NDLI: Chromatographic resolution, chiroptical characterization and urinary excretion of the enantiomers of sulindac

Content Provider	Springer Nature Link
Author	Slováková, A. Maltzan, X. Freiin Patel, B. K. Drake, A. F. Hutt, A. J.
Copyright Year	1998
Abstract	The chromatographic resolution of the enantiomers of sulindac has been achieved using a Chiralpak AD CSP (10 μm, 250×4.6 mm) with a mobile phase of hexane: ethanol (85∶15 v/v) containing trifluoroacetic acid (0.05% v/v) at a flow rate of 1.0 mL min−1. Under these conditions the enantiomers eluted with separation and resolution factors of 1.43 and 2.46 respectively. Semipreparative isolation of the enantiomers and their characterization by circular dichroism spectroscopy and NMR, in the presence of a chiral shift reagent, indicated that the elution order was (−)-(S)- before (+)-(R)-sulindac. The enantiomeric composition of sulindac in urine following administration of the racemic drug to man was determined by sequential achiral-chiral chromatography. Achiral analysis was carried out using a Spherisorb S5 ODS2 stationary phase (5 μm, 250×4.6 mm) and a mobile phase of aqueous acetic acid (2% v/v; pH 3.5): acetonitrile: THF (50∶48∶2 by volume) at a flow rate of 1.0 mL min−1. The HPLC eluate containing sulindac (retention time 4.9 min) was collected and following workup, the enantiomeric composition of the drug was determined using the CSP. Over the 24 h collection period sulindac was excreted predominantly as theR-enantiomer, but the enantiomeric composition was found to vary markedly with time which is presumably associated with the complex metabolism of the drug.
Starting Page	369
Ending Page	376
Page Count	8
File Format	PDF
ISSN	00095893
Journal	Chromatographia
Volume Number	48
Issue Number	5-6
e-ISSN	16121112
Language	English
Publisher	Vieweg Verlag
Publisher Date	1998-01-01
Publisher Place	Wiesbaden
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Enantiospecific chromatography Sequential achiral-chiral liquid chromatography Sulindac enantiomers Chiral stationary phase Circular dichroism Analytical Chemistry Organic Chemistry Pharmacy Biochemistry Plant Sciences Measurement Science, Instrumentation
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Analytical Chemistry Biochemistry Clinical Biochemistry

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