CHEBI:6129 - ketorolac

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ChEBI Name ketorolac
ChEBI ID CHEBI:6129
Definition A 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 It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure.
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Formula C15H13NO3
Net Charge 0
Average Mass 255.269
Monoisotopic Mass 255.090
InChI InChI=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)
InChIKey OZWKMVRBQXNZKK-UHFFFAOYSA-N
SMILES N12C(C(C(=O)O)CC1)=CC=C2C(=O)C3=CC=CC=C3
Roles Classification
Biological Role(s): cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
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.
Application(s): 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.
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ChEBI Ontology
Outgoing 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 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 Sources
ketorolac ChemIDplus
kétorolac WHO MedNet
ketorolaco ChemIDplus
ketorolacum ChemIDplus
Synonyms Sources
(±)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid ChemIDplus
(±)-ketorolac ChemIDplus
rac-ketorolac ChEBI
Manual Xrefs Databases
BE856681 Patent
C07062 KEGG COMPOUND
D08104 KEGG DRUG
DB00465 DrugBank
HMDB0014608 HMDB
Ketorolac Wikipedia
US4089969 Patent
US4347186 Patent
View more database links
Registry Numbers Types Sources
413572 Reaxys Registry Number Reaxys
74103-06-3 CAS Registry Number KEGG COMPOUND
74103-06-3 CAS Registry Number ChemIDplus
74103-06-3 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
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Last Modified
15 June 2017
General Comment
2013-11-07 This is the entry for racemic ketorolac. There are separate entries for the individual enantiomers and for 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid with unspecified stereochemistry.