Pharmacokinetics of nateglinide enantiomers and their metabolites in Goto-Kakizaki rats, a model for type 2 diabetes mellitus.

Abstract:

:The pharmacokinetics of (-)-N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine (nateglinide) and its enantiomer (L-enantiomer) was studied in Goto-Kakizaki (GK) rats after intravenous administration of nateglinide or L-enantiomer at a dose of 40 micromol/kg body weight. Nateglinide, its L-enantiomer and their metabolites in serum, bile and urine were determined. The total clearance (CL(tot)) and the volume of distribution (Vd) was slightly higher for nateglinide than those for L-enantiomer in control rats, although the differences were not statistically significant. The cumulative excretions of L-M1 (major metabolite of L-enantiomer) and L-M2 (major metabolite of L-enantiomer) into bile were almost the same as that of M1 (major metabolite of nateglinide)and M2 (major metabolite of nateglinide). In GK rats, CL(tot) and Vd were higher for nateglinide than those for L-enantiomer. The cumulative excretion of L-M1 and L-M2 were not different from those of M1 and M2, respectively, into bile or urine. CL(tot) and Vd for nateglinide or L-enantiomer in GK rats were not different from those in control rats. The total excretion of M1, M2, L-M1, and L-M2 into bile or urine in GK rats was not substantially different from that of control rats. These results suggest that the L-enantiomer of nateglinide shows higher CL(tot) and Vd compared with nateglinide, especially in the diabetic state.

journal_name

Chirality

journal_title

Chirality

authors

Tamura M,Shiba S,Kudo N,Kawashima Y

doi

10.1002/chir.20711

subject

Has Abstract

pub_date

2010-01-01 00:00:00

pages

92-8

issue

1

eissn

0899-0042

issn

1520-636X

journal_volume

22

pub_type

杂志文章
  • 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

  • Chiroptical property tuning of supramolecular assemblies in polymer matrices.

    abstract::Chiroptical materials have received much attention in diverse fields for applications such as displays, sensors, smart memory devices, and catalysis. Here, we develop a simple fabrication method for polymer films with tunable chiroptical properties using small amounts of self-assembling fluorescent dye as an additive....

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23201

    authors: Jintoku H,Ihara H

    更新日期:2020-05-01 00:00:00

  • Conformational and Chiral Properties of Cyclic-tri(N-methyl-meta-benzamide) Bearing Amidino Groups.

    abstract::Cyclic triamides bearing amidino groups at the meta position of the phenyl rings were synthesized, and their conformational properties in the crystal and in solution were examined. Compound exists as a capsule-type dimer of the enantiomers with a bowl-shaped syn conformation in the crystal state. Compound exists mainl...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22476

    authors: Nishiyama S,Urushibara K,Masu H,Azumaya I,Kagechika H,Tanatani A

    更新日期:2015-08-01 00:00:00

  • Separation and toxicity of salithion enantiomers.

    abstract::Enantioseletive toxicities of chiral pesticides have become an environmental concern recently. In this study, we evaluated the enantiomeric separation of salithion on a suite of commercial chiral columns and assessed the toxicity of enantiomers toward butyrylcholinesterase and Daphnia magna. Satisfactory separations o...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20690

    authors: Zhou S,Lin K,Li L,Jin M,Ye J,Liu W

    更新日期:2009-11-01 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

  • 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:4<199::AID-CHIR6>3

    authors: Urbanova M,Setnicka V V,Volka K

    更新日期:2000-05-01 00:00:00

  • Viewing and inducing symmetry breaking at the single-molecule limit.

    abstract::Symmetry breaking by photons, electrons, and molecular interactions lies at the heart of many important problems as varied as the origin of homochiral life to enantioselective drug production. Herein we report a system in which symmetry breaking can be induced and measured in situ at the single-molecule level using sc...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22096

    authors: Tierney HL,Jewell AD,Baber AE,Iski EV,Sykes EC

    更新日期:2012-12-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530040807

    authors: Valente EJ,Zubkowski J,Eggleston DS

    更新日期:1992-01-01 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

  • Highly enantioselective asymmetric autocatalysis of 2-alkenyl- and 2-vinyl-5-pyrimidyl alkanols with significant amplification of enantiomeric excess.

    abstract::2-Alkenyl- and 2-vinyl-5-pyrimidyl alkanols are highly enantioselective asymmetric autocatalysts with significant amplification of enantiomeric excess in the enantioselective addition of diisopropylzinc to 2-alkenyl- and 2-vinylpyrimidine-5-carbaldehydes. Consecutive asymmetric autocatalysis starting from 7% ee increa...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10068

    authors: Sato I,Yanagi T,Soai K

    更新日期:2002-02-01 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

  • Enantioselective separation of (±)-β-hydroxy-1,2,3-triazoles by supercritical fluid chromatography and high-performance liquid chromatography.

