Chiral Separation of Fluoxetine and Its Analogs with Charged Cyclodextrins by Capillary Electrophoresis

Inoue, Takayo; Chang, Jen P.

doi:10.1081/jlc-120023251

Cited by 12 publications

(14 citation statements)

References 25 publications

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“…, except for terfenadine, baseline resolution was achieved for all the analytes studied and high Rs values were obtained. The Rs values obtained were similar to or higher than those reported in the literature for these compounds with other cyclodextrins, but obtained in most cases using higher CD concentrations than here (Castro‐Puyana et al ., ; Van Eeckhaut et al ., ; Matsunaga et al ., ; Inoue and Chang, ; Rudaz et al ., ; Bonato et al ., ; Perrin et al ., ; Li and Vigh, ; Asensi‐Bernardi et al ., ; Yang et al ., ; Liao et al ., ; Chen et al ., ; Wei et al ., ).…”

Section: Resultsmentioning

confidence: 99%

Characterizing the interaction between enantiomers of eight psychoactive drugs and highly sulfated‐β‐cyclodextrin by counter‐current capillary electrophoresis

Asensi-Bernardi

Escuder-Gilabert

Martı́n-Biosca

et al. 2013

Biomedical Chromatography

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The estimation of apparent binding constants and limit mobilities of the complexes of the enantiomers that characterize the interaction of enantiomers with chiral selectors, in this case highly sulfated β-cyclodextrin, was approached using a simple and economic electrophoretic modality, the complete filling technique (CFT) in counter-current mode. The enantiomers of eight psychoactive drugs, four antihistamines (dimethindene, promethazine, orphenadrine and terfenadine) and four antidepressants (bupropion, fluoxetine, nomifensine and viloxazine) were separated for the first time for this cyclodextrin (CD). Estimations of thermodynamic and electrophoretic enantioselectivies were also performed. Results indicate that, in general, thermodynamic enantioselectivity is the main component explaining the high resolution found, but also one case suggests that electrophoretic enantioselectivity itself is enough to obtain a satisfactory resolution. CFT results advantageous compared with conventional capillary electrophoresis (CE) and partial filling technique (PFT) for the study of the interaction between drugs and chiral selectors. It combines the use of a simple fitting model (as in CE), when the enantiomers do not exit the chiral selector plug during the separation (i.e. mobility of electroosmotic flow larger than mobility of CD), and drastic reduction of the consumption (and cost; ~99.7%) of the CD reagent (as in PFT) compared with the conventional CE.

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Section: Resultsmentioning

confidence: 99%

Characterizing the interaction between enantiomers of eight psychoactive drugs and highly sulfated‐β‐cyclodextrin by counter‐current capillary electrophoresis

Asensi-Bernardi

Escuder-Gilabert

Martı́n-Biosca

et al. 2013

Biomedical Chromatography

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“…Finally, the enantioseparation of FLU and four analogues was carried out using charged and neutral CDs [31]. Good results were obtained with both kinds of CDs; however, as expected charged selectors at low pH values gave stronger interaction and thus higher resolution.…”

Section: Selective Serotonin Reuptake Inhibitorsmentioning

confidence: 90%

Advances in the enantioseparation of second‐generation antidepressant drugs by electrodriven methods

Mandrioli

Raggi

2006

Electrophoresis

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Stereochemistry is steadily increasing in importance in the development of new drugs, and the availability of pure enantiomer drugs can make therapy safer and more efficacious. In particular, almost all second-generation antidepressant drugs possess one or more chiral centres; however, only some of them are administered as single enantiomers. A fundamental part of the quality control of pharmaceutical formulations is the determination of enantiomeric excess and enantiomeric purity; this is also important for the therapeutic drug monitoring of depressed patients. For this purpose, efficient and reliable analytical methods are needed and electrodriven techniques (most of all CE, CEC and MEKC) are very efficient and inexpensive candidates for the role. In this review, the enantioselective electrodriven methods available for the analysis of second-generation antidepressant are presented and discussed. In particular, the following pharmacological classes of antidepressants will be considered: selective serotonin reuptake inhibitors (fluoxetine, citalopram, paroxetine, sertraline); norepinephrine reuptake inhibitors (reboxetine); serotonin and norepinephrine reuptake inhibitors (venlafaxine, milnacipran, duloxetine); and noradrenergic and specific serotonergic antidepressants (mirtazapine).

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“…Inoue and Chang () performed a complex CD screening using 11 different CDs including neutral and charged derivatives as chiral selectors in order to establish the optimal chiral selector for the separation of FLX enantiomers. Four FLX analogs that have different substituents on the amine moiety were also analyzed by in order to study the structural effects on chiral recognition; three of them that have simple alkyl substituents showed similar separation behavior to that of FLX, while addition of a carboxyl group on the amine moiety caused a significant change in chiral separation.…”

Section: Methodsmentioning

confidence: 99%

“…The low concentration of CD employed together with the use of a high-sensitivity detection cell (the so-called 'zeta-cell'), allowed limits of detection of 0.005 and 0.01 μg/mL for FLX and NFLX, respectively, comparable with those obtained by chromatographic techniques, allowing the determination of FLX and NFLX enantiomers at therapeutic levels in plasma. The FLX and NFLX ratio confirmed the stereoselectivity of the metabolic process Inoue and Chang (2003). performed a complex CD screening using 11 different CDs including neutral and charged derivatives as chiral selectors in order to establish the optimal chiral selector for the separation of FLX enantiomers.…”

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confidence: 94%

Analytical methodologies for the stereoselective determination of fluoxetine: An overview

Hancu

Cârcu-Dobrin

Budău³

et al. 2017

Biomedical Chromatography

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Fluoxetine is a widely used antidepressant belonging to the selective serotonin reuptake inhibitor class; it is used in the treatment of major depression, obsessive compulsive, premenstrual dysphoric, panic and post-traumatic stress disorders. Fluoxetine is an optical active pharmaceutical substance, which is used as a racemate in therapy, but stereospecific interactions associated with the serotonin-reuptake carrier, for both the parent drug and its active metabolite, norfluoxetine, have been described in the literature. Therefore, the stereoselective analysis of fluoxetine and norfluoxetine is important in order to characterize the pharmacokinetic and pharmacodynamic profile of the analytes. Several chromatographic and electrophoretic methods have been published in the literature for the chiral discrimination of fluoxetine enantiomers from different matrices. The purpose of the current review is to provide a systematic survey of the analytical techniques used for the chiral determination of fluoxetine and norfluoxetine covering a period of~25 years.

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Chiral Separation of Fluoxetine and Its Analogs with Charged Cyclodextrins by Capillary Electrophoresis

Cited by 12 publications

References 25 publications

Characterizing the interaction between enantiomers of eight psychoactive drugs and highly sulfated‐β‐cyclodextrin by counter‐current capillary electrophoresis

Characterizing the interaction between enantiomers of eight psychoactive drugs and highly sulfated‐β‐cyclodextrin by counter‐current capillary electrophoresis

Advances in the enantioseparation of second‐generation antidepressant drugs by electrodriven methods

Analytical methodologies for the stereoselective determination of fluoxetine: An overview

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