CHEBI:76228 - (S)-ketorolac

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ChEBI Name (S)-ketorolac
ChEBI ID CHEBI:76228
ChEBI ASCII Name (S)-ketorolac
Definition A 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid that has S configuration. While (S)-ketorolac is a COX1 and COX2 inhibitor, both enantiomers exhibit analgesic effects. Racemic ketorolac, known simply as ketorolac, is used (mainly as the tromethamine salt) as a potent analgesic for the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C15H13NO3
Net Charge 0
Average Mass 255.26860
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)/t11-/m0/s1
InChIKey OZWKMVRBQXNZKK-NSHDSACASA-N
SMILES OC(=O)[C@H]1CCn2c1ccc2C(=O)c1ccccc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
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.
Application(s): 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.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (S)-ketorolac (CHEBI:76228) has role analgesic (CHEBI:35480)
(S)-ketorolac (CHEBI:76228) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
(S)-ketorolac (CHEBI:76228) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
(S)-ketorolac (CHEBI:76228) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
(S)-ketorolac (CHEBI:76228) is a 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid (CHEBI:76223)
(S)-ketorolac (CHEBI:76228) is enantiomer of (R)-ketorolac (CHEBI:76227)
Incoming ketorolac (CHEBI:6129) has part (S)-ketorolac (CHEBI:76228)
(R)-ketorolac (CHEBI:76227) is enantiomer of (S)-ketorolac (CHEBI:76228)
IUPAC Name
(1S)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
Synonyms Sources
(−)-ketorolac ChemIDplus
(S)-(−)-ketorolac ChEBI
Registry Numbers Types Sources
6064296 Reaxys Registry Number Reaxys
66635-92-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10027870 PubMed citation Europe PMC
10223774 PubMed citation Europe PMC
10593468 PubMed citation Europe PMC
15584071 PubMed citation Europe PMC
17456651 PubMed citation Europe PMC
19281996 PubMed citation Europe PMC
23447046 PubMed citation Europe PMC
9549656 PubMed citation Europe PMC
Last Modified
08 November 2013