CHEBI:31162 - acemetacin

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ChEBI Name acemetacin
ChEBI ID CHEBI:31162
Definition A carboxylic ester that is the carboxymethyl ester of indometacin. A non-steroidal anti-inflammatory drug, it is used in the treatment of rheumatoid arthritis, osteoarthritis, and low back pain, as well as for postoperative pain and inflammation. Its activity is due to both acemetacin and its major metabolite, indometacin.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H18ClNO6
Net Charge 0
Average Mass 415.82400
Monoisotopic Mass 415.082
InChI InChI=1S/C21H18ClNO6/c1-12-16(10-20(26)29-11-19(24)25)17-9-15(28-2)7-8-18(17)23(12)21(27)13-3-5-14(22)6-4-13/h3-9H,10-11H2,1-2H3,(H,24,25)
InChIKey FSQKKOOTNAMONP-UHFFFAOYSA-N
SMILES COc1ccc2n(C(=O)c3ccc(Cl)cc3)c(C)c(CC(=O)OCC(O)=O)c2c1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
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.
Application(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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 acemetacin (CHEBI:31162) has functional parent indometacin (CHEBI:49662)
acemetacin (CHEBI:31162) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
acemetacin (CHEBI:31162) has role non-narcotic analgesic (CHEBI:35481)
acemetacin (CHEBI:31162) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
acemetacin (CHEBI:31162) has role prodrug (CHEBI:50266)
acemetacin (CHEBI:31162) is a N-acylindole (CHEBI:75884)
acemetacin (CHEBI:31162) is a carboxylic ester (CHEBI:33308)
acemetacin (CHEBI:31162) is a indol-3-yl carboxylic acid (CHEBI:24810)
acemetacin (CHEBI:31162) is a monocarboxylic acid (CHEBI:25384)
acemetacin (CHEBI:31162) is a monochlorobenzenes (CHEBI:83403)
IUPAC Name
{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxy}acetic acid
INNs Sources
acemetacin ChemIDplus
acemetacina ChemIDplus
acemetacine ChemIDplus
acemetacinum ChemIDplus
Synonyms Sources
indometacin carboxymethyl ester ChEBI
indometacin glycolic ester ChEBI
indomethacin carboxymethyl ester ChEBI
indomethacin glycolic ester ChEBI
K 708 ChemIDplus
K-708 ChemIDplus
TV-1322 ChEBI
TVX 3322 ChemIDplus
Brand Names Sources
Acemix ChEBI
Emflex ChEBI
Rantudil ChEBI
Solart ChEBI
Manual Xrefs Databases
47 DrugCentral
Acemetacin Wikipedia
D01582 KEGG DRUG
DE2234651 Patent
LSM-5753 LINCS
US3910952 Patent
View more database links
Registry Numbers Types Sources
501672 Reaxys Registry Number Reaxys
53164-05-9 CAS Registry Number ChemIDplus
Last Modified
22 February 2017