The Impact of Stereochemistry on Drug Development and Use

by Aboul-Enein, Hassan Y.; Wainer, Irving W.

• ISBN13: 9780471596448
• ISBN10: 0471596442
• Edition: 1st
• Format: Hardcover
• Copyright: 1997-04-11
• Publisher: Wiley-Interscience
• More Book Details

Summary

Provides an authoritative source of practical information on stereochemistry and its impact on drug development. Unlike other books which focus on synthesis, this work explores analytical, pharmacological, and regulatory topics in dealing with the theory and practice of stereochemistry in the pharmaceutical industry today. It specifically addresses how the body metabolizes chiral molecules; the varying effects of different chiral molecules; and provides detailed evaluations of current seperation techniques. Includes regulatory information.

Author Biography

About the editors<br> <br> Hassan Y. Aboul-Enein holds a PhD in pharmaceutical and medicinal chemistry from the University of Mississippi. He is currently involved in biomedical and pharmaceutical research at King Faisal Specialist Hospital & Research Centre in Riyadh, Saudi Arabia. He is a member of the editorial boards of several journals, including Chirality, Biomedical Chromatography, Journal of Liquid Chromatography, and Analytical Letters. Dr. Aboul-Enein is a member of the World Health Organization Expert Advisory Panel on Pharmaceuticals. He is the author of numerous professional papers and several book chapters in the fields of medicinal chemistry and pharmaceutical analysis.<br> <br> W. Wainer is Professor and Director of the Division of Pharmacokinetics in the Department of Oncology at McGill University in Montreal, Canada. He received his PhD in synthetic organic chemistry from Cornell University in 1970. Dr. Wainer is author or coauthor of more than 200 scientific publications and eight books. He was editor in chief of the journal Chirality from its inception in 1989 to 1994, when he became editor of the Journal of Chromatography, Biomedical Applications. The recipient of numerous awards and honors and a Fellow of the American Association of Pharmaceutical Sciences, Dr. Wainer is a member of the United States Pharmacopoeial Convention Committee of Revision for 1995-2000.

