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Drug Stereochemistry. Analytical Methods and Pharmacology.
BOOK REVIEWS
Drug Stereochemistry.Analytical Methods and Pharmacology. Edited by Irving W. Wainer and Dennis E. Drayer. Marcel Dekker: New York. 1988. 377 pages. 15 x 23 cm. ISBN 0-8247-7837-5.$125.00. This book, Volume 11 of the “Clinical Pharmacology” series, consists of 15 articles divided into four sections. Drayer begins the introductory section by reviewing the history of stereochemistry. This paper contains long passages from speeches delivered by late 19th century chemists including Pasteur. Then Wainer and A. L. Marcotteis skillfully refresh the reader’s knowledge of stereochemistry. Section 11, “Separation and Preparation of Stereochemically Pure Drugs”, begins with a readable article by C.E. Cook in which the topics of immunoreceptor and receptor binding assays are discussed. J. Gal thoroughly discusses the concept and methodology of resolution of enantiomers via formation of diastereoisomer. The subsequent article, although entitled “Stereochemical Aspect of Pharmaceuticals”, only reviews the application of chiral stationary GC phases. In the following article, Wainer acquaints the reader with the available chiral stationary HPLC phases. Several useful tables and illustrations are included in this paper. Next, J. W. Scott touches upon concepts such as “asymmetric synthesis”, the “chiral carbon pool” and the “Stork synthesis” in his article “Synthesis of Enantiomerically Pure Drugs”. The first article of the subsequent section, “Pharmacokinetic and Pharmacodynamic Differences between Drug Stereoisomers”, is devoted by Drayer to the mechanisms of stereoselective pharmacokinetics. However, he concentrates only on plasma protein binding and tubular secretion. W. E. Muller thoroughly reviews the topic “Stereoselective Plasma Protein Binding” at the expense of repeating the previous author. In the next article J. R. Powell et al. discuss the pharmacokinetics and toxicology of a series of chiral drugs. Subsequently D. R. Thakker et al. concentrate on the chemical aspects in “Stereoselective Biotransformation of Polycyclical Aromatic Hydrocarbon to Ultimate Carcinogens”. The last four articles present “Perspectives on the Use of Stereochemically Pure Drugs”. In an excellent paper C. S. Kumkumian deals with the regulatory complications of the matter. This is followed by another readable article by J. J. Baldwin and W. B. Abrams, who discuss, from a research and development point of view, the basis for decision making in production of stereochemically pure or racemic drugs. J. E. Carter deals with the cost versus risk and/or benefit of the question. A “pragmatic” viewpoint is presented by M. M. Reidenberg who takes an approach similar to that of Carter. This book contains some well-written articles, particularly in the area of stereochemistry. However, redundancies occur, especially with regard to the pharmacokinetics and pharmacodynamjcs of chiral drugs. The intriguing pharmacokinetics of chiral nonsteroidal anti-inflammatory drugs are completely ignored. This book is recommended for senior pharmaceutical science students and researchers interested in initiating studies in the relevant areas. F. Jamali Faculty of Pharmacy University of Alberta Edmonton, Alberta Canada T6G 2N8 998 /Journal of Pharmaceutical Sciences Vol. 77, No. 7 7 , November 7988
Relevance of NNitroso Compounds to Human Cancer. Exposures and Mechanisms. Proceedings of the IX International Symposium on KNitroso Compounds, Baden, Austria, September 1-5, 1986. Edited by H. Bartsch, 1. K. O’Neill, and R. Schulte-Hermann. International Agency for Research on Cancer: Lyon, France, 1987.663 pp. ISBN 92-832-1184-7. $98.00. This is the most recent of a series of IARC monographs on various aspects of carcinogenesis by N-nitroso compounds. It is based, as were most of the earlier volumes, on the proceedings of the more-or-less biennial international meetings on this topic sponsored by the International Agency for Research on Cancer. The current volume contains a number of features that make it in many respects one of the best of the series. The individual manuscripts have been kept uniformly short, rewritten in some cases for continuity of style, and have been typeset rather than photo-reproduced. The technical production is generally excellent, although the attractive paperback format may ultimately prove less practical than the previous hard-cover publications because of the typically heavy use of these monographs as a quick and convenient source of general information on almost any topic in nitrosamine chemistry or biochemistry. There is a good author index and an excellent subject index. All of the references have been collected into a single section at the end of the book. This section, in addition, contains over 1000 citations dating from as early as 1939 and with about 30 percent dating from 1984-1987 and is a good, relatively up-to-date, general reference source for N-nitroso compounds. The book contains well over 100 articles including sections on some of the more traditional areas such as analysis of Nnitroso-containing compounds and in vitro nitrosation reactions. It also includes extensive sections on the molecular and biochemical mechanisms of action of N-nitroso compounds, metabolism, interactions with biological macromolecules, biological effects, endogenous formation of N-nitroso compounds, and clinical and epidemiologicalstudies. One section is specifically devoted to both human and animal studies on tobacco and betel-quid carcinogenesis. The individual articles are generally well written, and the book as a whole constitutes a good overview of the scope and complexity of current research on N-nitroso compounds as well as a complete introduction to who is doing the research and where it is being done; there are few major individuals or laboratories not represented in this volume. The book will be useful to anyone interested in nitrosamine and/or nitrosamide carcinogenicity and indispensible to anyone considering entering the field.
