Stereoselective Renal Elimination

Recent progress has been made in understanding the role of membrane transporters in drug absorption and elimination. In particular, we are gaining an understanding of membrane transporters in drug elimination by both the kidney and the liver. In the past

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Volume 153 Edi tor-in -Chief K. Starke, Freiburg i. Br.

Editorial Board G.Y.R. Born, London M. Eichelbaum, Stuttgart D. Ganten, Berlin H. Herken, Berlin F. Hofmann, Miinchen L.E. Limbird, Nashville, TN W. Rosenthal, Berlin G. Rubanyi, Richmond, CA

Springer-Verlag Berlin Heidelberg GmbH

Stereochemical Aspects of Drug Action and Disposition Contributors S.K. Branch, C.M. Brett, P.-A. Carrupt, C. Dressler, M. Eichelbaum, G. Geisslinger K.M. Giacomini, D.IW. Grant, A. Gross, C.-H. Gu, P.I Hayball, K. Hostettmann, A.P. Ijzerman, G. Klebe, C. Leisen, D. Maule6n, IM. Mayer, R.I Ott, M. Reist, s. Rudaz, R.R. Shah, A. Somogyi, w. Soudijn, H. Spahn-Langguth, 1. Tegeder, C. Terreaux, B. Testa, C. Valenzuela, N.P.E. Vermeulen, I-L. Veuthey, P. Vogel, 1. van Wijngaarden, K. Williams

Editors

Michel Eichelbaum, Bemard Testa and Andrew Somogyi

i

Springer

Praf. Dr. Michel Eichelbaum Dr. Margarete-Fischer-Bosch Institut fur Klinische Pharmakologie Auerbachstr. 112 70376 Stuttgart Germany e-mail: michel.eichelbaum@ikp-stuttgarLde

Praf. Dr. Bernard Testa University of Lausanne School of Pharmacy 1015 Lausanne Switzerland e-mail: [email protected]

Praf. Dr. Andrew Somogyi University of Adelaide Dept. of Clinical and Experimental Pharmacology 5005 Adelaide Australia e-mail: [email protected]

With 96 Figures and 32 Tables

ISBN 978-3-642-62575-6 ISBN 978-3-642-55842-9 (eBook) DOI 10.1007/978-3-642-55842-9 Cataloging-in-Publication Data applied for Bibliographic information published by Die Deutsche Bibliothek Die Deutsche Bibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data is available in the Internet at . This work is subject to copyright. All rights are reserved. whether the whole or part of the material is concerned. specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilm or in other ways, and storage in data banks. Duplication of this publication or parts thereof is permitted only under the provisions of the German Copyright Law of September 9, 1965, in its current version, and permission for use must always be obtained from Springer-Verlag. Violations are liable for prosecution act under German Copyright Law. http://www.springer.de © Springer-Verlag Berlin Heidelberg 2003 Originally published by Springer-Verlag Berlin Heidelberg New York in 2003 Softcover feprint of the hardcover lst edition 2003 The use of general descriptive names, registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. Typesetting: SNP Best-set Typesetter Ud., Hong Kong Cover-Design: design & production GmbH, Heidelberg Printed on acid-free paper 27/3020/kk 5 4 3 2 1 O

Preface

State-of-the-Art Chirality Stereochemistry in general and chirality in particular have long been recognized as major structural factors influencing pharmacological