Resolution of enantiomers of bupropion and its metabolites by liquid chromatography

Batra, Sonika; Bhushan, Ravi

doi:10.1002/bmc.3572

Cited by 17 publications

(13 citation statements)

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“…Both direct and indirect approaches of separation of enantiomers (using LC) have their own advantages and limitations depending upon the situation, particularly, in terms of the source and amount of sample availability, chemical structure of the analyte and the ease of availability of laboratory facilities. Various reviews on separation of enantiomers of ( RS )‐baclofen (Batra & Bhushan, ), ( RS )‐bupropion (Batra & Bhushan, ), ( RS )‐Naproxen (Batra & Bhushan, ) and dl ‐penicillamine (Bhushan & Kumar, ), have discussed various issues related to ‘direct’ and ‘indirect’ (modes of) enantioseparation; therefore, such general aspects are not being discussed in this paper.…”

Section: Introductionmentioning

confidence: 99%

Bioassay, determination and separation of enantiomers of atenolol by direct and indirect approaches using liquid chromatography: A review

Batra

Bhushan

2017

Biomedical Chromatography

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Atenolol, a β-adrenergic receptor antagonist, is a chiral compound used for the treatment of cardiovascular diseases and to treat hypertension, coronary heart disease, arrhythmias, sinus tachycardia and myocardial infarction, where it acts preferentially upon the β-adrenergic receptors in the heart. It is marketed as a racemate, but only the (S)-enantiomer of (RS)-atenolol is responsible for the β-adrenoceptor blocking activity. Different chromatographic methods have been applied for the separation and determination of enantiomers. In this article a review is presented on liquid chromatographic methods for enantioseparation of (RS)-atenolol by both direct and indirect approaches involving practical applications of several chiral stationary phases, chiral derivatization reagents and ligand exchange and impregnation methods. These include methods using both HPLC and TLC for separation, determination and bioassay of enantiomers of atenolol. In addition, some aspects of enantioseparation under achiral phases of liquid chromatography have been briefly mentioned as applicable to (RS)-atenolol. This review provides current available enantioseparation choices not only for (RS)-atenolol but also for other applicable racemic drugs.

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Section: Introductionmentioning

confidence: 99%

Bioassay, determination and separation of enantiomers of atenolol by direct and indirect approaches using liquid chromatography: A review

Batra

Bhushan

2017

Biomedical Chromatography

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“…The aim of this review article was to gather all main CLEC studies that appeared in the literature over the last ten years. Some interesting reviews and book chapters have already been published in the literature during this time frame , whereas none of these contain a comprehensive overview of the applications in all the possible ways to perform CLEC analyses. Accordingly, in the present contribution, both CSPs‐ and CMPAs‐based applications have been briefly described and commented giving also the deserved focus on the new alternative ways to exploit the ligand‐exchange concept for the enantioselective analysis in liquid chromatography settings.…”

Section: Discussionmentioning

confidence: 99%

Last ten years (2008–2018) of chiral ligand‐exchange chromatography in HPLC: An updated review

Ianni

Pucciarini

Carotti

et al. 2018

J of Separation Science

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Chiral ligand-exchange chromatography is one of the elective strategies for the direct enantioresolution of small chelating compounds: amino acids, diamines, amino alcohols, diols, small peptides, etc. Unlike other methods, the interaction between chiral selector and analyte enantiomers is mediated by a cation, thus producing diastereomeric ternary complexes. Two main approaches are conventionally applied in chiral ligand-exchange chromatography. The first relies upon chiral stationary phases where the chiral selector is either covalently immobilized or physically adsorbed onto suitable packing materials (coated phases). In the second approach, chiral molecules are added to the eluent, thus generating chiral eluent systems. Among the advantages of chiral ligand-exchange chromatography, the generation of UV/vis-active metal complexes, and the use of commercially available or easy-to-synthesize chiral selectors, in combination to rather inexpensive achiral columns for coated phases and chiral eluents, are noteworthy. Besides amino acids and amino alcohols, other species have proven suitable for chiral ligand-exchange chromatography applications. Recently, the use of either chiral ionic liquids or micellar liquid chromatography systems as well as the successful off-column formation of diastereomeric complexes have expanded the selectivity profiles and application fields. All of these issues are touched in the review, shedding light to the contributions appeared in the last decade.

