CHEBI:76127 - cimicoxib

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ChEBI Name cimicoxib
ChEBI ID CHEBI:76127
Definition An imidazole substituted at positions 1, 4 and 5 by 4-aminosulfonylphenyl, chloro and 3-fluoro-4-methyoxyphenyl groups respectively. A selective cyclooxygenase 2 inhibitor, it is used in veterinary medicine for the control of pain and inflammation associated with osteoarthritis in dogs.
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Formula C16H13ClFN3O3S
Net Charge 0
Average Mass 381.80900
Monoisotopic Mass 381.03502
InChI InChI=1S/C16H13ClFN3O3S/c1-24-14-7-2-10(8-13(14)18)15-16(17)20-9-21(15)11-3-5-12(6-4-11)25(19,22)23/h2-9H,1H3,(H2,19,22,23)
InChIKey KYXDNECMRLFQMZ-UHFFFAOYSA-N
SMILES COc1ccc(cc1F)-c1c(Cl)ncn1-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.
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.
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ChEBI Ontology
Outgoing cimicoxib (CHEBI:76127) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
cimicoxib (CHEBI:76127) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
cimicoxib (CHEBI:76127) is a aromatic ether (CHEBI:35618)
cimicoxib (CHEBI:76127) is a imidazoles (CHEBI:24780)
cimicoxib (CHEBI:76127) is a organochlorine compound (CHEBI:36683)
cimicoxib (CHEBI:76127) is a organofluorine compound (CHEBI:37143)
cimicoxib (CHEBI:76127) is a sulfonamide (CHEBI:35358)
IUPAC Name
4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl]benzenesulfonamide
INN Source
cimicoxib ChemIDplus
Synonym Source
UR-8880 ChemIDplus
Manual Xrefs Databases
Cimicoxib Wikipedia
NZ556707 Patent
WO2005020895 Patent
WO2005021004 Patent
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Registry Numbers Types Sources
265114-23-6 CAS Registry Number ChemIDplus
9505967 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12877584 PubMed citation Europe PMC
23076019 PubMed citation Europe PMC
23685411 PubMed citation Europe PMC
23710692 PubMed citation Europe PMC
Last Modified
29 October 2013