Stereoselective determination of metoprolol and its metabolite α-hydroxymetoprolol in plasma by LC-MS/MS: application to pharmacokinetics during pregnancy.

Abstract:

:Metoprolol is available for clinical use as a racemic mixture. The S-(-)-metoprolol enantiomer is the one expressing higher activity in the blockade of the β(1)-adrenergic receptor. The α-hydroxymetoprolol metabolite also has activity in the blockade of the β(1)-adrenergic receptor. The present study describes the development and validation of a stereoselective method for sequential analysis of metoprolol and of α-hydroxymetoprolol in plasma using high-performance liquid chromatography with tandem mass spectrometry (LC-MS/MS). 1-ml aliquots of plasma were extracted with dichloromethane : diisopropyl ether (1:1, v/v). Metoprolol enantiomers and α-hydroxymetoprolol isomers were separated on a Chiralpak AD column (Daicel Chemical Industries, New York, NY, USA) and quantitated by LC-MS/MS. The limit of quantitation obtained was 0.2 ng of each metoprolol enantiomer/ml plasma and 0.1 ng/ml of each α-hydroxymetoprolol isomer/ml plasma. The method was applied to the study of kinetic disposition of metoprolol in plasma samples collected up to 24 h after the administration of a single oral dose of 100-mg metoprolol tartrate to a hypertensive parturient with a gestational age of 42 weeks. The clinical study showed that the metoprolol pharmakokinetics is enantioselective, with the observation of higher area under the curve (AUC)(0-∞) values for S-(-)-metoprolol (AUC(S-(-)) /AUC(R-(+))  = 1.81) and the favoring of the formation of the new chiral center 1'R of α-hydroxymetoprolol (AUC(0-∞) (1'R/1'S)  = 2.78).

journal_name

Chirality

journal_title

Chirality

authors

Antunes Nde J,Cavalli RC,Marques MP,Lanchote VL

doi

10.1002/chir.22102

subject

Has Abstract

pub_date

2013-01-01 00:00:00

pages

1-7

issue

1

eissn

0899-0042

issn

1520-636X

journal_volume

25

pub_type

杂志文章
  • Development of vacuum-ultraviolet circular dichroism measurement system using a polarizing undulator.

    abstract::We have developed an improved circular dichroism (CD) and linear dichroism (LD) simultaneous measurement system for the vacuum ultraviolet (VUV) region by polarization modulation techniques using a four-period Onuki-type crossed undulator as a polarized light source. The system has been constructed at the VUV beamline...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20234

    authors: Tanaka M,Yagi-Watanabe K,Yamada T,Kaneko F,Nakagawa K

    更新日期:2006-02-01 00:00:00

  • NMR chiral discrimination of chalcogen containing secondary alcohols.

    abstract::Here, we report the general strategies by which NMR spectroscopy can be used to determine the enantiopurity and absolute configuration of chalcogen containing secondary alcohols, including the evaluation of the use of chiral solvating and chiral derivatizing agents. The BINOL/DMAP ternary complex demonstrated a simple...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23030

    authors: Marques NBG,Jacob RG,Perin G,Lenardão EJ,Alves D,Silva MS

    更新日期:2019-01-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23293

    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

  • Synthesis and circular dichroism studies of N,N-bis(2-quinolylmethyl)amino acid Cu(II) complexes: determination of absolute configuration and enantiomeric excess by the exciton coupling method.

    abstract::We report a method to determine the absolute configuration of alpha-amino acids by exciton coupled circular dichroism (ECCD). Naturally occurring amino acids were successfully derivatized with 2-bromomethylquinoline. Complexation of these conformationally flexible ligands with Cu(II) salts yielded defined propeller-li...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10079

    authors: Holmes AE,Zahn S,Canary JW

    更新日期:2002-06-01 00:00:00

  • Polarization in France.

