Enantioselective HPLC analysis of escitalopram oxalate and its impurities using a cellulose-based chiral stationary phase under normal- and green reversed-phase conditions.
absolute configuration
cellulose tris(4-methylbenzoate)
citalopram
escitalopram
green high-performance liquid chromatography
Journal
Journal of separation science
ISSN: 1615-9314
Titre abrégé: J Sep Sci
Pays: Germany
ID NLM: 101088554
Informations de publication
Date de publication:
Mar 2022
Mar 2022
Historique:
revised:
22
12
2021
received:
16
11
2021
accepted:
23
12
2021
pubmed:
28
12
2021
medline:
8
4
2022
entrez:
27
12
2021
Statut:
ppublish
Résumé
Normal-phase and reversed-phase high-performance liquid chromatography methods for the separation of the active pharmaceutical ingredient escitalopram from its (R)-enantiomer impurity have been developed on the cellulose-based Chiralcel OJ-H chiral stationary phase. Both methods share two features: they use ethanol as a cosolvent and are able to give a complete enantioseparation without interference from other associated chiral impurities. With the green eluent mixture ethanol-water-diethylammine 70:30:0.1 (v/v/v), the resolution between escitalopram and (R)-enantiomer was 2.09 at 30°C. The limits of quantification for the (S) and (R) enantiomers were 4.5 and 3.8 μg mL
Identifiants
pubmed: 34958717
doi: 10.1002/jssc.202100913
doi:
Substances chimiques
Oxalates
0
Escitalopram
4O4S742ANY
Cellulose
9004-34-6
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
1059-1066Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
The European Pharmacopoeia. Monograph: escitalopram oxalate 07/2016:2733. 2020, 2546-8.
Budău M, Hancu G, Rusu A, Cârcu-Dobrin M, Muntean DL Chirality of modern antidepressants: an overview. Adv Pharm Bull. 2017;7:495-500.
Sethi S, Bhushan R, Enantioselective LC analysis and determination of selective serotonin reuptake inhibitors. Biomed Chromatogr. 2020;34:1-18.
Hegstad S, Havnen H, Helland A, Falch BMH, Spigset O Enantiomeric separation and quantification of citalopram in serum by ultrahigh performance supercritical fluid chromatography-tandem mass spectrometry. J Chromatogr B. 2017;1061-1062:103-9.
Gupta VK, Ali I, Agarwa S, Enantiomeric analysis of citalopram in human plasma by SPE and chiral HPLC method. Int. J. Electrochem. Sci. 2011;6:5639-48.
Soliman SM, Enantiomeric assay of escitalopram S(+)-enantiomer and its “in-process impurities” using two different techniques. Chirality 2019;31:185-201.
Rahman A, Haque MR, Rahman MM, Rashid MA, Development and validation of a chiral HPLC method for quantitative analysis of enantiomeric escitalopram. Dhaka Univ. J. Pharm. Sci. 2017;16:165-72.
Rocha A, Marques MP, Coelho EB, Lanchote VL, Enantioselective analysis of citalopram and demethylcitalopram in human and rat plasma by chiral LC-MS/MS: application to pharmacokinetics. Chirality 2007;19:793-801.
Rochat B, Amey M, Van Gelderen H, Testa B, Bauma P, Determination of the enantiomers of citalopram, its demethylated and propionic acid metabolites in human plasma by chiral HPLC. Chirality 1995;7:389-95.
Geryk R, Vozka J, Kalíková K, Tesařová E, HPLC method for chiral separation and quantification of antidepressant citalopram and its precursor citadiol. Chromatographia 2013;76:483-9.
Semreen MH, Aboul-Enein HY, Enantioselective separation and determination of citalopram enantiomers in pharmaceutical dosage form and bulk drug using experimental design approach on Chiralcel® OC as a chiral stationary phase. Acta Chromatogr. 2011;3:23389-401.
Ferretti R Zanitti L, Cirilli R, Development of a high-performance liquid chromatography method for the simultaneous determination of chiral impurities and assay of (S)-clopidogrel using a cellulose-based chiral stationary phase in methanol/water mode. J. Sep. Sci. 2018;41:1208-15.
Panella C, Ferretti R, Casulli A, Cirilli R, Temperature and eluent composition effects on enantiomer separation of carvedilol by high-performance liquid chromatography on immobilized amylose-based chiral stationary phases. J. Pharm. Anal. 2019;9:324-31.
Scapinello L, Grecchi S, Rossi S, Arduini F, Arnaboldi S, Penoni A, Cirilli R, Mussini PR, Benincori T, Modulating the enantiodiscrimination features of inherently chiral selectors by molecular design: a HPLC and voltammetry study case with atropisomeric 2,2’-biindole-based monomers and oligomer films. Chem. Eur. J. 2021;27:13190-202.
Rosetti A Ferretti R, Villani C, Pierini M, Cirilli R, Simultaneous enantio- and diastereo-selective high-performance liquid chromatography separation of paroxetine on an immobilized amylose-based chiral stationary phase under green reversed-phase conditions. J. Chromatogr. A. 2021;1653:462406.
Ferretti R, Zanitti L, Casulli A, Cirilli R, Green high-performance liquid chromatography enantioseparation of lansoprazole using a cellulose-based chiral stationary phase under ethanol/water mode. J. Sep. Sci. 2016;39:1418-24.
Capello C, Fischer U, Hungerbühlera K, What is a green solvent? A comprehensive framework for the environmental assessment of solvents. Green Chem. 2007;9:927-34.
Płotka J, Tobiszewski M, Sulej AM, Kupska M, Górecki T, Namieśnik J, Green chromatography. J. Chromatogr. A. 2013;1307:1-20.
Chen K, Lynen F, De Beer M, Hitzel L, Ferguson P, Hanna-Brown M, Sandra P, Selectivity optimization in green chromatography by gradient stationary phase optimized selectivity liquid chromatography. J. Chromatogr. A. 2010;1217:7222-30.
Colombo M, Ferretti R, Zanitti L, Cirilli R, Direct separation of the enantiomers of ramosetron on a chlorinated cellulose-based chiral stationary phase in hydrophilic interaction liquid chromatography mode. J. Sep. Sci. 2020;43:2589-93.
Cirilli R, Carradori S,. Casulli A, Pierini M, A chromatographic study on the retention behavior of the amylose tris(3-chloro-5-methylphenylcarbamate) chiral stationary phase under aqueous conditions. J. Sep. Sci. 2018;41:4014-21.