rofecoxib   

GtoPdb Ligand ID: 2893

Synonyms: Ceoxx® | MK 966 | Vioxx®
rofecoxib is an approved drug (FDA (1999))
Compound class: Synthetic organic
Comment: Rofecoxib is a non-steroidal anti-inflammatory (NSAID) drug.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 68.82
Molecular weight 314.06
XLogP 3.25
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C1OCC(=C1c1ccccc1)c1ccc(cc1)S(=O)(=O)C
Isomeric SMILES O=C1OCC(=C1c1ccccc1)c1ccc(cc1)S(=O)(=O)C
InChI InChI=1S/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17(18)16(15)13-5-3-2-4-6-13/h2-10H,11H2,1H3
InChI Key RZJQGNCSTQAWON-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
A non-steroidal anti-inflammatory drug previously used in the treatment of rheumatoid arthritis, osteoarthritis, primary dysmenorrhea, acture migraine and acute pain. Withdrawn from the US market in 2004 due to concerns about safety.
Mechanism Of Action and Pharmacodynamic Effects
While the exact mechanism of action of rofecoxib has not been determined, its anti-inflammatory properties appear to arise from its inhibition of prostaglandin synthesis via inhibition of COX-2 which is involved in the mediation of inflammation and pain.