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


: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.






Sun LN,Shen YW,Ying YW,Li D,Li TF,Zhang XH,Zhao P,Ding L,Wang YQ




Has Abstract


2018-12-01 00:00:00












  • Unusual temperature-induced retention behavior of constrained β-amino acid enantiomers on the zwitterionic chiral stationary phases ZWIX(+) and ZWIX(-).

    abstract::The effects of temperature on the chiral recognition of cyclic β-amino acid enantiomers on zwitterionic [Chiralpak ZWIX(+) and ZWIX(-)] chiral stationary phases were investigated. Experiments were performed at different mobile phase compositions and under 10°C column temperature increments in the temperature range 10-...


    pub_type: 杂志文章


    authors: Ilisz I,Pataj Z,Gecse Z,Szakonyi Z,Fülöp F,Lindner W,Péter A

    更新日期:2014-08-01 00:00:00

  • Evaluation of the enantiomeric composition of amino acids in tobacco.

    abstract::Despite the fact that several studies have reported the concentrations of various free amino acids in tobacco, their enantiomeric composition is unknown. Both the absolute and enantiomeric compositions of proline, alanine, asparagine, aspartic acid, valine, methionine, leucine,and phenylalanine were determined for thr...


    pub_type: 杂志文章


    authors: Kullman JP,Chen X,Armstrong DW

    更新日期:1999-01-01 00:00:00

  • Secondary phosphine oxides: tautomerism and chiral recognition monitored by multinuclear NMR spectroscopy of their Rh2[(R)-MTPA]4 adducts.

    abstract::Six secondary phosphine oxides and their tautomeric equilibria as free ligands and in the presence of an equimolar amount of the chiral dirhodium complex Rh* are described and discussed. Discrimination of enantiomers is easily possible by inspecting the (31)P NMR resonances; some (1)H and (13)C NMR resonances are usef...


    pub_type: 杂志文章


    authors: Magiera D,Szmigielska A,Pietrusiewicz KM,Duddeck H

    更新日期:2004-01-01 00:00:00

  • Comparative study on kynurenic acid production in the rat striatum by tryptophan enantiomers: an in vivo microdialysis study.

    abstract::Kynurenic acid (KYNA), an endogenous antagonist of N-methyl-D-aspartate and α(7) nicotinic acetylcholine receptors, is one of the L-tryptophan (Trp) metabolites. To compare the level of KYNA produced in the striatum of rats after independent administration of L-Trp and D-Trp, rats were intraperitoneally administered L...


    pub_type: 杂志文章


    authors: Ishii K,Iizuka H,Ogaya T,Song Z,Fukushima T

    更新日期:2011-01-01 00:00:00

  • Resolution of enantiomers of novel C2 -symmetric aminobisphosphinic acids via diastereomeric salt formation with quinine.

    abstract::C2 -symmetric N,N-bis(phosphinomethyl)amines were prepared by the thermal reaction of aromatic aldehydes with ammonia and hypophosphorus acid as previously described. Both enantiomers of C2 -symmetric N,N-bis(phosphinomethyl)amine were obtained in a high enantiomeric purity through the diastereomeric salt formation wi...


    pub_type: 杂志文章


    authors: Kaboudin B,Faghihi MR,Kazemi F,Yokomatsu T

    更新日期:2015-01-01 00:00:00

  • Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides.

    abstract::Synthetic pyrethroid insecticides are chiral compounds with multiple asymmetric positions. In this study, isomers of four commonly used pyrethroids were separated at the enantiomeric level by enantioselective high-performance liquid chromatography (HPLC), and differences between enantiomers in aquatic toxicity were ch...


    pub_type: 杂志文章


    authors: Liu W,Gan JJ,Qin S

    更新日期:2005-01-01 00:00:00

  • Discrimination in resolving systems: ephedrine-mandelic acid.

    abstract::Resolution of mandelic acid with (-)-(1R,2S)-ephedrine in water and ethanol produces intermediate diastereomeric salts with greatly disparate solubilities and melting points. Single crystal X-ray analysis of the less (L) and more (M) soluble (-)-ephedrinium mandelates (I, II) shows crystal structures which are isoster...


    pub_type: 杂志文章


    authors: Valente EJ,Zubkowski J,Eggleston DS

    更新日期:1992-01-01 00:00:00

  • Separation and determination of tetracycline hydrochloride in real water samples using binary small molecule alcohol-salt aqueous two-phase system coupled with high-performance liquid chromatography.

