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For over half a century, this book has served the discipline of medicinal chemistry for both graduate and undergraduate pharmacy and chemistry students as well as practicing pharmacists. Fully updated for the Eleventh Edition, coverage begins with the fundamental principles of chemistry, biochemistry, and biology that underlie the discipline of medicinal chemistry. These principles are then applied to understanding the properties, mode of action, therapeutic applications, and limitations of various pharmaceutical agents. The subject matter is organized by pharmaceutical and therapeutic classes, providing a bridge between the basic sciences and clinical practice. The text contains many tables for quick reference to names, formulations, dosages, and applications.
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Wilson and Gisvold's Textbook of ANIC MEDICINAL AND PHARMAC ICAL CHEMIS TRY E L E V E N T H E D I T I 0 N Wilson and Gisvold's Textbook of ORGANIC MEDICINAL AND PHARMACEUTICAL CHEMISTRY ELEVENTH EDITION Edited by John H. Block, Ph.D., R.Ph. Professor of Medicinal Chemistry Department of Pharmaceutical Sciences College of Pharmacy Oregon State University Corvallis. Oregon John M. Beale, Jr., Ph.D. Associate Professor of Medicinal Chemistry and Director of Pharmaceutical Sciences St. Louis College of Pharmacy St. Louis, Missouri WILLIAMS WILKINS A Wolters Kluwer Company Bahimore • New York • London Philadelphia Buenos Aires • Hong Kong • Sydney . Tokyo F4iwr: l)avid B. Tiny Managing Lthsar: Matthew J. Hauber Markrsing Ma,wger: Samantha S. Smith Production &Iitor: Bill Designer: Doug Smock Compositor: Maryland Composition Printer: Quehecor WOrld Copyright 2(8)4 Lippincott Williams & Wilkins 351 Wcct Camden Street Baltimore, MD 21201 530 Walnut Street Philadelphia. PA 19106 All rights reserved. This book is protected by copyright. No part of this book may be reproduced in any lOon or by any means, including photocopying. or by any infortnation storage and retrieval system without written permission rrom the copyright owner. The publisher is not responsible (as a matter of product liability, negligence, or otherwise) For any injury resulting from any material contained herein. This publication contains infonttation relating to general principles ui medical care that should not he construed a.s specific instructions for individual patiettts. Manuthcturers' prnduct information and package inserts should he reviewed lOr current information, including contraindicationt. dosages, and precautions. Prinle'rI in the Uniteg! Stale.s of Anwrieu First Editton, 1949 Second Edition. 1954 Third Edition. 1956 Filth Edition. 1966 Sixth Edition. 1971 Seventh Edition, 1977 Eighth Edition. 1982 Ninth Edition, 1991 Tenth Edition, 1998 rswrtli Edition, (962 Llbrnry or Congrnas Cataloglng.In.Publkatloit Data Wilson and Gisvold's textbook of organic medicinal and phartnaccutical chemistry.— 11th ed. / edited by John H. Block. John M. Beale Jr. p. cm, Includes bibliographical references attd index. ISBN 11-7817-34111-9 I. Pharmaceutical chemistry. 2. Chemistry. Organic. I. Title: Textbook of organic medicinal and pharmaceutical chemistry. II. Wilson. Charles Owens. 1911—2002 10. Gisvold. Ole. l904- IV. Block. John H. V. Ileak. John Marlowe. IDNLM: I. Chemistry. Pharmaceutical. 2. Chemistry. Organic. QV 744 W754 2ll(9J RS403. 143 2111)4 6 IS'. 19—dc2l 20031)48849 The puhlisher.s have tizade every effort to trace the c'opyri gut itolders for borrowed material. If they have inadvertently overlooked any. they will be pleased to make the n