173F13E4C5 n26:271B5B1F-363D-11E5-9242-09173F13E4C5 n26:271B5B20-363D-11E5-9242-09173F13E4C5 n26:271B5B21-363D-11E5-9242-09173F13E4C5 n26:271B5B22-363D-11E5-9242-09173F13E4C5 n26:271B5B23-363D-11E5-9242-09173F13E4C5 n26:271B5B24-363D-11E5-9242-09173F13E4C5 n26:271B5B25-363D-11E5-9242-09173F13E4C5 n26:271B5B17-363D-11E5-9242-09173F13E4C5 n26:271B5B18-363D-11E5-9242-09173F13E4C5 n26:271B5B19-363D-11E5-9242-09173F13E4C5 n26:271B5B1A-363D-11E5-9242-09173F13E4C5 n26:271B5B1B-363D-11E5-9242-09173F13E4C5 n26:271B5B1C-363D-11E5-9242-09173F13E4C5 n26:271B5B1D-363D-11E5-9242-09173F13E4C5 n26:271B5B1E-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Zawada ET Jr: Renal consequences of nonsteroidal antiinflammatory drugs. Postgrad Med. 1982 May;71(5):223-30. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/7041104 # 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":http://www.ncbi.nlm.nih.gov/pubmed/16195368 # 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":http://www.ncbi.nlm.nih.gov/pubmed/16240369 # 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":http://www.ncbi.nlm.nih.gov/pubmed/2777420 # Bergner T, Przybilla B: Photosensitization caused by ibuprofen. J Am Acad Dermatol. 1992 Jan;26(1):114-6. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/1531054 # Dill J, Patel AR, Yang XL, Bachoo R, Powell CM, Li S: A molecular mechanism for ibuprofen-mediated RhoA inhibition in neurons. J Neurosci. 2010 Jan 20;30(3):963-72. doi: 10.1523/JNEUROSCI.5045-09.2010. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/20089905
n3:group
approved
n3:halfLife
2-4 hours
n3: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.
owl:sameAs
n11:DB01050 n17:DB01050
dcterms:title
Ibuprofen
adms:identifier
n13:Ibuprofen n22:DB01050 n23:5855 n24:3544 n27:46507255 n28:PA449957 n29:3672 n30:0182-8688-89 n31:IBP n32:C01588 n33:D00126 n34:2713 n35:2713
n3:mechanismOfAction
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 <i>in vivo</i>. The S-enantiomer is believed to be the more pharmacologically active enantiomer.
n3:packager
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n3:patent
n18:6727286 n18:5215755
n3:routeOfElimination
Ibuprofen is rapidly metabolized and eliminated in the urine.
n3:synonym
Nuprin Mynosedin Trendar Motrin Suspren Brufen Nobgen Rufen Ibu-attritin Pediaprofen Dolgit Medipren (+-)-P-Isobutylhydratropic acid (4-Isobutylphenyl)-alpha-methylacetic acid Ibutid Advil Para-Isobutylhydratropic Acid Dolo-dolgit Liptan Apsifen Ebufac Nurofen Haltran 2-(4-Isobutylphenyl)propanoic acid Brufort (RS)-ibuprofen Nobfen alpha-(P-Isobutylphenyl)propionic acid (+-)-Ibuprofen Dolgirid Amibufen Ibuprocin Tabalon P-Isobutylhydratropic Acid Butylenin Anflagen Lamidon Bluton Dolgin Ibuprofen Roidenin Inabrin alpha-(4-Isobutylphenyl)propionic acid Ibuprophen Ibumetin Lebrufen Buburone Anco Epobron Urem 4-Isobutylhydratropic acid Femadon Seclodin Inoven (+-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid (+-)-2-(P-Isobutylphenyl)propionic acid Adran
n3:toxicity
<p>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. <p>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).</p> <p>LD<sub>50</sub>=1255mg/kg(orally in mice)</p>
n8:hasAHFSCode
n25:28-08-04-92
n3:foodInteraction
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. Avoid alcohol
n3:mixture
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n3:proteinBinding
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.
n3:synthesisReference
http://en.wikipedia.org/wiki/Ibuprofen#Synthesis
n19:hasConcept
n20:M0010965
foaf:page
n5:ibuprofen.html n16:ibup.htm
n3:IUPAC-Name
n7:271B5B2A-363D-11E5-9242-09173F13E4C5
n3:InChI
n7:271B5B30-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n7:271B5B2F-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n7:271B5B2C-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n7:271B5B2D-363D-11E5-9242-09173F13E4C5
n3:SMILES
n7:271B5B2E-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n7:271B5B3F-363D-11E5-9242-09173F13E4C5 n7:271B5B28-363D-11E5-9242-09173F13E4C5
n3:logP
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n3:logS
n7:271B5B42-363D-11E5-9242-09173F13E4C5 n7:271B5B27-363D-11E5-9242-09173F13E4C5
n3:pKa
n7:271B5B44-363D-11E5-9242-09173F13E4C5
n8:hasATCCode
n9:M01AE01 n9:M02AA13 n9:C01EB16 n9:G02CC01
n3:H-Bond-Acceptor-Count
n7:271B5B36-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n7:271B5B37-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n7:271B5B31-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n7:271B5B32-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n7:271B5B34-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n7:271B5B33-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n7:271B5B35-363D-11E5-9242-09173F13E4C5
n3:absorption
~ 80% absorbed from GI tract <p>Time to reach peak plasma concentration = 47 minutes (suspension), 62 minutes (chewable tablets), 120 minutes (conventional tablets)</p>
n3:affectedOrganism
Humans and other mammals
n3:caco2-Permeability
n7:271B5B43-363D-11E5-9242-09173F13E4C5
n3:casRegistryNumber
15687-27-1
n3:category
n3:containedIn
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n3:Bioavailability
n7:271B5B3B-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n7:271B5B3D-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n7:271B5B3E-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n7:271B5B40-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n7:271B5B3A-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n7:271B5B39-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n7:271B5B3C-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n7:271B5B2B-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n7:271B5B38-363D-11E5-9242-09173F13E4C5