- Overview
- Properties
- Related Genes
- Pathways
- Related Drugs
- Related Diseases
- Datasets
- Downloads/LinkOuts
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.
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AKR1C3 |
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AKT1 |
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CDKN1A |
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CTNNB1 |
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DDIT3 |
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MMP9 |
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PDK1 |
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PLA2G2A |
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PLA2G4A |
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PPARG |
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PTGDS |
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PTGS1 |
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TBXAS1 |
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VEGFA |
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Non-Curated Information
A list of non-curated publications that mention this drug along with other genes is available.
Metabolizing Enzymes
Drug Targets
PharmGKB Curated Pathways
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 | |
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Adenomatous Polyposis Coli |
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Arthritis, Rheumatoid |
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Asthma |
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Colonic Neoplasms |
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Dysmenorrhea |
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Fever |
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Inflammation |
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Osteoarthritis |
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Pain |
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Spondylitis, Ankylosing |
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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.
LinkOuts
Common Searches
Search PubMed
Search Medline Plus
Search PubChem
Search CTD
Non-Curated Publications
A list of non-curated publications that mention this drug is available.
