CHEBI:76255 - oxametacin

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ChEBI Name oxametacin
ChEBI ID CHEBI:76255
Definition A hydroxamic acid obtained by formal condensation of the carboxy group of indometacin with the amino group of hydroxylamine.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H15ClN2O4
Net Charge 0
Average Mass 358.77600
Monoisotopic Mass 358.072
InChI InChI=1S/C18H15ClN2O4/c1-25-14-6-7-16-15(9-14)12(8-17(22)20-24)10-21(16)18(23)11-2-4-13(19)5-3-11/h2-7,9-10,24H,8H2,1H3,(H,20,22)
InChIKey OHKBKALZIBYJEV-UHFFFAOYSA-N
SMILES COc1ccc2n(cc(CC(=O)NO)c2c1)C(=O)c1ccc(Cl)cc1
Roles Classification
Biological Role(s): EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor
A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
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.
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ChEBI Ontology
Outgoing oxametacin (CHEBI:76255) has functional parent indometacin (CHEBI:49662)
oxametacin (CHEBI:76255) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
oxametacin (CHEBI:76255) has role non-narcotic analgesic (CHEBI:35481)
oxametacin (CHEBI:76255) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
oxametacin (CHEBI:76255) is a N-acylindole (CHEBI:75884)
oxametacin (CHEBI:76255) is a aromatic ether (CHEBI:35618)
oxametacin (CHEBI:76255) is a hydroxamic acid (CHEBI:24650)
oxametacin (CHEBI:76255) is a organochlorine compound (CHEBI:36683)
IUPAC Name
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-hydroxyacetamide
INNs Sources
oxametacin KEGG DRUG
oxametacina ChemIDplus
oxamétacine WHO MedNet
oxametacinum ChemIDplus
Synonyms Sources
1-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-acetamide ChemIDplus
1-(p-Chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetohydroxamic acid ChemIDplus
1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetohydroxamic acid ChemIDplus
Indoxamic acid ChemIDplus
Manual Xrefs Databases
D07266 KEGG DRUG
DE2008332 Patent
EP1336602 Patent
FR1599495 Patent
GB2475359 Patent
Oxametacin Wikipedia
US3624103 Patent
US4455432 Patent
WO2006099416 Patent
View more database links
Registry Numbers Types Sources
27035-30-9 CAS Registry Number KEGG DRUG
27035-30-9 CAS Registry Number ChemIDplus
497721 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
1182055 PubMed citation Europe PMC
6297524 PubMed citation Europe PMC
6597800 PubMed citation Europe PMC
6613750 PubMed citation Europe PMC
6681967 PubMed citation Europe PMC
6778714 PubMed citation Europe PMC
6873149 PubMed citation Europe PMC
6944075 PubMed citation Europe PMC
7194675 PubMed citation Europe PMC
7194676 PubMed citation Europe PMC
7282104 PubMed citation Europe PMC
Last Modified
22 February 2017