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CHEBI:6129 - ketorolac

Default Structure
ChEBI IDCHEBI:6129
ChEBI Nameketorolac
Stars
DefinitionA racemate comprising equimolar amounts of (R)-(+)- and (S)-(−)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid. While only the (S)-(−) enantiomer is a COX1 and COX2 inhibitor, the (R)-(+) enantiomer exhibits potent analgesic activity. A non-steroidal anti-inflammatory drug, ketorolac is mainly used (generally as the tromethamine salt) for its potent analgesic properties in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis. It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure.
Last Modified15 June 2017
DownloadsMolfile
FormulaC15H13NO3
Net Charge0
Average Mass255.273
Monoisotopic Mass255.08954
SMILESO=C(c1ccccc1)c1ccc2n1CCC2C(=O)O
InChIInChI=1S/C15H13NO3/c17-14(10-4-2-1-3-5-10)13-7-6-12-11(15(18)19)8-9-16(12)13/h1-7,11H,8-9H2,(H,18,19)
InChIKeyOZWKMVRBQXNZKK-UHFFFAOYSA-N
Wikipedia
Roles Classification
Biological Roles:
cyclooxygenase 1 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
Applications:
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.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
ChEBI Ontology
Outgoing Relation(s)
ketorolac (CHEBI:6129) has part (R)-ketorolac (CHEBI:76227)
ketorolac (CHEBI:6129) has part (S)-ketorolac (CHEBI:76228)
ketorolac (CHEBI:6129) has role analgesic (CHEBI:35480)
ketorolac (CHEBI:6129) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
ketorolac (CHEBI:6129) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
ketorolac (CHEBI:6129) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
ketorolac (CHEBI:6129) is a racemate (CHEBI:60911)
ketorolac (CHEBI:6129) is conjugate acid of ketorolac(1−) (CHEBI:76229)
Incoming Relation(s)
ketorolac(1−) (CHEBI:76229) is conjugate base of ketorolac (CHEBI:6129)
IUPAC Name 
rac-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
INNs  Source
ketorolacChemIDplus
kétorolacWHO MedNet
ketorolacoChemIDplus
ketorolacumChemIDplus
Synonyms  Source
(±)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acidChemIDplus
rac-ketorolacChEBI
(±)-ketorolacChemIDplus
Manual XrefsDatabases
BE856681Patent
C07062KEGG COMPOUND
D08104KEGG DRUG
DB00465DrugBank
HMDB0014608HMDB
KetorolacWikipedia
US4089969Patent
US4347186Patent
Registry NumbersSources
Reaxys:413572Reaxys
CAS:74103-06-3KEGG DRUG
CAS:74103-06-3ChemIDplus
CAS:74103-06-3KEGG COMPOUND
Citations