CHEBI:4909 - etodolac

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ChEBI Name etodolac
ChEBI ID CHEBI:4909
Definition A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl moiety. A preferential inhibitor of cyclo-oxygenase 2 and non-steroidal anti-inflammatory, it is used for the treatment of rheumatoid arthritis and osteoarthritis, and for the alleviation of postoperative pain. Administered as the racemate, only the (S)-enantiomer is active.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:126431
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Formula C17H21NO3
Net Charge 0
Average Mass 287.35350
Monoisotopic Mass 287.152
InChI InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)
InChIKey NNYBQONXHNTVIJ-UHFFFAOYSA-N
SMILES CCc1cccc2c3CCOC(CC)(CC(O)=O)c3[nH]c12
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): cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
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): antipyretic
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing etodolac (CHEBI:4909) has role antipyretic (CHEBI:35493)
etodolac (CHEBI:4909) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
etodolac (CHEBI:4909) has role non-narcotic analgesic (CHEBI:35481)
etodolac (CHEBI:4909) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
etodolac (CHEBI:4909) is a monocarboxylic acid (CHEBI:25384)
etodolac (CHEBI:4909) is a organic heterotricyclic compound (CHEBI:26979)
Incoming (R)-etodolac (CHEBI:60370) is a etodolac (CHEBI:4909)
(S)-etodolac (CHEBI:60371) is a etodolac (CHEBI:4909)
IUPAC Name
(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid
INNs Sources
etodolac ChemIDplus
etodolaco ChemIDplus
etodolacum ChemIDplus
Synonyms Sources
(±)-1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid ChemIDplus
(1,8-Diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid ChEMBL
1,3,4,9-tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetic acid ChemIDplus
1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid ChemIDplus
1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-ylacetic acid ChEBI
ETODOLAC ChEMBL
ETODOLIC ACID ChEMBL
Manual Xrefs Databases
1103 DrugCentral
D00315 KEGG DRUG
DB00749 DrugBank
DE2301525 Patent
Etodolac Wikipedia
HMDB0014887 HMDB
LSM-1781 LINCS
US3939178 Patent
View more database links
Registry Numbers Types Sources
41340-25-4 CAS Registry Number ChemIDplus
41340-25-4 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
15369391 PubMed citation ChEMBL
2527995 PubMed citation ChEMBL
28166217 PubMed citation Europe PMC
2970548 PubMed citation ChEMBL
Last Modified
14 June 2017
General Comment
2014-07-15 Etodolac can be found in blood and urine samples of individuals who have taken this drug.