Textbook of Organic Medicinal and Pharmaceutical Chemistry

American Journal of Pharmaceutical Education,  Summer 1999  by Knittel, James J

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JAMIE N. DELGADO AND WILLIAM A. REMERS. Textbook of Organic Medicinal and Pharmaceutical Chemistry. Philadelphia, PA: Lippincott-Raven Publishers, 1998. xv + 974 pp., 254 figs., 113 tbls., $69.50.

The tenth edition of Wilson & Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry has undergone the most extensive revision since I first became acquainted with this text in 1983. As with many multi-authored texts, this book is a bit uneven in depth and presentation. However, the overall result still makes this one of the best textbooks available. Four completely new chapters have been added and others have been extensively revised. The new chapters are: Drug Latentiation and Prodrugs, Biotechnology and Drug Discovery, Fundamentals of Immunology and Immunizing Biologicals (Vaccines and Toxoids), and Agents for Diagnostic Imaging. The chapter on antibiotics in the ninth edition has now been broken into two chapters: Antibacterial Antibiotics and Antivirals. Some rearrangement of chapter order has also occurred. All in all the text maintains the same general style and format of the preceding editions of this text, even to the extent of not correcting typographical errors and misstatements present in the previous editions. For example in Chapter 2, (Physicochemical Properties in Relation to Biological Action) several errors in the structures are present. Bonds are missing in some and stereochemistry is not properly shown in others (e.g., methylprednisolone on p. 6). The stereochemistry section has relatively poor structures and in some instances (e.g., trimeperidine on pg. 31 ) it is very difficult to interpret the structure and point the author is trying to make with it. Today's students do not have a good grasp of stereochemistry to begin with, and poorly drawn structures make it even more difficult for them. On the plus side, three new sections have been added to this chapter (Combinatorial Chemistry, 3DQSAR, and Bioisosterism). Although brief, they do provide an introduction to these concepts that isn't present in many texts.

Throughout most of the text it is painfully obvious where new chemical structures have been added. Many of the structures appear blurred and are much bolder relative to the "older" structures. This is distracting to the reader and really shouldn't be a problem considering the chemical drawing programs now available. This is not a problem in most of the newer chapters or chapters that have been more extensively revised.

Chapter 3, Metabolic Changes of Drugs and Related Organic Compounds, follows the same format as previous editions even though it has a new author. Unfortunately the same errors of the previous edition have been retained. For example on page 61 the hydroxylation of monosubstituted cyclohexane results in cis and trans configurational stereoisomers, not conformational isomers as stated in the text. There is no discussion of the CYP families and causes for drug interactions as the result of inhibition or induction of certain CYPs. This is a glaring omission.

Chapter 4 is a new chapter dealing with drug latentiation and prodrugs. It discusses the major prodrugs grouped according to functional group (carboxylic acids and alcohols, amines, azo linkages and carbonyl compounds). A good general discourse of bioactivation of molecules is also provided. Drug delivery systems are also presented. Biotechnology and Drug Discovery is the topic of Chapter 5 and this is generally a nice introduction. I am glad to see it early in the text rather than buried in the back and running the risk of not being covered at all. The chapter covers the basic concepts of using DNA sequence information, drug screening strategies (e.g., high throughput screens), antibodies and antisense therapies and gene therapy. Several products are also described. Overall this chapter is a good introduction to the basics of biotechnology.

Chapter 6 provides a basic introduction to the principles of immunology, including the different types of antibodies and their roles in the immune response. Methods of vaccine production, types of vaccines and how they are dosed are also discussed. Products for both viral and bacterial vaccines are also presented. This is a nice addition to the text and should be useful as supplemental reading in other courses besides medicinal chemistry.

Agents for diagnostic imaging are discussed in Chapter 13. This chapter begins with a reasonable discourse on the basics of radiation and proceeds through the major isotopes used in radiopharmaceuticals. It also covers the principles of obtaining x-rays and magnetic resonance imaging. Radiologic contrast agents are also discussed.

Many of the other chapters follow the same format as previous editions of this text, although there are several instances where new authors have extensively rewritten some chapters or made significant additions to content. For example, the chapter on antineoplastic agents (Chapter 12) has an expanded description of the differences between normal and tumor cells as well as in vitro testing systems for antineoplastics. Unfortunately, this is one of the chapters that suffers from poorly reproduced structures. The chapter on local anesthetics (Chapter 20) has new authors and a completely rewritten historical background section that is much better than the previous edition. It also has a more sophisticated presentation of the nervous system and nerve conduction. Chapter 21 (Histamine and Antihistamine Agents) also has new authors and is essentially a complete revision of the previous edition. It provides a very good discussion of HI and H2 antagonists as well as a more extensive discussion of the role of histamine in the body. The section on H I antagonists is now divided into 1 st and 2nd generation agents, with the latter being primarily the non-sedating agents. A much better presentation of H2 antagonists as well as H+ pump inhibitors is also provided.