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Current Pharmaceutical Analysis

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ISSN (Print): 1573-4129
ISSN (Online): 1875-676X

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Review Article

Recent Trends in Chiral Separation-A Collective Paradigm of Selected Chiral Impurities

Author(s): Prachi Raikar and Gurupadayya Bannimath*

Volume 16, Issue 5, 2020

Page: [456 - 473] Pages: 18

DOI: 10.2174/1573412915666181219144507

Price: $65

Abstract

Chiral separation plays a very important role in the modern pharmaceutical analysis and will continue in upcoming years. Separation and identification of chiral impurities are indispensable. According to ICH guidelines, only the active enantiomer of the drug has to be marketed, so there is a focus on separation of the inactive enantiomer which acts as a chiral impurity. The impurities present in the enantiomers also pose various toxic adverse effects on bioavailability and efficacy, hence the need to separate these impurities will forever be trending. This review primarily focuses on the separation techniques like Capillary Electrophoresis (CE), High-Performance Liquid Chromatography (HPLC), Gas Chromatography (GC), and Supercritical Fluid Chromatography (SFC) followed by the year-wise trend in the separation of selected chiral impurities. In the coming years, researchers should work on using ultra-fast, selective, and sensitive methods for the effective separation of chiral impurities.

Keywords: Capillary Electrophoresis (CE), chiral impurities, chirality, Chiral Stationary Phase (CSP), enantiomers, High- Performance Liquid Chromatography (HPLC).

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Graphical Abstract

[1]
Görög, S. Identification and determination of impurities in drugs; Elsevier, 2000.
[2]
Cohen, M.N.; Christians, U.; Henthorn, T.; Vu Tran, Z.; Moll, V.; Zuk, J.; Galinkin, J. Pharmacokinetics of single-dose intravenous ketorolac in infants aged 2-11 months. Anesth. Analg., 2011, 112(3), 655-660.
[http://dx.doi.org/10.1213/ANE.0b013e3182075d04] [PMID: 21233498]
[3]
Chiral HPLC of Antihistamines Utility of Chirex™ Chiral Stationary Phases, Tom Cleveland Phenomenex Inc; Torrance: CA, USA, 2011.
[4]
Wadekar, K.R.; Bhalme, M.; Rao, S.S.; Reddy, K.V.; Kumar, L.S.; Balasubrahmanyam, E. Evaluating impurities in drugs (Part II of III). Pharm. Technol., 2012, 2(36), 58-72.
[5]
General chapters. Ordinary impurities and Impurities in official articles. USP 28-NF 23,
[6]
Rahman, N.; Khan, S. Circular dichroism spectroscopy: An efficient approach for the quantitation of ampicillin in presence of cloxacillin. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2016, 160, 26-33.
[http://dx.doi.org/10.1016/j.saa.2016.02.009] [PMID: 26909703]
[7]
Siddiqui, M.R.; AlOthman, Z.A.; Rahman, N. Analytical techniques in pharmaceutical analysis: a review. Arab. J. Chem., 2017, 10, 1409-1421.
[http://dx.doi.org/10.1016/j.arabjc.2013.04.016]
[8]
AlOthman, Z.A.; Rahman, N.; Siddiqui, M.R. Review on pharmaceutical impurities, stability studies and degradation products. Rev. Adv. Sci. Eng., 2013, 2, 155-166.
[http://dx.doi.org/10.1166/rase.2013.1039]
[9]
Rahman, N.; Azmi, S.N.H.; Wu, H.F. The importance of impurity analysis in pharmaceutical products: an integrated approach. Accredit. Qual. Assur., 2006, 11, 69-74.
[http://dx.doi.org/10.1007/s00769-006-0095-y]
[10]
Gübitz, G.; Schmid, M.G. Chiral separation principles in capillary electrophoresis. J. Chromatogr. A, 1997, 792, 179-225.
[http://dx.doi.org/10.1016/S0021-9673(97)00871-6]
[11]
Gassmann, E.; Kuo, J.E.; Zare, R.N. Electrokinetic separation of chiral compounds. Science, 1985, 230(4727), 813-814.
[http://dx.doi.org/10.1126/science.230.4727.813] [PMID: 17791795]
[12]
Mikuš, P.; Maráková, K. Advanced CE for chiral analysis of drugs, metabolites, and biomarkers in biological samples. Electrophoresis, 2009, 30(16), 2773-2802.
[http://dx.doi.org/10.1002/elps.200900173] [PMID: 19653234]
[13]
Waldhier, M.C.; Gruber, M.A.; Dettmer, K.; Oefner, P.J. Capillary electrophoresis and column chromatography in biomedical chiral amino acid analysis. Anal. Bioanal. Chem., 2009, 394(3), 695-706.
[http://dx.doi.org/10.1007/s00216-009-2792-y] [PMID: 19396430]
[14]
Ward, T.J.; Ward, K.D. Chiral separations: a review of current topics and trends. Anal. Chem., 2012, 84(2), 626-635.
[http://dx.doi.org/10.1021/ac202892w] [PMID: 22066781]
[15]
Li, B.; Haynie, D.T. Chiral drug separation. Encycl. Chem. Process., 2006, 1, 449-458.
[16]
Valliappan, K. Reflections on chiral chromatographic analysis. Indian J. Pharm. Sci., 2005, 67, 273.
[17]
Ward, T.J.; Ward, K.D. Chiral separations: fundamental review 2010. Anal. Chem., 2010, 82(12), 4712-4722.