    abstract::An environmental and sensitive sample pretreatment method was established and combined with high-performance liquid chromatography (HPLC) for the analysis of tetracycline hydrochloride (TC) in feed water and lake water. One element small molecule alcohol-salt aqueous two-phase system (ATPS) cannot effectively adjust t...


    pub_type: 杂志文章


    authors: Guo DG,Ni L,Wang L,Shao L

    更新日期:2019-09-01 00:00:00

  • Channel-like crystal structure of cinchoninium L-O-phosphoserine salt dihydrate.

    abstract::Studies on the interactions between L-O- phosphoserine, as one of the simplest fragments of membrane components, and the Cinchona alkaloid cinchonine, in the crystalline state were performed. Cinchoninium L-O-phosposerine salt dihydrate (PhSerCin) crystallizes in a monoclinic crystal system, space group P2(1), with un...


    pub_type: 杂志文章


    authors: Wesełucha-Birczyńska A,Oleksyn BJ,Watroba J

    更新日期:2010-06-01 00:00:00

  • Unexpected rearrangement of enantiomerically pure 3-aminoquinuclidine as a simple way of preparing diastereomeric octahydropyrrolo[2,3-c]pyridine derivatives.

    abstract::Reaction of (S)- or (R)-3-aminoquinuclidine with 2-chloropyrimidine or 2-bromopyrimidine led to an unexpected formation of both cis- and trans-octahydropyrrolo [2,3]pyridine derivatives. A single-step synthesis of two of the four stereoisomers of these octahydropyrrolo[2,3]pyridine derivatives provides a convenient wa...


    pub_type: 杂志文章


    authors: Goljer I,Molinari A,He Y,Nogle L,Sun W,Campbell B,McConnell O

    更新日期:2009-07-01 00:00:00

  • Enantioselective LC/MS method for the determination of an antimalarial agent Fenozan B07 in dog plasma.

    abstract::A chiral liquid chromatography/mass spectrometry (LC/MS) bioanalytical procedure has been developed for the analysis of the antimalaric agent Fenozan B07 in dog plasma. Normal-phase chromatography involving a phenylcarbamate derivative of cellulose coated on silica gel as the chiral stationary phase was used to resolv...


    pub_type: 杂志文章


    authors: Maraschiello C,Vilageliu J,Dorronsoro I,Martinez A,Floriano P,Gómez-Acebo E

    更新日期:2006-05-15 00:00:00

  • Separation of amino acid enantiomers by micelle-enhanced ultrafiltration.

    abstract::A Micelle-enhanced ultrafiltration (MEUF) separation process was investigated that can potentially be used for large-scale enantioseparations. Copper(II)-amino acid derivatives dissolved in nonionic surfactant micelles were used as chiral selectors for the separation of dilute racemic amino acids solutions. For the al...


    pub_type: 杂志文章


    authors: De Bruin TJ,Marcelis AT,Zuilhof H,Rodenburg LM,Niederländer HA,Koudijs A,Overdevest PE,Van der Padt A,Sudhölter EJ

    更新日期:2000-08-01 00:00:00

  • Tautomerism of 4-hydroxy-2,5-dimethyl-3(2H)-furanone: evidence for its enantioselective biosynthesis.

    abstract::Chiral natural flavor compounds exhibit characteristic enantiomeric excesses due to stereoselective, enzymatically catalyzed reactions during biogenesis. Although the enzymatic formation of the strawberry key flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF; Furaneol(R)) is anticipated, the naturally occurr...


    pub_type: 杂志文章


    authors: Raab T,Hauck T,Knecht A,Schmitt U,Holzgrabe U,Schwab W

    更新日期:2003-08-01 00:00:00

  • Preparative and analytical separation of the zopiclone enantiomers and determination of their affinity to the benzodiazepine receptor binding site.

    abstract::We report the preparative separation of rac-zopiclone using malic acid as the resolving agent. Furthermore, two different methods for the analytical determination of zopiclone enantiomers by HPLC on chiral stationary phases are described. The benzodiazepine receptor binding of the isolated enantiomers was investigated...


    pub_type: 杂志文章


    authors: Blaschke G,Hempel G,Müller WE

    更新日期:1993-01-01 00:00:00

  • Asymmetric Borane Reduction of Prochiral Ketones Catalyzed By Helical Poly[(S)-3-vinyl-2,2'-dihydroxy-1,1'-binaphthyl].

