Pure enantiomers are of large interest for several industries. This study was aimed to establish a method for separation of etodolac enantiomers by preferential crystallization after a conglomerate formation of its derivatives. S-(+)-etodolac and R-(-)-etodolac enantiomers were both prepared by classical resolution via crystallization of diastereoisomeric salt with (-)-brucine and (-)-cinchonidine. Enantiomeric purity of etodolac was determined by HPLC method using Chiralcel OD-H column. The pure diastereomeric salt collected from repeated recrystallization was further fractionated by liquid-liquid extraction to pure enantiomers. Etodolac enantiomers were recovered with overall yield more than 20% and the purities were over 99.9%.
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http://dx.doi.org/10.1007/s12272-009-2012-5 | DOI Listing |
Biochem Biophys Rep
July 2022
Stein Eye Institute, Department of Ophthalmology, David Geffen School of Medicine at University of California, Los Angeles, CA, 90095, USA.
Etodolac is an FDA-approved nonsteroidal anti-inflammatory drug (NSAID) used to treat a variety of inflammatory diseases. The drug is administered as a racemate (50/50 mixture of R- and S- enantiomers), however, studies have shown that the two enantiomers have distinct biologic and pharmacokinetic differences. Wnt signaling, which plays key roles in cell proliferation, polarity, and differentiation, has been shown to be inhibited by R-etodolac; however, comparative analyses of R- and S-etodolac in this function have not been conducted.
View Article and Find Full Text PDFJ Sep Sci
January 2020
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, India.
The control of enantiomeric purity and determination of individual enantiomeric drug molecules remains the subject of importance for clinical, analytical, and regulatory purposes and to facilitate an accurate evaluation of the risks posed by them to human health. A large number of pharmaceuticals are marketed and administered as racemates. Etodolac is among such nonsteroidal anti-inflammatory drugs.
View Article and Find Full Text PDFJ Chromatogr Sci
July 2019
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, India.
Direct resolution of (RS)-ketorolac and (RS)-etodolac has been achieved by ligand exchange thin layer chromatography. Cu(II) has been used as a complexing ion with three enantiomerically pure amino acids (namely, l-tryptophan, l-histidine and l-phenylalanine) as chiral dopants. Chromatograms were developed using different combinations of solvent systems in different ratio having no chiral additive.
View Article and Find Full Text PDFJ Assoc Physicians India
December 2017
Department of Chest and Tuberculosis, Vora Clinic, Mumbai, Maharashtra.
Chirally pure molecules or enantiomers are non-superimposable mirror images of each other with a chiral center (such as carbon, sulphur, nitrogen or phosphorous atom). An equimolar mixture of enantiomers forms a racemate. Chirally pure molecules (single enantiomers) are important in the field of drug discovery as the drug targets such as enzymes and receptors are enantioselective in nature.
View Article and Find Full Text PDFAAPS J
November 2017
Center for Pharmacometrics and Systems Pharmacology, Department of Pharmaceutics, College of Pharmacy, University of Florida, 6550 Sanger Road, Orlando, Florida, 32827, USA.
Cyclooxygenase-2 (COX-2) isoform has a critical role in the development of pain. Inhibition of COX-2 in vitro serves as a biomarker for nonsteroidal anti-inflammatory drugs (NSAIDs). The NSAID concentrations yielding 80% COX-2 inhibition (IC) correlate with therapeutic doses to achieve analgesia across multiple COX-2 inhibitors.
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