Lumiracoxib

Lumiracoxib
Clinical data
Trade names	Prexige
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: C;
Routes of; administration	Oral
ATC code	M01AH06 (WHO) ;
Legal status
Legal status	Rx-only, withdrawn (Australia, New Zealand, Canada, UK, Germany, Austria, Belgium, Cyprus, Brazil);
Pharmacokinetic data
Bioavailability	74-90%
Protein binding	>98%
Metabolism	Predominantly in the liver via oxidation and hydroxylation (CYP2C9)
Elimination half-life	5-8 hours
Excretion	Urine (54%) and faeces (43%)
Identifiers
	IUPAC name {2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid;
CAS Number	220991-20-8 ;
PubChem CID	151166;
IUPHAR/BPS	2897;
DrugBank	DB01283 ;
ChemSpider	133236 ;
UNII	V91T9204HU;
KEGG	D03714 ;
ChEBI	CHEBI:73044 ;
ChEMBL	ChEMBL404108 ;
PDB ligand	LUR (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID9049035 ;
Chemical and physical data
Formula	C15H13ClFNO2
Molar mass	293.72 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc2cccc(F)c2Nc1ccc(cc1CC(=O)O)C;
	InChI InChI=1S/C15H13ClFNO2/c1-9-5-6-13(10(7-9)8-14(19)20)18-15-11(16)3-2-4-12(15)17/h2-7,18H,8H2,1H3,(H,19,20) ; Key:KHPKQFYUPIUARC-UHFFFAOYSA-N ;
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Lumiracoxib is a COX-2 selective inhibitor nonsteroidal anti-inflammatory drug.

Its structure is different from that of other COX-2 inhibitors, such as celecoxib: lumiracoxib is an analogue 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 class of NSAIDs; it binds to a different site on the COX-2 enzyme than do other COX-2 inhibitors; it is the only acidic coxib and has the highest COX-2 selectivity of any NSAID.

It was patented in 1997 and approved for medical use in 2003. It was manufactured by Novartis and is still sold in few countries, including Mexico, Ecuador and the Dominican Republic, under the trade name Prexige. Lumiracoxib has been withdrawn from the market in several countries, mostly due to its potential for causing liver failure (sometimes requiring liver transplantation). It has never been approved for use in the United States.