    abstract::The special relationship between France and the polarization of light from the beginning of the 19th century until the present day is reviewed in the lives and works of Étienne Louis Malus, François Arago, Jean-Baptiste Biot, Augustin Fresnel, Louis Pasteur, Frédéric Wallerant, Aimé Cotton, Francis Perrin, and Alain A...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22818

    authors: Kahr B

    更新日期:2018-04-01 00:00:00

  • Gas chromatographic separation of saturated aliphatic hydrocarbon enantiomers on permethylated beta-cyclodextrin.

    abstract::Enantiomers of chiral aliphatic hydrocarbons are generally difficult to separate because they lack functional groups to be derivatized in order to generate diastereomers. The systematic and quantitative separation of a series of branched hydrocarbon enantiomers using a chiral cyclodextrin stationary phase and a cryost...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10269

    authors: Meierhenrich UJ,Nguyen MJ,Barbier B,Brack A,Thiemann WH

    更新日期:2003-01-01 00:00:00

  • Surface-enhanced chiroptical spectroscopy with superchiral surface waves.

    abstract::We study the chiroptical properties of one-dimensional photonic crystals supporting superchiral surface waves by introducing a simple formalism based on the Fresnel reflection matrix. We show that the proposed framework provides useful insights on the behavior of all the relevant chiroptical quantities, allowing for a...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22971

    authors: Pellegrini G,Finazzi M,Celebrano M,Duò L,Biagioni P

    更新日期:2018-07-01 00:00:00

  • Stereoselective metabolism of benalaxyl in liver microsomes from rat and rabbit.

    abstract::Benalaxyl (BX), methyl-N-phenylacetyl-N-2,6-xylyl alaninate, is a potent acylanilide fungicide and consist of a pair of enantiomers. The stereoselective metabolism of BX was investigated in rat and rabbit microsomes in vitro. The degradation kinetics and the enantiomer fraction (EF) were determined using normal high-p...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20879

    authors: Zhang P,Zhu W,Dang Z,Shen Z,Xu X,Huang L,Zhou Z

    更新日期:2011-02-01 00:00:00

  • Enantioselectivity in the steady-state pharmacokinetics and transplacental distribution of pindolol at delivery in pregnancy-induced hypertension.

    abstract::Nine patients taking oral doses of 10 mg/12 h rac-pindolol as part of their treatment for hypertension in pregnancy were recruited for the study. Maternal and fetal gestational age ranged from 20-38 years and 28-41 weeks, respectively. Blood was collected from the umbilical cord vein and from the mother from zero to 1...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10124

    authors: Gonçalves PV,Matthes Ado C,Da Cunha SP,Lanchote VL

    更新日期:2002-08-01 00:00:00

  • Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism.

    abstract::Advances in the measurement, calculation, and application of vibrational circular dichroism (VCD) for the determination of absolute configuration are described. The purpose of the review is to provide an up-to-date perspective on the capability of VCD to solve problems of absolute stereochemistry for chiral molecules ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10287

    authors: Freedman TB,Cao X,Dukor RK,Nafie LA

    更新日期:2003-11-01 00:00:00

  • From cosmic chirality to protein structure: Lord Kelvin's legacy.

    abstract::A selection of my work on chirality is sketched in two distinct parts of this lecture. Symmetry and Chirality explains how the discrete symmetries of parity P, time reversal T, and charge conjugation C may be used to characterize the properties of chiral systems. The concepts of true chirality (time-invariant enantiom...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22017

    authors: Barron LD

    更新日期:2012-11-01 00:00:00

  • Circular dichroism and the interactions of water soluble porphyrins with DNA.

    abstract::The size, sign, and profile of induced circular dichroism (CD) features in the Soret region are reliable indicators of the binding modes of porphyrins and metalloporphyrins to DNA. Porphyrins shown (using such CD criteria) to be intercalators in monodispersed DNA duplexes prove extremely useful for the detection and c...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.10206

    authors: Pasternack RF

    更新日期:2003-05-05 00:00:00

  • The biological activities of prothioconazole enantiomers and their toxicity assessment on aquatic organisms.