[http://dx.doi.org/10.1021/ac1010926] [PMID: 20496871]
[18]
He, L.; Beesley, T.E. Applications of Enantiomeric Gas Chromatography: A Review. J. Liq. Chromatogr. Relat. Technol., 2005, 28, 1075-1114.
[http://dx.doi.org/10.1081/JLC-200052997]
[19]
Stalcup, A.M.; Gahm, K.H. Application of sulfated cyclodextrins to chiral separations by capillary zone electrophoresis. Anal. Chem., 1996, 68(8), 1360-1368.
[http://dx.doi.org/10.1021/ac950764a] [PMID: 8651498]
[20]
Dette, C.; Ebel, S.; Terabe, S. Neutral and anionic cyclodextrins in capillary zone electrophoresis: enantiomeric separation of ephedrine and related compounds. Electrophoresis, 1994, 15(6), 799-803.
[http://dx.doi.org/10.1002/elps.11501501112] [PMID: 7982402]
[21]
Assi, K.H.; Abushoffa, A.M.; Altria, K.D.; Clark, B.J. Determination of trace enantiomeric impurities in chiral compounds by capillary electrophoresis with uncoated, cationic, anionic and neutral surface modified capillaries. J. Chromatogr. A, 1998, 817, 83-90.
[http://dx.doi.org/10.1016/S0021-9673(98)00245-3]
[22]
Fillet, M.; Fotsing, L.; Crommen, J. Enantioseparation of uncharged compounds by capillary electrophoresis using mixtures of anionic and neutral β-cyclodextrin derivatives. J. Chromatogr. A, 1998, 817, 113-119.
[http://dx.doi.org/10.1016/S0021-9673(98)00442-7]
[23]
Cai, H.; Vigh, G. Capillary electrophoretic separation of enantiomers using the single isomer heptakis-(2, 3-dimethyl-6-sulfato)-β-cyclodextrin as chiral resolving agent in methanol-water background electrolytes. J. Chromatogr. A, 1998, 827, 121-132.
[http://dx.doi.org/10.1016/S0021-9673(98)00767-5]
[24]
Murdoch, D.; McTavish, D. Sertraline. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in depression and obsessive-compulsive disorder. Drugs, 1992, 44(4), 604-624.
[http://dx.doi.org/10.2165/00003495-199244040-00007] [PMID: 1281075]
[25]
Lucangioli, S.E.; Hermida, L.G.; Tripodi, V.P.; Rodríguez, V.P.; López, E.E.; Rouge, P.D.; Carducci, C.N. Analysis of cis-trans isomers and enantiomers of sertraline by cyclodextrin-modified micellar electrokinetic chromatography. J. Chromatogr. A, 2000, 871(1-2), 207-215.
[http://dx.doi.org/10.1016/S0021-9673(99)00881-X] [PMID: 10735301]
[26]
Bicker, W.; Hebenstreit, D.; Lämmerhofer, M.; Lindner, W. Enantiomeric impurity profiling in ephedrine samples by enantioselective capillary electrochromatography. Electrophoresis, 2003, 24(15), 2532-2542.
[http://dx.doi.org/10.1002/elps.200305489] [PMID: 12900865]
[27]
Sweetman, S.C. The Complete Drug Reference; Pharmaceutical Press: London, 2002, pp. 553-557.
[28]
Gotti, R.; El-Hady, D.A.; Andrisano, V.; Bertucci, C.; El-Maali, N.A.; Cavrini, V. Determination of the chiral and achiral related substances of methotrexate by cyclodextrin-modified micellar electrokinetic chromatography. Electrophoresis, 2004, 25(16), 2830-2837.
[http://dx.doi.org/10.1002/elps.200405926] [PMID: 15352016]
[29]
Abushoffa, A.M.; Fillet, M.; Marini, R.D.; Hubert, P.; Crommen, J. Enantiomeric separation of amino glutethimide by capillary electrophoresis using native cyclodextrins in single and dual systems. J. Sep. Sci., 2003, 26, 536-542.
[http://dx.doi.org/10.1002/jssc.200390073]
[30]
Marini, R.D.; Matthijs, N.; Vander, Heyden, Y.; Smeyers-Verbeke, J.; Dehouck, P.; Hoogmartens, J.; Silvestre, P.; Ceccato, A.; Goedert, P.; Saevels, J.; Herbots, C. Collaborative study of an liquid chromatographic method for the determination of R-Timolol and other related substances in S-Timolol maleate. Anal. Chim. Acta, 2005, 546, 182-192.
[http://dx.doi.org/10.1016/j.aca.2005.05.026]
[31]
Yates, R.; Nairn, K.; Dixon, R.; Kemp, J.V.; Dane, A.L. Pharmacokinetics, dose proportionality, and tolerability of single and repeat doses of a nasal spray formulation of zolmitriptan in healthy volunteers. J. Clin. Pharmacol., 2002, 42(11), 1244-1250.
[http://dx.doi.org/10.1177/009127002762491334] [PMID: 12412823]
[32]
Oldman, A.D.; Smith, L.A.; McQuay, H.J.; Moore, R.A. Pharmacological treatments for acute migraine: quantitative systematic review. Pain, 2002, 97(3), 247-257.
[http://dx.doi.org/10.1016/S0304-3959(02)00024-6] [PMID: 12044621]
[33]
Srinivasu, M.K.; Rao, B.M.; Sridhar, G.; Kumar, P.R.; Chandrasekhar, K.B.; Islam, A. A validated chiral LC method for the determination of zolmitriptan and its potential impurities. J. Pharm. Biomed. Anal., 2005, 37(3), 453-460.
