GW406381   

GtoPdb Ligand ID: 9850

Synonyms: compound 8 [PMID: 15454242] | GW-406381
Compound class: Synthetic organic
Comment: GW406381 is a cyclooxygenase inhibitor that is selective for the COX2 isozyme, that has clinical potential for the treatment of inflammatory pain [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 81.94
Molecular weight 393.11
XLogP 4.33
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCOc1ccc(cc1)c1nn2c(c1c1ccc(cc1)S(=O)(=O)C)cccn2
Isomeric SMILES CCOc1ccc(cc1)c1nn2c(c1c1ccc(cc1)S(=O)(=O)C)cccn2
InChI InChI=1S/C21H19N3O3S/c1-3-27-17-10-6-16(7-11-17)21-20(19-5-4-14-22-24(19)23-21)15-8-12-18(13-9-15)28(2,25)26/h4-14H,3H2,1-2H3
InChI Key NXMZBNYLCVTRGB-UHFFFAOYSA-N
Immunopharmacology Comments
COX2 selective inhibitors have demonstrated clinical efficacy equivalent to NSAIDs in the treatment of inflammatory pain, but are not associated with the gastrointestinal toxicity typical of NSAID use.
Immunopharmacology Disease
Disease X-Refs Comment References
Rheumatoid arthritis Disease Ontology: DOID:7148
OMIM: 180300
Phase 3 clinical candidate for RA- see NCT00113308.
Osteoarthritis Disease Ontology: DOID:8398
Phase 3 clinical candidate for OA- see NCT00120900. However GW406381 failed to demonstrate clinically meaningful efficacy in pain related to OA of the knee. 2