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Microfilms International 300 N INFORMATION TO USERS This w u produced from a copy of a document sent to us for microfilming. While the most advanced technological means to photograph and reproduce this document have been used, the quality is heavily dependent upon the quality of the material submitted. The following explanation of techniques is provided to help you understand markings or notations which may appear on this reproduction. 1.The sign or “target” for pages apparently lacking from the document photographed is “Missing Page(s)”. If it was possible to obtain the missing page(s) or section, they are spliced into the film along with adjacent p8ges. This may have necessitated cutting through an image and duplicating adjacent pages to assure you of complete continuity. 2. When an image on the film is obliterated with a round black mark it is an indication that the film inspector noticed either blurred copy because of movement during exposure, or duplicate copy. 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Ml 4B106 18 BEDFORD ROW. LONDON WC1R 4EJ. ENGLAND 8115100 ENEANYA, DENNIS ILOZULIKE DIETHYLDITHIOCARBAMIC ACID: DOSE DEPENDENT KINETICS, BILIARY SECRETION OF METABOLITES AND CHOLERETIC EFFECTS The Ohio State University PH.D. 1981 University Microfilms International 300 N. Zeeb Road, Ann Arbor, MI 48106 Copyright 1981 by ENEANYA, DENNIS ILOZULIKE All Rights Reserved PLEASE NOTE: In all cases this material has been filmed in the best possible way from the available copy. Problems encountered with this document have been identified here with a check mark V 1. Glossy photographs or pages ______ 2. Colored illustrations, paper or print _____ 3. Photographs with dark background _____ 4. Illustrations are poor copy ______ 5. Pages with black marks, not original copy ______ 6. Print shows through as there is text on both sides of page ______ 7. Indistinct, broken or small print on several pages ^ 8. Print exceeds margin requirements _____ 9. Tightly bound copy with print lost in spine ______ 10. Computer printout pages with Indistinct print ______ 11. Page(s)___________ lacking when material received, and not available from school or author. 12. Page(s)___________ iseem to be mtssing in numbering only as text follows. 13. Two pages numbered I__________ . Text follows. 14. Curling and wrinkled pages 15. Other University Microfilms International DIETKYLDITHIOCARBAMIC ACID; DOSE DEPENDENT KINETICS, BILIARY SECRETION OF METABOLITES AND CHOLERETIC EFFECTS DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in The Graduate School of The Ohio State University. By Dennis Ilozulike Eneanya, B.S. The Ohio State University 1981 Reading Committee: Approved by Dr. Joseph R. Bianchine Dr. Brian D. Andresen Adviser Dr. Richard H. Fertel rtment of Pharmacology Dr. Rao Panganamala ACKNOWLEDGEMENTS I would like to thank Doctor Joseph R. Bianchine, ay academic adviser with whom I have been priviledged. to work; whose counsel, criticism and support have been invaluable. I will continue to have the highest regards for him. I would wish to extend my gratitude to Dr. Nicholas Gerber. My experiments have borrowed from his prestigious works and his suggestions have been of immense help to me. I have also been priviledged to work with him. My sincere thanks to Drs. Brian Andresen, Richard Fertel and Rao Panganamala. They have taught, challenged and enlightened me. To my family (especially my wife, Comfort; my daughter, son and mother) I express my deepest appreciation for their closeness, encour­ agement, understanding and prayers. I also thank the Sterrett's family whose friendship, kindness and support, I will remain indebted to. I would’ like to thank Dr. B.M. Hanumaiah for technical laboratory assistance, I thank Mrs. Carol Jones for her patience and expertise in the preparation of this manuscript, and Miss Dorothy Brickman for her educational help. The aupporc o£ the predoctoral scholarship from the Federal Govern** meat of Nigeria is acknowledged. Finally, to all who helped me during my graduate school career, I gratefully acknowledge. VITA September 8, 1952 Born- Nri, Nigeria 1976 B.S., Denison University Granville, Ohio 1976-1981 Graduate Research Associate Department of Pharmacology The Ohio State University Columbus, Ohio PUBLICATIONS AND PRESENTATIONS