| Identification | Back Directory | [Name]
(S)-Ketorolac | [CAS]
66635-92-5 | [Synonyms]
Ketorolac S-IsoMer
(S)-Ketorolac ISO 9001：2015 REACH
Ketorolac impurity 2/Ketorolac S-Isomer
1H-Pyrrolizine-1-carboxylic acid, 5-benzoyl-2,3-dihydro-, (1S)- | [Molecular Formula]
C15H13NO3 | [MDL Number]
MFCD00871493 | [MOL File]
66635-92-5.mol | [Molecular Weight]
255.27 |
| Chemical Properties | Back Directory | [Melting point ]
160-167?C | [Boiling point ]
493.2±40.0 °C(Predicted) | [density ]
1.33±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
Chloroform: Slightly; Ethanol: >1mg/ml; Methanol: Slightly | [form ]
A crystalline solid | [pka]
4.29±0.20(Predicted) | [color ]
White to off-white | [Optical Rotation]
[α]/D -165 to -185°, c =0.5 in methanol | [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]
[n]21c(ccc2C(=O)c3ccccc3)[C@H](CC1)C(=O)O |
| Hazard Information | Back Directory | [Description]
(S)-Ketorolac is a non-selective COX inhibitor and non-steroidal anti-inflammatory drug (NSAID; IC50s = 0.1 and 2.7 μM for COX-1 and COX-2, respectively). (S)-Ketorolac is approximately twice as potent as the racemic mixture and 60 times more potent than (R)-ketorolac in a rat pain assay. (S)-Ketorolac is cleared from rat kidney and liver more quickly than (R)-ketorolac. Formulations containing ketorolac have been used to manage postoperative pain as well as an ophthalmic solution to treat ocular pain and inflammation. | [Chemical Properties]
Off-White Solid | [Uses]
(S)-Ketorolac is the S-enantiomer of Ketorolac. The (S)-enantiomer is about 60 times more potent than (R)-enantiomer. Prostaglandin biosynthesis inhibitor. Analgesic; anti-inflammatory. | [Uses]
The R-enantiomer of Ketorolac. The (S)-enantiomer is about 60 times more potent than (R)-enantiomer. Prostaglandin biosynthesis inhibitor. Analgesic; anti-inflammatory. | [Definition]
ChEBI: 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 s
mply 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. | [References]
[1] DR. DEAN A. HANDLEY PHD. Preclinical Enantioselective Pharmacology of (R)- and (S)- Ketorolac[J]. The Journal of Clinical Pharmacology, 2013, 38 2S: 25S-35S. DOI: 10.1002/j.1552-4604.1998.tb04414.x
[2] ANGEL GUSMAN. Absolute configuration of (-)-5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid, the active enantiomer of ketorolac[J]. Journal of Medicinal Chemistry, 1986, 29 4: 589-591. DOI: 10.1021/jm00154a027
[3] S K DUBEY R N S A Anand. Enantioselective Tissue Distribution of Ketorolac and its Enantiomers in Rats.[J]. Drug Research, 2015, 65 8: 428-431. DOI: 10.1055/s-0034-1389913
[4] DDS S M G, MPH Jaime S B D, MS Janet R R, et al. Peripheral prostanoid levels and nonsteroidal anti-inflammatory drug analgesia: Replicate clinical trials in a tissue injury model[J]. Clinical Pharmacology & Therapeutics, 2002, 72 2: 175-183. DOI: 10.1067/mcp.2002.126501 |
|
|