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CHEBI:63634 - valdecoxib

ChEBI IDCHEBI:63634
ChEBI Namevaldecoxib
Stars
DefinitionA 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used as a nonsteroidal anti-inflammatory drug (NSAID) for the treatment of arthritis from 2001 until 2005, when it was withdrawn following concerns of an associated increased risk of heart attack and stroke.
Secondary ChEBI IDCHEBI:41662
Last Modified22 February 2017
DownloadsMolfile
FormulaC16H14N2O3S
Net Charge0
Average Mass314.366
Monoisotopic Mass314.07251
SMILESCc1onc(-c2ccccc2)c1-c1ccc(S(N)(=O)=O)cc1
InChIInChI=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)
InChIKeyLNPDTQAFDNKSHK-UHFFFAOYSA-N
Wikipedia
Roles Classification
Biological Roles:
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.
Applications:
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.
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.
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
parecoxib (CHEBI:73038) has functional parent valdecoxib (CHEBI:63634)
IUPAC Name 
4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide
INNs  Source
valdecoxibWHO MedNet
valdecoxibWHO MedNet
valdecoxibumWHO MedNet
valdécoxibWHO MedNet
Synonyms  Source
p-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamideChemIDplus
4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamideChemIDplus
Brand Name  Source
BextraChEBI
Manual XrefsDatabases
ValdecoxibWikipedia
D02709KEGG DRUG
DB00580DrugBank
HMDB0005033HMDB
COXPDBeChem
LSM-5305LINCS
2799DrugCentral
Registry NumbersSources
Reaxys:8563786Reaxys
CAS:181695-72-7ChemIDplus
CAS:181695-72-7KEGG DRUG
Citations