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Legal status	℞-only, withdrawn (Australia, New Zealand, Canada, UK, Germany, Austria, Belgium, Cyprus, Brazil)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)
Biological 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 N
PubChem CID	151166
IUPHAR/BPS	2897
DrugBank	DB01283 N
ChemSpider	133236 Y
UNII	V91T9204HU
KEGG	D03714 Y
ChEBI	CHEBI:73044 N
ChEMBL	CHEMBL404108 Y
PDB ligand	LUR (PDBe, RCSB PDB)
Chemical and physical data
Formula	C15H13ClFNO2
Molar mass	293,72 g/mol
3D model (Jmol)	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) Y Key:KHPKQFYUPIUARC-UHFFFAOYSA-N Y
NY (what is this?)

Lumiracoxib (rINN) is a carboxylic acid COX-2 selective inhibitor non-steroidal anti-inflammatory drug, manufactured by Novartis and still sold in few countries, including Mexico, Ecuador and the Dominican Republic, under the trade name Prexige (sometimes misquoted as "Prestige" by the media).

Lumiracoxib has several distinctive features. 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.

Since its original approval, lumiracoxib has been withdrawn from the market in several countries, mostly due to its potential for causing liver failure (sometimes requiring liver transplantation).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.

The TARGET study (Therapeutic Arthritis Research and Gastrointestinal Event Trial) was conducted with more than 18,000 patients to test its gastrointestinal and cardiovascular safety against naproxen and ibuprofen and also study its efficacy against these two NSAIDs.

In November 2006, Prexige received marketing approval for all European Union countries through a common procedure called MRP. However, in August 2007, Prexige was withdrawn from the market in Australia following 8 serious liver adverse events, including 2 deaths and 2 liver transplants. On September 27, 2007, the US Food and Drug Administration issued a not approvable letter for lumiracoxib, requiring additional safety data. Canada withdrew Prexige (approved at 100 mg dose only) in October 2007. Several European Union countries followed suit in November 2007.