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 administration of the morning dose, with discontinuation of the subsequent doses during the study period. Plasma concentrations of N-hydroxymexiletine glucuronide were calculated as the difference between the concentrations of unchanged and total (unchanged + conjugated) MEX enantiomers. Total plasma MEX concentrations were analyzed by HPLC after enzymatic hydrolysis with beta-glucuronidase, the formation of diastereomeric derivatives with the chiral reagent N-acetyl-L-cysteine/o-phthalaldehyde, and fluorescence detection. The differences in the pharmacokinetic parameters of the enantiomers were evaluated by the paired t-test. The plasma concentrations of the (+)-(S)-MEX did not differ before and after enzymatic hydrolysis. The pharmacokinetic parameters calculated for (-)-(R)-N-hydroxymexiletine glucuronide are presented as means (95% confidence interval): maximum plasma concentration Cmax = 194.0 ng.ml-1 (154.3-233.7), time to maximum plasma concentration tmax = 1.4 hr (0.3-2.5), area under the plasma concentration versus time curve AUC0-24 = 2099.2 ng.h.ml-1 (1585.6-2612.6), elimination half-life t1/2 beta = 12.8 hr (9.9-15.6) and extent of conjugation of 31.6% (24.3-38.9%). The present data indicate stereospecific conjugation of (-)-(R)-N-hydroxymexiletine in the female patients with the arrhythmic form of Chagas' heart disease.
journal_name
Chiralityjournal_title
Chiralityauthors
Lanchote VL,Cesarino EJ,Santos VJ,Mere Júnior Y,Santos SRdoi
10.1002/(SICI)1520-636X(1999)11:1<29::AID-CHIR5>3.subject
Has Abstractpub_date
1999-01-01 00:00:00pages
29-32issue
1eissn
0899-0042issn
1520-636Xpii
10.1002/(SICI)1520-636X(1999)11:1<29::AID-CHIR5>3.journal_volume
11pub_type
临床试验,杂志文章相关文献
CHIRALITY文献大全abstract::Recent discovery of asymmetric desymmetrization of meso-heterocycles using (R,R)-(salen)manganese complex 2 as a catalyst allowed easy access to optically active 2,3,4-trisubstituted pyrrolidines. Taking advantage of this new reaction, we could achieve the short-step synthesis of (-)-swainsonine 1. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(2000)12:5/6<464::AID-CHIR2
更新日期:2000-06-01 00:00:00
abstract::The objective of this brief highlight is to point out the central role of the exciton chirality method to gain insights on the structural basis of the recently achieved ligand gating of synthetic ion channels. This unprecedented ligand gating was achieved with an equally unprecedented transmembrane rigid-rod pi-stack ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20221
更新日期:2006-02-01 00:00:00
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
更新日期:2012-12-01 00:00:00
abstract::Human carboxylesterase 1 (hCES1) is an enzyme that plays an important role in hydrolysis of pharmaceuticals in the human liver. In this study, elucidation of the chiral recognition ability of hCES1 was attempted using indomethacin esters in which various chiral alcohols were introduced. Indomethacin was condensed with...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23141
更新日期:2020-01-01 00:00:00
abstract::A statement has been formulated that chirality is an indispensable inherent property of all material objects, at one level of organization of matter or another. The translation of chirality from one level of material objects to another deserves our attention. The parity violation of weak interactions can be discussed ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20271
更新日期:2006-08-01 00:00:00
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...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10230
更新日期:2003-05-15 00:00:00
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
更新日期:2019-01-01 00:00:00
abstract::Novel enantiopure 1,2,4-trizole-3-thiones containing a benzensulfonamide moiety were synthesized via multistep reaction sequence starting with D-phenylalanine methyl ester and L-phenylalanine ethyl ester as a source of chirality. The chemical structures of all compounds were characterized by elemental analysis, UV, IR...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22607
更新日期:2016-06-01 00:00:00
abstract::The attempts of applying chiroptical spectroscopy to supramolecular chirality are reviewed with a focus on vibrational circular dichroism (VCD). Examples were taken from gels, solids, and monolayers formed by low-molecular mass weight chiral gelators. Particular attention was paid to a group of gelators with perfluoro...
journal_title:Chirality
pub_type: 杂志文章,评审
doi:10.1002/chir.22482
更新日期:2015-10-01 00:00:00
abstract::A variety of reactions can be categorized under the global concept of the "interconversion of stereoisomers." Thus, racemization or epimerization can result from inversion of labile chiral centers. From the examples available, some predictive rules are suggested for a chiral center of the type R"R'RC-H undergoing base...