[http://dx.doi.org/10.1016/j.jpba.2004.10.021] [PMID: 15740903]
[34]
Roussel, C.; Del Rio, A.; Pierrot-Sanders, J.; Piras, P.; Vanthuyne, N. Chiral liquid chromatography contribution to the determination of the absolute configuration of enantiomers. J. Chromatogr. A, 2004, 1037(1-2), 311-328.
[http://dx.doi.org/10.1016/j.chroma.2004.01.065] [PMID: 15214673]
[35]
Okamoto, M. Reversal of elution order during the chiral separation in high performance liquid chromatography. J. Pharm. Biomed. Anal., 2002, 27(3-4), 401-407.
[http://dx.doi.org/10.1016/S0731-7085(01)00646-X] [PMID: 11755741]
[36]
Gasparrini, F.; Misiti, D.; Villani, C. High-performance liquid chromatography chiral stationary phases based on low-molecular-mass selectors. J. Chromatogr. A, 2001, 906(1-2), 35-50.
[http://dx.doi.org/10.1016/S0021-9673(00)00953-5] [PMID: 11215896]
[37]
Franco, P.; Senso, A.; Oliveros, L.; Minguillón, C. Covalently bonded polysaccharide derivatives as chiral stationary phases in high-performance liquid chromatography. J. Chromatogr. A, 2001, 906(1-2), 155-170.
[http://dx.doi.org/10.1016/S0021-9673(00)00531-8] [PMID: 11215885]
[38]
Felix, G. Regioselectively modified polysaccharide derivatives as chiral stationary phases in high-performance liquid chromatography. J. Chromatogr. A, 2001, 906(1-2), 171-184.
[http://dx.doi.org/10.1016/S0021-9673(00)00943-2] [PMID: 11215886]
[39]
Ward, T.J.; Baker, B.A. Chiral separations. Anal. Chem., 2008, 80(12), 4363-4372.
[http://dx.doi.org/10.1021/ac800662y] [PMID: 18481872]
[40]
Sellers, J.A.; Olsen, B.A.; Owens, P.K.; Gavin, P.F. Determination of the enantiomer and positional isomer impurities in atomoxetine hydrochloride with liquid chromatography using polysaccharide chiral stationary phases. J. Pharm. Biomed. Anal., 2006, 41(4), 1088-1094.
[http://dx.doi.org/10.1016/j.jpba.2006.01.063] [PMID: 16533585]
[41]
Vincent, J.; Elliott, H.L.; Meredith, P.A.; Reid, J.L. Doxazosin, an alpha 1-adrenoceptor antagonist: pharmacokinetics and concentration-effect relationships in man. Br. J. Clin. Pharmacol., 1983, 15(6), 719-725.
[http://dx.doi.org/10.1111/j.1365-2125.1983.tb01556.x] [PMID: 6135439]
[42]
Nageswara Rao, R.; Nagaraju, D.; Narasa Raju, A. Enantiomeric resolution of doxazosin mesylate and its process-related substances on polysaccharide chiral stationary phases. J. Pharm. Biomed. Anal., 2006, 41(3), 766-773.
[http://dx.doi.org/10.1016/j.jpba.2006.01.019] [PMID: 16495033]
[43]
Castro-Puyana, M.; Crego, A.L.; Marina, M.L. Enantiomeric separation of ketoconazole and terconazole antifungals by electrokinetic chromatography: Rapid quantitative analysis of ketoconazole in pharmaceutical formulations. Electrophoresis, 2005, 26(20), 3960-3968.
[http://dx.doi.org/10.1002/elps.200500100] [PMID: 16217826]
[44]
Castro-Puyana, M.; García-Ruiz, C.; Cifuentes, A.; Crego, A.L.; Marina, M.L. Identification and quantitation of cis-ketoconazole impurity by capillary zone electrophoresis-mass spectrometry. J. Chromatogr. A, 2006, 1114(1), 170-177.
[http://dx.doi.org/10.1016/j.chroma.2006.02.030] [PMID: 16516899]
[45]
Zheng, J.; Norton, D.; Shamsi, S.A. Fabrication of internally tapered capillaries for capillary electrochromatography electrospray ionization mass spectrometry. Anal. Chem., 2006, 78(4), 1323-1330.
[http://dx.doi.org/10.1021/ac051480l] [PMID: 16478129]
[46]
De Rossi, A.; Desiderio, C. Fast capillary electrochromatographic analysis of parabens and 4-hydroxybenzoic acid in drugs and cosmetics. Electrophoresis, 2002, 23(19), 3410-3417.
[http://dx.doi.org/10.1002/1522-2683(200210)23:19<3410:AID-ELPS3410>3.0.CO;2-I] [PMID: 12373771]
[47]
Kvasnicková, L.; Glatz, Z.; Sterbová, H.; Kahle, V.; Slanina, J.; Musil, P. Application of capillary electrochromatography using macroporous polyacrylamide columns for the analysis of lignans from seeds of Schisandra chinensis. J. Chromatogr. A, 2001, 916(1-2), 265-271.
[http://dx.doi.org/10.1016/S0021-9673(01)00556-8] [PMID: 11382300]
[48]
Desiderio, C.; De Rossi, A.; Sinibaldi, M. Analysis of flavanone-7-O-glycosides in citrus juices by short-end capillary electrochromatography. J. Chromatogr. A, 2005, 1081(1), 99-104.
[http://dx.doi.org/10.1016/j.chroma.2005.01.009] [PMID: 16013605]
[49]
Ganzera, M.; Stöggl, W.M.; Bonn, G.K.; Khan, I.A.; Stuppner, H. Capillary electro chromatography of boswellic acids in BoswelliaserrataRoxb. J. Sep. Sci., 2003, 26, 1383-1388.
