(S)-Ketorolac

Base Information

• Chemical Name: (S)-Ketorolac
• CAS No.: 66635-92-5
• Molecular Formula: C15H13 N O3
• Molecular Weight: 255.273
• UNII: 5H3TJ0A81K
• DSSTox Substance ID: DTXSID901317534
• Nikkaji Number: J269.531F
• Wikidata: Q27145822
• Mol file: 66635-92-5.mol

Synonyms:(S)-Ketorolac;66635-92-5;(-)-Ketorolac;(1S)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid;Ketorolac, (S)-;UNII-5H3TJ0A81K;5H3TJ0A81K;1H-Pyrrolizine-1-carboxylicacid, 5-benzoyl-2,3-dihydro-, (1S)-;1H-Pyrrolizine-1-carboxylic acid, 5-benzoyl-2,3-dihydro-, (S)-;S-(-)-Ketorolac;(S)-(-)-ketorolac;SCHEMBL14892;CHEBI:76228;HY-B0580A;DTXSID901317534;AKOS030240797;MS-23597;CS-0084964;EN300-18567395;Q27145822;(S)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid;1H-Pyrrolizine-1-carboxylic acid, 5-benzoyl-2,3-dihydro-, (1S)-

Chemical Property of (S)-Ketorolac

Chemical Property:

• Vapor Pressure: 1.52E-10mmHg at 25°C
• Melting Point: 160-167?C
• Boiling Point: 493.2°Cat760mmHg
• Flash Point: 252.1°C
• PSA: 59.30000
• Density: 1.33g/cm³
• LogP: 2.29100
• Storage Temp.: Refrigerator
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 255.08954328
• Heavy Atom Count: 19
• Complexity: 376

Purity/Quality:

97% ^*data from raw suppliers

(S)-Ketorolac ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2C(=CC=C2C(=O)C3=CC=CC=C3)C1C(=O)O
• Isomeric SMILES: C1CN2C(=CC=C2C(=O)C3=CC=CC=C3)[C@H]1C(=O)O
• 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.
• 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. The R-enantiomer of Ketorolac. The (S)-enantiomer is about 60 times more potent than (R)-enantiomer. Prostaglandin biosynthesis inhibitor. Analgesic; anti-inflammatory.

Technology Process of (S)-Ketorolac

There total 18 articles about (S)-Ketorolac which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

C15H13NO3*C18H39NO → S-ketorolac (66635-92-5)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate; at 20 ℃; for 0.5h; pH=6 - 7;

Reference yield:

C29H25NO5 → (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) + R-(+)-ketorolac (66635-93-6) + S-ketorolac (66635-92-5)

Guidance literature:

With sulfuric acid; In methanol; Sealed tube; Microwave irradiation;

DOI:10.1039/c7nj02898a

Reference yield:

Ketorolac (74103-06-3) → S-ketorolac (66635-92-5)

Guidance literature:

Yield given;

DOI:10.1021/jm00154a027

upstream raw materials:

Ketorolac

5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid methyl ester

ketorolac acid ethyl ester

2-methyl-propan-1-ol

Downstream raw materials:

diacetone 6'-O-ketorolac-D-galactopyranoside

Refernces

• 1、 Fuelling, Gerd,Sih, Charles J.. "Enzymatic Second-Order Asymmetric Hydrolysis of Ketorolac Esters: In Situ Racemization". . p. 2845 - 2846. Retrieved 1987.
• 2、 Juaristi, Eusebio,Pérez-Venegas, Mario,Rodríguez-Trevi?o, Agustín Mario. "Dual Mechanoenzymatic Kinetic Resolution of (±)-Ketorolac". . . Retrieved 2020/02/15.