Drug/Small Molecule:
valdecoxib

2D structure

Overview

Generic Names: valdecoxib
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. (source: Drug Bank)

Indication

For the treatment of osteoarthritis and dysmenorrhoea (source: Drug Bank)

ATC Therapeutic Category

  • M01AH:Coxibs

Pharmacology, Interactions, and Contraindications

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. (source: Drug Bank)

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. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic (involves CYP3A4 and 2C9) (source: Drug Bank)

Protein Binding

98% (source: Drug Bank)

Absorption

Oral bioavailability is 83%. (source: Drug Bank)

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. (source: Drug Bank)

Isomeric SMILES Code:

Cc1c(c(no1)c2ccccc2)c3ccc(cc3)S(=O)(=O)N (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
PTGIR
  • CO
  •   
  •   
  •   
  • GN
Publications
Phenotype data available No genotype data Literature annotations available Has annotations
PTGS2
  • CO
  •   
  •   
  • FA
  • GN
Publications

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

Drug Targets

Gene Description
PTGS2 Uncurated Annotation (source: Drug Bank)

PharmGKB Curated Pathways

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
Phenotype data available Genotype Data Available Literature annotations available Not annotated
Cardiovascular Diseases
  • CO
  •   
  •   
  •   
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Pain
  •   
  • PD
  • PK
  •   
  •   
Publications

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

Web Resource:
Wikipedia
DrugBank:
DB00580
PubChem Compound ID:
119607
PubChem Substance ID:
696308

Common Searches

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Non-Curated Publications

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

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