ketorolac (CHEBI:6129)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

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 It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Wikipedia	License

Read full article at Wikipedia

Formula

C15H13NO3

Net Charge

Average Mass

255.269

Monoisotopic Mass

255.08954

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.

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

Synonyms	Sources
(±)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid	ChemIDplus
(±)-ketorolac	ChemIDplus
rac-ketorolac	ChEBI

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.