valdecoxib   

GtoPdb Ligand ID: 2894

Synonyms: Bextra® | SC-65872
valdecoxib is an approved drug (FDA (2001))
Compound class: Synthetic organic
Comment: Valdecoxib is a non-steroidal anti-inflammatory drug (NSAID).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 94.57
Molecular weight 314.07
XLogP 3.15
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES Cc1onc(c1c1ccc(cc1)S(=O)(=O)N)c1ccccc1
Isomeric SMILES Cc1onc(c1c1ccc(cc1)S(=O)(=O)N)c1ccccc1
InChI InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)
InChI Key LNPDTQAFDNKSHK-UHFFFAOYSA-N
References
1. Sethi KK, Vullo D, Verma SM, Tanç M, Carta F, Supuran CT. (2013)
Carbonic anhydrase inhibitors: synthesis and inhibition of the human carbonic anhydrase isoforms I, II, VII, IX and XII with benzene sulfonamides incorporating 4,5,6,7-tetrabromophthalimide moiety.
Bioorg. Med. Chem., 21 (19): 5973-82. [PMID:23965175]
2. Talley JJ, Brown DL, Carter JS, Graneto MJ, Koboldt CM, Masferrer JL, Perkins WE, Rogers RS, Shaffer AF, Zhang YY et al.. (2000)
4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2.
J. Med. Chem., 43 (5): 775-7. [PMID:10715145]