AZAPROPAZONE. 20 years of clinical use
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1 AZAPROPAZONE 20 years of clinical use
2 AZAPROPAZONE 20 years of clinical use Edited by KD Rainsford Department of Biomedical Sciences McMaster University Faculty of Health Sciences Hamilton, Ontario Canada... KLUWER ACADEMIC PUBLISHERS ~ DORDRECHTI BOSTON I LONDON
3 Distributors for the United States and Canada: Kluwer Academic Publishers, PO Box 358, Accord Station, Hingham, MA , for all other countries: Kluwer Academic Publishers Group, Distribution Center, PO Box 322, 3300 AH Dordrecht, The Netherlands British Library Cataloguing in Publication Data Azapropazone. 1. Azapropazone I. Rainsford, K.D. (Kim D.), '.7 ISBN-13: DOl: / e-isbn-13: Copyright 1989 by Kluwer Academic Publishers Softcover reprint of the hardcover 1st edition 1989 All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form of by any means, electronic, mechanical, photocopying, recording or otherwise, without prior permission from the publishers, Kluwer Academic Publishers BV, PO Box 17, 3300 AA Dordrecht, The Netherlands Published in the United Kingdom by Kluwer Academic Publishers, PO Box 55, Lancaster,. Kluwer Academic Publishers BV incorporates the publishing programmes of D. Reidel, Martinus Nijhoff, Dr W. Junk and MTP Press.
4 CONTENTS List of Contributors Preface KD Rainsford Vll Xl Section I EXPERIMENTAL 1 Introduction to therapy with azapropazone KD Rainsford 2 The chemical classification of azapropazone FM Dean 3 Survey of toxicological investigations of azapropazone U Jahn 4 The mode of action of azapropazone in relation to its therapeutic actions in rheumatic conditions and its major side-effects KD Rainsford 5 Pharmacokinetic properties of azapropazone in comparison to other NSAIDs K Brune 6 The pharmacokinetics of azapropazone JC McElnay and FS Walker 7 Mathematical model for assessing risk of gastrointestinal reactions to NSAIDs K McCormack 8 Reduction of irreversible injury in animal models of myocardial ischaemia by treatment with azapropazone RM Knabb, MJMC Thoolen, SA Mousa and PBMWM Timmermans 95 9 Dual inhibitory effects of azapropazone on both neutrophil migration and function: relation to cardiovascular function SA M ousa, R Brown, WM Mackin, P Turlapaty, RD Smith and PBMWM Timmermans 107 v
5 10 Aspects of clinical pharmacology and bioavailability of azapropazone KK M aggon and G M Lam 11 Immunochemical studies on azapropazone CH Schneider Section II THERAPEUTIC ACTIONS 12 Untersuchungen zur Arthrose [Studies in osteoarthritis] o Kniisel Studies on gout and urate elimination by azapropazone G Nuki, F Grinlington, J Palit and R Wallace Die Analgetische Wirksamkeit von Azapropazon [Analgesic effects of azapropazonej H Spring, JLHeidecker, A J#ight, I ab I Davis, FS Walker, JG Riddel, RU Bauer, D Eggli, E Gilleman and J Steens Oberblick tiber die Anwendung von Azapropazon nach operativen Eingriffen und bei traumatisierten Patienten [Review of application of azapropazone in post-operative and traumatic conditions] E Schneider and FU Niethard Clinical trial methodology in rheumatoid arthritis: azapropazone studies WW Buchanan and N Bellamy Comparative effects of azapropazone on the progression of joint pathology on osteoarthritis FS Walker, A Hemingway, KD Rainsford, P Revell, FLow and S Rashad Serious gastrointestinal reactions to azapropazone: an estimate of the risk B Simon and JF Hort Tolerance of azapropazone: allergic and pseudo-allergic reactions and comparison with other NSAIDs A Szczeklik, E Nizankowska and G Czerniawska-Mysik Haematological reactions JF Hort Epilogue, with some thoughts for research on azapropazone KD Rainsford 281 Index 291 vi
6 List of contributors FU Bauer Siegfried AG CH-4BOO Zofingen N Bellamy Department of Rheumatology Victoria Hospital, Westminster Campus 777 Baseline Road East London, Ontario N6A 4G2 Canada R Brown E.I. dupont de Nemours and Co. PO Box B0400, Wilmington DE 19B80 K Brune Department of Pharmacology University of Erlangen-Nurnberg Universitiitstr. 22 D-B525 Erlangen FRG WW Buchanan Department of Medicine McMaster University Faculty of Health Sciences 1200 Main St W, Hamilton Ontario LBN 3Z5 Canada G Czerniawska-Mysik Outpatient Allergological Clinic City Hospital Skawinska Krakow Poland I ab I Davies School of Pharmacy Queen's University of Belfast Belfast BT9 7BL Northern Ireland FM Dean Department of Chemistry University of Liverpool Box 147 Liverpool L69 3BX D Eggli Leumberger Medizin Technik AG CH-B152 GlaUbrugg FC Geerling Siegfried AG CH-4BOO Zofingen E Gilleman Rheuma- und Rehabilitations Klinik CH-3954 Leukerbad F Grinlington Rheumatic Diseases Unit University of Edinburgh Northern General Hospital Edinburgh EH5 2DQ JL Heidecker Department of Medical Services Siegfried AG CH-4800 Zofingen A Hemingway Department of Diagnostic Radiology Royal Hallamshire Hospital Sheffield S102JF JF Hort A H Robins Co. Ltd. Sussex Manor Business Park Gatwick Road Crawley, W. Sussex RH10 2NH vii