[http://dx.doi.org/10.1002/jssc.200301562]
[50]
Mangelings, D.; Saevels, J.; Vander Heyden, Y. Enantiomeric impurity determination of levetiracetam using capillary electrochromatography. J. Sep. Sci., 2006, 29(18), 2827-2836.
[http://dx.doi.org/10.1002/jssc.200600190] [PMID: 17305245]
[51]
Hong, J.W.; Hu, C.Q. Determination of Enantiomeric Impurity of Antofloxacin Hydrochloride by Capillary Electrophoresis. J. Instr. Anal., 2007, 26, 888.
[52]
Tellez, S.; Colpaert, F.; Marien, M. The α 2-adrenoceptor antagonist, (+)-efaroxan, enhances acetylcholine release in the rat cortex in vivo. Eur. J. Pharmacol., 1995, 277(1), 113-116.
[http://dx.doi.org/10.1016/0014-2999(95)00110-7] [PMID: 7635166]
[53]
Silveira, G.P.; Coelho, F. Enantioselective synthesis of 2-ethyl-2, 3-dihydrobenzofuran carboxylic acid, direct precursor of (+)-Efaroxan, from a Baylis-Hillman adduct. Tetrahedron Lett., 2005, 46, 6477-6781.
[http://dx.doi.org/10.1016/j.tetlet.2005.07.099]
[54]
Pena, R.; Ribet, J.P.; Maurel, J.L.; Volta, L.; Lacoulonche, F.; Chauvet, A. Sublimation and vaporization processes of S (-) Efaroxan hydrochloride. Thermochim. Acta, 2003, 408, 85-96.
[http://dx.doi.org/10.1016/S0040-6031(03)00321-6]
[55]
Lorin, M.; Delepee, R.; Maurizot, J.C.; Ribet, J.P.; Morin, P. Sensitivity improvement of circular dichroism detection in HPLC by using a low-pass electronic noise filter: Application to the enantiomeric determination purity of a basic drug. Chirality, 2007, 19(2), 106-113.
[http://dx.doi.org/10.1002/chir.20352] [PMID: 17096379]
[56]
Lorin, M.; Delépée, R.; Ribet, J.P.; Morin, P. Validation of a method using an achiral liquid chromatography sorbent and a circular dichroism detector. Analysis of the efaroxan enantiomers. J. Chromatogr. A, 2007, 1141(2), 244-250.
[http://dx.doi.org/10.1016/j.chroma.2006.12.036] [PMID: 17207805]
[57]
Lorin, M.; Delépée, R.; Morin, P.; Ribet, J.P. Quantification of very low enantiomeric impurity of efaroxan using a dual cyclodextrin system by capillary electrophoresis. Anal. Chim. Acta, 2007, 592(2), 139-145.
[http://dx.doi.org/10.1016/j.aca.2007.04.018] [PMID: 17512818]
[58]
Cheng, F.C.; Tsai, T.R.; Chen, Y.F.; Hung, L.C.; Tsai, T.H. Pharmacokinetic study of levofloxacin in rat blood and bile by microdialysis and high-performance liquid chromatography. J. Chromatogr. A, 2002, 961(1), 131-136.
[http://dx.doi.org/10.1016/S0021-9673(02)00506-X] [PMID: 12186384]
[59]
Yan, H.; Row, K.H. Rapid chiral separation and impurity determination of levofloxacin by ligand-exchange chromatography. Anal. Chim. Acta, 2007, 584(1), 160-165.
[http://dx.doi.org/10.1016/j.aca.2006.11.023] [PMID: 17386599]
[60]
Hedeland, Y.; Lehtinen, J.; Pettersson, C. Ketopinic acid and diisoproylideneketogulonic acid as chiral ion-pair selectors in capillary electrophoresis. Enantiomeric impurity analysis of S-timolol and 1R,2S-ephedrine. J. Chromatogr. A, 2007, 1141(2), 287-294.
[http://dx.doi.org/10.1016/j.chroma.2006.12.013] [PMID: 17187814]
[61]
Baumann, P. Pharmacology and pharmacokinetics of citalopram and other SSRIs. Int. Clin. Psychopharmacol., 1996, 11(Suppl. 1), 5-11.
[http://dx.doi.org/10.1097/00004850-199603001-00002] [PMID: 8732438]
[62]
Hyttel, J.; Bøgesø, K. P.; Perregaard, J.; Sanchez, C. The pharmacological effect of citalopram resides in the (S)-(+)-enantiomer. Journal of Neural Transmission/General Section JNT, 1992, 88, 157-160.
[63]
Sungthong, B.; Jác, P.; Scriba, G.K. Development and validation of a capillary electrophoresis method for the simultaneous determination of impurities of escitalopram including the R-enantiomer. J. Pharm. Biomed. Anal., 2008, 46(5), 959-965.
[http://dx.doi.org/10.1016/j.jpba.2007.05.029] [PMID: 17629435]
[64]
Dung, P.T.; Ko, M.Y.; Choi, H.J.; Sin, K.S.; Kim, K.H. Determination of enantiomeric impurity of etodolac by capillary electrophoresis using (2-hydroxypropyl)-β-cyclodextrin. Arch. Pharm. Res., 2008, 31(9), 1218-1223.
[http://dx.doi.org/10.1007/s12272-001-1292-4] [PMID: 18806967]
[65]
Clemett, D.; Markham, A. Linezolid. Drugs, 2000, 59(4), 815-827.
