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
SMILES
OC(=O)[C@@H]1CCN2C1=CC=C2C(=O)C3=CC=CC=C3
InChI
InChIKey=OZWKMVRBQXNZKK-LLVKDONJSA-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-/m1/s1
(R)- enantiomer does not exhibit COX inhibition – it was > 100-fold less active than (S)- enantiomer on both COX subtypes. (R)- enantiomer is about 60 times less potent than the (-)-S isomer in the carrageenan edema test and ca. 230 times less active than the (-)-S isomer in the mouse phenylquinone writhing assay. R-ketorolac is an inhibitor of fatty acid amide hydrolase, but not at physiological concentrations.
Originator
Approval Year
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 |
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| Determination of ketorolac enantiomers in plasma using enantioselective liquid chromatography on an alpha 1-acid glycoprotein chiral stationary phase and ultraviolet detection. | 1994 Aug 5 |
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| Racemization of ketorolac in aqueous solution. | 1995 Sep |
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| Preclinical enantioselective pharmacology of (R)- and (S)- ketorolac. | 1998 Feb |
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66635-93-6
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SUBSTANCE RECORD
