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Isomer Ratio (isomer + ratio)

Distribution by Scientific Domains

Life Sciences	50%
Chemistry	50%

Selected Abstracts

Analysis of oxycodol and noroxycodol stereoisomers in biological samples by capillary electrophoresis

ELECTROPHORESIS, Issue 10 2005
Andrea Baldacci
Abstract A capillary electrophoresis (CE) method for the separation of the diastereoisomers of 6-oxycodol (6OCOL) and nor-6-oxycodol (N6OCOL), the 6-keto-reduced metabolites of oxycodone (OCOD) and noroxycodone (NOCOD), respectively, is reported and employed to assess the stereoselectivity of these metabolic steps in vivo, in vitro, and in chemical synthesis. CE in an untreated fused-silica capillary with acidic buffers containing 2-hydroxypropyl-,-cyclodextrin, randomly sulfated ,-cyclodextrin, or single isomer heptakis(2,3-diacetyl-6-sulfato)-,-cyclodextrin (HDAS-,-CD) is shown to permit the simultaneous separation of the stereoisomers of 6OCOL and N6OCOL. A 100 mM phosphate buffer of pH 2.0 containing 2.05% w/v HDAS-,-CD provides a medium for rapid analysis and unambiguous identification of these stereoisomers in solid-phase extracts of (i) urines stemming from patients under pharmacotherapy with OCOD, (ii) incubations of OCOD and NOCOD with human liver cytosol and the human liver S9 fraction, and (iii) after chemical synthesis from OCOD and NOCOD using NaBH4. In all cases, ,-N6OCOL is shown to be the predominant stereoisomer of N6OCOL. For 6OCOL, the same is true for in vitro formation and for chemical synthesis. In urine, however, ,-6OCOL is observed to be excreted in a higher amount than ,-6OCOL. For the urinary ,-/,-isomer ratio of 6OCOL and N6OCOL, there are no differences between the data obtained for nonhydrolyzed and enzymatically hydrolyzed urines. The data document the stereoselectivity of the 6-keto-reduction of OCOD and NOCOD in man. [source]

Quantitative 1H NMR spectroscopic determination of the E/Z isomer ratio of the antidepressant drug fluvoxamine for use in pharmaceutical analysis

MAGNETIC RESONANCE IN CHEMISTRY, Issue 12 2002
Ralph Deubner
Abstract High-resolution NMR spectroscopy is a powerful tool in the elucidation of a structure with respect to constitution, configuration and conformation. In recent years, NMR has been increasingly used in quantitative analysis. In this study, we show the ability of 1H NMR to determine the isomeric composition of the antidepressant drug fluvoxamine. The activity of fluvoxamine resides on the E -isomer, and the current British Pharmacopoeia limits the content of the Z -isomer to 0.5%. The NMR method described here is able to determine the content of the Z -isomer down to the 0.2% level on a total amount of 15 mg of the substance. Copyright © 2002 John Wiley & Sons, Ltd. [source]

Environmental factors affecting the levels of legacy pesticides in the airshed of Delaware and Chesapeake Bays, USA

ENVIRONMENTAL TOXICOLOGY & CHEMISTRY, Issue 9 2010
Anubha Goel
Abstract Organochlorine insecticides and their degradation products contribute to toxicity in Chesapeake Bay, USA, sediments and affect the reproductive health of avian species in the region; however, little is known of atmospheric sources or temporal trends in concentrations of these chemicals. Weekly air (n,=,265) and daily rain samples (n,=,494) were collected over 2000 to 2003 from three locations in the Delmarva Peninsula, USA. Pesticides were consistently present in the gas phase with infrequent detection in the particle phase. Hexachlorocyclohexanes (HCHs) and cis - and trans -chlordane were detected most frequently (95,100%), and cis - and trans -nonachlor, oxychlordane, heptachlor, heptachlor epoxide, dieldrin, and 1-chloro-4-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene (4,4,-DDE) were also detected frequently. The highest mean air concentrations were for dieldrin (60,84,pg/m3), ,-HCH (37,83,pg/m3), and 4,4,-DDE (16,80,pg/m3). Multiple regression analyses of air concentrations with temperature and wind conditions using modified Clausius-Clapeyron equations explained only 30 to 60% of the variability in concentration for most chemicals. Comparison of the air concentrations and enthalpy of air,surface exchange values at the three sites indicate sources of chlordanes and ,-HCH sources are primarily from long-range transport. However, examination of chlordane isomer ratios indicates some local and regional contributions, and ,-HCH, 4,4,-DDE, dieldrin, heptachlor, heptachlor epoxide, and oxychlordane also have local or regional sources, possibly from contaminated soils. Median rain sample volumes of 1 to 3 L led to infrequent detections in rain; however, average measured concentrations were 2 to 10 times higher than in the Great Lakes. Dissipation half-lives in air were well below 10 years for all chemicals and below published values for the Great Lakes except dieldrin, which did not decline during the sample period. Environ. Toxicol. Chem. 2010;29:1893,1906. © 2010 SETAC [source]

Stereoselective pharmacokinetics of clausenamide enantiomers and their major metabolites after single intravenous and oral administration to rats

CHIRALITY, Issue 8 2003
Chuan Jiang Zhu
Abstract The pharmacokinetics of clausenamide (CLA) enantiomers and their metabolites were investigated in Wistar rat. After intravenous and oral administration at a dose of 80 and 160 mg/kg each enantiomer, plasma concentrations of (,)- or (+)-CLA and its major metabolites were simultaneously determined by reverse-phase HPLC with UV detection. Notably, stereoselective differences in pharmacokinetics were found. The mean plasma levels of (+)-CLA were higher at almost all time points than those of (,)-CLA. (+)-CLA also exhibited greater tmax, Cmax, t1/2,, AUC0,12h, and AUC0,, and smaller CL (or CL/F) and Vd (or Vd/F), than its antipode. The (+)/(,) isomer ratios for t1/2,, tmax, AUC0,12 h, and AUC0,,, which ranged from 1.26 to 2.08. The ratio for CL (or CL/F) was about 0.5, and there were significant differences in these values between CLA enantiomers (P < 0.05), implying that the absorption, distribution, and elimination of (,)-CLA were more rapid than those of (+)-CLA. Similar findings for (,)-7-OH-CLA, the major metabolite of (,)-CLA, and (+)-4-OH-CLA, the major metabolite of (+)-CLA, can be also seen in rat plasma. The contributing factors for the differences in stereoselective pharmacokinetics of CLA enantiomers appeared to be involved in their different plasma protein binding, first-pass metabolism and interaction with CYP enzymes, especially with their metabolizing enzyme CYP 3A isoforms. Chirality 15:668,673, 2003. © 2003 Wiley-Liss, Inc. [source]