CHEBI:49662 - indometacin

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ChEBI Name indometacin
Definition A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:49660, CHEBI:5918
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Formula C19H16ClNO4
Net Charge 0
Average Mass 357.78800
Monoisotopic Mass 357.07679
InChI InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)
SMILES COc1ccc2n(C(=O)c3ccc(Cl)cc3)c(C)c(CC(O)=O)c2c1
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): drug metabolite

xenobiotic metabolite
Any metabolite produced by metabolism of a xenobiotic compound.
EC (prostaglandin-endoperoxide synthase) inhibitor
A compound or agent that combines with cyclooxygenases (EC and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
gout suppressant
A drug that increases uric acid excretion by the kidney (uricosuric drug), decreases uric acid production (antihyperuricemic), or alleviates the pain and inflammation of acute attacks of gout.
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 indometacin (CHEBI:49662) has role analgesic (CHEBI:35480)
indometacin (CHEBI:49662) has role drug metabolite (CHEBI:49103)
indometacin (CHEBI:49662) has role EC (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
indometacin (CHEBI:49662) has role environmental contaminant (CHEBI:78298)
indometacin (CHEBI:49662) has role gout suppressant (CHEBI:35845)
indometacin (CHEBI:49662) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
indometacin (CHEBI:49662) has role xenobiotic (CHEBI:35703)
indometacin (CHEBI:49662) has role xenobiotic metabolite (CHEBI:76206)
indometacin (CHEBI:49662) is a N-acylindole (CHEBI:75884)
indometacin (CHEBI:49662) is a aromatic ether (CHEBI:35618)
indometacin (CHEBI:49662) is a indole-3-acetic acids (CHEBI:24803)
indometacin (CHEBI:49662) is a monochlorobenzenes (CHEBI:83403)
Incoming acemetacin (CHEBI:31162) has functional parent indometacin (CHEBI:49662)
oxametacin (CHEBI:76255) has functional parent indometacin (CHEBI:49662)
proglumetacin (CHEBI:76263) has functional parent indometacin (CHEBI:49662)
[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
INNs Sources
indometacin ChemIDplus
indometacina ChemIDplus
indometacine ChemIDplus
indometacinum ChemIDplus
Synonyms Sources
1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid ChemIDplus
Indocin ChemIDplus
Indomethacin KEGG COMPOUND
{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid PDBeChem
Brand Names Sources
Manual Xrefs Databases
1440 DrugCentral
BE379378 Patent
C00030512 KNApSAcK
CPD-10545 MetaCyc
DB00328 DrugBank
HMDB0014473 HMDB
Indometacin Wikipedia
US3161654 Patent
View more database links
Registry Numbers Types Sources
1446006 Gmelin Registry Number Gmelin
497341 Beilstein Registry Number Beilstein
497341 Reaxys Registry Number Reaxys
53-86-1 CAS Registry Number NIST Chemistry WebBook
53-86-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22931205 PubMed citation Europe PMC
23992308 PubMed citation Europe PMC
28166217 PubMed citation Europe PMC
5952296 PubMed citation Europe PMC
6039425 PubMed citation Europe PMC
Last Modified
15 June 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag