etodolac (CHEBI:4909)

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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

Average Mass

287.35350

Monoisotopic Mass

287.15214

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.

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

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

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.