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13-Cis-Retinoic Acid WORLD HEALTH ORGANIZATION INTERNATIONAL AGENCY FOR RESEARCH ON CANCER IARC Handbooks of Cancer Prevention Retinoids Volume 4 This publication represents the views and expert opinions of an IARC Working Group on the Evaluation of Cancer-preventive Agents, which met in Lyon, 24-30 March 1999 Published by the International Agency for Research on Cancer, 150 cours Albert Thomas, F-69372 Lyon cedex 08, France © International Agency for Research on Cancer, 1999 Distributed by Oxford University Press, Walton Street, Oxford, 0X2 6DP, UK (Fax: +44 1865 267782) and in the USA by Oxford University Press, 2001 Evans Road, Carey, NC 27513, USA (Fax: +1 919 677 1303). All IARC publications can also be ordered directly from IARCPress (Fax: +33 4 72 73 83 02; E-mail: [email protected]). Publications of the World Health Organization enjoy copyright protection in accordance with the provisions of Protocol 2 of the Universal Copyright Convention. All rights reserved. The designations used and the presentation of the material in this publication do not imply the expression of any opinion whatsoever on the part of the Secretariat of the World Health Organization concerning the legal status of any country, territory, city, or area or of its authorities, or concerning the delimitation of its frontiers or boundaries. The mention of specific companies or of certain manufacturers' products does not imply that they are endorsed or recommended by the World Health Organization in preference to others of a similar nature that are not mentioned. Errors and omissions excepted, the names of proprietary products are distinguished by initial capital letters. The authors alone are responsible for the views expressed in this publication. The International Agency for Research on Cancer welcomes requests for permission to reproduce or translate its publications, in part or in full. Applications and enquiries should be addressed to the Editorial & Publications Service, International Agency for Research on Cancer, which will be glad to provide the latest information on any changes made to the text, plans for new editions, and reprints and translations already available. IARC Library Cataloguing in Publication Data Retinoids! IARC Working Group on the Evaluation of Cancer Preventive Agents (1999 : Lyon, France) (IARC handbooks of cancer prevention ; 4) 1. Retinoids - congresses. I. IARC Working Group on the Evaluation of Cancer Preventive Agents Il Series ISBN 92 832 3004 3 (NLM Classification: Wi) 155M 1027-5622 Printed in France International Agency For Research On Cancer The International Agency for Research on Cancer (IARC) was established in 1965 by the World Health Assembly, as an independently financed organization within the framework of the World Health Organization. The headquarters of the Agency are in Lyon, France. The Agency conducts a programme of research concentrating particularly on the epi- demiology of cancer and the study of potential carcinogens in the human environment. Its field studies are supplemented by biological and chemical research carried out in the Agency's laboratories in Lyon and, through collaborative research agreements, in national research institutions in many countries. The Agency also conducts a programme for the education and training of personnel for cancer research. The publications of the Agency contribute to the dissemination of authoritative infor- mation on different aspects of cancer research. A complete list is printed at the back of this book. Information about IARC publications, and how to order them, is also available via the Internet at: http/Iwww.iarc.fr/ Note to the Reader Anyone who is aware of published data that may influence any consideration in these Handbooks is encouraged to make the information available to the Unit of Chemoprevention, International Agency for Research on Cancer, 150 Cours Albert Thomas, 69372 Lyon Cedex 08, France Although all efforts are made to prepare the Handbooks as accurately as possible, mis- takes may occur. Readers are requested to communicate any errors to the Unit of Chemoprevention, so that corrections can be reported in future volumes. Acknowledgements The Foundation for Promotion of Cancer Research, Japan, is gratefully acknowledged for its generous support to the meeting of the Working Group and the production of this volume of the IARC Handbooks of Cancer Prevention. Contents List of Participants .................... 1 8.3 Cancer-preventive effects ......... 130 Preamble ............................3 8.4 Other beneficial effects ........... 131 General Remarks ....................... 15 8.5 Carcinogenicity ................. 131 8.6 Other toxic effects ............... 131 Handbook 1 All-trans-Retinoic Acid 95 9. Recommendations for Research .. 