KETOROLAC, (S)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H13NO3
Molecular Weight	255.2686
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)[C@H]1CCN2C1=CC=C2C(=O)C3=CC=CC=C3

InChI

InChIKey=OZWKMVRBQXNZKK-NSHDSACASA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9549656 | https://www.ncbi.nlm.nih.gov/pubmed/3959034 | https://www.ncbi.nlm.nih.gov/pubmed/10027870

(S)-ketorolac is the enantiomer of ketorolac, a nonsteroidal anti-inflammatory drug. (S)-ketorolac exhibited potent cyclooxygenase (COX1 and COX2) enzyme inhibition. (S)-ketorolac is considered to be active enantiomer of racemic ketorolac.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-1 127 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9549656	Inhibitor 8297		0.46 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9549656	Inhibitor 8297		1.46 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9549656 https://www.ncbi.nlm.nih.gov/pubmed/10422661 https://www.ncbi.nlm.nih.gov/pubmed/10027870	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Absolute configuration of (-)-5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-alpha]pyrrole-1-carboxylic acid, the active enantiomer of ketorolac.	1986 Apr	3959034
The pharmacokinetics of ketorolac enantiomers following intramuscular administration of the racemate.	1994 Jan	8148223
Preclinical enantioselective pharmacology of (R)- and (S)- ketorolac.	1998 Feb	9549656
Inhibition of anandamide hydrolysis by the enantiomers of ibuprofen, ketorolac, and flurbiprofen.	1999 Feb 15	9989926
Synergistic antiallodynic effects of spinal morphine with ketorolac and selective COX1- and COX2-inhibitors in nerve-injured rats.	1999 Jul	10422661
Characterization of the analgesic and anti-inflammatory activities of ketorolac and its enantiomers in the rat.	1999 Mar	10027870
Body weight, gender and pregnancy affect enantiomer-specific ketorolac pharmacokinetics.	2017 Sep	28429492

Sample Use Guides

In Vivo Use Guide

rats: 0.01–1 mg/kg s.c.

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

KETOROLAC, (S)-

Common Name

English

(-)-KETOROLAC

Common Name

English

1H-PYRROLIZINE-1-CARBOXYLIC ACID, 5-BENZOYL-2,3-DIHYDRO-, (1S)-

Systematic Name

English

S-(-)-KETOROLAC

Common Name

English

(1S)-5-BENZOYL-2,3-DIHYDRO-1H-PYRROLIZINE-1-CARBOXYLIC ACID

Systematic Name

English

(S)-KETOROLAC

Common Name

English

1H-PYRROLIZINE-1-CARBOXYLIC ACID, 5-BENZOYL-2,3-DIHYDRO-, (S)-

Common Name

English

Code System Code Type Description

CHEBI

76228