journal_title:Chirality
pub_type: 杂志文章,评审
doi:10.1002/chir.530050302
更新日期:1993-01-01 00:00:00
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
更新日期:2015-12-01 00:00:00
abstract::Numbers of resolving factors were investigated to improve resolution of venlafaxine 1. An effective resolving agent, O,O'-di-p-toluoyl-(R, R)-tartaric acid 2, was screened using similar method of 'Dutch resolution' from tartaric acid derivatives. The resolution efficiency was up to 88.4%, when the ratio of rac-1 and 2...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22790
更新日期:2018-03-01 00:00:00
abstract::Fluoroquinolones are popular class of antibiotics with distinct chemical functionality. Most of them are ampholytes with one chiral center. Stereogeneic center is located either in the side ring of Gatifloxacin (GFLX) or in the quinolone core of Ofloxacin (OFLX). These two amphoteric fluoroquinolones have terminal ami...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22861
更新日期:2018-06-01 00:00:00
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
更新日期:2002-08-01 00:00:00
abstract::The separation methods of the enantiomers of two β-blockers and tryptophan were studied using capillary electrochromatography with heparin covalently as well as non-covalently, bonded onto the capillary inner wall as stationary phase and electrokinetic chromatography with heparin as pseudostationary phase. In the case...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22972
更新日期:2018-06-25 00:00:00
abstract::Efficient synthesis of several new atropisomeric amino alcohols having 1-phenyl-1H-pyrrole skeleton are reported. Steric arrangements of the products were confirmed by a single-crystal X-ray measurement. The consequences of the size of the N-substituents on enantioinduction were examined by employing the enantioselect...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22415
更新日期:2015-03-01 00:00:00
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
更新日期:1997-01-01 00:00:00
abstract::A new enantiomerically pure P-chiral phosphine, (S)-cyclohexylmethyl- (1-naphthyl)phosphine (1) was prepared by phosphine-borane methodology and used in a mechanistic study of the Mitsunobu reaction. Enantiomerically enriched (S)-cyclo- hexylmethyl(1-naphtyl)phosphine oxide (8) is obtained if the reaction proceeds thr...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(2000)12:5/6<346::AID-CHIR8
更新日期:2000-06-01 00:00:00
abstract::Environmental enantioselectivity information is important to fate assessment of chiral contaminants. Warfarin, a rodenticide and prescription medicine, is a chiral chemical but used in racemic form. Little is known about its enantioselective behavior in the environment. In this study, enantioselective degradation of w...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.21023
更新日期:2012-01-01 00:00:00
abstract::The adsorption of heptahelicene, a helically shaped polyaromatic hydrocarbon (C(30)H(18)), on a Cu(111) surface was studied by means of thermal desorption mass spectrometry (TDMS) and low energy electron diffraction (LEED) at temperatures between 130-1,000 K under ultrahigh vacuum (UHV) conditions. The molecule in the...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10006
更新日期:2001-01-01 00:00:00
abstract::Racemic 1-phenylethylamine was optically resolved by its own derivative formed with glutaric acid namely (+)-(R)-N-(1-phenylethyl)glutaramic acid. The amide acid resolving agent was synthesized from (+)-(R)-1-phenylethylamine by N-derivatization. The glutaric acid derivative was the next in a homologous series of dica...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20377
更新日期:2007-03-01 00:00:00
abstract::The epimeric diterpenes (+)-(1S,3E,7E,11S,12S)-verticilla-3,7-dien-12-ol (1), isolated from Bursera suntui, and (+)-(1S,3E,7E,11S,12R)-verticilla-3,7-dien-12-ol (2), isolated from Bursera kerberi, gave the same Wagner-Meerwein rearrangement product (-)-(1E,4Z,8Z,11S,12R)-phomacta-1,(15)4,8-triene (3). The Et2 O:BF3 -i...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23061
更新日期:2019-11-01 00:00:00
abstract::The simultaneous disposition of fenoprofen enantiomers in synovial fluid and plasma was studied in 11 patients with arthritis and chronic knee effusions treated with a single oral dose of 600 mg rac-fenoprofen. A plasma sample and a synovial fluid sample were collected simultaneously from each patient up to 16 h after...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20374
更新日期:2007-05-05 00:00:00
abstract::Spontaneous symmetry breaking in reactive systems, known as a rare physical phenomenon and for the Soai autocatalytic irreversible reaction, might in principle also occur in other, more common asymmetric reactions when the chiral product is capable to promote its formation and an element of "nonlinearity" is involved ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20474
更新日期:2007-11-01 00:00:00
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
更新日期:1997-01-01 00:00:00
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...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.1053
更新日期:2001-08-01 00:00:00
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 ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22630
更新日期:2016-10-01 00:00:00
abstract::Solid phase extraction (SPE)-chiral separation of the important drugs pheniramine, oxybutynin, cetirizine, and brinzolamide was achieved on the C18 cartridge and AmyCoat (150 x 46 mm) and Chiralpak AD (25 cm x 0.46 cm id) chiral columns in human plasma. Pheniramine, oxybutynin, cetirizine, and brinzolamide were resolv...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22276
更新日期:2014-03-01 00:00:00
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
更新日期:2011-09-01 00:00:00
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
更新日期:2018-04-01 00:00:00