132 1. Chemical and Physical 10. Evaluation .................... 133 Characteristics .................95 10.1 Cancer-preventive activity ......... 133 1.1 Nomenclature ...................95 10.2 Overall evaluation ............... 133 1.2 Name .........................95 1.3 Structural and molecular formulae and 11. References ..................... 133 relative molecular mass ............ 95 Handbook 2 13-cis-Retinoic Acid . 145 1.4 Physical and chemical properties ........95 1. Chemical and Physical 2. Occurrence, Production, Use, Characteristics ................ 145 Human Exposure and Analysis .....96 1.1 Nomenclature .................. 145 2.1 Occurrence .....................96 1.2 Name ........................ 145 2.2 Production ..................... 96 1.3 Structural and molecular formulae and 2.3 Use .......................... 96 relative molecular mass ........... 145 2.4 Human exposure ................. 97 1.4 Physical and chemical properties ....... 145 2.5 Analysis ...................... 97 2. Occurrence, Production, Use, Metabolism, Kinetics and Genetic Human Exposure and Analysis . 145 Variation ...................... 97 2.1 Occurrence .................... 145 3.1 Humans ...................... 97 2.2 Production ..................... 146 3.2 Experimental models .............. 98 2.3 Use .......................... 146 4. Cancer-Preventive Effects ....... 100 2.4 Human exposure ................ 146 4.1 Humans ..................... 100 2.5 Analysis ..................... 147 4.2 Experimental models ............. 101 3. Metabolism, Kinetics and Genetic 4.3 Mechanisms of cancer prevention . 117 Variation ....................147 3.1 Humans ..................... 147 5. Other Beneficial Effects ......... 120 3.2 Experimental models ............. 149 6. Carcinogenicity ................ 120 4. Cancer-preventive Effects ........ 152 6.1 Humans ..................... 120 4.1 Humans ..................... 152 6.2 Experimental models ............. 120 4.2 Experimental models ............. 154 7. Other Toxic Effects ..............120 4.3 Mechanisms of cancer prevention . 163 7.1 Adverse effects ................. 120 5. Other Beneficial Effects ......... 163 7.2 Reproductive and developmental effects 124 7.3 Genetic and related effects ........ 127 6. Carcinogenicity ............... 164 6.1 Humans ..................... 164 8. Summary of Data ............... 128 6.2 Experimental models ............. 164 8.1 Chemistry, occurrence and human exposure ..................... 128 7. Other Toxic Effects ............. 164 8.2 Metabolism and kinetics .......... 128 7.1 Adverse effects ................. 164 7 ARC Handbooks of Cancer Prevention 7.2 Reproductive and developmental 6.1 Humans ..................... 197 effects ........................168 6.2 Experimental models .............197 7.3 Genetic and related effects ........ 173 7. Other Toxic Effects ............. 198 8. Summary of Data .............. 173 7.1 Toxic and other adverse effects ..... 198 8.1 Chemistry, occurrence and human 7.2 Reproductive and developmental exposure .................... 173 effects ......................... 200 8.2 Metabolism and kinetics .......... 173 7.3 Genetic and related effects ........ 201 8.3 Cancer-preventive effects ......... 174 8. Summary of Data .............. 201 8.4 Other beneficial effects ........... 175 8.1 Chemistry, occurrence and human 8.5 Carcinogenicity ................. 175 exposure .................... 201 8.6 Other toxic effects ............... 175 8.2 Metabolism and kinetics .......... 201 9. Recommendations for Research .. 176 8.3 Cancer-preventive effects ......... 202 8.4 Other beneficial effects ........... 202 10. Evaluation ....................176 8.5 Carcinogenicity ................. 202 10.1 Cancer-preventive activity .........176 8.6 Other toxic effects ............... 202 10.2 Overall evaluation ...............176 9. Recommendations for Research . 203 11. References ......................176 10. Evaluation .................... 203 Handbook 3 9-cis-Retinoic Acid .. 187 10.1 Cancer-preventive activity ......... 203 10.2 Overall evaluation 1. Chemical and Physical ............... 203 Characteristics ................187 11. References .................... 203 1.1 Nomenclature ..................187 1.2 Name ........................187 Handbook 4 4-Hydroxyphenyl- 1.3 Structural and molecular formulae and retinamide .......... 209 relative molecular mass ...........187 1. Chemical and Physical 1.4 Physical and chemical properties .......187 Characteristics ............... 209 1.1 Nomenclature .................. 209 2. Occurrence, Production, Use, 1.2 Name ........................ 209 Human Exposure and Analysis . 188 1.3 Structural and molecular formulae and 2.1 Occurrence .................... 188 relative molecular mass ..........
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