    abstract::Chiral fungicide prothioconazole has a wide range of antifungal spectrum; however, little research has been conducted to evaluate prothioconazole on an enantiomeric level. Five target pathogens and three common aquatic organisms were tested for the enantioselective bioactivity and toxicity of prothioconazole in this w...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23075

    authors: Zhai W,Zhang L,Cui J,Wei Y,Wang P,Liu D,Zhou Z

    更新日期:2019-06-01 00:00:00

  • A systematic study of chiral homoprolinols and their derivatives in the catalysis of enantioselective addition of diethylzinc to aldehydes.

    abstract::Homoprolinol analogs, a class of optically active γ-amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these γ-amino alcohols with those by the β-amino alcohols based on pyrrolidine architecture reported in the ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.21017

    authors: Liu CL,Wei CY,Wang SW,Peng YG

    更新日期:2011-11-01 00:00:00

  • Time-resolved circular dichroism in carbonmonoxy-myoglobin: the central role of the proximal histidine.

    abstract::A calculation of the circular dichroism (CD) spectra of carbonmonoxy- and deoxy-myoglobin is carried out in relation to a time-resolved CD experiment. This calculation allows us to assign a dominant role to the proximal histidine in the definition of the electronic normal modes and to interpret the transient CD struct...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20254

    authors: Dartigalongue T,Hache F

    更新日期:2006-05-05 00:00:00

  • Effect of the mobile phase on the retention behavior of optical isomers of the mandelic acid derivative methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate by chiral HPLC.

    abstract::Conditions for separation of enantiomers of a mandelic acid derivative, methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate (the analyte) were studied. Because of the presence of two chiral carbons, the analyte consists of four stereoisomers stable at ambient temperature. Chiral HPLC of the analyte resulted in four peaks...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20304

    authors: Shen B,Xu X,Chen J,Zhang X,Xu B

    更新日期:2006-09-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20938

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

    更新日期:2011-01-01 00:00:00

  • Physicochemical properties, binary and ternary phase diagrams of ketoprofen.

    abstract::Compared to simulated moving bed (SMB) chromatography, fractional crystallization is a simple and economical method for enantioseparation. Therefore, the coupling of SMB chromatography and fractional crystallization is suggested for enantioseparation of racemic compounds. In this work, a nonsteroidal antiinflammatory ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20075

    authors: Hong Lu Y,Bun Ching C

    更新日期:2004-10-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20985

    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

  • 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20663

    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

  • Enantioselectivity of esterases in human brain.

    abstract::Subcellular fractions of three human brain specimens were found to contain esterase activities which hydrolyzed racemic oxazepam 3-acetate (rac-OXA). All three human brain preparations were highly selective toward the S-enantiomer of rac-OXA. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530050714

    authors: Yang SK,Huang A,Huang JD

    更新日期:1993-01-01 00:00:00

  • Asymmetric reduction of β-ketoesters and chiral β-iminoesters: impact of a α-quaternary stereocenter.

    abstract::Diastereomeric reduction of nonactivated, hindered β-keto and chiral β-iminoesters are described. The influence of a α-stereocontrolled center on the efficiency and stereoselectivity of the reduction was studied. Reaction conditions were optimized to synthesize β-hydroxy- and β-aminoesters in good yields. In the case ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20909

    authors: Almahli H,Hendra F,Troufflard C,Cavé C,Joseph D,Delarue-Cochin S

    更新日期:2011-03-01 00:00:00

  • Improving enantiomeric resolutions by avoiding peak distortion effects in on-line coupled liquid chromatography to gas chromatography.

    abstract::In this work, we study the effect of different variables affecting elution profile distortion on the enantiomeric resolution eventually achievable when working with on-line coupled liquid chromatography to gas chromatography (LC-GC). Specifically, the proposed configuration combines achiral reversed-phase liquid chrom...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23121

    authors: Martínez RM,Barba C,Robredo S,Herraiz M

    更新日期:2019-10-01 00:00:00

  • Vibrational Circular Dichroism (VCD) Reveals Subtle Conformational Aspects and Intermolecular Interactions in the Carnitine Family.