    abstract::This paper reports the enantioseparation of β-hydroxy-1,2,3-triazole derivatives, which present a broad range of biological properties, by supercritical fluid chromatography (SFC) and high-performance liquid chromatography techniques (HPLC). Polysaccharide-based chiral columns (cellulose and amylose) were used to eval...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22851

    authors: Alvarenga N,Porto ALM,Barreiro JC

    更新日期:2018-07-01 00:00:00

  • Simultaneous Chiral Separation of Flavanone, Naringenin, and Hesperetin Enantiomers by RP-UHPLC-DAD.

    abstract::A rapid and effective RP-UHPLC-DAD method for enantioseparation of three flavanones, i.e., flavanone, naringenin, and hesperetin, was developed and validated. Chromatographic separation of the analytes was performed using a Chiralpak AD-3R analytical column under reverse phase conditions with methanol as the mobile ph...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22559

    authors: Baranowska I,Hejniak J,Magiera S

    更新日期:2016-02-01 00:00:00

  • The enantioselective enrichment, metabolism, and toxicity of fenoxaprop-ethyl and its metabolites in zebrafish.

    abstract::To investigate the impacts of the widely used chiral herbicide fenoxaprop-ethyl (FE) on aquatic organisms, the enrichment, metabolism, acute toxicity, and oxidative stress of fenoxaprop-ethyl and its main metabolites fenoxaprop (FA), ethyl-2-(4-hydroxyphenoxy)propanoate (EHPP), 2-(4-hydroxyphenoxy)propanoic acid (HPPA...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23222

    authors: Xu Y,Jing X,Zhai W,Li X

    更新日期:2020-07-01 00:00:00

  • N,N-dimethylcarbamyl derivatives of oxazepam.

    abstract::Three N,N-dimethylcarbamyl derivatives of oxazepam (1-(N,N-dimethylcarbamyl)oxazepam, 3-O-(N,N-dimethylcarbamyl)oxazepam, and 1,3-O-bis(N,N-dimethylcarbamyl) oxazepam) and a 3-O-acyl-1-(N,N-dimethylcarbamyl)-oxazepam were synthesized from either oxazepam or demoxepam. Enantiomeric pairs of these derivatives and of cam...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530030313

    authors: Yang SK,Lu XL

    更新日期:1991-01-01 00:00:00

  • Stereoselective renal secretion of carbenicillin in rabbits: role of the organic anion transporter at the renal brush border membrane.

    abstract::Stereoselectivity in the renal secretion of carbenicillin (CBPC) was studied in rabbits. Significant renal secretion of CBPC was observed in vivo, with the secretion of the S-epimer being greater than that of the R-epimer. Stereoselective transport of CBPC was further studied in vitro using basolateral and brush borde...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1998)10:4<349::AID-CHIR10>

    authors: Itoh T,Nakaura H,Koyano S,Tsuda Y,Yamada H

    更新日期:1998-01-01 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

  • 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

  • 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:8<669::AID-CHIR10>

    authors: Kullman JP,Chen X,Armstrong DW

    更新日期:1999-01-01 00:00:00

  • Chiroptical properties of cation complexes of chiral phenazino-18-crown-6 ether-type hosts.

    abstract::Herein we report CD spectroscopic studies on complexes of (R,R)-dimethyl-, (R,R)-diisobutyl-, and (S,S)-di-sec-butyl-phenazino-18-crown-6 ligands (Scheme 1) with selected alkali (Na+, K+), alkaline earth (Mg2+, Ca2+), and transition-metal (Ag+, Zn2+, Ni2+, Cd2+, Pb2+) cations. The complexation was monitored in the 300...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20162

    authors: Szarvas S,Szalay L,Vass E,Hollósi M,Samu E,Huszthy P

    更新日期:2005-06-01 00:00:00

  • Copper(II) complexes of N2-alkyl-(S)-amino acid amides as chiral selectors for dynamically coated chiral stationary phases in RP-HPLC.

    abstract::Copper(II) complexes of N2-octyl-(S)-phenylalaninamide (Noc-Phe-NH2), N2-dodecyl-(S)-phenylalaninamide (Ndo-Phe-NH2), and N2-octyl-(S)-norleucinamide (Noc-NLeu-NH2), dynamically adsorbed on a reversed-phase C18 column, were able to perform the direct enantiomeric separation of unmodified amino acids, amino acid amides...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1996)8:2<189::AID-CHIR3>3.

    authors: Galaverna G,Corradini R,Dossena A,Marchelli R,Dallavalle F

    更新日期:1996-01-01 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

  • Stereoselective intramolecular cyclization to 4-(hydroxymethyl)-3-(1H-indolyl)oxazolidin-2-ones.

