CHEBI:60371 - (S)-etodolac

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ChEBI Name (S)-etodolac
ChEBI ID CHEBI:60371
ChEBI ASCII Name (S)-etodolac
Definition The S-enantiomer of etodolac. It is a preferential inhibitor of cyclo-oxygenase 2 and a non-steroidal anti-inflammatory, whereas the enantiomer, (R)-etodolac, is inactive. The racemate is commonly used for the treatment of rheumatoid arthritis and osteoarthritis, and for the alleviation of postoperative pain.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C17H21NO3
Net Charge 0
Average Mass 287.359
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)/t17-/m0/s1
InChIKey NNYBQONXHNTVIJ-KRWDZBQOSA-N
SMILES C=12NC=3C(=CC=CC3C1CCO[C@]2(CC(=O)O)CC)CC
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.
(via etodolac )
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
(via etodolac )
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.
(via etodolac )
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.
(via etodolac )
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.
(via etodolac )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (S)-etodolac (CHEBI:60371) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
(S)-etodolac (CHEBI:60371) has role non-narcotic analgesic (CHEBI:35481)
(S)-etodolac (CHEBI:60371) is a etodolac (CHEBI:4909)
(S)-etodolac (CHEBI:60371) is enantiomer of (R)-etodolac (CHEBI:60370)
Incoming (R)-etodolac (CHEBI:60370) is enantiomer of (S)-etodolac (CHEBI:60371)
IUPAC Name
[(1S)-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]indol-1-yl]acetic acid ChEBI
(+)-etodolac ChEBI
(S)-(+)-etodolac ChEBI
Manual Xref Database
8QP PDBeChem
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Citations Waiting for Citations Types Sources
20557835 PubMed citation Europe PMC
26723001 PubMed citation Europe PMC
28875479 PubMed citation Europe PMC
Last Modified
21 November 2019