Separation of stereoisomers of sertraline and its related enantiomeric impurities on a dimethylated β-cyclodextrin stationary phase by HPLC

Rao, R. Nageswara; Talluri, M.V.N. Kumar; Maurya, Pawan K.

doi:10.1016/j.jpba.2009.04.038

Cited by 29 publications

(13 citation statements)

References 19 publications

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“…In general, the hydroxyl groups on CD rims can be substituted with diverse functionalities like methyl [21,22], phenyl [23] and phenyl isocyanate [24,25]. These functionalities can effectively enable the enantioseparation under mixed modes in HPLC by constructing multiple intermolecular interactions such as -conjugation, dipole-dipole, ion-pairing, hydrogen bonding, and electrostatic and steric repulsion interactions besides inclusion complexation.…”

Section: Introductionmentioning

confidence: 99%

Cationic cyclodextrin clicked chiral stationary phase for versatile enantioseparations in high-performance liquid chromatography

Zhou

Yang

Tang

2016

Journal of Chromatography A

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Section: Introductionmentioning

confidence: 99%

Cationic cyclodextrin clicked chiral stationary phase for versatile enantioseparations in high-performance liquid chromatography

Zhou

Yang

Tang

2016

Journal of Chromatography A

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“…The method described by Rao et al for the separation and quantitation of stereoisomers and related enantiomeric impurities of sertraline ( 2 ) by means of a dimethylated β‐cyclodextrine material as stationary phase was considered a suitable starting point. The column employed in this study, an Astec Cylcobond I 2000 DM, seemed to be promising for our purpose due to the structural analogy of indatraline ( 1 ) compared to sertraline ( 2 ).…”

Section: Resultsmentioning

confidence: 99%

“…The column employed in this study, an Astec Cylcobond I 2000 DM, seemed to be promising for our purpose due to the structural analogy of indatraline ( 1 ) compared to sertraline ( 2 ). The described mobile phase, however, employing 0.4% (v/v) trifluoroacetic acid (TFA) at pH 3.0 can be considered relatively harsh and possibly destructive for the stationary phase as these conditions are at or even not within the manufacturer's advice for handling of the Astec Cylcobond I 2000 DM. Additionally, for TFA a memory effect was found by Ye et al which was assumed to impair a rapid switching between different kinds of buffers.…”

Section: Resultsmentioning

confidence: 99%

Enantiopurity Determination of the Enantiomers of the Triple Reuptake Inhibitor Indatraline

et al. 2013

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The present study describes the development of two approaches for the determination of the enantiopurity of both enantiomers of indatraline. Initially, a method was developed using different chiral solvating agents (CSAs) for diastereomeric discrimination regarding signal separation in (1)H nuclear magnetic resonance (NMR) spectroscopy, revealing MTPA as a promising choice for the differentiation of the indatraline enantiomers. This CSA was also tested for its ideal molar ratio, temperature, and solvent. Optimized conditions could be achieved that made determination of enantiopurity for (1R,3S)-indatraline up to 98.9% enantiomeric excess (ee) possible. To quantify even higher enantiopurities, a high-performance liquid chromatography (HPLC) method based on a modified β-cyclodextrine phase was established. The influence of buffer type, concentration, pH value, percentage and kind of organic modifier, temperature, injection volume as well as sample solvent on chromatographic parameters was investigated. Afterwards, the reliability of the established HPLC method was demonstrated by validation according to the ICH guideline Q2(R1) regarding specificity, accuracy, precision, linearity, and quantitation limit. The developed method proved to be strictly linear within a concentration range of 1.25-1000 μM for the (1R,3S)-enantiomer and 1.25-750 μM for its mirror image that enables a reliable determination of enantiopurities up to 99.75% ee for the (1R,3S)-enantiomer and up to 99.67% ee for the (1S,3R)-enantiomer.

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“…A RPHPLC method was developed and validated for enantioseparation of sertraline HCl and related enantiomers using the Cyclobond I 2000 DM column ( l × i.d., 25 cm × 4.6 mm, 5 μm particle size) packed with dimethyl‐ β ‐CD as stationary phase (Rao et al, ). The method allowed separation and determination of the potency and enantiomeric purity of cis ‐( 1S , 4S )‐, cis ‐( 1R , 4R )‐, trans ‐( 1S , 4R )‐ and trans ‐( 1R , 4S )‐enantiomers of sertraline hydrochloride in the presence of five other related potential enantiomeric impurities in drug substances and products owing to the high selectivity of the chromatographic system.…”

Section: Sertralinementioning

confidence: 99%

EnantioselectiveLCanalysis and determination of selective serotonin reuptake inhibitors

Sethi

Bhushan

2019

Biomedical Chromatography

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LC separation of biologically and pharmaceutically important enantiomers (from racemic or non‐racemic mixtures) remains a subject of importance. The present review article deals with the liquid chromatographic enantioseparation of chiral selective serotonin reuptake inhibitors (SSRIs), namely citalopram, paroxetine, sertraline and fluoxetine. It is now known that the enantiomers of numerous psychotropic drugs exhibit distinct pharmacodynamics, pharmacokinetic patterns and receptor binding properties, and psychiatric patients are frequently taking more than one medication. Therefore, monitoring of the levels of these analytes in biological fluids is important to determine the levels of enantiomer concentrations; the present paper may be helpful in understanding the present state of available methods (along with a critical discussion of applicability of the methods) and in developing the new ones for this purpose. Different approaches using LC discussed herein may be applied for determining the enantiomeric composition (and enantiomeric purity) of SSRIs and numerous other racemic drugs, of current/future pharmaceutical importance and utility, using simple separation methods, instrumentation, inexpensive reagents and potentially significant analytical approaches. The contents cover the essential data to understand the various separation techniques and associated issues, if any, with documented examples.

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Separation of stereoisomers of sertraline and its related enantiomeric impurities on a dimethylated β-cyclodextrin stationary phase by HPLC

Cited by 29 publications

References 19 publications

Cationic cyclodextrin clicked chiral stationary phase for versatile enantioseparations in high-performance liquid chromatography

Cationic cyclodextrin clicked chiral stationary phase for versatile enantioseparations in high-performance liquid chromatography

Enantiopurity Determination of the Enantiomers of the Triple Reuptake Inhibitor Indatraline

EnantioselectiveLCanalysis and determination of selective serotonin reuptake inhibitors

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