Determination of rabeprazole enantiomers in dog plasma by supercritical fluid chromatography tandem mass spectrometry and its application to a pharmacokinetic study

Su, Chong; Yang, Hong; Meng, Xiangjun; Fawcett, J. Paul; Cao, Jianming; Yang, Yan; Gu, Jingkai

doi:10.1002/jssc.201601232

Cited by 26 publications

(14 citation statements)

References 20 publications

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“…HPLC with chiral stationary phases is far and away the most powerful and widely used technique for solvent‐based enantiomeric separations at both analytical and preparative scales. Chromatography hyphenated with mass spectrometry has increasingly become a popular technique for the determination of chiral drugs because of its potential for high‐throughput screening . However, most of the previously reported techniques for the analysis of chiral drugs involve the use of chiral stationary phases, which are made by coating or bonding the chiral selectors, usually to silica gel supports.…”

Section: Introductionmentioning

confidence: 99%

Quantification of enantiomers by mass spectrometry based on chemical derivatization and spectral shape deformation quantitative theory

et al. 2019

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A facile mass spectrometric kinetic method for quantitative analysis of chiral compounds was developed by integrating mass spectrometry based on chemical derivatization and the spectral shape deformation quantitative theory. Chemical derivatization was employed to introduce diastereomeric environments to the chiral compounds of interest, resulting in different abundance distribution patterns of fragment ions of the derivatization products of enantiomers in mass spectrometry.The quantitative information of the chiral compounds of interest was extracted from complex mass spectral data by an advanced calibration model derived based on the spectral shape deformation quantitative theory. The performance of the proposed method was tested on the quantitative analysis of R-propranolol in propranolol tablets. Experimental results demonstrated that it could achieve accurate and precise concentration ratio predictions for R-propranolol with an average relative predictive error (ARPE) of about 4%, considerably better than the corresponding results of the mass spectrometric method based on chemical derivatization and the univariate ratiometric model (ARPE: about 12%). The limit of detection (LOD) and limit of quantification (LOQ) of the proposed method for the concentration ratio of R-propranolol were estimated to be 1.5% and 6.0%, respectively. The proposed method is complementary to the existing methods designed for the quantification of enantiomers such as the Cooks kinetic method.

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Section: Introductionmentioning

confidence: 99%

Quantification of enantiomers by mass spectrometry based on chemical derivatization and spectral shape deformation quantitative theory

et al. 2019

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“…The development and improvement of SFC separation technology are drawing an increasing attention in the field of research study and practical application [14][15][16]. According to the available literature, the SFC enantioseparation of racemic compounds has been mostly applied in one or two chiral carbon atoms drugs [17][18][19][20][21] and pesticides [22][23][24]; however, the use of SFC in the chiral S/P atoms was rarely reported [25,26].…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of six chiral pesticides that contain chiral sulfur/phosphorus atoms by supercritical fluid chromatography

Zhang

Miao

Lin

2018

J of Separation Science

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Six chiral pesticides containing chiral sulfur/phosphorus atoms were separated by supercritical fluid chromatography with supercritical CO as the main mobile phase component. The effect of the chiral stationary phase, different type and concentration of modifiers, column temperature, and backpressure on the separation efficiency was investigated to obtain the appropriate separation condition. Five chiral pesticides (isofenphos-methyl, isocarbophos, flufiprole, fipronil, and ethiprole) were baseline separated under experimental conditions, while isofenphos only obtained partial separation. The Chiralpak AD-3 column showed a better chiral separation ability than others for chiral pesticides containing chiral sulfur/phosphorus atoms. When different modifiers at the same concentration were used, the retention factor of pesticides except flufiprole decreased in the order of isopropanol, ethanol, methanol; meanwhile, the retention factor of flufiprole increased in the order of isopropanol, ethanol, methanol. For a given modifier, the retention factor and resolution decreased on the whole with the increase of its concentration. The enantiomer separation of five chiral pesticides was an "enthalpy-driven" process, and the separation factor decreased as the temperature increased. The backpressure of the mobile phase had little effect on the separation factor and resolution.

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“…There were four articles focusing on the enantiomeric determination of the racemic rabeprazole in vivo. Only one chiral method has been reported to simultaneously assay racemic rabeprazole in human plasma.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective pharmacokinetics of (R)‐(+)‐ and (S)‐(−)‐rabeprazole in human using chiral LC‐MS/MS after administration of rabeprazole sodium enteric‐coated tablet

et al. 2018

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Rabeprazole is an effective proton pump inhibitor to treat acid‐related diseases. To achieve the simultaneous determination of rabeprazole enantiomers in human plasma, a chiral LC‐MS/MS method was developed and validated. Acetonitrile including 0.1% ammonium were used as protein precipitating agent. Analytes were separated within 8 minutes on a Chiralpak IC column (4.6 mm × 150 mm, 5 μm). The mobile phase was 10 mM ammonium acetate including 0.2% acetic acid‐acetonitrile (35:65, v/v). An API 4000 mass spectrometer was used as detector for the analysis, and the multiple reactions monitoring transitions of m/z 360.1 → 242.2 and 346.1 → 198.1 were opted for quantifying rabeprazole enantiomers and internal standard. Matrix effects were not apparent for each enantiomer and internal standard (esomeprazole), the calibration curves were linear over the concentration of 0.500 to 400 ng·mL−1, the intra‐run precisions were below 5.4%, the inter‐run precisions were below 9.9%, and the accuracy was between −9.2% and 9.3%. There was no chiral inversion observed during sample storage, preparation procedure, and analysis, demonstrating that analytes were stable in this study. This method was applied to the stereoselective pharmacokinetic study of (R)‐(+)‐ and (S)‐(−)‐rabeprazole after oral administration of 10‐mg rabeprazole sodium enteric‐coated tablet in healthy Chinese subjects.

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Determination of rabeprazole enantiomers in dog plasma by supercritical fluid chromatography tandem mass spectrometry and its application to a pharmacokinetic study

Cited by 26 publications

References 20 publications

Quantification of enantiomers by mass spectrometry based on chemical derivatization and spectral shape deformation quantitative theory

Quantification of enantiomers by mass spectrometry based on chemical derivatization and spectral shape deformation quantitative theory

Enantiomeric separation of six chiral pesticides that contain chiral sulfur/phosphorus atoms by supercritical fluid chromatography

Stereoselective pharmacokinetics of (R)‐(+)‐ and (S)‐(−)‐rabeprazole in human using chiral LC‐MS/MS after administration of rabeprazole sodium enteric‐coated tablet

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