U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H13ClFNO2
Molecular Weight 293.721
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LUMIRACOXIB

SMILES

CC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C1

InChI

InChIKey=KHPKQFYUPIUARC-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

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. It has never been approved for use in the United States. 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. 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. Lumiracoxib is used for the acute and chronic treatment of the signs and symptoms of osteoarthritis of the knee in adults.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.5 nM [IC50]
3.22 µM [IC50]
1.9 µM [IC50]
3.3 µM [IC50]
833.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Prexige
Palliative
Prexige

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Oral Osteoarthritis of the knee Adult: 100 mg once daily. Max: 400 mg/day.
Route of Administration: Oral
In Vitro Use Guide
Lumiracoxib (15 - 240 umol/L) has an inhibitory effect on the proliferation of A549 and NCI-H460 cell lines in concentration- and time-dependent manners with the IC50 values of 2597 umol/L and 833 umol/L, respectively.