    abstract::The application of helical poly[(S)-3-vinyl-2,2'-dihydroxy-1, 1'-binaphthyl] (L*) in the asymmetric borane reduction of prochiral ketones was studied. The results showed that L* had excellent catalytic activity as well as enantioselectivity, giving up to 96% yield and up to 99% enantiomeric excess (ee) of the correspo...


    pub_type: 杂志文章


    authors: Qin G,Chen Y,Yang L,Yang N,Yang Z

    更新日期:2015-07-01 00:00:00

  • Chiral counter-current chromatography: A survey of its instrument, mechanism, procedure, and applications.

    abstract::The chiral separation by counter-current chromatography has made great progress in the past three decades. It has become increasingly popular in the field of chiral separation, and many applications have been introduced during the last years. This review mainly focuses on the current topics, applications, and trends i...


    pub_type: 杂志文章,评审


    authors: Duan WD,Huang XY,Di DL

    更新日期:2020-10-01 00:00:00

  • Enantiomeric recognition of amino acids using a chiral spiropyran derivative.

    abstract::An optically active spiropyran 1 with a binaphthol moiety as a chiral source was synthesized. The colored merocyanine form of (R)-1 obtained by the UV irradiation remained in the presence of D-amino acids longer than with L-amino acids. ...


    pub_type: 杂志文章


    authors: Tsubaki K,Mukoyoshi K,Morikawa H,Kinoshita T,Fuji K

    更新日期:2002-10-01 00:00:00

  • Structural Basis and Mechanism of Chiral Benzedrine Molecules Interacting With Third Dopamine Receptor.

    abstract::In order to investigate the chiral benzedrine molecules corresponding to their different characteristics in biochemical systems, we studied their interaction with D3 R using the docking method, molecular dynamic simulation, and quantum chemistry. The obtained results indicate that the active residues for R-benzedrine ...


    pub_type: 杂志文章


    authors: Wang M,Xie W,Li A,Xu S

    更新日期:2016-10-01 00:00:00

  • Measurements of concentration dependence and enantiomeric purity of terpene solutions as a test of a new commercial VCD spectrometer

    abstract::Vibrational circular dichroism (VCD) spectra of (+)-alpha-pinene solutions in carbon tetrachloride have been measured in the range of volume fractions 5-100% (v/v) in the mid-infrared region. The concentration dependence measured was statistically analyzed with the aim of obtaining a reliable correlation between the V...


    pub_type: 杂志文章


    authors: Urbanova M,Setnicka V V,Volka K

    更新日期:2000-05-01 00:00:00

  • Modulatory effect of chiral nonsteroidal anti-inflammatory drugs on apoptosis of human neutrophils.

    abstract::Polymorphonuclear neutrophils (PMNs) are short-lived leukocytes that die by apoptosis. Although PMNs are crucial in the defense against infection, they have been implicated in the pathogenesis of tissue injury observed in inflammatory diseases. The induction or prevention of PMN apoptosis is currently discussed as a k...


    pub_type: 杂志文章


    authors: Zielińska-Przyjemska M,Główka FK,Klaczyńska J

    更新日期:2008-02-01 00:00:00

  • Unequivocal Enantiomeric Identification and Analysis of 10 Chiral Pesticides in Fruit and Vegetables by QuEChERS Method Combined With Liquid Chromatography-Quadruple/Linear Ion Trap Mass Spectrometry Determination.

    abstract::In this research, 10 chiral pesticides in fruits and vegetables were simultaneously determined using chiral liquid chromatography triple quadrupole-linear ion trap hybrid mass spectrometry (LC-QqLIT). The QuEChERS method was applied for sample preparation, and an enhanced product ion (EPI) scan was used to acquire tan...


    pub_type: 杂志文章


    authors: He Z,Peng Y,Wang L,Luo M,Liu X

    更新日期:2015-12-01 00:00:00

  • Normal phase chiral HPLC of methylphenidate: comparison of different polysaccharide-based chiral stationary phases.

    abstract::A comparison of the enantiomeric resolution of (+/-)-threo-methylphenidate (MPH) (Ritalin) was achieved on different polysaccharide based chiral stationary phases. The mobile phase used was hexane-ethanol-methanol-trifluoroacetic acid (480:9.75:9.75:0.5, v/v/v/v). Benzoic acid and phenol were used as the mobile phase ...


    pub_type: 杂志文章


    authors: Aboul-Enein HY,Ali I

    更新日期:2002-01-01 00:00:00

  • The possible role of enantiodiscrimination in bilirubin toxicity.

    abstract::The possibility that enantiodiscrimination of bilirubin might be involved in neuronal membrane destabilization, and therefore in bilirubin toxicity, was investigated, by circular dichroism, on model membranes composed of phospholipids. The equilibrium between bilirubin enantiomers is displaced at some extent by the in...


