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Namespace Prefixes

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Statements

Subject Item
n2:DB00712
rdf:type
n3:Drug
n3:description
Flurbiprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with antipyretic and analgesic activity. Oral formulations of flurbiprofen may be used for the symptomatic treatment of rheumatoid arthritis, osteoarthritis and anklylosing spondylitis. Flurbiprofen may also be used topically prior to ocular surgery to prevent or reduce intraoperative miosis. Flurbiprofen is structurally and pharmacologically related to fenoprofen, ibuprofen, and ketoprofen.
n3:dosage
n33:271B4B65-363D-11E5-9242-09173F13E4C5 n33:271B4B66-363D-11E5-9242-09173F13E4C5 n33:271B4B67-363D-11E5-9242-09173F13E4C5 n33:271B4B68-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Geerts H: Drug evaluation: (R)-flurbiprofen--an enantiomer of flurbiprofen for the treatment of Alzheimer's disease. IDrugs. 2007 Feb;10(2):121-33. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17285465 # Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19515014 # Calapai G, Imbesi S, Cafeo V, Ventura Spagnolo E, Minciullo PL, Caputi AP, Gangemi S, Milone L: Fatal hypersensitivity reaction to an oral spray of flurbiprofen: a case report. J Clin Pharm Ther. 2013 Aug;38(4):337-8. doi: 10.1111/jcpt.12073. Epub 2013 May 13. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/23668805 # Mironov GG, Logie J, Okhonin V, Renaud JB, Mayer PM, Berezovski MV: Comparative study of three methods for affinity measurements: capillary electrophoresis coupled with UV detection and mass spectrometry, and direct infusion mass spectrometry. J Am Soc Mass Spectrom. 2012 Jul;23(7):1232-40. doi: 10.1007/s13361-012-0386-y. Epub 2012 Apr 28. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/22544663
n3:group
investigational approved
n3:halfLife
R-flurbiprofen, 4.7 hours; S-flurbiprofen, 5.7 hours
n3:indication
Flurbiprofen tablets are indicated for the acute or long-term symptomatic treatment of rheumatoid arthritis, osteorarthritis and anklosing spondylitis. It may also be used to treat pain associated with dysmenorrhea and mild to moderate pain accompanied by inflammation (e.g. bursitis, tendonitis, soft tissue trauma). Topical ophthalmic formulations may be used pre-operatively to prevent intraoperative miosis.
n3:manufacturer
n11:271B4B54-363D-11E5-9242-09173F13E4C5 n11:271B4B4C-363D-11E5-9242-09173F13E4C5 n11:271B4B4D-363D-11E5-9242-09173F13E4C5 n11:271B4B50-363D-11E5-9242-09173F13E4C5 n11:271B4B51-363D-11E5-9242-09173F13E4C5 n11:271B4B4E-363D-11E5-9242-09173F13E4C5 n11:271B4B4F-363D-11E5-9242-09173F13E4C5 n11:271B4B55-363D-11E5-9242-09173F13E4C5 n11:271B4B52-363D-11E5-9242-09173F13E4C5 n11:271B4B53-363D-11E5-9242-09173F13E4C5
owl:sameAs
n27:DB00712 n31:DB00712
dcterms:title
Flurbiprofen
adms:identifier
n16:3277 n17:DB00712 n18:5130 n19:4194 n20:D00330 n21:4194 n22:PA449683 n23:3394 n25:46505550 n28:Flurbiprofen n29:16590-096-30
n3:mechanismOfAction
Similar to other NSAIAs, the anti-inflammatory effect of flurbiprofen occurs via reversible inhibition of cyclooxygenase (COX), the enzyme responsible for the conversion of arachidonic acid to prostaglandin G2 (PGG2) and PGG2 to prostaglandin H2 (PGH2) in the prostaglandin synthesis pathway. This effectively decreases the concentration of prostaglandins involved in inflammation, pain, swelling and fever. Flurbiprofen is a non-selective COX inhibitor and inhibits the activity of both COX-1 and -2. It is also one of the most potent NSAIAs in terms of prostaglandin inhibitory activity.
n3:packager
n11:271B4B4A-363D-11E5-9242-09173F13E4C5 n11:271B4B4B-363D-11E5-9242-09173F13E4C5 n11:271B4B37-363D-11E5-9242-09173F13E4C5 n11:271B4B36-363D-11E5-9242-09173F13E4C5 n11:271B4B3B-363D-11E5-9242-09173F13E4C5 n11:271B4B3C-363D-11E5-9242-09173F13E4C5 n11:271B4B2E-363D-11E5-9242-09173F13E4C5 n11:271B4B39-363D-11E5-9242-09173F13E4C5 n11:271B4B3A-363D-11E5-9242-09173F13E4C5 n11:271B4B35-363D-11E5-9242-09173F13E4C5 n11:271B4B38-363D-11E5-9242-09173F13E4C5 n11:271B4B33-363D-11E5-9242-09173F13E4C5 n11:271B4B34-363D-11E5-9242-09173F13E4C5 n11:271B4B31-363D-11E5-9242-09173F13E4C5 n11:271B4B48-363D-11E5-9242-09173F13E4C5 n11:271B4B49-363D-11E5-9242-09173F13E4C5 n11:271B4B32-363D-11E5-9242-09173F13E4C5 n11:271B4B46-363D-11E5-9242-09173F13E4C5 n11:271B4B2F-363D-11E5-9242-09173F13E4C5 n11:271B4B47-363D-11E5-9242-09173F13E4C5 n11:271B4B30-363D-11E5-9242-09173F13E4C5 n11:271B4B44-363D-11E5-9242-09173F13E4C5 n11:271B4B45-363D-11E5-9242-09173F13E4C5 n11:271B4B42-363D-11E5-9242-09173F13E4C5 n11:271B4B43-363D-11E5-9242-09173F13E4C5 n11:271B4B40-363D-11E5-9242-09173F13E4C5 n11:271B4B41-363D-11E5-9242-09173F13E4C5 n11:271B4B3E-363D-11E5-9242-09173F13E4C5 n11:271B4B3F-363D-11E5-9242-09173F13E4C5 n11:271B4B3D-363D-11E5-9242-09173F13E4C5
n3:routeOfElimination
Flurbiprofen is poorly excreted into human milk. Following dosing with flurbiprofen, less than 3% of flurbiprofen is excreted unchanged in the urine, with about 70% of the dose eliminated in the urine as parent drug and metabolites. Renal elimination is a significant pathway of elimination of flurbiprofen metabolites.
