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QuickView for Flurbiprofen (compound)

Summary
General Info

PubChem

PubChem Compound 3394

PubChem Compound 3394

Name:	Flurbiprofen
PubChem Compound ID:	3394
Description:	An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.
Molecular formula:	C₁₅H₁₃FO₂
Molecular weight:	244.261 g/mol
Synonyms:	R-Flurbiprofen; DivK1c_000804; MLS000028441; Spectrum3_000435; Flurbiprofene [INN-French]; FP 70; NSC685699; Spectrum4_000558; Ocufen; Yakuban. show more » R-Flurbiprofen; DivK1c_000804; MLS000028441; Spectrum3_000435; Flurbiprofene [INN-French]; FP 70; NSC685699; Spectrum4_000558; Ocufen; Yakuban; CCRIS 3708; Anmetarin; Flurofen; Ansaid; U-27182; BTS 18322; 3-Fluoro-4-phenylhydratropic acid; [1,1'-Biphenyl]-4-acetic acid, 2-fluoro-.alpha.-methyl-; SPBio_002983; Flurbiprofen; EINECS 257-262-6; Spectrum_001096; EINECS 225-827-6; Cebutid; CHEBI:5130; Prestwick1_000917; MLS000040873; Flurbiprofen [USAN:BAN:INN:JAN]; KBio2_001576; Flugalin; KBioGR_001255; KBio3_001270; KBioSS_001576; Froben; S-Flurbiprofen; 5104-49-4; D00330; Spectrum2_001025; NCI60_030812; KBio2_006712; NINDS_000804; MKS-11; U 27,182; Flurbiprofenum [INN-Latin]; BTS-18322; (+-)-2-(2-Fluoro-4-biphenylyl)propionic acid; (1,1'-Biphenyl)-4-acetic acid, 2-fluoro-alpha-methyl-, (+-)-; Ansaid (TN); 51543-38-5; KBio1_000804; Flurbiprofen (JP15/USP); 4-Biphenylacetic acid, 2-fluoro-alpha-methyl-; NSC685700; 2-(2-fluoro-[1,1'-biphenyl-4-yl])propanoic acid; 2-Fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetic acid; (1)-2-Fluoro-alpha-methyl(1,1'-biphenyl)-4-acetic acid; Prestwick0_000917; Ocuflur; Flurbiprofeno [INN-Spanish]; SPBio_001209; KBio2_004144; (+-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid; Antadys; SMR000042823 show less «

DrugBank

Identification

Name:	Flurbiprofen
Name (isomeric):	DB00712
Drug Type:	small molecule
Description:	An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.
Synonyms:	Flurbiprofenum [INN-Latin]; Flurbiprofeno [INN-Spanish]; FLP; Flurbiprofen Sodium; Flurbiprofene [INN-French]
Brand:	Zepolas, Novo-Flurprofen, Froben Sr, Cebutid, Froben, Flurbiprofen Axetil, Ansaid, Adfeed, Ocufen, Flurofen, Apo-Flurbiprofen, Antadys, Nu-Flurbiprofen, Stayban
Category:	Analgesics, Non-Narcotic, Antipyretics, Cyclooxygenase Inhibitors, Analgesics, Anti-inflammatory Agents, Nonsteroidal Anti-inflammatory Agents (NSAIAs)
CAS number:	5104-49-4

