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 the administration of fenoprofen. A stereospecific assay for fenoprofen using LC-MS-MS was developed and applied successfully to the analysis of the enantiomers in plasma (LOQ = 10 ng of each enantiomer/ml) and synovial fluid (LOQ = 25 ng of each enantiomer/ml). The values of the area under the curve (AUC) for the S-(+)-fenoprofen eutomer were approximately 2.5 times higher in plasma than in synovial fluid (256 vs 104 microg h/ml), while the values for the R-(-)-fenoprofen distomer were about four times higher in plasma than in synovial fluid (42.5 vs 10.5 microg h/ml). These data demonstrate accumulation of the S-(+)-fenoprofen eutomer in plasma and in synovial fluid, with concentrations versus time AUC (+)/(-) ratios of 6.0 in plasma and 9.9 in synovial fluid, suggesting a greater accumulation of the eutomer at the active site represented by synovial fluid than in plasma. This result demonstrates the importance of enantioselective methods and of analysis of synovial fluid rather than plasma in studies of the pharmacokinetics-pharmacodynamics of fenoprofen.
journal_name
Chiralityjournal_title
Chiralityauthors
De Miranda Silva C,Marques MP,Barissa GR,Donadi EA,Da Silva LM,Lanchote VLdoi
10.1002/chir.20374subject
Has Abstractpub_date
2007-05-05 00:00:00pages
255-63issue
4eissn
0899-0042issn
1520-636Xjournal_volume
19pub_type
杂志文章相关文献
CHIRALITY文献大全abstract::About 30% of a chemically diverse set of compounds were found to separate on four polysaccharide chiral stationary phases using polar organic mobile phases. No structural features appeared to correlate to successful separations. Titrations between normal and polar organic mobile phases suggested that separation mechan...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20212
更新日期:2006-01-01 00:00:00
abstract::Allyl nitrite, O=NOCH(2)CH=CH(2), can exist in conformations which include syn (S) and anti (A) configurations of O=N-O-C, anti or gauche (G) configurations of N-O-C-C, and syn or skew (Sk) configurations of O-C-C=C. Four of them have been observed and characterized by their microwave spectra and quantum chemical calc...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10065
更新日期:2002-02-01 00:00:00
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
更新日期:2006-05-05 00:00:00
abstract::This article describes a very useful extension of an unique column switching technique called "Simulated Moving Columns" (SMC) that was previously reported for chiral high performance liquid chromatography (HPLC) (Zhang and McConnell, Journal of Chromatography A 2004;1028:227-238). SMC uses two or three short chiral c...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20409
更新日期:2007-09-01 00:00:00
abstract::Fourier transform infrared vibrational circular dichroism (FTIR-VCD) measurements have gone through major advances in the last decade. A major thrust in these advances was to find ways that can minimize the VCD spectral artifacts and obtain the VCD signals at enhanced signal quality. However, all these advances are no...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20999
更新日期:2011-10-01 00:00:00
abstract::Treatment of benzoate, formate, or trifluoroacetate esters with silyldibromomethyllithiums provides alkyl silyl mixed acetals via the 1,3-rearrangement of a silyl group from carbon to oxygen. A high level of asymmetric induction onto the acetal carbon is observed when chiral alkyl esters are employed. The stereochemic...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10152
更新日期:2003-01-01 00:00:00
abstract::Enantioselective catalytic epoxidation of olefins is an important problem from both practical and mechanistic points of view. The origins of chiral induction by asymmetric porphyrin and salen complexes were investigated by FT-NMR T1 relaxation techniques. A new chiral vaulted porphyrin (1) that carries (S)-binaphthyl-...