    abstract::A simple high-yield three-steps route to optically active 4-hydroxymethyl-3-(1H-indolyl)oxazolidin-2-ones from (S)-glycidol is described. The key intermediates (R)-oxiran-2-ylmethyl 1H-indol-4/-5-ylcarbamates are obtained in high yields from (S)-glycidol. These are readily transformed to oxazolidin-2-ones, very intere...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22003

    authors: Chiummiento L,Funicello M,Tramutola F

    更新日期:2012-04-01 00:00:00

  • Chiral recognition ability and solvent versatility of bonded amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase: enantioselective liquid chromatographic resolution of racemic N-alkylated barbiturates and thalidomide analogs.

    abstract::The chiral recognition ability and solvent versatility of a new chiral stationary phase containing amylose 3,5-dimethylphenylcarabamate immobilized onto silica gel (CHIRALPAK IA) is investigated. Thus, the direct enantioselective separation of a set of racemic N-alkylated barbiturates and 3-alkylated analogs of thalid...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20398

    authors: Ghanem A,Al-Humaidi E

    更新日期:2007-06-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20122

    authors: Liu W,Gan JJ,Qin S

    更新日期:2005-01-01 00:00:00

  • (R,R)-N,N'-dimethylcyclohexyl-1,2-diazaseleno-phospholidine as a chiral derivatizing agent for the evaluation of chiral alcohols.

    abstract::Previously, a diazaphospholidine has been synthesized and evaluated as a chiral derivatizing reagent for the determination of the optical purity of chiral alcohols via 31P NMR spectroscopy (Alexakis et al., J. Org. Chem. 57:1224-1237, 1992). Our laboratory is interested in the advantageous and practical applications o...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530060306

    authors: House KL,O'Connor MJ,Silks LA 3rd,Dunlap RB,Odom JD

    更新日期:1994-01-01 00:00:00

  • Stereoselective effect of warfarin and bilirubin on the binding of 5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2- one enantiomers to human serum albumin.

    abstract::The binding of the title benzodiazepine enantiomers and its modulation by warfarin and bilirubin were studied by chromatography on human serum albumin (HSA) immobilized on Sepharose 4B, and also by a combination of ultrafiltration and circular dichroism (UF-CD) methods. In the absence of warfarin and bilirubin the bin...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530020307

    authors: Fitos I,Visy J,Magyar A,Kajtár J,Simonyi M

    更新日期:1990-01-01 00:00:00

  • Excitatory amino acid receptor antagonists: resolution, absolute stereochemistry, and pharmacology of (S)- and (R)-2-amino-2-(5-tert-butyl-3-hydroxyisoxazol-4-yl)acetic acid (ATAA).

    abstract::We have previously shown that (RS)-2-amino-2-(5-tert-butyl-3-hydroxyisoxazol-4-yl)acetic acid (ATAA) is an antagonist at N-methyl-D-aspartic acid (NMDA) and (RS)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) receptors. We have now resolved ATAA via diastereomeric salt formation using N-BOC protected...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1997)9:5/6<529::AID-CHIR20

    authors: Johansen TN,Frydenvang K,Ebert B,Madsen U,Krogsgaard-Larsen P

    更新日期:1997-01-01 00:00:00

  • Enantioselectivity in the metabolism of mexiletine by conjugation in female patients with the arrhythmic form of chronic Chagas' heart disease.

    abstract::The phenomenon of enantioselectivity in the metabolism of mexiletine (MEX) conjugation was investigated in eight female patients with the arrhythmic form of chronic Chagas' heart disease treated with racemic mexiletine hydrochloride (two 100 mg capsules every 8 hr). Blood samples were collected up to 24 hr after the a...

    journal_title:Chirality

    pub_type: 临床试验,杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:1<29::AID-CHIR5>3.

    authors: Lanchote VL,Cesarino EJ,Santos VJ,Mere Júnior Y,Santos SR

    更新日期:1999-01-01 00:00:00

  • A chiral enantioseparation generic strategy for anti-Alzheimer and antifungal drugs by short end injection capillary electrophoresis using an experimental design approach.

    abstract::The present study describes a generic strategy using capillary electrophoretic (CE) method for chiral enantioseparation of anti-Alzheimer drugs, namely, donepezil (DON), rivastigmine (RIV), and antifungal drugs, namely, ketoconazole (KET), Itraconazole (ITR), fluconazole (FLU), and sertaconazole (SRT) in which these d...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22777

    authors: Abdel-Megied AM,Hanafi RS,Aboul-Enein HY

    更新日期:2018-02-01 00:00:00