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The Metabolism of Anabolic Agents in the Racing Greyhound

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The Metabolism of Anabolic Agents in the Racing Greyhound The Metabolism of Anabolic Agents In the Racing Greyhound A thesis submitted in partial fulfilment of the requirements for the Degree of Doctor of Philosophy by Mr. Keith Robert Williams, B.Sc. July 1999 Department of Forensic Medicine & Science University of Glasgow Copyright © 1999 by Keith R. Williams. All rights reserved. No part o f this thesis may be reproduced in any forms or by any means without the written permission o f the author. I ProQuest Number: 13833925 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a com plete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. uest ProQuest 13833925 Published by ProQuest LLC(2019). Copyright of the Dissertation is held by the Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States C ode Microform Edition © ProQuest LLC. ProQuest LLC. 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, Ml 48106- 1346 GLASGOW UNIVERSITY LIBRARY 111-X (coK To my parents for all their help, support and encouragement i Table of Contents i List of Figures V List of Tables VIII Summary IX Chapter 1: Drugs in Sport ...............................................................................................................................1 Introduction .................................................................................................................................................. 1 The Use of Anabolic Agents in Sport .......................................................................................................2 Greyhound Racing in the United Kingdom ...............................................................................................5 Aims of Study ..............................................................................................................................................7 Chapter 2 Steroid Hormones .........................................................................................................................10 Steroid Nomenclature and Structure ....................................................................................................... 10 Basic Mechanisms of Hormone Action ................................................................................................... 13 Mechanism of Steroid Action ................................................................................................................... 13 Structure of a Steroid Receptor ................................................................................................................15 Biosynthesis of Steroids ............................................................................................................................ 18 Conversion of Cholesterol to Pregnenolone ............................................................................................18 Regulation of Steroidogenesis ..................................................................................................................25 Excretion of Steroids .................................................................................................................................30 Anabolic Androgenic Steroids (AAS) ....................................................................................................32 Metabolism of Exogenous Anabolic Steroids .........................................................................................35 metabolites..................................................................................................................................................39 Side Effects of Anabolic/Androgenic Steroids .......................................................................................39 Greyhounds and Steroids .........................................................................................................................40 Beta 2 Agonists ......................................................................................................................................... 43 Chapter 3 Analytical Techniques .................................................................................................................47 Chromatography Theory ...........................................................................................................................47 Mass Spectrometry .................................................................................................................................... 53 Extraction Techniques ...............................................................................................................................62 Chapter 4 Analytical Techniques Practical .................................................................................................65 III Chapter 5 Elucidation of Endogenous Steroid Biochemistry of the Racing Greyhound .........................81 Introduction ................................................................................................................................................81 Elucidation of the background steroid profile of the racing greyhound .............................................. 85 glucuronide Metabolism of Testosterone in the Racing Greyhound ....................................................92 Dosing with Radiolabelled testosterone .................................................................................................. 99 Conclusions ..............................................................................................................................................103 Chapter 6 Metabolism ofNandrolone and Boldenone .............................................................................107 Introduction ..............................................................................................................................................107 Dosing of anabolic steroids .................................................................................................................... 107 Nandrolone ...............................................................................................................................................110 Boldenone ................................................................................................................................................128 Conclusions .............................................................................................................................................. 129 Chapter 7 The analysis of clenbuterol in the plasma and urine of the racing greyhound. ....................130 Introduction ..............................................................................................................................................130 Mass Spectrometry Studies .................................................................................................................... 130 Conclusions ..............................................................................................................................................141 Chapter 8 Conclusions ................................................................................................................................151 Acknowledgements ..................................................................................................................................... 158 References .................................................................................................................................................... 159 Appendix 1 Paper published in Analytica Chimica Acta Appendix 2 Two papers presented at the international association of Forensic Science, Dusseldorf, August 1993 Appendix 3 Greyhounds used in metabolism studies IV List of Figures Figure 2.1a Basic Steroid Hydrocarbon Skeleton 11 Figure 2.1 b Numbering System of Steroid Rings 11 Figure 2.3 Proposed Mechanisms for the Action of Hormones 14 Figure 2.4 Mechanism of Steroid Action. 16 Figure 2.5 Structure of Steroid Receptor 17 Figure 2.6 Synthesis of Cholesterol from Acetyl CoA. 19 Synthesis of testosterone from pregnenolone 217 Figure 2.8 Biosynthesis of Corticosteroids 23 Figure 2.9 Biosynthesis of Oestrogens 24 Figure 2.10 The Inhibition of Steroid Synthesis by Steroids 27 Figure 2.11 Metabolism of Testosterone 29 Figure 2.12 Mode of action of Beta agonists 46 Figure 3.1 Schematic Diagram of an Electron Impact Source. 54 Figure 3.2 Various Types of Mass Spectrometers 56 Figure 3.3 Definitions of Resolution 60 Figure 5.1 Urinary steroid profile of a male racing greyhound 86 Figure 5.2 Urinary steroid profile of a female racing greyhound 87 Figure 5.3 Sample chromatogram showing the separation of 17p-Oestradiol and 17p-Oestradiol glucuronide 92 Figure 5.4a Concentration of testosterone in the urine of Dog 1 as determined by RIA 97 Figure 5.4b Concentration of testosterone in the urine of Dog 2 as determined by RIA 98 Figure 5.5 Disintegration per minute per millilitre of plasma versus time after dosing following an intravenous injection of a greyhound with H- testosterone 101 Figure 5.6: Radioactivity in urine up to 144 hours post-dose 102 Figure 5.7 Graph of the ratio between labelled and unlabelled testosterone following administration of approximately 2 mg of deutero-labelled testosterone 106 Figure 6.1 Structures of Nandrolone, Nandrolone Laurate and Boldenone
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