Pharmacology

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.
Pharmacology:	Flurbiprofen, a nonsteroidal anti-inflammatory agent (NSAIA) of the propionic acid class, is structually and pharmacologically related to fenoprofen, ibuprofen, and ketoprofen, and has similar pharmacological actions to other prototypica NSAIAs. Flurbiprofen exhibits antiinflammatory, analgesic, and antipyretic activities. The commercially availabl... show more » Flurbiprofen, a nonsteroidal anti-inflammatory agent (NSAIA) of the propionic acid class, is structually and pharmacologically related to fenoprofen, ibuprofen, and ketoprofen, and has similar pharmacological actions to other prototypica NSAIAs. Flurbiprofen exhibits antiinflammatory, analgesic, and antipyretic activities. The commercially available flurbiprofen is a racemic mixture of (+)S- and (-) R-enantiomers. The S-enantiomer appears to possess most of the anti-inflammatory, while both enantiomers may possess analgesic activity. show less «
Mechanism of Action:	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 prostagla... show more » 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. show less «
Absorption:	Fluribiprofen is rapidly and almost completely absorbed following oral administration. Peak plasma concentrations are reached 0.5 - 4 hours after oral administration.
Protein binding:	> 99% bound, primarily to albumin. Binds to a different primary binding site on albumin than anticoagulants, sulfonamides and phenytoin.
Biotransformation:	Hepatic. Cytochrome P450 2C9 plays an important role in the metabolism of flurbiprofen to its major metabolite, 4’-hydroxy-flurbiprofen. The 4’-hydroxy-flurbiprofen metabolite showed little anti-inflammatory activity in animal models of inflammation.
Route of elimination:	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.
Half Life:	R-flurbiprofen, 4.7 hours; S-flurbiprofen, 5.7 hours
Toxicity:	LD₅₀=10 mg/kg (orally in dogs). 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.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Avoid alcohol.

Take with food to reduce gastric irritation.

Drug interaction:

Trimethoprim	The strong CYP2C9 inhibitor, Flurbiprofen, 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 Flurbiprofen is initiated, discontinued or dose changed.
Anisindione	The NSAID, flurbiprofen, may increase the anticoagulant effect anisindione.
Acenocoumarol	The NSAID, flurbiprofen, may increase the anticoagulant effect of acenocoumarol.
Dicumarol	The NSAID, flurbiprofen, may increase the anticoagulant effect of dicumarol.
Tamoxifen	Flurbiprofen may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Flurbiprofen is initiated, discontinued or dose changed.

Trimethoprim	The strong CYP2C9 inhibitor, Flurbiprofen, 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 Flurbiprofen is initiated, discontinued or dose changed.
Anisindione	The NSAID, flurbiprofen, may increase the anticoagulant effect anisindione.
Acenocoumarol	The NSAID, flurbiprofen, may increase the anticoagulant effect of acenocoumarol.
Dicumarol	The NSAID, flurbiprofen, may increase the anticoagulant effect of dicumarol.
Tamoxifen	Flurbiprofen may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Flurbiprofen is initiated, discontinued or dose changed.
Methotrexate	The NSAID, flurbiprofen, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
Tolbutamide	Flurbiprofen, 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 Flurbiprofen is initiated, discontinued or dose changed.
Timolol	The NSAID, Flurbiprofen, may antagonize the antihypertensive effect of Timolol.
Voriconazole	Flurbiprofen, 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 flurbiprofen is initiated, discontinued or dose changed.
Colesevelam	Bile acid sequestrants may decrease the absorption of Nonsteroidal Anti-Inflammatory Agents. Monitor for decreased serum concentrations/therapeutic effects of nonsteroidal anti-inflammatory agents (NSAID) if coadministered with bile acid sequestrants. Separating the administration of doses by 2 or more hours may reduce (but not eliminate) the risk of interaction. The manufacturer of colesevelam recommends that drugs should be administered at least 1 hour before or 4 hours after colesevelam.
Ginkgo biloba	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Trandolapril	The NSAID, Flurbiprofen, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Flurbiprofen is initiated, discontinued or dose changed.
Alendronate	Increased risk of gastric toxicity
Torasemide	Flurbiprofen, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing Torasemide metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Flurbiprofen is initiated, discontinued or dose changed.
Telmisartan	Concomitant use of Telmisartan and Flurbiprofen may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Warfarin	Flurbiprofen, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. The antiplatelet effect of flurbiprofen 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 flurbiprofen is initiated, discontinued or dose changed.
Cyclosporine	Monitor for nephrotoxicity
Treprostinil	The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Flurbiprofen. Monitor for increased bleeding during concomitant thearpy.

Targets

Prostaglandin G/H synthase 1

Prostaglandin G/H synthase 2

Enzymes

Cytochrome P450 2C9

UDP-glucuronosyltransferase 2B7

UDP-glucuronosyltransferase 1-1

UDP-glucuronosyltransferase 1-3

UDP-glucuronosyltransferase 1-9

UDP-glucuronosyltransferase 2B4

Transporters

Multidrug resistance-associated protein 4

Solute carrier family 22 member 6

Carriers