    pub_type: 杂志文章


    authors: Bernardini C,D'Arrigo P,Elemento G,Mancini G,Servi S,Sorrenti A

    更新日期:2009-01-01 00:00:00

  • Deracemization of an axially chiral biphenylic derivative as a tool for investigating chiral recognition in self-assemblies.

    abstract::Two diastereomeric cationic surfactants derived from L-proline, in which the second chiral center is a quaternary nitrogen, have been separated and fully characterized. The recognition properties of the aggregates formed by the two diastereomeric surfactants have been investigated by circular dichroism and (1)H NMR th...


    pub_type: 杂志文章


    authors: Borocci S,Ceccacci F,Galantini L,Mancini G,Monti D,Scipioni A,Venanzi M

    更新日期:2003-05-15 00:00:00

  • Lack of metabolic racemisation of ropivacaine, determined by liquid chromatography using a chiral AGP column.

    abstract::Ropivacaine hydrochloride monohydrate (ropivacaine) is a new local anaesthetic agent which is administered exclusively as the (-)-(S)-form. The aim of the study was to determine whether metabolic racemisation of (-)-(S)-ropivacaine occurs. This was tested in man, rat, dog, and sheep after different routes of administr...


    pub_type: 杂志文章


    authors: Arvidsson T,Bruce HF,Halldin MM

    更新日期:1995-01-01 00:00:00

  • Improved chiral electrochemical recognition of tryptophan enantiomers based on three-dimensional molecularly imprinted overoxidized polypyrrole/MnO2 /carbon felt composites.

    abstract::A three-dimensional molecularly imprinted overoxidized polypyrrole/MnO2 /carbon felt (MIOPPy/MnO2 /CF) composites were fabricated, which results in increased active area of the surface of the molecularly imprinted polymers film and greatly improved electrochemical chiral recognition effect for tryptophan isomers. The ...


    pub_type: 杂志文章


    authors: Dong L,Liu X,Xu H,Wu D,Gao S,Zhong L,Kong Y

    更新日期:2019-11-01 00:00:00

  • Solid-state circular dichroism and hydrogen bonding: absolute configuration of massarigenin A from Microsphaeropsis sp.

    abstract::Massarigenin A (1) and papyracillic acids A (2) and B (3) were isolated from the endophytic fungus Microsphaeropsis sp. Their structures were elucidated by multidimensional nuclear magnetic resonance spectroscopy; the structure of massarigenin A (1) was also confirmed by X-ray crystallography. The absolute configurati...


    pub_type: 杂志文章


    authors: Hussain H,Ahmed I,Schulz B,Draeger S,Flörke U,Pescitelli G,Krohn K

    更新日期:2011-09-01 00:00:00

  • Variable stereochemistry in highly branched isoprenoids from diatoms.

    abstract::C(25) highly branched isoprenoid (HBI) alkenes are ubiquitous lipids found in geochemical samples around the globe. The origins of these widespread geochemicals are believed to be restricted to a limited number of diatoms, including Haslea ostrearia (and related species), Rhizosolenia setigera, and Pleurosigma interme...


    pub_type: 杂志文章


    authors: Belt ST,Allard WG,Johns L,König WA,Massé G,Robert JM,Rowland S

    更新日期:2001-08-01 00:00:00

  • Time-resolved circularly polarized luminescence of Eu3+ -based systems.

    abstract::Chiral Eu3+ -based systems are frequently studied via circularly polarized luminescence spectroscopy. The emission lifetimes of each circular polarization, however, are virtually always ignored, because in a homogeneous sample of emitters, there should be no difference between the two. However, we show that in less ro...


    pub_type: 杂志文章


    authors: Hananel U,Schwartz G,Paiss G,Arrico L,Zinna F,Di Bari L,Cheshnovsky O,Markovich G

    更新日期:2020-12-30 00:00:00

  • Applications of the Cartesian coordinate tensor transfer technique in the simulations of vibrational circular dichroism spectra of oligonucleotides.

    abstract::The application of the Cartesian coordinate tensor transfer (CCT) technique for simulations of the IR absorption and vibrational circular dichroism (VCD) spectra of relatively large nucleic acid fragments is demonstrated on several case studies. The approach is based on direct ab initio calculations of atomic tensors,...


    pub_type: 杂志文章,评审


    authors: Andrushchenko V,Bouř P

    更新日期:2010-01-01 00:00:00