Table of Contents

CONTRIBUTORS	xi	(4)
PREFACE	xv	(8)
CUMULATIVE LISTING OF VOLUMES IN SERIES	xxiii
CHAPTER 1 CHIRALITY AND DRUG HAZARDS	1	(20)
HASSAN Y. ABOUL-ENEIN
LAILA I. ABOU BASHA
CHAPTER 2 STEREOCHEMISTRY IN THE DRUG DEVELOPMENT PROCESS: ROLE OF CHIRALITY AS A DETERMINANT OF DRUG ACTION, METABOLISM, AND TOXICITY	21	(24)
THOMAS A. BAILLIE
KATHLEEN M. SCHULTZ
CHAPTER 3 STEREOCHEMICAL ASPECTS OF DRUG METABOLISM	45	(62)
JONATHAN P. MASON
ANDREW J. HUTT
CHAPTER 4 SOME EXAMPLES FOR STEREOSELECTIVE BIOTRANSFORMATION OF DRUGS	107	(18)
GOTTFRIED BLASCHKE
CHAPTER 5 KINETICS OF REACTIVE PHASE II METABOLITES: STEREOCHEMICAL ASPECTS OF FORMATION OF EPIMERIC ACYL GLUCURONIDES AND THEIR REACTIVITY	125	(48)
HILDEGARD SPAHN-LANGGUTH
LESLIE Z. BENET
PARNIAN ZIA-AMIRHOSSEINI
SEIGO IWAKAWA
PETER LANGGUTH
CHAPTER 6 STUDIES ON THE STEREOSELECTIVITY OF THE BIOLOGICALLY IMPORTANT METABOLISM OF ALKENE-ALKENE OXIDE (OXIRANE)-ALKANEDIOL	173	(28)
DOROTHEE WISTUBA
CHAPTER 7 CHIRAL BARBITURATES: SYNTHESIS, CHROMATOGRAPHIC RESOLUTIONS, AND BIOLOGICAL ACTIVITY	201	(34)
JACEK BOJARSKI
CHAPTER 8 ETHAMBUTOL AND TUBERCULOSIS, A NEGLECTED AND CONFUSED CHIRAL PUZZLE	235	(28)
BERNARD BLESSINGTON
CHAPTER 9 STEREOGENIC ELEMENTS OF PHARMACEUTICAL COMPOUNDS: SOME ASPECTS ON ISOMERISM, RESOLUTION, AND STEREOCHEMICAL INTEGRITY	263	(24)
STIG G. ALLENMARK
CHAPTER 10 THE IMPORTANCE OF CHIRAL SEPARATIONS IN PHARMACEUTICALS	287	(30)
SUT AHUJA
CHAPTER 11 SEPARATION OF OPTICALLY ACTIVE PHARMACEUTICALS USING CAPILLARY ELECTROPHORESIS	317	(28)
TIMOTHY J. WARD
KAREN D. WARD
CHAPTER 12 CHIRAL RECOGNITION MECHANISM OF POLYSACCHARIDES CHIRAL STATIONARY PHASES	345	(32)
EJI YASHIMA
YOSHIO OKAMOTO
CHAPTER 13 MICELLE-MEDIATED CAPILLARY ELECTROPHORETIC SEPARATION OF ENANTIOMERIC COMPOUNDS	377	(24)
MICHAEL E. SWARTZ
PHYLLIS R. BROWN
CHAPTER 14 UNIFIED ENANTIOSELECTIVE CHROMATOGRAPHY INVOLVING CHIRASIL-DEX	401	(14)
VOLKER SCHURIG
SABINE MAYER
MARTIN JUNG
MARKUS FLUCK
HANSJORG JAKUBETZ
ALEXANDRA GLAUSCH
SIMONA NEGURA
CHAPTER 15 DERIVATIZED CYCLODEXTRINS AS CHIRAL GAS CHROMATOGRAPHIC STATIONARY PHASES AND THEIR POTENTIAL APPLICATIONS IN THE PHARMACEUTICAL INDUSTRY	415	(22)
WEIYONG LI
THOMAS M. ROSSI
CHAPTER 16 CHIRAL DERIVATIZATION REAGENTS IN THE BIOANALYSIS OF OPTICALLY ACTIVE DRUGS WITH CHROMOPHORE-BASED DETECTION	437	(56)
RALF BUSCHGES
HASSAN Y. ABOUL-ENEIN
ERIC MARTIN
PETER LANGGUTH
HILDEGARD SPAHN-LANGGUTH
CHAPTER 17 CIRCULAR DISCHROISM SPECTROSCOPY IN THE ANALYSIS OF CHIRAL DRUGS	493	(28)
PIERA SALVADORI
CARLO ROSINI
CARLO BERTUCCI
CHAPTER 18 CIRCULAR DICHROISM IN THE STUDY OF STEREOSELECTIVE BINDING OF DRUGS TO SERUM PROTEINS	521	(24)
CARLO BERTUCCI
PIERO SALVADORI
ENRICO DOMENICI
CHAPTER 19 CURRENT REGULATORY GUIDELINES OF STEREOISOMERIC DRUGS: NORTH AMERICAN, EUROPEAN AND JAPANESE POINT OF VIEW	545	(20)
SYLVIE LAGANIERE
CHAPTER 20 ENANTIOSELECTIVE ANALYSIS AND THE REGULATION OF CHIRAL DRUGS	565	(8)
MICHAEL GROSS
CHAPTER 21 FIRST PASS PHENOMENA: SOURCES OF STEREOSELECTIVITIES AND VARIABILITIES OF CONCENTRATION-TIME PROFILES AFTER ORAL DOSAGE	573	(38)
HILDEGARD SPAHN-LANGGUTH
LESLIE Z. BENET
WERNER MOHRKE
PETER LANGGUTH
CHAPTER 22 GASTROINTESTINAL TRANSPORT PROCESSES: POTENTIALS FOR STEREOSELECTIVITIES AT SUBSTRATE-SPECIFIC AND NONSPECIFIC EPITHELIAL TRANSPORT SYSTEMS	611	(22)
PETER LANGGUTH
GORDON L. AMIDON
ELKE LIPKA
HILDEGARD SPAHN-LANGGUTH
CHAPTER 23 PREPARATION OF DRUG ENANTIOMERS BY CHROMATOGRAPHIC RESOLUTION ON CHIRAL STATIONARY PHASES	633
ERIC FRANCOTTE