[http://dx.doi.org/10.2165/00003495-200059040-00007] [PMID: 10804037]
[66]
Michalska, K.; Pajchel, G.; Tyski, S. Determination of enantiomeric impurity of linezolid by capillary electrophoresis using heptakis-(2,3-diacetyl-6-sulfato)-β-cyclodextrin. J. Chromatogr. A, 2008, 1180(1-2), 179-186.
[http://dx.doi.org/10.1016/j.chroma.2007.11.110] [PMID: 18164025]
[67]
Andersson, T. Pharmacokinetics, metabolism and interactions of acid pump inhibitors. Focus on omeprazole, lansoprazole and pantoprazole. Clin. Pharmacokinet., 1996, 31(1), 9-28.
[http://dx.doi.org/10.2165/00003088-199631010-00002] [PMID: 8827397]
[68]
Guan, J.; Yang, J.; Bi, Y.; Shi, S.; Yan, F.; Li, F. Determination of the enantiomeric impurity in S-(-)pantoprazole using high performance liquid chromatography with sulfobutylether-beta-cyclodextrin as chiral additive. J. Sep. Sci., 2008, 31(2), 288-293.
[http://dx.doi.org/10.1002/jssc.200700369] [PMID: 18196525]
[69]
Dworkin, R.H.; Corbin, A.E.; Young, J.P., Jr; Sharma, U.; LaMoreaux, L.; Bockbrader, H.; Garofalo, E.A.; Poole, R.M. Pregabalin for the treatment of postherpetic neuralgia: a randomized, placebo-controlled trial. Neurology, 2003, 60(8), 1274-1283.
[http://dx.doi.org/10.1212/01.WNL.0000055433.55136.55] [PMID: 12707429]
[70]
Chen, X.; Zhang, D.; Deng, J.; Fu, X. Determination of optical impurity of pregabalin by HPLC with pre-column chiral derivatization. J. Chromatogr. Sci., 2008, 46(1), 42-44.
[http://dx.doi.org/10.1093/chromsci/46.1.42] [PMID: 18218187]
[71]
Bertaina-Anglade, V.; La Rochelle, C.D.; Scheller, D.K. Antidepressant properties of rotigotine in experimental models of depression. Eur. J. Pharmacol., 2006, 548(1-3), 106-114.
[http://dx.doi.org/10.1016/j.ejphar.2006.07.022] [PMID: 16959244]
[72]
Chu, B.L.; Guo, B.; Zuo, H.; Wang, Z.; Lin, J.M. Simultaneous enantioseparation of antiparkinsonian medication Rotigotine and related chiral impurities by capillary zone electrophoresis using dual cyclodextrin system. J. Pharm. Biomed. Anal., 2008, 46(5), 854-859.
[http://dx.doi.org/10.1016/j.jpba.2007.02.010] [PMID: 17383843]
[73]
Richter, T.; Mürdter, T.E.; Heinkele, G.; Pleiss, J.; Tatzel, S.; Schwab, M.; Eichelbaum, M.; Zanger, U.M. Potent mechanism-based inhibition of human CYP2B6 by clopidogrel and ticlopidine. J. Pharmacol. Exp. Ther., 2004, 308(1), 189-197.
[http://dx.doi.org/10.1124/jpet.103.056127] [PMID: 14563790]
[74]
Fayed, A.S.; Weshahy, S.A.; Shehata, M.A.; Hassan, N.Y.; Pauwels, J.; Hoogmartens, J.; Van Schepdael, A. Separation and determination of clopidogrel and its impurities by capillary electrophoresis. J. Pharm. Biomed. Anal., 2009, 49(2), 193-200.
[http://dx.doi.org/10.1016/j.jpba.2008.10.031] [PMID: 19081694]
[75]
Prakash, A.; Faulds, D. Rabeprazole. Drugs, 1998, 55(2), 261-267.
[http://dx.doi.org/10.2165/00003495-199855020-00009] [PMID: 9506245]
[76]
Cirilli, R.; Ferretti, R.; Gallinella, B.; Turchetto, L.; Zanitti, L.; La Torre, F. Development and validation of an enantioselective and chemoselective HPLC method using a Chiralpak IA column to simultaneously quantify (R)-(+)- and (S)-(-)-lansoprazole enantiomers and related impurities. J. Pharm. Biomed. Anal., 2009, 50(1), 9-14.
[http://dx.doi.org/10.1016/j.jpba.2009.03.021] [PMID: 19411156]
[77]
Doogan, D.P.; Caillard, V. Sertraline: a new antidepressant. J. Clin. Psychiatry, 1988, 49(Suppl.), 46-51.
[PMID: 2842321]
[78]
Rao, R.N.; Talluri, M.V.; Maurya, P.K. Separation of stereoisomers of sertraline and its related enantiomeric impurities on a dimethylated β-cyclodextrin stationary phase by HPLC. J. Pharm. Biomed. Anal., 2009, 50(3), 281-286.
[http://dx.doi.org/10.1016/j.jpba.2009.04.038] [PMID: 19502000]
[79]
Gillberg, P.G.; Sundquist, S.; Nilvebrant, L. Comparison of the in vitro and in vivo profiles of tolterodine with those of subtype-selective muscarinic receptor antagonists. Eur. J. Pharmacol., 1998, 349(2-3), 285-292.
[http://dx.doi.org/10.1016/S0014-2999(98)00214-3] [PMID: 9671109]
[80]
Krishna, S.R.; Rao, B.M.; Rao, N.S. A validated stability-indicating HPLC method for the determination of related substances and assay of Tolterodinetartrate. Rasayan J. Chem., 2009, 2, 144-150.
