Systematic approach to treatment of enantiomeric separations in capillary electrophoresis and liquid chromatography II. A study of the enantiomeric separation of fluoxetine and norfluoxetine

Piperaki, Stavroula; Penn, Sharron G.; Goodall, David M.

doi:10.1016/0021-9673(95)00113-2

Cited by 55 publications

(33 citation statements)

References 16 publications

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“…Under these conditions relative- [23,24], a first screening of the enantiomeric resolution of Flx and Nflx was performed using dimethylated-…”

Section: Preliminary Experimentsmentioning

confidence: 99%

“…Fluoxetine enantiomers were separated by CE with the direct method using oligosaccharide [21], maltosaccharide [22] or cyclodextrins [23,24] as chiral selectors, but no applications to biofluids have been reported to date. In the direct method the chiral selector is simply dissolved in the buffer and interacts selectively, during the run, with the two enantiomers forming reversible and labile diastereoisomeric complexes of different mobility (if complexes of different stability are formed).…”

Section: Introductionmentioning

confidence: 99%

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Enantiomeric separation of fluoxetine and norfluoxetine in plasma and serum samples with high detection sensitivity capillary electrophoresis

et al. 1999

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A capillary electrophoresis method was optimized for the stereoselective analysis of the antidepressant drug fluoxetine and its main demethylated metabolite norfluoxetine using a cyclodextrin‐modified sodium phosphate buffer at pH 2.5. The combination of a neutral and a negatively charged cyclodextrin, dimethylated‐β‐ and phosphated‐γ‐respectively, provided the baseline enantiomeric separation of the two compounds. The very low concentrations of chiral selectors employed together with the use of a high sensitivity detection cell of special design (zeta‐shaped) in a diode array UV detector allowed us to reach a limit of detection of 0.005 and 0.01 μg/mL for fluoxetine and norfluoxetine, respectively. Analysis of fluoxetine and norfluoxetine standard mixtures showed a reproducibility of migration times and peak area and linearity in the concentration range of 0.1—2.0 μg/mL. The optimized method was applied to the analysis of clinical serum and plasma samples of patients under depression therapy. In all the analyzed samples the enantiomeric forms of fluoxetine and norfluoxetine were easily identified. The fluoxetine and metabolite enantiomeric ratio confirmed the stereoselectivity of the metabolic process of the fluoxetine drug in accordance with the literature data.

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“…Under these conditions relative- [23,24], a first screening of the enantiomeric resolution of Flx and Nflx was performed using dimethylated-…”

Section: Preliminary Experimentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of fluoxetine and norfluoxetine in plasma and serum samples with high detection sensitivity capillary electrophoresis

et al. 1999

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“…However, in most of these, FLU is only a tool for theoretical or practical studies regarding enantioseparation, or studies of the enantioseparative power of newly synthesised chiral selectors [22][23][24][25][26][27]. An example of the latter is the enantioseparation of FLU (as well as pindolol and chlorcyclizine) by means of N-(3-sulfo-3-carboxy)-propionylchitosan [22].…”

Section: Selective Serotonin Reuptake Inhibitorsmentioning

confidence: 99%

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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“…Piperaki et al have studied a b-cyclodextrin chiral stationary phase (CSP) for direct separation of fluoxetine enantiomers [9,10]. Investigations using capillary electrophoresis with cyclodextrins [11,12] or malto-oligosaccharides [13] as chiral selectors have also been reported.…”

Section: Introductionmentioning

confidence: 97%

Enantiomeric Separation of Fluoxetine Derivatives on Polysaccharide‐Based Chiral Columns

Mei-Li

Jie-Guo

2006

Archiv der Pharmazie

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A high performance liquid chromatography (HPLC) method employing amylose-based chiral columns (Chiralpak AD-RH and Chiralpak AD) and cellulose-based chiral columns (Chiralcel OD) as chiral stationary phases have been developed for the enantiomeric separation of fluoxetine (FLX) derivatives. The FLX was derivatized with 4-(N-chloroformylmethyl-N-methyl)amino-7-nitro-2,1,3-benzoxadiazole (NBD-COCl) and 4-(N-chloroformylmethyl-N-methyl)amino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole (DBD-COCl), respectively. Influence of the mobile phase composition and column temperature on the enantioseparation was discussed during the separation. On the basis of separation of derivatized FLX enantiomers, the paper also discussed the separation mechanism on the chiral stationary phases used.

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Systematic approach to treatment of enantiomeric separations in capillary electrophoresis and liquid chromatography II. A study of the enantiomeric separation of fluoxetine and norfluoxetine

Cited by 55 publications

References 16 publications

Enantiomeric separation of fluoxetine and norfluoxetine in plasma and serum samples with high detection sensitivity capillary electrophoresis

Enantiomeric separation of fluoxetine and norfluoxetine in plasma and serum samples with high detection sensitivity capillary electrophoresis

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

Enantiomeric Separation of Fluoxetine Derivatives on Polysaccharide‐Based Chiral Columns

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