Drug Stereochemistry: Analytical Methods and Pharmacology

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Maintaining and enhancing its focus on key issues in the development, regulatory approval and use of stereoisomeric compounds, this edition continues to cover in detail all aspects of chiral drugs from the academic, governmental, industrial and clinical points of view.;Completely rewritten and updated throughout, Drug Stereochemistry: illustrates current indirect chromatographic methods for the resolution of drug enantiomers; treats the rapidly growing area of enantioselective gas chromatography; discusses the ...
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Overview

Maintaining and enhancing its focus on key issues in the development, regulatory approval and use of stereoisomeric compounds, this edition continues to cover in detail all aspects of chiral drugs from the academic, governmental, industrial and clinical points of view.;Completely rewritten and updated throughout, Drug Stereochemistry: illustrates current indirect chromatographic methods for the resolution of drug enantiomers; treats the rapidly growing area of enantioselective gas chromatography; discusses the latest in HPLC resolution of enantiomeric drugs; uses verapamil as a model to show how stereoselective pharmacokinetics affect pharmacodynamics; and supplies an in-depth study on the effect of stereoselective plasma protein binding.;This edition offers entirely new chapters that: discuss the recent decisions and present position of the US Food and Drug Administration on the development of stereoisomeric drugs; explicate enzymatic synthesis of stereochemically pure drugs; review the toxicological, pharmacokinetic and pharmacodynamic differences found among stereoisomers; elucidate the stereoselective transport of drugs across epithelia; and give a physician's perspective on the questions and problems caused by stereoisomeric drugs in practice as well as the pharmaceutical industry's collective viewpoint based on a national survey.

This book contains black-and-white illustrations.

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Editorial Reviews

Doody's Review Service
Reviewer: M. Victor Nora, PharmD, PhD (Rush Medical College of Rush University)
Description: This book examines the synthesis, resolution, therapeutic, and toxicological consequences of chirality in drugs. This is a second edition, with new coverage in the areas of synthesis, resolution, and kinetics, and it has updated areas in chiral separation, protein binding, and FDA guidelines.
Purpose: This book is one of a continuing series of books entitled Clinical Pharmacology. It is aimed at pharmaceutical chemists, biologists, and clinicians who are interested in stereoisomerism of drugs. This book attempts to cover too broad an area and consequently spreads itself too thin. Because this is a contributed book the coverage tends vary. Some chapters try to cover an area on which multiple books have been written (e.g., chiral drug synthesis) and consequently produce too sparse acoverage. Other cha pters, though well written, appear to be aimed at a medical student learning basic pharmacology and therefore are too elementary for a medicinal chemist. Other than for several well-known examples, the clinical relevance of the use of either racemic mixtures or pure isomers as drugs is still largely investigational.
Audience: Because of the unevenness of coverage and the wide scope of the book, this a book in search of an audience. Different chapters would be appropriate for different audiences.
Features: The book is amply illustrated by black-and-white structures, chromatograms, graphs, and tables of varying quality. The chemical structures are well drawn, and the stereochemistry is easily identified, but some of the diagrams and graphs (e.g., p 289) appear to be hand drawn and detract from the general appearance. In some chromatograms (e.g., p.118), the originals have not been completely cleaned up for publication.
Assessment: The typeface is easily readable, and the index is detailed and satisfactory. As individual chapters some are well written and informative, but as a book it does not reach its stated goals. For a clinician there is very little that would be applicable to his or her practice.
Journal of Medicinal Chemistry
...an excellent book, edited by a recognized leader in the field...a valuable source of information.
Journal of the American Chemical Society
...well written and referenced...a must for libraries.
Analytica Chimica Acta
...Much of the information is new or has been rewritten, so that the new edition will be a constant companion to all working with chiral drug molecules.
Booknews
Addresses the academic, industrial, and regulatory aspects of drug stereochemistry, covering the separation and preparation of stereochemically pure drugs, the pharmacokinetic and pharmacodynamic differences between drug stereoisomers, and perspectives on the use of stereochemically pure drugs. The date of the first edition is not noted, but the second edition includes several new topics, including enzymatic synthesis and resolution, toxicological consequences and implications of stereoselective biotransformations, and bioavailability and bioequivalence. Annotation c. Book News, Inc., Portland, OR (booknews.com)

2 Stars from Doody
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Product Details

  • ISBN-13: 9780824788193
  • Publisher: CRC Press
  • Publication date: 1/1/1993
  • Series: Clinical Pharmacology Series , #18
  • Edition description: 2nd ed., rev. and expanded
  • Edition number: 2
  • Pages: 436
  • Product dimensions: 7.00 (w) x 10.00 (h) x 0.50 (d)

Table of Contents

Part 1 Introduction: The early history of stereochemistry - from the discovery of molecular asymmetry and the first resolutionof a racemate by pasteur to the asymmetrical carbon of Van't Hoff and Le Bel, Dennis E. Drayer; stereochemical terms and concepts - an overview, Irving W. Wainer and Alice A. Marcotte. Part 2 The separation and preparation of stereochemically pure drugs: enantiomer analysis by competitive binding methods, C. Edgar Cook; indirect methods for the chromatographic resolution of drug enantiomers synthesis and separation of diastereomeric derivatives, Joseph Gal; the direct resolution of enantiomeric drugs by chiral-phase gas chromatography, Wilfried A. Koenig; HPLC chiral stationary phases for the stereochemical resolution of enantiomeric compounds - the current state of the art, Irving W. Wainer; synthesis of enantiomerically pure drugs, John W. Scott; enzymatic synthesis and resolution of enantiomerically pure compounds, David I. Stirling. Part 3 Pharmacokinetic and pharmacodynamic differences between drug stereoisomers: stereoselective biotransformation toxicological consequences and implications, Nico P.E. Vermeulen and Johan M. te Koppele; stereoselective transport of drugs across epithelia, Ronda J. Ott and Kathleen M. Giacomini; verapamil - a chiral challenge to the pharmacokinetic and pharmacodynamic assessment of bioavailability and bioequivalence, James A. Longstreth; enantioselective binding of drugs to plasma proteins, Terence A.G. Noctor. Part 4 Perspectives on the use of stereochemically pure drugs: FDA perspective on the development of new stereoisomeric drugs - chemistry, manufacturing, and control issues, Wilson H. de Camp; stereochemically pure drugs - an overview, Fakhreddin Jamali; stereoisomeric drugs in therapeutics - clinical perspectives, Darrell R. Abernathy and Nabil S. Andrawis; development of stereoisomeric drugs - an industrial perspective, Mitchell N. Cayen.
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