Home > Compound List > Product Information
Click picture or here to close


Catalog No. DB01283 Name DrugBank
CAS Number 220991-20-8 Website http://www.ualberta.ca/
M. F. C15H13ClFNO2 Telephone (780) 492-3111
M. W. 293.7206232 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 1141


IUPAC name
2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid
IUPAC Traditional name
Brand Name
Prexige (Novartis)
COX 189


CAS Number 220991-20-8
PubChem CID 151166
PubChem SID 46506378


Hydrophobicity(logP) 3.9


Description (English)
Item Information
Drug Groups approved; investigational
Description Lumiracoxib is a COX-2 selective inhibitor non-steroidal anti-inflammatory drug. On August 11, 2007, Australia's Therapeutic Goods Administration (TGA, the Australian equivalent of the FDA) cancelled the registration of lumiracoxib in Australia due to concerns that it may cause liver failure. New Zealand and Canada have also followed suit in recalling the drug.
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 COX-2 receptor than the standard COX-2 inhibitors. It displays extremely high COX-2 selectivity.
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
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.
Absorption Rapidly absorbed following oral administration, with an absolute oral bioavailablity of 74%.
Half Life Terminal half-life is approximately 4 hours.
Protein Binding Highly bound to plasma proteins (>= 98%).
External Links