Two‐dimensional chromatography method applied to the enantiomeric determination of lansoprazole in human plasma by direct sample injection

Gomes, Ricardo F.; Cassiano, Neila M.; Pedrazzoli, José; Cass, Quézia B.

doi:10.1002/chir.20701

Cited by 25 publications

(21 citation statements)

References 19 publications

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“…In all cases, reversed‐phase mode of elution was used in the second dimension for the enantioseparation. The complete descriptions of the analytical methods have been previously published 13–15. Briefly, all three methods showed excellent linearity, precision, accuracy, recovery, and limit of quantification for each of the enantiomers, as follow: pantoprazole 0.20 μg/ml, omeprazole 0.05 μg/ml, and lansoprazole 0.10 μg/ml.…”

Section: Methodsmentioning

confidence: 99%

Enantioselective disposition of omeprazole, pantoprazole, and lansoprazole in a same Brazilian subjects group

Cassiano

Oliveira

Bernasconi³

et al. 2012

Chirality

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This work reports the result of the enantioselective disposition of pantoprazole, omeprazole, and lansoprazole in a same group of Brazilian health subjects. Ten nongenotyped healthy subjects were used for this study. Each subject received a single oral dose of 80 mg of pantoprazole, 40 mg of omeprazole, and 30 mg of lansoprazole, and the plasma concentrations of the enantiomers were measured for 8 h postdose. For pantoprazole and omeprazole, among the 10 volunteers investigated, only one volunteer (Subject # 4) presented higher plasma concentrations of the (+)-enantiomer than those of (-)-enantiomer. Nevertheless, the area under the concentration-time curve of the (+)-lansoprazole was higher than those the (-)-lansoprazole for all subjects. The comparison of proton pump inhibitors' enantiomers disposition from a single group volunteer demonstrated that pantoprazole and omeprazole can be used to differentiate extensive from poor CYP2C19 metabolizer while lansoprazole cannot do it.

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Section: Methodsmentioning

confidence: 99%

Enantioselective disposition of omeprazole, pantoprazole, and lansoprazole in a same Brazilian subjects group

Cassiano

Oliveira

Bernasconi³

et al. 2012

Chirality

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“…It has been reported that the plasma concentration of each LAN enantiomer appeared to be influenced by enantioselective metabolism in liver and, by enantioselective protein binding . On the enantioselective pharmacokinetics of LAN, the plasma concentration of (+)‐LAN was higher than (–)‐LAN . Therefore, LAN enantiomers may have different pharmacokinetic properties, pharmacodynamics, and toxicology.…”

Section: Introductionmentioning

confidence: 99%

“…A significant number of HPLC and SFC methods for the determination of LAN enantiomers in biological matrix have been reported . But the selectivity and sensitivity of UV detection has obvious disadvantages compared with MS, the analysis time and the LODs of these methods were not so satisfactory.…”

Section: Introductionmentioning

confidence: 99%

Determination of lansoprazole enantiomers in dog plasma by column‐switching liquid chromatography with tandem mass spectrometry and its application to a preclinical pharmacokinetic study

Wang

Sun

Meng

et al. 2015

J of Separation Science

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Lansoprazole, a selective proton pump inhibitor, has a chiral benzimidazole sulfoxide structure and is used for the treatment of gastric acid hypersecretory related diseases. To investigate its stereoselective pharmacokinetics, a column-switching liquid chromatography with tandem mass spectrometry method was developed for the determination of lansoprazole enantiomers in dog plasma using (+)-pantoprazole as an internal standard. After a simple protein precipitation procedure with acetonitrile, matrix components left behind after sample preparation were further eliminated from the sample by reversed-phase chromatography on a C18 column. The fluent was fed to a chiral column for the separation of lansoprazole enantiomers. Baseline separation of lansoprazole enantiomers was achieved on a Chiralcel OZ-RH column using acetonitrile/0.1% formic acid in water (35:65, v/v) as the mobile phase at 40°C. The linearity of the calibration curves ranged from 3 to 800 ng/mL for each enantiomer. Intra- and inter-day precisions ranged from 2.1 to 7.3% with an accuracy of ±1.7% for (+)-lansoprazole, and from 1.6 to 6.9% with an accuracy of ±3.5% for (-)-lansoprazole, respectively. The validated method was successfully applied for the stereoselective pharmacokinetic study of lansoprazole in beagle dog after intravenous infusion.

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“…However, the differences in stereochemical properties of the two enantiomers had pronounced impacts on their pharmacodynamics and pharmacokinetics. As a consequence of the numerous merits of R-(+)-lansoprazole, such as the slower metabolism, higher plasma concentration, longer elimination half-time and greater systemic exposure, it was developed and approved for marketing as a novel proton-pump inhibitor with the trade name Dexilant in 2009 (Gomes, Cassiano, Pedrazzoli, & Cass, 2010;Hershcovici, Jha, & Fass, 2011;Katsuki, Hamada, Nakamura, Arimori, & Nakano, 2001;Metz, Vakily, & Dixit, 2009). In addition, research on the extent of enantioselective binding of lansoprazole enantiomers to human serum proteins demonstrated that R-(+)lansoprazole was more tightly bound to serum proteins than S-(−)lansoprazole (Zhou, Yan, Pan, & Zeng, 2008).…”

Section: Introductionmentioning

confidence: 99%

Enantioselective analysis of lansoprazole in rat plasma by LC–MS/MS: Application to a stereoselective pharmacokinetic study

Wen

et al. 2018

Biomedical Chromatography

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A rapid, sensitive and enantioselective method was developed and fully validated for the separation and determination of lansoprazole enantiomers in rat plasma by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The analytes and the internal standard (esomeprazole) were both extracted from plasma samples by liquid-liquid extraction with diethyl ether-dichloromethane (70:30; v/v). Satisfactory resolution (R = 2.0) was achieved within 7.3 min on a Chiralpak ID column (250 × 4.6 mm, 5 μm) employing acetonitrile-water (60:40, v/v) as the mobile phase at a flow rate of 0.6 mL/min. The acquisition of mass spectrometric data was performed in the multiple reaction monitoring mode coupled with a positive electrospray ionization source. A comprehensive validation of this method was rigorously conducted over the concentration range of 1.00-500.0 ng/mL for both enantiomers. All of the validation data demonstrated that the desirable linearity, sensitivity, accuracy, precision, recovery and stability were attained from the proposed approach. The established method was successfully applied to a stereoselective pharmacokinetic study of lansoprazole enantiomers in rat plasma after oral administration of 3 mg/kg racemic lansoprazole or dexlansoprazole. No chiral inversion was observed during the experimental procedure.

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Two‐dimensional chromatography method applied to the enantiomeric determination of lansoprazole in human plasma by direct sample injection

Cited by 25 publications

References 19 publications

Enantioselective disposition of omeprazole, pantoprazole, and lansoprazole in a same Brazilian subjects group

Enantioselective disposition of omeprazole, pantoprazole, and lansoprazole in a same Brazilian subjects group

Determination of lansoprazole enantiomers in dog plasma by column‐switching liquid chromatography with tandem mass spectrometry and its application to a preclinical pharmacokinetic study

Enantioselective analysis of lansoprazole in rat plasma by LC–MS/MS: Application to a stereoselective pharmacokinetic study

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