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CHEBI:60371 - (S)-etodolac

Default Structure
ChEBI IDCHEBI:60371
ChEBI Name(S)-etodolac
Stars
ASCII Name(S)-etodolac
DefinitionThe 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.
Last Modified21 November 2019
SubmitterGareth Owen
DownloadsMolfile
FormulaC17H21NO3
Net Charge0
Average Mass287.359
Monoisotopic Mass287.15214
SMILESCCc1cccc2c3c(nc12)[C@](CC)(CC(=O)O)OCC3
InChIInChI=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
InChIKeyNNYBQONXHNTVIJ-KRWDZBQOSA-N
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
Applications:
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
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-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
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.
ChEBI Ontology
Outgoing Relation(s)
(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 Relation(s)
(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  Source
(+)-[1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl]acetic acidChEBI
(+)-etodolacChEBI
(S)-(+)-etodolacChEBI
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