(S)-ketorolac (CHEBI:76228)

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CHEBI:76228 - (S)-ketorolac

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ChEBI ID	CHEBI:76228
ChEBI Name	(S)-ketorolac
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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.
Last Modified	8 November 2013
Submitter	Gareth Owen
Downloads	Molfile

Formula	C15H13NO3
Net Charge	0
Average Mass	255.273
Monoisotopic Mass	255.08954
SMILES	O=C(c1ccccc1)c1ccc2n1CC[C@@H]2C(=O)O
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

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. 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 1 inhibitor A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
Applications:	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.

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
(−)-ketorolac	ChemIDplus
(S)-(−)-ketorolac	ChEBI

Registry Numbers	Sources
Reaxys:6064296	Reaxys
CAS:66635-92-5	ChemIDplus

Citations