n3:synonym
Flurbiprofenum 3-Fluoro-4-phenylhydratropic acid Flurbiprofen S-flurbiprofen 2-Fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetic acid Ansaid Flurbiprofeno 2-(2-Fluorobiphenyl-4-yl)propanoic acid Flurbiprofene FLP (+-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid
n3:toxicity
LD<sub>50</sub>=10 mg/kg (orally in dogs). <p>Selective COX-2 inhibitors have been associated with increased risk of serious cardiovascular events (e.g. myocardial infarction, stroke) in some patients. Current data is insufficient to assess the cardiovascular risk of flurbiprofen. Flurbiprofen may increase blood pressure and/or cause fluid retention and edema. Use caution in patients with fluid retention or heart failure. Risk of GI toxicity including bleeding, ulceration and perforation. Risk of direct renal injury, including renal papillary necrosis. Anaphylactoid and serious skin reactions (e.g. exfoliative dermatitis, Stevens-Johnson syndrome, toxic epidermal necrolysis) may occur. Common adverse events include abdominal pain, constipation, diarrhea, dyspepsia, flatulence, GI bleeding, GI perforation, nausea, peptic ulcer, vomiting, renal function abnormalities, anemia, dizziness, edema, liver function test abnormalities, headache, prolonged bleeding time, pruritus, rash, tinnitus. Although rarely documented in the case of flurbiprofen, oral propionic acid derivatives have been associated with a relatively high frequency of allergic reactions.</p>
n3:volumeOfDistribution
* 14 L [Normal Healthy Adults] * 12 L [Geriatric Arthritis Patients] * 10 L [End Stage Renal Disease Patients] * 14 L [Alcoholic Cirrhosis Patients] * 0.12 L/kg
n8:hasAHFSCode
n12:28-08-04-92 n12:52-08-20
n3:foodInteraction
Take with food to reduce gastric irritation. Avoid alcohol.
n3:mixture
n5:271B4B2D-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
> 99% bound, primarily to albumin. Binds to a different primary binding site on albumin than anticoagulants, sulfonamides and phenytoin.
n3:salt
n3:synthesisReference
Yutaka Mizushima, Hiroyuki Okamoto, Shigetoshi Sugio, Kazumasa Yokoyama, Tadakazu Suyama, Masao Tohno, Makoto Okumura, Yoshiaki Konishi, Kiyonoshin Ichikawa, Katsuhiro Uchida, "Flurbiprofen derivative ophthalmic preparation." U.S. Patent US5171566, issued January, 1984.
n6:hasConcept
n7:M0008647
foaf:page
n14:flurbipro.htm n24:ans1023.shtml n32:flurbiprofen-drops.html
n3:IUPAC-Name
n4:271B4B6D-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B4B73-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B4B72-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B4B6F-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B4B70-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B4B71-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B4B6B-363D-11E5-9242-09173F13E4C5 n4:271B4B82-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B4B84-363D-11E5-9242-09173F13E4C5 n4:271B4B6C-363D-11E5-9242-09173F13E4C5 n4:271B4B69-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B4B85-363D-11E5-9242-09173F13E4C5 n4:271B4B6A-363D-11E5-9242-09173F13E4C5
n8:hasATCCode
n9:S01BC04 n9:R02AX01 n9:M02AA19 n9:M01AE09
n3:H-Bond-Acceptor-Count
n4:271B4B79-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B4B7A-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B4B74-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B4B75-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B4B77-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B4B76-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B4B78-363D-11E5-9242-09173F13E4C5
n3:absorption
Fluribiprofen is rapidly and almost completely absorbed following oral administration. Peak plasma concentrations are reached 0.5 - 4 hours after oral administration.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
5104-49-4
n3:category
n3:containedIn
n10:271B4B57-363D-11E5-9242-09173F13E4C5 n10:271B4B58-363D-11E5-9242-09173F13E4C5 n10:271B4B56-363D-11E5-9242-09173F13E4C5 n10:271B4B63-363D-11E5-9242-09173F13E4C5 n10:271B4B64-363D-11E5-9242-09173F13E4C5 n10:271B4B61-363D-11E5-9242-09173F13E4C5 n10:271B4B62-363D-11E5-9242-09173F13E4C5 n10:271B4B5F-363D-11E5-9242-09173F13E4C5 n10:271B4B60-363D-11E5-9242-09173F13E4C5 n10:271B4B5D-363D-11E5-9242-09173F13E4C5 n10:271B4B5E-363D-11E5-9242-09173F13E4C5 n10:271B4B5B-363D-11E5-9242-09173F13E4C5 n10:271B4B5C-363D-11E5-9242-09173F13E4C5 n10:271B4B59-363D-11E5-9242-09173F13E4C5 n10:271B4B5A-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B4B7E-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B4B80-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B4B81-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B4B83-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B4B7D-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B4B7C-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B4B7F-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B4B6E-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B4B7B-363D-11E5-9242-09173F13E4C5