Metabolic Basis of Detoxication
Metabolism of Functional Groups
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Metabolic Basis of Detoxication: Metabolism of Functional Groups considers the possible fates of the relatively circumscribed number of functional groups that xenobiotics bear. An understanding of the possible reactions, and the chemical and biological factors influencing them, will contribute to the overall predictability of the fate of "real" molecules. This approach attempts to knit together the understanding of metabolic pathways with that of the enzymes that catalyze the specific steps. The book contains 18 chapters and begins with a discussion of the biological oxidation of carbon atoms. This is followed by separate chapters on the metabolism of halogenated aliphatic hydrocarbons, aryl halides, heterocyclic rings, alcohols, aldehydes, and ketones. Subsequent chapters cover oxidative processes such as metabolic dealkylations and biological oxidation at nitrogen centers; the reduction of nitro and azo compounds and tertiary amine N-oxides; the oxidation, alkylation, acylation, and glycosylation of mercaptans; epoxide metabolism; and conjugation of phenols. The book aims to inform and interest the pharmacologist and toxicologist concerning the biochemical aspects and to orient the biochemist to the pharmacological insights required in dealing with the metabolism of xenobiotics.
Table of Contents
Contributors
Preface
Introduction
Text
1. Oxidation of Foreign Compounds at Carbon Atoms
I. Introduction
II. Enzymes Involved in Foreign Compound Oxidation at Carbon Atoms
III. Cytochrome P-450-Catalyzed Reactions
IV. Examples of Oxidation Reactions at Carbon
V. Factors That Affect the Rate and Site of Oxidation at Carbon
References
2. Aliphatic Halogenated Hydrocarbons
I. Introduction
II. Chemistry of the Carbon-Halogen Bond
III. Metabolic Reactions
References
3. Aryl Halides
I. Introduction
II. Halogenated Benzenes
III. Halogenated Biphenyls
IV. Halogenated Naphthalenes
V. Comments
References
4. Oxidative Metabolism of Heterocyclic Ring Systems
I. Introduction
II. Nitrogen Heterocycles
III. Sulfur Heterocycles
IV. Oxygen Heterocycles
References
5. Alcohols, Aldehydes, and Ketones
I. Introduction
II. Interconversion of Primary Alcohols and Aldehydes
III. Oxidation of Aldehydes
IV. Interconversion of Secondary Alcohols and Ketones
V. Reduction of Ketones
VI. Comments
References
6. N-Dealkylation and Deamination
I. Introduction and Definitions
II. Chemical Reactions Leading to C—Ν Bond Cleavages
III. Enzymes Promoting C—Ν Bond Cleavages
IV. Distinctions between Alternative Mechanisms of Enzymatic C—Ν Bond Cleavage
V. Properties of Substrates for N-Dealkylation
VI. Metabolic Significance and Pharmacological Consequences of N-Dealkylation
References
7. Oxidation at Nitrogen Centers
I. Introduction
II. Chemical Aspects of Nitrogen Oxidation
III. Biochemical Aspects of Nitrogen Oxidation
IV. Enzyme Systems Involved in Metabolic Nitrogen Oxidation
V. Role of Nitrogen Oxidation in the Detoxication and Toxication of Xenobiotics
References
8. Reductive Metabolism of Nitrogen-Containing Functional Groups
I. Introduction
II. Reduction of Aromatic Nitro Groups
III. Reduction of Azo Compounds
IV. Tertiary Amine N-Oxide Reduction
V. Factors Affecting Nitro, Azo, and TV-Oxide Reductions
VI. Toxicological and Clinical Implications of the Biological Reduction of Organic Nitrogen
References
9. Functional Groups Bearing Sulfur
I. Introduction
II. Biotransformation of Functional Groups Bearing Sulfur
III. Identification of Toxic Metabolites
References
10. Mercaptans
I. Introduction
II. Oxidation of Mercaptans
III. Alkylation of Mercaptans
IV. Acylation of Mercaptans
V. Glycosylation of Mercaptans
VI. Integrative Aspects of the Metabolism of Mercaptans
References
11. Metabolism of Epoxides
I. Introduction
II. Chemistry of Epoxides
III. In Vitro Epoxide Metabolism
IV. Comments
References
12. Hydrolysis of Carboxylic Esters and Amides
I. Susceptibility of Carboxyl Esters and Amides to Hydrolysis
II. Hydrolytic Detoxication of Esters and Amides In Vivo
III. Hydrolytic Toxications and Bioactivations
References
13. Conjugation of Phenols
I. Chemistry of the Phenolic Hydroxy 1 Group
II. Inventory of Substrates
III. Factors Determining Conjugation In Vivo and in Isolated Cell Preparations
IV. Inhibition of Conjugation In Vivo and in Isolated Cell Preparations
References
14. Conjugation of Xenobiotic Carboxylic Acids
I. Introduction
II. The Carboxylic Acid Group
III. Decarboxylation
IV. Reduction
V. Conjugation with Glucuronic Acid
VI. Conjugations with Sugars
VII. Conjugations with Amino Acids
VIII. Methyl Ester Formation
IX. Amide Formation
X. Elimination Unchanged
XI. Chemical and Biological Factors Governing the Relative Extents of Glucuronic Acid and Amino Acid Conjugations of an Acid
XII. Consequences of the Conjugation of Carboxylic Acids
References
15. Conjugation Reactions of Nitrogen Centers
I. Carbamate Formation
II. Acylation Reactions
III. Sulfation at Nitrogen
IV. Sugar Conjugations at Nitrogen
V. N-Methylation
VI. Concluding Remarks
References
16. Metabolism of Organic Hydroperoxides
I. Introduction
II. Chemical and Physical Properties of Organic Hydroperoxides
III. Enzymatic Basis for Organic Hydroperoxide Reduction
IV. Antioxidants
V. Assessment of Hydroperoxide Status in Metabolic Systems
References
17. Role of the Intestinal Microflora
I. Description of the Flora
II. Some of the Detoxication Reactions of the Flora
III. The Flora in Health and Disease
IV. Comment
References
18. Metabolism and Urinary Excretion
I. Introduction
II. Renal Function
III. Examples of Interaction of Metabolism and Urinary Excretion
IV. Comments
References
Index
Product details
- No. of pages: 375
- Language: English
- Copyright: © Academic Press 1982
- Published: June 28, 1982
- Imprint: Academic Press
- eBook ISBN: 9780323137997
About the Author
William B. Jakoby
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