7 AZAPROPAZONE 20 YEARS OF CLINICAL USE U Jahn Department of Biology Siegfried AG CH-4800 Zofingen RM Knabb E.!. dupont de Nemours and Co. o Kniisel Stv. Chefarzt der Rheumaklinik Zurzach Quellenstrasse CH-8437 Zurzach GM Lam E.!. dupont de Nemours and Company (Inc.) Pharmaceuticals Division Drug Metabolism Section Stine-Haskell Research Center Elkton Road Newark DE EM Lemmel Staatliches Rheumakrankenhaus Baden-Baden FRG FLow X-ray Department West Middlesex University Hospital Isleworth TW7 6AF WM Mackin E.!. dupont de Nemours and Co. KK Maggon Clinical Research Du Pont de Nemours International PO Box Le Grand Saconnex K McCormack McCormack Ltd. Church House Church Square Leighton Buzzard, Beds LU7 7AE JC McElnay School of Pharmacy Queen's University of Belfast 97 Lisburn Road Belfast BT9 7BL, Northern Ireland SA Mousa E.!. dupont de Nemours and Co. FU Niethard Orthopadische Universitatsklinik Schlierbacher Landstrasse D-6900 Heidelberg FRG E Nizankowska Department of Allergy and Clinical Immunology Copernicus Academy of Medicine Skawinska Krakow Poland G Nuki Rheumatic Diseases Unit University of Edinburgh Northern General Hospital Edinburgh EH5 2DQ J Palit Rheumatic Diseases Unit University of Edinburgh Northern General Hospital Edinburgh EH5 2DQ JA Pfister Clinique Rheumatologique Lavey-Ies-Bains viii
8 LIST OF CONTRIBURORS KD Rainsford Dept of Biomedical Sciences McMaster University Faculty of Health Sciences 1200 Main St W, Hamilton Ontario L8N 3Z5 Canada S Rashad Department of Orthopaedic Surgery West Middlesex University Hospital Isleworth TW7 6AF P Revell Bone and Joint Research Unit The London Hospital Medical College London E1 2AD JG Riddell School of Pharmacy Queen's University of Belfast Belfast BT9 7BL Northern Ireland E Schneider Orthopadische Universitatsklinik Schlierbacher Landstrasse 200a D-6900 Heidelberg FRG CH Schneider University of Bern Institute for Clinical Immunology I nselspital CH-3010 Bern B Simon Ruprecht-Karls-Universitat Heidelberg Medizinische Klinik Abt Gastroenterologie Bergheimerstrasse 58 D-6900 Heidelberg FRG A Szczeklik Department of Allergy and Clinical Immunology Copernicus Academy of Medicine Skawinska Krakow Poland MJM Thoolen inen E.I. dupont de Nemours and Co. N. Billerica Mass. PBMWM Timmermans E.I. dupont de Nemours and Co. P Turlapaty E.I. dupont de Nemours and Co. M Waldburger Hopital cantonal Fribourg FS Walker A H Robins Co. Ltd. Sussex Manor Business Park Gatwick Road Crawley, W. Sussex RH10 2NH ix
9 LIST OF CONTRIBURORS RD Smith E.!. dupont de Nemours and Co. H Spring Rheuma- und Rehabilitations Klinik CH-3954 Leukerbad J Steens Rumelinbackweg 20 CH-4054 Basel R Wallace Rheumatic Diseases Unit University of Edinburgh Northern General Hospital Edinburgh EH5 2DQ A Wright School of Pharmacy Queen's University of Belfast Belfast B19 7BL Northern Ireland
10 Preface Azapropazone is a chemically unique non-steroidal anti-inflammatory drug (benzotriazine oxide) which has found successful clinical applications in the therapy of a wide variety of arthritic conditions. This book summarizes the progress and critically reviews the clinical use and experimental studies since its introduction 20 years ago. Several studies focus on the physiochemical, pharmacological and toxicological properties of this drug. The studies suggest that it has some unique properties compared with other non-steroidal anti-inflammatory drugs. Among these the novel observations are that azapropazone inhibits several non-prostaglandin-related leucocyte functions, especially superoxide anion production. These serve as a basis for investigations which are reviewed showing the potential for the drug to prevent the pathological consequencies of myocardial ischaemia. The preparation of this book would not have been possible without the cooperation of the four companies who produce, market, or have research involvement with azapropazone, namely Siegfried AG (the manufacturers of the drug), A.H. Robins (U.K.) Co. Ltd., Robapharm AG () and E.!. dupont de Nemours (U.S.A., and F.R.G.). I thank, in particular, Dr J.F. Hort and Mr F.S. Walker of A.H. Robins (U.K.) Co. Ltd., Drs 1. Heidecker and A. von Korponay of Siegfried AG and Dr K.K. Maggon of E.I. dupont Europe (Geneva) for their invaluable help in organizing the contributions and their esteemed advice. My thanks also to the Publishing Director at Kluwer Academic Publishers, Lancaster,, Dr Peter Clarke, and his Editor, Mr Phil Johnstone, for all their efforts and also those of their colleagues which have enabled smooth publication of this volume. Finally, my sincere thanks to the contributors who had to meet strict deadlines against the inevitable problem of competing professional and practical needs, and the editorial help of Mrs Veronica Rainsford-Koechli. K.D. Rainsford, PhD, MRCPath, FRSC Professor of Pharmacology and Pathology Director -- Pharmacology of Rheumatic Diseases McMaster University Faculty of Health Sciences Hamilton, Ontario, Canada, L8N 3Z5 Azapropazone - 20 years of clinical use. Rainsford, KD (ed) Kluwer Academic Publishers. xi
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