[81]
Elzanfaly, E.S.; Zaazaa, H.E.; Soudi, A.T.; Salem, M.Y. Validated chiral chromatographic methods for clopidogrel bisulphate and its related substances in bulk drug and pharmaceutical dosage forms. Chem. Pap., 2015, 69, 1541-1547.
[http://dx.doi.org/10.1515/chempap-2015-0179]
[82]
Durga Rao, D.; Kalyanaraman, L.; Sait, S.S.; Venkata Rao, P. A validated stability-indicating normal phase LC method for clopidogrel bisulfate and its impurities in bulk drug and pharmaceutical dosage form. J. Pharm. Biomed. Anal., 2010, 52(1), 160-165.
[http://dx.doi.org/10.1016/j.jpba.2009.12.027] [PMID: 20074888]
[83]
Walter, P.; Schaffhauser, A.O. L-Carnitine, a ‘Vitamin-like Substance’ for functional food. Proceedings Of the symposium on L-carnitine, april 28 to may 1, 2000, zermatt, switzerland. Ann. Nutr. Metab., 2000, 44(2), 75-96.
[http://dx.doi.org/10.1159/000012825] [PMID: 10970996]
[84]
Sánchez-Hernández, L.; García-Ruiz, C.; Crego, A.L.; Marina, M.L. Sensitive determination of D-carnitine as enantiomeric impurity of levo-carnitine in pharmaceutical formulations by capillary electrophoresis-tandem mass spectrometry. J. Pharm. Biomed. Anal., 2010, 53(5), 1217-1223.
[http://dx.doi.org/10.1016/j.jpba.2010.03.031] [PMID: 20392588]
[85]
Kale-Pradhan, P.B.; Landry, H.K.; Sypula, W.T. Esomeprazole for acid peptic disorders. Ann. Pharmacother., 2002, 36(4), 655-663.
[http://dx.doi.org/10.1345/aph.1A104] [PMID: 11918517]
[86]
Andersson, T. Single-isomer drugs: true therapeutic advances. Clin. Pharmacokinet., 2004, 43(5), 279-285.
[http://dx.doi.org/10.2165/00003088-200443050-00001] [PMID: 15080761]
[87]
Zanitti, L.; Ferretti, R.; Gallinella, B.; La Torre, F.; Sanna, M.L.; Mosca, A.; Cirilli, R. Direct HPLC enantioseparation of omeprazole and its chiral impurities: application to the determination of enantiomeric purity of esomeprazole magnesium trihydrate. J. Pharm. Biomed. Anal., 2010, 52(5), 665-671.
[http://dx.doi.org/10.1016/j.jpba.2010.02.021] [PMID: 20338705]
[88]
Murthy, M.V.; Krishnaiah, C.; Jyothirmayi, K.; Srinivas, K.; Mukkanti, K.; Kumar, R. Enantioseparation of Palonosetron hydrochloride and its related enantiomeric impurities by computer simulation and validation. Am. J. Anal. Chem., 2011, 2, 437.
[http://dx.doi.org/10.4236/ajac.2011.24053]
[89]
Wang, W.; Xiang, S.; Zhou, X.; Ji, Y.; Xiang, B. Enantiomeric separation and determination of the enantiomeric impurity of armodafinil by capillary electrophoresis with sulfobutyl ether-β-cyclodextrin as chiral selector. Molecules, 2011, 17(1), 303-314.
[http://dx.doi.org/10.3390/molecules17010303] [PMID: 22210169]
[90]
Chang, M.H.; Fung, H.B. Besifloxacin: a topical fluoroquinolone for the treatment of bacterial conjunctivitis. Clin. Ther., 2010, 32(3), 454-471.
[http://dx.doi.org/10.1016/j.clinthera.2010.03.013] [PMID: 20399984]
[91]
Wang, Z.; Wang, S.; Zhu, F.; Chen, Z.; Yu, L.; Zeng, S. Determination of enantiomeric impurity in besifloxacin hydrochloride by chiral high-performance liquid chromatography with precolumn derivatization. Chirality, 2012, 24(7), 526-531.
[http://dx.doi.org/10.1002/chir.22042] [PMID: 22593028]
[92]
Deng, X.; De Wolf, J.; Vervoort, R.; Pamperin, D.; Adams, E.; Schepdael, A.V. Development and validation of a capillary electrophoresis method for the determination of escitalopram and sensitive quantification of its enantiomeric impurity in formulations. Electrophoresis, 2012, 33(11), 1648-1651.
[http://dx.doi.org/10.1002/elps.201100580] [PMID: 22736368]
[93]
Centers for Disease Control and Prevention.. https://www.cdc.gov/(2011)2018.
[94]
Dahab, A.A.; Smith, N.W. Determination of trace amount of enantiomeric impurity in therapeutic nicotine derivative using capillary electrophoresis with new imaging technology detection. J. Sep. Sci., 2012, 35(1), 66-72.
[http://dx.doi.org/10.1002/jssc.201100513] [PMID: 22128114]
[95]
Meredith, P.A.; Elliott, H.L. Clinical pharmacokinetics of amlodipine. Clin. Pharmacokinet., 1992, 22(1), 22-31.
[http://dx.doi.org/10.2165/00003088-199222010-00003] [PMID: 1532771]
[96]
Murdoch, D.; Heel, R.C. Amlodipine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in cardiovascular disease. Drugs, 1991, 41(3), 478-505.