Tejwani, G.A., Pertel, R., Hart, R.W*, Eneanya, D., Allison, D.: Asbestos Induced Changes in the Concentrations of Cyclic Nucleotides in Normal Human Fibroblasts. Federation Proceedings 2 J J 1536, 1978. Eneanya, D.I., Daniel, F.B., Hart, R.W.: Effects of Asbestos (chrysotile intermediate) on the Metabolism of Benzo(a)pyrene to DNA of Syrian Hamster Embryo Cells. Federation Proceedings a3§,: 1653, 1979. Eneanya, D.I., Daniel, F.B., Hart, R.W.: Asbestos (chrysotile intermediate) Alters the Metabolism of Benso(a)pyrene in Syrian Hamster Embryo Cells. Xlth International Congress of Biochemistry 7932003, Toronto, Canada July 1979 Eneanya, D.I., Duran, D.O., Wu, J., Andresen, B., Bianchine, J.: Characterisation of the Glucuronide of Diethyldithiocarbamic Acid Using Gas Chromatography and Mass Spectrometry. Pharmacologist 22: 458, 1980. Eneanya, D.I., Bianchine, J.R., Duran, D.O., Andresen, B.: The Actions and Metabolic Fate of Disulfiram. Annual Review of Pharmacology and Toxicology 21: (1981) In Press. iv Bianchine, J.R., Brys, D.A., Schwarz, R.D., Eneanya, D.I., Duran, D.O., Greenwald, J.E., Andresen, B.D.: Clinical Correlates of Changes in Receptors During Aging, In Neural Regulatory Mechanisms During Aging, Edited by Roberts, J. C19B0T FIELDS OF STUDY Major Field: Pharmacology Drug Metabolism ........... Dr. J.R. Bianchine and Dr. N. Cerber t Gas Chromatography and Mass Spectrometry......... Dr. B. Andresen Biochemical Pharmacology. Dr. R. Fertel Pharmacokinetics ........... Dr. N. Gerber Physiological Chemistry . Dr. R. Panganamaia R a d i o l o g y ............... Dr. R. Hart and Dr. B, Daniel Tissue Culture............ Dr* R. Hart and Dr. B. Daniel TABLE OF CONTENTS Page ACKNOWLEDGEMENTS Li VITA iv LIST OF TABLES ix LIST OF FIGURES x LIST OF ABBREVIATIONS ............................ xii INTRODUCTION 1 Literature Review ............................ I Chemistry of D i s u l f i r a a .......................... .2 Pharmacokinetics of Disulfiram ................. 4 Administration ............................ 4 Absorption 4 Distribution ........... 4 Metabolism ............................ 5 Reduction of disulfiram ............... 5 Glucuronidation ...................... 9 Non-enzymatic degradation ............. 9 Methylation............................10 O x i d a t i o n ............................. 11 Disulfiram and the Enzymes of the B o d y ............ 12 The Dehydrogenases ........ 12 The Oxidases ............................. 13 Dopamine p-Hydroxylase ..................... 14 Other Enzymes Inhibited by Disulfiram .... 14 General Mechanism of Enzyme Inhibition .... 14 Pharmacodynamics of Disulfiram.................... IS The Disulfiram - Ethanol Reaction .......... 15 Acetaldehyde and D E R .................. 16 vi Page Disulfiram and Biogenic Amines ........... 18 Disul£iram~Induced Hepatotoxicity ...... 20 Carbon Disulfide and DS Neuropathies........ 20 Disulfiram Induced Psychosis ........ 22 Disulfiram Induced Acetonemia ............. 23 Inhibition of Oxidative Phosphorylation . 23 Other Side Effects of Disulfiram ...... 24 Disulfiram Interaction With Other Drugs ..... 24 Other Drugs with Disulfiram-Like A c t i o n ....... 26 Methods for the Determination of Disulfiram and Its Metabolites 28 Colorimetric methods ................... 28 Other methods .......................... 29 Chromatographic assays ................... 29 STATEMENT OF PROBLEM: AN OVERVIEW...................... 30 MATERIALS AND METHODS 32 Synthesis of Dithiocarbamic Acids ............. 33 Assay Procedure ............................ 33 Extraction 36 Liver Perfusion Experiments ................... 37 Kinetic studies .......................... 38 Choleretic effects ....................... 40 Excretion of metabolites ................. 41 Intact Animal Experiment ....................... 41 Decline of DDC in blood of rat at I.V. dose of 250 mg/kg .......................... 42 Effect of Choleresis on Composition of Bile . 42 Analytical Methods ........................ 42 Unmetabolized DDC ...................... 43 DDC-conjugate by alkali hydrolysis ........ 43 Perfusate samples .............. 43 Page Analysis of DDC-glucuronide ............. 44 Permethylation....................... 44 Silylation ........................ 45 Decline of DDC in IntactAn i m a l ...........
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