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QuickView for Lumiracoxib (compound)


PubChem
Name: lumiracoxib
PubChem Compound ID: 151166
Molecular formula: C15H13ClFNO2
Molecular weight: 293.72 g/mol
Synonyms:
Prexige; COX189; 2-((2-Chloro-6-fluorophenyl)amino)-5-methylbenzeneacetic acid; Benzeneacetic acid, 2-((2-chloro-6-fluorophenyl)amino)-5-methyl-; Lumiracoxib (USAN); D03714; 220991-20-8; Lumiracoxib; COX 189; COX-189.
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DrugBank
Identification
Name: lumiracoxib
Name (isomeric): DB01283
Drug Type: small molecule
Synonyms:
COX 189
Brand: Prexige, Prexige (Novartis)
Category: Cyclooxygenase Inhibitors, Cyclooxygenase 2 Inhibitors
CAS number: 220991-20-8
Pharmacology
Indication: For the acute and chronic treatment of the signs and symptoms of osteoarthritis of the knee in adults.
Pharmacology:
Lumiracoxib has a different structure from the standard COX-2 inhibitors (e.g. celecoxib). It more closely resembles the structure of diclofenac (one chlorine substituted by fluorine, the phenylacetic acid has another methyl group in meta position), making it a member of the arylalkanoic acid family of NSAIDs. It binds to a different site on the CO...
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Mechanism of Action: The mechanism of action of lumiracoxib is due to inhibition of prostaglandin synthesis via inhibition of cyclooygenase-2 (COX-2). Lumiracoxib does not inhibit COX-1 at therapeutic concentrations.
Absorption: Rapidly absorbed following oral administration, with an absolute oral bioavailablity of 74%.
Protein binding: Highly bound to plasma proteins (>= 98%).
Biotransformation: Hepatic oxidation and hydroxylation via CYP2C9. Three major metabolites have been identified in plasma: 4'-hydroxy-lumiracoxib, 5-carboxy-lumiracoxib, and 4'-hydroxy-5-carboxy-lumiracoxib.
Half Life: Terminal half-life is approximately 4 hours.
Toxicity: Single oral doses in mice and rats resulted in mortality and/or moribundity at doses of 600 mg/kg and 500 mg/kg, respectively. Single intraperitoneal doses in mice and rats results in mortality/moribundity at 750 mg/kg and 1000 mg/kg, respectively. The maximum non-lethal single oral and intraperitoneal dose in mouse was 300 mg/kg and 250 mg/kg, respectively. In the rat it was 150 mg/kg and 250 mg/kg, respectively.
Affected organisms: Humans and other mammals
Interactions
Food interaction:
Take with or without food. Food has no effect on the absorption of the product.
Drug interaction:
DicumarolLumiracoxib may increase the anticoagulant effect of dicumarol.
AnisindioneLumiracoxib may increase the anticoagulant effect of anisindione.
TolbutamideTolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Lumiracoxib. Consider alternate therapy or monitor for changes in Lumiracoxib therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
WarfarinLumiracoxib may increase the anticoagulant effect of warfarin.
TreprostinilThe prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Lumiracoxib. Monitor for increased bleeding during concomitant thearpy.
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