John S. Wishnok Department of Applied Biological Sciences Massachusetts Institute of Technology Cambridge, MA 02139
0022-3549/88/11O@0998$01.0010
0 1988, American Pharmaceutical Association
Drug Stereochemistry.Analytical Methods and Pharmacology. Edited by Irving W. Wainer and Dennis E. Drayer. Marcel Dekker: New York. 1988. 377 pages. 15 x 23 cm. ISBN 0-8247-7837-5.$125.00. This book, Volume 11 of the “Clinical Pharmacology” series, consists of 15 articles divided into four sections. Drayer begins the introductory section by reviewing the history of stereochemistry. This paper contains long passages from speeches delivered by late 19th century chemists including Pasteur. Then Wainer and A. L. Marcotteis skillfully refresh the reader’s knowledge of stereochemistry. Section 11, “Separation and Preparation of Stereochemically Pure Drugs”, begins with a readable article by C.E. Cook in which the topics of immunoreceptor and receptor binding assays are discussed. J. Gal thoroughly discusses the concept and methodology of resolution of enantiomers via formation of diastereoisomer. The subsequent article, although entitled “Stereochemical Aspect of Pharmaceuticals”, only reviews the application of chiral stationary GC phases. In the following article, Wainer acquaints the reader with the available chiral stationary HPLC phases. Several useful tables and illustrations are included in this paper. Next, J. W. Scott touches upon concepts such as “asymmetric synthesis”, the “chiral carbon pool” and the “Stork synthesis” in his article “Synthesis of Enantiomerically Pure Drugs”. The first article of the subsequent section, “Pharmacokinetic and Pharmacodynamic Differences between Drug Stereoisomers”, is devoted by Drayer to the mechanisms of stereoselective pharmacokinetics. However, he concentrates only on plasma protein binding and tubular secretion. W. E. Muller thoroughly reviews the topic “Stereoselective Plasma Protein Binding” at the expense of repeating the previous author. In the next article J. R. Powell et al. discuss the pharmacokinetics and toxicology of a series of chiral drugs. Subsequently D. R. Thakker et al. concentrate on the chemical aspects in “Stereoselective Biotransformation of Polycyclical Aromatic Hydrocarbon to Ultimate Carcinogens”. The last four articles present “Perspectives on the Use of Stereochemically Pure Drugs”. In an excellent paper C. S. Kumkumian deals with the regulatory complications of the matter. This is followed by another readable article by J. J. Baldwin and W. B. Abrams, who discuss, from a research and development point of view, the basis for decision making in production of stereochemically pure or racemic drugs. J. E. Carter deals with the cost versus risk and/or benefit of the question. A “pragmatic” viewpoint is presented by M. M. Reidenberg who takes an approach similar to that of Carter. This book contains some well-written articles, particularly in the area of stereochemistry. However, redundancies occur, especially with regard to the pharmacokinetics and pharmacodynamjcs of chiral drugs. The intriguing pharmacokinetics of chiral nonsteroidal anti-inflammatory drugs are completely ignored. This book is recommended for senior pharmaceutical science students and researchers interested in initiating studies in the relevant areas. F. Jamali Faculty of Pharmacy University of Alberta Edmonton, Alberta Canada T6G 2N8 998 /Journal of Pharmaceutical Sciences Vol. 77, No. 7 7 , November 7988
Relevance of NNitroso Compounds to Human Cancer. Exposures and Mechanisms. Proceedings of the IX International Symposium on KNitroso Compounds, Baden, Austria, September 1-5, 1986. Edited by H. Bartsch, 1. K. O’Neill, and R. Schulte-Hermann. International Agency for Research on Cancer: Lyon, France, 1987.663 pp. ISBN 92-832-1184-7. $98.00. This is the most recent of a series of IARC monographs on various aspects of carcinogenesis by N-nitroso compounds. It is based, as were most of the earlier volumes, on the proceedings of the more-or-less biennial international meetings on this topic sponsored by the International Agency for Research on Cancer. The current volume contains a number of features that make it in many respects one of the best of the series. The individual manuscripts have been kept uniformly short, rewritten in some cases for continuity of style, and have been typeset rather than photo-reproduced. The technical production is generally excellent, although the attractive paperback format may ultimately prove less practical than the previous hard-cover publications because of the typically heavy use of these monographs as a quick and convenient source of general information on almost any topic in nitrosamine chemistry or biochemistry. There is a good author index and an excellent subject index. All of the references have been collected into a single section at the end of the book. This section, in addition, contains over 1000 citations dating from as early as 1939 and with about 30 percent dating from 1984-1987 and is a good, relatively up-to-date, general reference source for N-nitroso compounds. The book contains well over 100 articles including sections on some of the more traditional areas such as analysis of Nnitroso-containing compounds and in vitro nitrosation reactions. It also includes extensive sections on the molecular and biochemical mechanisms of action of N-nitroso compounds, metabolism, interactions with biological macromolecules, biological effects, endogenous formation of N-nitroso compounds, and clinical and epidemiologicalstudies. One section is specifically devoted to both human and animal studies on tobacco and betel-quid carcinogenesis. The individual articles are generally well written, and the book as a whole constitutes a good overview of the scope and complexity of current research on N-nitroso compounds as well as a complete introduction to who is doing the research and where it is being done; there are few major individuals or laboratories not represented in this volume. The book will be useful to anyone interested in nitrosamine and/or nitrosamide carcinogenicity and indispensible to anyone considering entering the field.
John S. Wishnok Department of Applied Biological Sciences Massachusetts Institute of Technology Cambridge, MA 02139
0022-3549/88/11O@0998$01.0010
0 1988, American Pharmaceutical Association