[http://dx.doi.org/10.2165/00003495-199141030-00009] [PMID: 1711448]
[97]
Auditore, R.; Santagati, N.A.; Aturki, Z.; Fanali, S. Enantiomeric separation of amlodipine and its two chiral impurities by nano-liquid chromatography and capillary electrochromatography using a chiral stationary phase based on cellulose tris(4-chloro-3-methylphenylcarbamate). Electrophoresis, 2013, 34(17), 2593-2600.
[http://dx.doi.org/10.1002/elps.201300157] [PMID: 23775281]
[98]
McKeage, K.; Blick, S.K.; Croxtall, J.D.; Lyseng-Williamson, K.A.; Keating, G.M. Esomeprazole: a review of its use in the management of gastric acid-related diseases in adults. Drugs, 2008, 68(11), 1571-1607.
[http://dx.doi.org/10.2165/00003495-200868110-00009] [PMID: 18627213]
[99]
Estevez, P.; Flor, S.; Boscolo, O.; Tripodi, V.; Lucangioli, S. Development and validation of a capillary electrophoresis method for determination of enantiomeric purity and related substances of esomeprazole in raw material and pellets. Electrophoresis, 2014, 35(6), 804-810.
[http://dx.doi.org/10.1002/elps.201300334] [PMID: 24258683]
[100]
Qi, Y.; Zhang, X. Determination of enantiomeric impurity of levamlodipine besylate bulk drug by capillary electrophoresis using carboxymethyl-β-cyclodextrin. Cell Biochem. Biophys., 2014, 70(3), 1633-1637.
[http://dx.doi.org/10.1007/s12013-014-0106-2] [PMID: 25269770]
[101]
Wang, S.Z.; Zhao, Y.F.; Sun, J.Y.; Guo, X.J. Determination of enantiomeric impurity in levocetirizine tablets by capillary electrophoresis. Zhejiang da xuexuebao. Yi xue ban. Journal of Zhejiang University. Med. Sci., 2014, 43, 150-154.
[102]
Zhu, Q.Y.; Yu, L.S.; Zheng, G.G.; Xie, S.G.; Tao, Q.F. Determination of enantiomeric impurity of Timolol maleate in bulk substances and eye drops. Zhejiang da xuexuebao. Yi xue ban. J. Zhejiang Univ. Med. Sci., 2014, 43, 160-163.
[103]
Balamurugan, P.; Anver Bash, K.; Jayachandran, J.E.; Gangrade, M.A.; Parthiban, P. A simple RP-HPLC method for simultaneous estimation of organic impurities, enantiomer and assay of Dexlansoprazole. Int. J. Pharma Sci., 2015, 7, 347-352.
[104]
Liang, X.; Zhao, L.; Deng, M.; Liu, L.; Ma, Y.; Guo, X. Separation of Ofloxacin and Its Six Related Substances Enantiomers by Chiral Ligand-Exchange Chromatography. Chirality, 2015, 27(11), 843-849.
[http://dx.doi.org/10.1002/chir.22527] [PMID: 26382212]
[105]
European Medicines Agency. Assessment report for Volibris Doc., http://www.ema.europa.eu/docs/en GB/document library/EPAR- Public assessment report/human/000839/WC500053063.pdf2008.
[106]
Orlandini, S.; Pasquini, B.; Caprini, C.; Del Bubba, M.; Douša, M.; Pinzauti, S.; Furlanetto, S. Enantioseparation and impurity determination of ambrisentan using cyclodextrin-modified micellar electrokinetic chromatography: Visualizing the design space within quality by design framework. J. Chromatogr. A, 2016, 1467, 363-371.
[http://dx.doi.org/10.1016/j.chroma.2016.06.082] [PMID: 27425759]
[107]
Xu, L.; Cui, Z.; Jiang, K. Determination of enantiomeric impurity in R-verapamil active pharmaceutical ingredient using carboxymethyl-β-cyclodextrin as a chiral selector by CE. Yaowu Fenxi Zazhi, 2016, 36, 541-546.
[108]
Gallinella, B.; Ferretti, R.; Zanitti, L.; Sestili, I.; Mosca, A.; Cirilli, R. Comparison of reversed-phase enantioselective HPLC methods for determining the enantiomeric purity of (S)-omeprazole in the presence of its related substances. J. Pharm. Anal., 2016, 6(2), 132-136.
[http://dx.doi.org/10.1016/j.jpha.2015.11.001] [PMID: 29403973]
[109]
Kumar, G.P.; Srivastava, V.; Khandelwal, K.; Kumar, R.; Hiriyanna, S.G.; Kumar, A.; Kumar, P. Simple Isocratic HPLC Method for Determination of Enantiomeric Impurity in Besifloxacin Hydrochloride. Chirality, 2016, 28(9), 628-632.
[http://dx.doi.org/10.1002/chir.22626] [PMID: 27563753]
[110]
Sadutto, D.; Ferretti, R.; Zanitti, L.; Casulli, A.; Cirilli, R. Analytical and semipreparative high performance liquid chromatography enantioseparation of bicalutamide and its chiral impurities on an immobilized polysaccharide-based chiral stationary phase. J. Chromatogr. A, 2016, 1445, 166-171.
[http://dx.doi.org/10.1016/j.chroma.2016.04.011] [PMID: 27067494]
[111]
Ferretti, R.; Zanitti, L.; Cirilli, R. Development of an HPLC 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., 2017, 41, 1208-1215.
[http://dx.doi.org/10.1002/jssc.201701191] [PMID: 29193750]
[112]
Kamalzadeh, Z.; Babanezhad, E.; Ghaffari, S.; Mohseni Ezhiyeh, A.; Mohammadnejad, M.; Naghibfar, M.; Bararjanian, M.; Attar, H. Determination of Bortezomib in API Samples Using HPLC: Assessment of Enantiomeric and Diastereomeric Impurities. J. Chromatogr. Sci., 2017, 55(7), 697-705.
