CHEBI:71941 - tolmetin

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ChEBI Name tolmetin
ChEBI ID CHEBI:71941
Definition A monocarboxylic acid that is (1-methylpyrrol-2-yl)acetic acid substituted at position 5 on the pyrrole ring by a 4-methylbenzoyl group. Used in the form of its sodium salt dihydrate as a nonselective nonsteroidal anti-inflammatory drug.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:9618
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Formula C15H15NO3
Net Charge 0
Average Mass 257.28450
Monoisotopic Mass 257.105
InChI InChI=1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18)
InChIKey UPSPUYADGBWSHF-UHFFFAOYSA-N
SMILES Cc1ccc(cc1)C(=O)c1ccc(CC(O)=O)n1C
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): 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-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 tolmetin (CHEBI:71941) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
tolmetin (CHEBI:71941) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
tolmetin (CHEBI:71941) is a aromatic ketone (CHEBI:76224)
tolmetin (CHEBI:71941) is a monocarboxylic acid (CHEBI:25384)
tolmetin (CHEBI:71941) is a pyrroles (CHEBI:26455)
tolmetin (CHEBI:71941) is conjugate acid of tolmetin(1−) (CHEBI:72213)
Incoming tolmetin(1−) (CHEBI:72213) is conjugate base of tolmetin (CHEBI:71941)
IUPAC Name
[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid
INNs Sources
tolmetin KEGG DRUG
tolmetine DrugBank
tolmetino DrugBank
tolmetinum DrugBank
Synonyms Sources
1-Methyl-5-(4-methylbenzoyl)-pyrrole-2-acetic acid ChemIDplus
1-Methyl-5-p-toluoylpyrrole-2-acetic acid ChemIDplus
5-(p-Toluoyl)-1-methylpyrrole-2-acetic acid ChemIDplus
tolmetina DrugBank
Manual Xrefs Databases
2699 DrugCentral
C07149 KEGG COMPOUND
D02355 KEGG DRUG
DB00500 DrugBank
DE2836902 Patent
HMDB0014643 HMDB
LSM-3852 LINCS
MX2010012712 Patent
TLT PDBeChem
Tolmetin Wikipedia
WO2004069782 Patent
WO2008017903 Patent
WO2009072139 Patent
View more database links
Registry Numbers Types Sources
26171-23-3 CAS Registry Number KEGG COMPOUND
26171-23-3 CAS Registry Number NIST Chemistry WebBook
26171-23-3 CAS Registry Number ChemIDplus
485305 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
1206489 PubMed citation Europe PMC
19181568 PubMed citation Europe PMC
19505209 PubMed citation Europe PMC
20529813 PubMed citation Europe PMC
20582193 PubMed citation Europe PMC
20853464 PubMed citation Europe PMC
21936545 PubMed citation Europe PMC
22005020 PubMed citation Europe PMC
22943177 PubMed citation Europe PMC
23333829 PubMed citation Europe PMC
3390998 PubMed citation Europe PMC
445955 PubMed citation Europe PMC
6686452 PubMed citation Europe PMC
8472518 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-05-01 Tolmetin can be found in blood and urine sample of individuals who have taken this drug.