Drug/Small Molecule:

valdecoxib

Overview

Generic Names:	valdecoxib
IUPAC Name:	4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide
Trade Names:	Bextra
PharmGKB Accession Id:	PA10226

Description

Valdecoxib was removed from the Canadian, U.S., and E.U. markets in 2005 due to concerns about possible increased risk of heart attack and stroke.

Indication

For the treatment of osteoarthritis and dysmenorrhoea

ATC Therapeutic Category

• M01AH:Coxibs

Pharmacology and Interactions

Mechanism Of Action

Both COX-1 and COX-2 catalyze the conversion of arachidonic acid to prostaglandin (PG) H2, the precursor of PGs and thromboxane. Valdecoxib selectively inhibits the cyclooxygenase-2 (COX-2) enzyme, important for the mediation of inflammation and pain. Unlike non-selective NSAIDs, valdecoxib does not inhibit platelet aggregation.

Pharmacology

Valdecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor, is classified as a nonsteroidal anti-inflammatory drug (NSAID). Valdecoxib is used for its anti-inflammatory, analgesic, and antipyretic activities in the management of osteoarthritis (OA) and for the treatment of dysmenorrhea or acute pain. Unlike celecoxib, valdecoxib lacks a sulfonamide chain and does not require CYP450 enzymes for metabolism.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic (involves CYP3A4 and 2C9)

Protein Binding

98%

Absorption

Oral bioavailability is 83%.

Half Life

8-11 hours

Toxicity

Symptoms following acute NSAID overdoses are usually limited to lethargy, drowsiness, nausea, vomiting, and epigastric pain, which are generally reversible with supportive care. Gastrointestinal bleeding can occur. Hypertension, acute renal failure, respiratory depression and coma may occur, but are rare.

Chemical Properties

Chemical Formula:

C₁₆H₁₄N₂O₃S

SMILES Code:

Cc1c(c(no1)c2ccccc2)c3ccc(cc3)S(=O)(=O)N

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

314.359 / 314.0725

Curated Information

The following genes are in curated knowledge about this drug.

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Metabolizing Enzymes

• CYP3A4
• CYP2C9

Drug Targets

• PTGS2

PharmGKB Curated Pathways

• Celecoxib Pathway

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Curated Information

The following diseases are in curated knowledge about this drug.

	Disease	Relationship	Evidence
	Adenomatous Polyposis Coli	PD PK	Pathways
	Arthritis, Rheumatoid	PD PK	Pathways
	Asthma	PD PK	Pathways
	Colonic Neoplasms	PD PK	Pathways
	Dysmenorrhea	PD PK	Pathways
	Fever	PD PK	Pathways
	Inflammation	PD PK	Pathways
	Osteoarthritis	PD PK	Pathways
	Pain	PD PK	Publications, Pathways
	Spondylitis, Ankylosing	PD PK	Pathways

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.