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“…Additionally, stereoselective LC-UV analytical methods were developed for bupropion and hydroxybupropion enantiomers utilizing achiral-chiral chromatography [17], with ovomucoid [18], cyclobond I 2000 [9], cellulose [19], and α 1 -acid glycoprotein[20] columns, electrokinetic chromatography [21], and isothiocyanate-based chiral derivatization [22]. Previously, our group utilized an α 1 -acid glycoprotein chiral column in a validated LC-MS/MS assay for bupropion and hydroxybupropion enantiomers in plasma [5].…”

Section: Introductionmentioning

confidence: 99%

Development and validation of a high-throughput stereoselective LC–MS/MS assay for bupropion, hydroxybupropion, erythrohydrobupropion, and threohydrobupropion in human plasma

Teitelbaum

Flaker

Kharasch

2016

Journal of Chromatography B

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A stereoselective analytical method was developed and validated for the quantification of bupropion, and principle metabolites hydroxybupropion, erythrohydrobupropion and threohydrobupropion in human plasma. Separation of individual enantiomers (R)-bupropion, (S)-bupropion, (R,R)-hydroxybupropion, (S,S-hydroxybupropion), (1S,2S)-threohydrobupropion, (1R,2R)-threohydrobupropion, (1R,2S)-erythrohydrobupropion, and (1S,2R)-erythrohydrobupropion was achieved utilizing an α1-acid glycoprotein column within a 12-minute run time. Chromatograph separation was significantly influenced by mobile phase pH and variability between columns. Analytes were quantified by positive ion electrospray tandem mass spectrometry following plasma protein precipitation with 20% trichloroacetic acid. Identification of erythrohydrobupropion enantiomer peaks and threohydrobupropion enantiomer peaks was achieved by sodium borohydride reduction of enantiopure (R)- and (S)-bupropion. Initial assay validation and sensitivity determination was on AB Sciex 3200, 4000 QTRAP, and 6500 mass spectrometers. Accuracy and precision were within 15% for each analyte. The assay was fully validated over analyte-specific concentrations using an AB Sciex 3200 mass spectrometer. Intra- and inter-assay precision and accuracy were within 12% for each analyte. The limits of quantification for bupropion (R and S), hydroxybupropion (R,R and S,S), threohydrobupropion (1S,2S and 1R,2R), and erythrohydrobupropion (1R,2S and 1S,2R) were 0.5, 2, 1, and 1 ng/mL, respectively. All analytes were stable following freeze thaw cycles at −80°C and while stored at 4°C in the instrument autosampler. This method was applicable to clinical pharmacokinetic investigations of bupropion in patients. This is the first chromatographic method to resolve erythrohydrobupropion and threohydrobupropion enantiomers, and the first stereoselective LC-MS/MS assay to quantify bupropion, and principle metabolites hydroxybupropion, erythrohydrobupropion, and threohydrobupropion in human plasma.

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Resolution of enantiomers of bupropion and its metabolites by liquid chromatography

Cited by 17 publications

References 53 publications

Bioassay, determination and separation of enantiomers of atenolol by direct and indirect approaches using liquid chromatography: A review

Bioassay, determination and separation of enantiomers of atenolol by direct and indirect approaches using liquid chromatography: A review

Last ten years (2008–2018) of chiral ligand‐exchange chromatography in HPLC: An updated review

Development and validation of a high-throughput stereoselective LC–MS/MS assay for bupropion, hydroxybupropion, erythrohydrobupropion, and threohydrobupropion in human plasma

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