Direct resolution of a new antifungal agent, voriconazole (UK-109,496) and its potential impurities, by use of coupled achiral-chiral high-performance liquid chromatography

Ferretti, Rosella; Gallinella, Bruno; Torre, Francesco La; Zanitti, Leo

doi:10.1007/bf02467448

Cited by 26 publications

(7 citation statements)

References 19 publications

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“…The serial coupling strategy was also successfully exploited by Angelo et al [12] for the quantitative LC determination of the methadone enantiomers and of some of its related cyclic N-demethylated metabolites. Analogously, Ferretti et al [13] reported on the simultaneous chemo-and enantioseparation for the identification and determination of the antifungal agent Voriconazole, its stereoisomers and potential impurities by LC. Bicker et al [14] treated the problem of limited diastereoselectivity, i. e. insufficient chemoselectivity for diastereomeric forms of pyrethroic acids by a serial chiral -chiral in-line coupling of two distinct quinine carbamate-based anionexchangers one of which delivered the diastereoselectivity increment which was missing on the other column that however showed better enantioselectivity.…”

Section: Introductionmentioning

confidence: 96%

In‐line coupling of a reversed‐phase column to cope with limited chemoselectivity of a quinine carbamate‐based anion‐exchange type chiral stationary phase

Sardella

Lämmerhofer²,

Natalini

et al. 2008

J of Separation Science

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A chiral stationary phase based on tert-butylcarbamoyl quinine has shown remarkable enantiomer separation capability for the thyroid hormone thyroxine (T(4)) and its structural analogue triiodothyronine (T(3)) employing hydroorganic buffered mobile phases (typical RP conditions). To overcome the problem of a somehow limited chemoselectivity for the critical peak pair between adjacent L-thyroxine (L-T(4)) and D-thyroxine (D-T(4)) peaks on the chiral anion-exchanger CSP when all four compounds need to be analysed simultaneously like in impurity profiling of L-T(4 )drug products, an RP column (Gemini C18) was serially coupled with the chiral anion-exchanger column to add a hydrophobic selectivity increment and to improve thereby the critical resolution between L-T(3) and D-T(4). Various parameters such as organic modifier content, pH, buffer concentration and type, type of achiral column as well as sequence of achiral and chiral column have been investigated with individual and tandem columns. With the optimized conditions and use of the tandem column a significantly improved separation, as compared to the chiral anion-exchanger column alone, with a critical resolution as high as 3.7 and an almost equal band spacing of the four components of the test mixture could be obtained. The sequence of the columns (achiral-chiral or chiral-achiral) had no significant effect on the separation performance.

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Section: Introductionmentioning

confidence: 96%

In‐line coupling of a reversed‐phase column to cope with limited chemoselectivity of a quinine carbamate‐based anion‐exchange type chiral stationary phase

Sardella

Lämmerhofer²,

Natalini

et al. 2008

J of Separation Science

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“…One potential solution to overcome this limitation is to use multidimensional liquid chromatography (2D-LC) approaches, where the two dimensions are often based on different separation mechanisms [10][11][12]. Much more rarely, tandem column systems consisting of columns connected in series showed promising results with a significantly improved overall separation performance [13][14][15][16].…”

Section: Introductionmentioning

confidence: 98%

Diastereo- and enantioseparation of a Nα-Boc amino acid with a zwitterionic quinine-based stationary phase: Focus on the stereorecognition mechanism

Ianni

Carotti

Marinozzi

et al. 2015

Analytica Chimica Acta

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“…Since 1990, high-performance liquid chromatography (HPLC) with ultraviolet, fluorescence, or electrochemical detection has been used extensively for the determination of antifungal drugs in biological samples (e.g., ketoconazole [7,8], clotrimazole [9], itraconazole [10][11][12][13], fluconazole [14][15][16][17], and voriconazole [18,19]), although other analytical methods including bioassays and gas chromatography using electron-capture or nitrogen-selective detection have also been described. On the other hand, the use of capillary electrophoresis (CE) continues to grow rapidly as an alternative and complementary analytical technique to HPLC for the separation of small organic molecules such as pharmaceutical agents and drug metabolites.…”

Section: Introductionmentioning

confidence: 99%

Application of capillary zone electrophoresis with off-line solid-phase extraction toin vitro metabolism studies of antifungals

Crego¹,

Gómez²,

Marina³

et al. 2001

Electrophoresis

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A simple and robust solid-phase extraction (SPE) procedure for the cleanup and sample preconcentration of antifungals (ketoconazole, clotrimazole, itraconazole, fluconazole, and voriconazole) and their metabolites after incubation with human liver microsomes, as well as a simplified capillary zone electrophoresis (CZE) method for their rapid analysis, have been developed to determine the stability of these compounds in in vitro samples. Three different sample pretreatment procedures using SPE with reversed-phase sorbents (100 mg C8, 100 mg C18, and 30 mg Oasis-HLB) were studied. The highest and most reproducible recoveries were obtained using a 30 mg Oasis-HLB sorbent and methanol containing 2% acetic acid as eluent. Enrichment by a factor of about four times was achieved by reconstituting the final SPE eluates to a small volume. For the CZE separation, good separations without interfering peaks due to the in vitro matrix were obtained with a simple running electrolyte using a fused-silica capillary. The best separation for all components originated by each tested drug after incubation with human liver microsomes (unmetabolized parent drug and its metabolites) was obtained using a 0.05 M phosphate running buffer (pH 2.2) without additives. The effect of the injection volume was also investigated in order to obtain the best sensitivity. Performance levels in terms of precision, linearity, limits of detection, and robustness were determined.

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Direct resolution of a new antifungal agent, voriconazole (UK-109,496) and its potential impurities, by use of coupled achiral-chiral high-performance liquid chromatography

Cited by 26 publications

References 19 publications

In‐line coupling of a reversed‐phase column to cope with limited chemoselectivity of a quinine carbamate‐based anion‐exchange type chiral stationary phase

In‐line coupling of a reversed‐phase column to cope with limited chemoselectivity of a quinine carbamate‐based anion‐exchange type chiral stationary phase

Diastereo- and enantioseparation of a Nα-Boc amino acid with a zwitterionic quinine-based stationary phase: Focus on the stereorecognition mechanism

Application of capillary zone electrophoresis with off-line solid-phase extraction toin vitro metabolism studies of antifungals

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