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
No information available.
Summary of Clinical Use
Prior to manufacturer's withdrawl from the US and EU markets, valdecoxib was approved to treat osteoarthritis, rheumatoid arthritis and primary dysmennorhea. Reasons for withdrawl included increased cardiovascular risk (heart attack and stroke) and risk of a serious/fatal skin reaction. A prodrug of valdecoxib, parecoxib, is approved for use in several countries other than the US.
Mechanism Of Action and Pharmacodynamic Effects
Valdecoxib is a second-generation cyclooxygenase 2 (COX2) inhibitor which inhibits the synthesis of prostaglandins and thromboxane(s) from arachidonic acid.