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ASPIRIN AND RELATED DRUGS EDITED BY K. D. Rainsford PhD, FRCP Edin, FRCPath, FRSC, FIBiol, FIBMS, Dr(hc) Biomedical Research Centre Sheffield Hallam University Sheffield, UK CRC PR E S S Boca Raton London New York Washington, D.C. © 2004 K.D. Rainsford Aspirin and Related Drugs © 2004 K.D. Rainsford Aspirin and Related Drugs K . D. R ai n s fo r d P h D, F R CP E di n , F R C Pa t h , F R S C , F I B i o l , F I B M S , D r ( h c ) B i o m ed i c a l R es ea r c h C en t r e S h ef f i el d H a l l a m U n i v er s i t y S h ef f i el d , U K © 2004 K.D. Rainsford First published 2004 by Taylor & Francis 11 New Fetter Lane, London EC4P 4EE Simultaneously published in the USA and Canada by Taylor & Francis Inc, 29 West 35th Street, New York, NY 10001 Taylor & Francis is an imprint of the Taylor & Francis Group © 2004 K.D. Rainsford Typeset in Baskerville by Wearset Ltd, Boldon, Tyne and Wear Printed and bound in Great Britain by TJ International Ltd, Padstow, Cornwall All rights reserved. No part of this book may be reprinted or reproduced or utilised in any form or by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying and recording, or in any information storage or retrieval system, without permission in writing from the publishers. Every effort has been made to ensure that the advice and information in this book is true and accurate at the time of going to press. However, neither the publisher nor the authors can accept any legal responsibility or liability for any errors or omissions that may be made. In the case of drug administration, any medical procedure or the use of technical equipment mentioned within this book, you are strongly advised to consult the manufacturer’s guidelines. British Library Cataloguing in Publication Data A catalogue record for this book is available from the British Library Library of Congress Cataloging in Publication Data A catalog record for this book has been requested ISBN 0–7484–0885–1 © 2004 K.D. Rainsford ‘To those who have gone before’ In recognition of those who have contributed so much to the explosion of science and clinical practice on the actions and uses of aspirin and the salicylates as well as other related analgesic/anti-inflammatory/ antipyretic drugs © 2004 K.D. Rainsford Contents Contributors Preface Abbreviations and nomenclature 1 HISTORY AND DEVELOPMENT OF THE SALICYLATES K.D. Rainsford Introduction Early Use of Salicylate-containing Plants Chemical Development of Salicylates Clinical Observations on the Use of Salicylates in the Nineteenth Century Early Clinical Studies with Salicylates in the Treatment of Rheumatoid Arthritis Chemical Development and Early Clinical Studies with Aspirin Aspects of the Commercial Development of Aspirin Other Salicylates References 2 THE INDUSTRIAL HISTORY OF ANALGESICS: THE EVOLUTION OF ANALGESICS AND ANTIPYRETICS J.R. McTavish Recognition of Pain Therapeutic Nihilism and Fevers The Organic Chemical Industry The Salicylates The Value of a Good Name Conclusion References 3 OCCURRENCE, PROPERTIES AND SYNTHETIC DEVELOPMENTS OF THE SALICYLATES K.D. Rainsford Introduction Naturally Occurring Salicylates Chemical Properties Commercial Synthesis and Properties of the Salicylates Experimental Drugs © 2004 K.D. Rainsford Various Chemical Applications Conclusions References 4 PHARMACOKINETICS AND METABOLISM OF THE SALICYLATES G.G. Graham, M.S. Roberts, R.O. Day and K.D. Rainsford Introduction Absorption of Aspirin and Salicylate Distribution of Aspirin and Salicylate Elimination of Aspirin Elimination of Salicylate Metabolic Pathways of Salicylate Factors Controlling the Elimination of Aspirin and Salicylate Kinetics of Elimination of Salicylate Pro-Drugs Analytical Methods for the Salicyl