EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:76228 - (S)-ketorolac

Default Structure
ChEBI IDCHEBI:76228
ChEBI Name(S)-ketorolac
Stars
ASCII Name(S)-ketorolac
DefinitionA 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.
Last Modified8 November 2013
SubmitterGareth Owen
DownloadsMolfile
FormulaC15H13NO3
Net Charge0
Average Mass255.273
Monoisotopic Mass255.08954
SMILESO=C(c1ccccc1)c1ccc2n1CC[C@@H]2C(=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)/t11-/m0/s1
InChIKeyOZWKMVRBQXNZKK-NSHDSACASA-N
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
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.
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.
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)
(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 Relation(s)
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  Source
(S)-(−)-ketorolacChEBI
(−)-ketorolacChemIDplus
Registry NumbersSources
Reaxys:6064296Reaxys
CAS:66635-92-5ChemIDplus
Citations