journal_title:Chirality
pub_type: 杂志文章
doi:
更新日期:1998-01-01 00:00:00
abstract::The versatility of a previously developed method for the synthesis of chiral carbene-based palladacycles is demonstrated through the synthesis of two new chiral pyridine-functionalized N-heterocyclic carbene palladacycles with different wingtip groups. The efficiency in their resolution with different counter anions a...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22116
更新日期:2013-03-01 00:00:00
abstract::A new colorimetric chiral sensor material consisting of three different functional sites such as chromophore (2,4-dinitrophenylazophenol dye), binding site (crown ether), and chiral barrier (3,3'-diphenyl-1,1'-binaphthyl group) was prepared and applied to the recognition of the two enantiomers of primary amino alcohol...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20928
更新日期:2011-04-01 00:00:00
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
更新日期:1992-01-01 00:00:00
abstract::Chirality is often glossed over in theoretical or experimental discussions concerning the origin of life, but the ubiquity of homochiral building blocks in known biological systems demands explanation. Information theory can provide a quantitative framework for understanding the role of chirality in biology. Here I sh...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20590
更新日期:2009-03-01 00:00:00
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...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10247
更新日期:2003-08-01 00:00:00
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...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20516
更新日期:2008-02-01 00:00:00
abstract::The straightforward synthesis of a series of enantiomerically pure Lewis basic amides by simple condensation of commercially available enantiopure diamines with picolinic acid is reported. These compounds were shown to promote the enantioselective reduction of ketoimines with trichlorosilane. Working with the model su...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20615
更新日期:2009-01-01 00:00:00
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...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.530050605
更新日期:1993-01-01 00:00:00
abstract::Ninety isolates of microorganisms belonging to different taxonomical groups (30 bacteria, 20 yeast, and 40 fungi) were previously isolated from various samples. These isolates were screened as reducing agents for acetophenone 1a to phenylethanol 2a. It was found that the isolate EBK-10 was the most effective biocataly...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20846
更新日期:2010-10-01 00:00:00
abstract::8-Prenylnaringenin (8PN) is a naturally occurring bioactive chiral prenylflavonoid found most commonly in the female flowers of hops (Humulus lupulus L.). A stereospecific method of analysis for 8PN in biological fluids is necessary to study the pharmacokinetic disposition of each enantiomer. A novel and simple liquid...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22343
更新日期:2014-08-01 00:00:00
abstract::We present a new concept of synthesis for preparation of molecularly imprinted polymers using a functionalized initiator to replace the traditional functional monomer. Using propranolol as a model template, a carboxyl-functionalized radical initiator was demonstrated to lead to high-selectivity polymer particles prepa...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23167
更新日期:2020-03-01 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::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
更新日期:2006-09-01 00:00:00
abstract::A new water soluble zinc-salophen complex with appended D-glucose moieties was synthesized and characterized. Its binding properties toward six aminoacids were investigated by UV-vis spectrophotometric titrations. Association constants showed to be unfavorably affected by increasing steric hindrance of the side chain....
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20614
更新日期:2009-01-01 00:00:00
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 ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10028
更新日期:2002-01-01 00:00:00
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
更新日期:2011-02-01 00:00:00
abstract::A summary of selected NMR studies of enantiodiscrimination phenomena regarding the use of quinine-based chiral solvating agents (CSAs) for the determination of the enantiomeric compositions in solution is reported, with explanations of their multireceptorial character offered. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20134
更新日期:2005-01-01 00:00:00
abstract::A molecular docking study, using molecular mechanics calculations with AutoDock and semi-empirical PM3 calculations, was used to predict the enantiodiscrimination of heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TMβCD) and ketoconazole (KTZ) enantiomers. A Density Functional Theory (DFT) single-point calculation at the...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22554
更新日期:2016-03-01 00:00:00
abstract::Although the organocatalytic direct asymmetric Michael reactions of carbonyl compounds to nitroalkenes have been investigated intensely, the Michael reaction of the thioether-based donors remains a rather undeveloped field. This work concerns the asymmetric Michael addition of aryl sulfanyl-propan-2-one to nitroalkene...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20689
更新日期:2010-07-01 00:00:00
abstract::Separations of six dihydropyridine enantiomers on three commercially available cellulose-based chiral stationary phases (Chiralcel OD-RH, Chiralpak IB, and Chiralpak IC) were evaluated with high-performance liquid chromatography (HPLC). The best enantioseparation of the six chiral drugs was obtained with a Chiralpak I...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22690
更新日期:2017-03-01 00:00:00
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.
更新日期:1999-01-01 00:00:00
abstract::The chiral fungicide furametpyr is widely used in the rice field to control rice sheath blight; however, furametpyr enantiomers are treated as just one compound in traditional achiral analysis, which gives only partial information. An effective chiral analytical method was developed for the resolution and determinatio...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22232
更新日期:2013-12-01 00:00:00
abstract::Many drugs contain a chiral centre, or such a centre is introduced during metabolism of the drug in man and in animals. If a single chiral centre is present, the drug will normally exist as a mixture of two enantiomers, of which one may have quite different pharmacologic and/or toxic effects than the other. Chiral dru...
journal_title:Chirality
pub_type: 杂志文章,评审
doi:10.1002/chir.530010204
更新日期:1989-01-01 00:00:00