    abstract::Vibrational circular dichroism spectra (VCD) in the mid-IR region and electronic circular dichroism (ECD) spectra for three carnitine derivatives in the form of hydrochloride salts were recorded in deuterated methanol solutions. Density Functional Theory calculations help one to understand the significance of the obse...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22532

    authors: Mazzeo G,Abbate S,Longhi G,Castiglioni E,Villani C

    更新日期:2015-12-01 00:00:00

  • Effect of serum lipoproteins on stereoselective halofantrine metabolism by rat hepatocytes.

    abstract::Experimental hyperlipidemia has shown to decrease cytochrome P450 3A4 and 2C11 expression and to increase liver concentrations and the plasma protein binding of halofantrine (HF) enantiomers. The present study examined the effect of hyperlipidemic (HL) serum on the metabolism of HF enantiomers by primary rat hepatocyt...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22054

    authors: Patel JP,Hamdy DA,El-Kadi AO,Brocks DR

    更新日期:2012-07-01 00:00:00

  • Substituent effects in the selective reductive opening of epoxides with borohydrides in the presence of beta-cyclodextrin

    abstract::The opening of ortho-substituted phenyl oxiranes by borohydrides is described both in aqueous and solid phases. Some remarkable differences in the regioselectivity and inversion of enantioselectivity of oxirane ring-opening are reported. The results obtained are compared with previous studies and have allowed some fac...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:7<541::AID-CHIR5>3

    authors: Doussot J,Guy A,Siaugue JM,Ferroud C,Guieres AF

    更新日期:1999-01-01 00:00:00

  • Solid-state circular dichroism and hydrogen bonding, part 2: the case of hypothemycin re-investigated.

    abstract::The impact of crystalline forces on the solid-state circular dichroism (CD) spectrum of hypothemycin (), a biologically active molecule extracted from natural sources, has been analyzed by means of time-dependent density functional theory CD calculations. Input structures were extracted from the X-ray geometry of and ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22008

    authors: Pescitelli G

    更新日期:2012-09-01 00:00:00

  • Configuration of heptopyranoside and heptofuranoside side chains: 2-anthroate, a powerful chromophore for exciton coupled CD.

    abstract::The absolute configuration of the acyclic side chain of heptopyranosides and heptofuranosides was determined by exciton coupled CD, employing the strongly fluorescent 2-anthroate chromophore. The usage of this chromophore offers significant improvements over previous chemical and spectroscopic procedures since its int...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1997)9:7<699::AID-CHIR11>3

    authors: Akritopoulou-Zanze I,Nakanishi K,Stepowska H,Grzeszczyk B,Zamojski A,Berova N

    更新日期:1997-01-01 00:00:00

  • Spectroscopic studies on nicotine and nornicotine in the UV region.

    abstract::The UV absorption and electronic circular dichroism (ECD) spectra of (R)- and (S)-nicotine and (S)-nornicotine in aqueous solution were measured to a significantly lower wavelength range than previously reported, allowing the identification of four previously unobserved electronic transitions. The ECD spectra of the t...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22141

    authors: Clayton PM,Vas CA,Bui TT,Drake AF,McAdam K

    更新日期:2013-05-01 00:00:00

  • Enantioselective Friedel-Crafts reaction of indoles with trifluoroacetaldehyde catalyzed by Cinchona alkaloids.

    abstract::The first direct asymmetric synthetic preparation of trifluoro-1-(indol-3-yl)ethanols (TFIEs) is described by an enantioselective organocatalytic method from indoles and inexpensive trifluoroacetaldehyde methyl hemiacetal. The reaction is catalyzed by hydroquinine to produce TFIEs in an almost quantitative yield and w...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20982

    authors: Borkin DA,Landge SM,Török B

    更新日期:2011-09-01 00:00:00