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
References
1. Beswick P, Bingham S, Bountra C, Brown T, Browning K, Campbell I, Chessell I, Clayton N, Collins S, Corfield J et al.. (2004)
Identification of 2,3-diaryl-pyrazolo[1,5-b]pyridazines as potent and selective cyclooxygenase-2 inhibitors.
Bioorg. Med. Chem. Lett., 14 (21): 5445-8. [PMID:15454242]
2. Boswell DJ, Ostergaard K, Philipson RS, Hodge RA, Blum D, Brown JC, Quessy SN. (2008)
Evaluation of GW406381 for treatment of osteoarthritis of the knee: two randomized, controlled studies.
Medscape J Med, 10 (11): 259. [PMID:19099009]
3. Varner J, Lomax M, Blum D, Quessy S. (2009)
A randomized, controlled, dose-ranging study investigating single doses of GW406381, naproxen sodium, or placebo in patients with acute pain after third molar tooth extraction.
Clin J Pain, 25 (7): 577-83. [PMID:19692798]