[http://dx.doi.org/10.1093/chromsci/bmx023] [PMID: 28369337]
[113]
Chung, H.K.; Truong, Q.K.; Mai, X.L.; Choi, Y.; Kang, J.S.; Mar, W.; Kim, K.H. Determination of S-(-)-lansoprazole in dexlansoprazole preparation by capillary zone electrophoresis. Arch. Pharm. Res., 2017, 40(8), 962-971.
[http://dx.doi.org/10.1007/s12272-017-0936-8] [PMID: 28766240]
[114]
Niedermeier, S.; Scriba, G.K.E. A quality by design-based approach to a capillary electrokinetic assay for the determination of dextromepromazine and levomepromazine sulfoxide as impurities of levomepromazine. J. Pharm. Biomed. Anal., 2017, 146, 402-409.
[http://dx.doi.org/10.1016/j.jpba.2017.09.003] [PMID: 28926734]
[115]
Szabó, Z.I.; Foroughbakhshfasaei, M.; Gál, R.; Horváth, P.; Komjáti, B.; Noszál, B.; Tóth, G. Chiral separation of lenalidomide by liquid chromatography on polysaccharide-type stationary phases and by capillary electrophoresis using cyclodextrin selectors. J. Sep. Sci., 2018, 41(6), 1414-1423.
[http://dx.doi.org/10.1002/jssc.201701211] [PMID: 29211341]
[116]
Zhu, B.; Xu, S.; Guo, X.; Wei, L.; Yu, J.; Wang, T. Use of various β-cyclodextrin derivatives as chiral selectors for the enantiomeric separation of ofloxacin and its five related substances by capillary electrophoresis. J. Sep. Sci., 2017, 40(8), 1784-1795.
[http://dx.doi.org/10.1002/jssc.201601403] [PMID: 28168817]
[117]
Meng, R.; Kang, J. Determination of the stereoisomeric impurities of sitafloxacin by capillary electrophoresis with dual chiral additives. J. Chromatogr. A, 2017, 1506, 120-127.
[http://dx.doi.org/10.1016/j.chroma.2017.05.010] [PMID: 28551019]
[118]
Foroughbakhshfasaei, M.; Szabó, Z.I.; Tóth, G.; Validated, L.C. Method for Determination of Enantiomeric Purity of Apremilast Using Polysaccharide-Type Stationary Phases in Polar Organic Mode. Chromatographia, 2018, 1613-1621.
[http://dx.doi.org/10.1007/s10337-018-3546-9]
[119]
Foroughbakhshfasaei, M.; Szabó, Z.I.; Mirzahosseini, A.; Horváth, P.; Tóth, G. Enantiomeric quality control of R-Tofisopam by HPLC using polysaccharide-type chiral stationary phases in polar organic mode. Electrophoresis, 2018, 39(20), 2566-2574.
[http://dx.doi.org/10.1002/elps.201800220] [PMID: 29999177]
[120]
Ferretti, R.; Zanitti, L.; Casulli, A.; Cirilli, R. Unusual retention behavior of omeprazole and its chiral impurities B and E on the amylose tris (3-chloro-5-methylphenylcarbamate) chiral stationary phase in polar organic mode. J. Pharm. Anal., 2018, 8(4), 234-239.
[http://dx.doi.org/10.1016/j.jpha.2018.04.001] [PMID: 30140487]
[121]
Niedermeier, S.; Matarashvili, I.; Chankvetadze, B.; Scriba, G.K.E. Simultaneous determination of dextromepromazine and related substances 2-methoxyphenothiazine and levomepromazine sulfoxide in levomepromazine on a cellulose tris(4-methylbenzoate) chiral column. J. Pharm. Biomed. Anal., 2018, 158, 294-299.
[http://dx.doi.org/10.1016/j.jpba.2018.06.012] [PMID: 29906685]
[122]
Kirkpatrick, D.; Fain, M.; Yang, J.; Trehy, M. Enantiomeric impurity analysis using circular dichroism spectroscopy with United States Pharmacopeia liquid chromatographic methods. J. Pharm. Biomed. Anal., 2018, 156, 366-371.
[http://dx.doi.org/10.1016/j.jpba.2018.04.033] [PMID: 29754067]
[123]
Pasquini, B.; Orlandini, S.; Villar-Navarro, M.; Caprini, C.; Del Bubba, M.; Douša, M.; Giuffrida, A.; Gotti, R.; Furlanetto, S. Chiral capillary zone electrophoresis in enantioseparation and analysis of cinacalcet impurities: Use of Quality by Design principles in method development. J. Chromatogr. A, 2018, 1568, 205-213.
[http://dx.doi.org/10.1016/j.chroma.2018.07.021] [PMID: 30005942]
[124]
Krait, S.; Scriba, G.K.E. Quality by design-assisted development of a capillary electrophoresis method for the chiral purity determination of dexmedetomidine. Electrophoresis, 2018, 39(20), 2575-2580.
[http://dx.doi.org/10.1002/elps.201800100] [PMID: 29600596]
[125]
Harnisch, H.; Scriba, G.K. Capillary Electrophoresis Method for the Determination of (R)-Dapoxetine, (3S)-3-(Dimethylamino)-3-phenyl-1-propanol, (S)-3-Amino-3-phenyl-1-propanol and 1-Naphthol as impurities of Dapoxetine Hydrochloride. J. Pharm. Biomed. Anal., 2018, 162, 257-263.
[PMID: 30273816]

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