CHEBI:63634 - valdecoxib

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ChEBI Name valdecoxib
ChEBI ID CHEBI:63634
Definition A member of the class of isoxazoles that is isoxazole which is substituted at positions 3, 4 and 5 by phenyl, p-sulfamoylphenyl and methyl groups, respectively. A selective cyclooxygenase 2-inhibitor, it used as a nonsteroidal anti-inflammatory drug (NSAID) for the treatment of arthritis from 2001 until 2005, when it was withdrawn following concerns of an associated increased risk of heart attack and stroke.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:41662
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Formula C16H14N2O3S
Net Charge 0
Average Mass 314.35900
Monoisotopic Mass 314.073
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)
InChIKey LNPDTQAFDNKSHK-UHFFFAOYSA-N
SMILES Cc1onc(-c2ccccc2)c1-c1ccc(cc1)S(N)(=O)=O
Roles Classification
Biological Role(s): cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
antirheumatic drug
A drug used to treat rheumatoid arthritis.
antipyretic
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
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ChEBI Ontology
Outgoing valdecoxib (CHEBI:63634) has role antipyretic (CHEBI:35493)
valdecoxib (CHEBI:63634) has role antirheumatic drug (CHEBI:35842)
valdecoxib (CHEBI:63634) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
valdecoxib (CHEBI:63634) has role non-narcotic analgesic (CHEBI:35481)
valdecoxib (CHEBI:63634) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
valdecoxib (CHEBI:63634) is a isoxazoles (CHEBI:55373)
valdecoxib (CHEBI:63634) is a sulfonamide (CHEBI:35358)
Incoming parecoxib (CHEBI:73038) has functional parent valdecoxib (CHEBI:63634)
IUPAC Name
4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide
INNs Sources
valdécoxib WHO MedNet
valdecoxib WHO MedNet
valdecoxib WHO MedNet
valdecoxibum WHO MedNet
Synonyms Sources
4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide ChemIDplus
p-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide ChemIDplus
Brand Name Source
Bextra ChEBI
Database Links Databases
2799 DrugCentral
COX PDBeChem
D02709 KEGG DRUG
DB00580 DrugBank
HMDB0005033 HMDB
LSM-5305 LINCS
Valdecoxib Wikipedia
View more database links
Registry Numbers Types Sources
181695-72-7 CAS Registry Number KEGG DRUG
181695-72-7 CAS Registry Number ChemIDplus
8563786 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20467258 PubMed citation Europe PMC
20717044 PubMed citation Europe PMC
21073910 PubMed citation Europe PMC
21720517 PubMed citation Europe PMC
21769548 PubMed citation Europe PMC
Last Modified
22 February 2017