Drug Metabolism Chemical and Enzymatic Aspects 1st Edition by Jack Uetrecht, William Trager 1420061038 9781420061031

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ISBN 10: 1420061038

ISBN 13: 9781420061031

Author: Jack P. Uetrecht; William Trager

In order to understand drug metabolism at its most fundamental level, pharmaceutical scientists must be able to analyze drug compound structures and predict possible metabolic pathways in order to avoid the risk of adverse reactions that lead to the withdrawal of a drug from the market. This comprehensive textbook will aid in guiding students

Drug Metabolism Chemical and Enzymatic Aspects 1st Table of contents:

1 Introduction

References

2 Background for Nonchemists

Using The Structure Of A Drug To Predict Properties Such As Water Solubility

Prediction Of Charge From Pka

Factors Such As Charge That Affect Drug Absorption, Distribution, And Excretion

Hints For Understanding Chemical Mechanisms

References

3 Background for Chemists

Basic Aspects Of Pharmacokinetics

Drug Transporters

Enzyme Kinetics

In Vitro–In Vivo Correlation Of Drug Behavior

Deuterium Isotope Effects

References

4 Oxidation Pathways and the Enzymes That Mediate Them

Oxidative Enzymes

Cytochrome P450s

Cytochrome P450: General Properties and Mechanism of Oxygen Action

Cytochrome P450 Nomenclature

Peroxidases

Horseradish Peroxidase

Prostaglandin H Synthase

Myeloperoxidase

Miscellaneous Peroxidases

Flavin Monooxygenase

Alcohol Dehydrogenase

Aldehyde Dehydrogenases

Monoamine Oxidase

Xanthine Oxidase

Aldehyde Oxidase

Oxidative Pathways

Oxidation of sp3 Carbon–Hydrogen Bonds of Simple Alkanes

Oxidation of Benzylic and Allylic sp3 Carbon–Hydrogen Bonds

Oxidation α to a Heteroatom (N, O, S, Halogen)

N-Dealkylation/Deamination

O-Dealkylation

S-Dealkylation

Halogen Dealkylation

Oxidative Cleavage of Esters and Amides

Oxidative Cleavage of Nitriles

Oxidative Dehydrogenation

Oxidative Addition to Unsaturated Carbon

Alkenes

Alkynes

Aromatic Rings

Ipso Substitution

FeO2+—An Active P450 Oxidant

Oxidation of Alcohols

Oxidation of Aldehydes

Oxidative Decarboxylation

Oxidation of Heteroatoms

Oxidation of Nitrogen

Oxidation of Sulfur

References

5 Reductive Pathways

Major Reducing Enzymes

Aldo/Keto Reductases

Carbonyl Reductases

Cytochrome P450

Xanthine Oxidase and Aldehyde Oxidase

NAD(P)H Quinone Oxidoreductase

Reductive Metabolic Pathways

Reduction of Nitro, Nitroso, and Hydroxylamine Groups

Reduction of Amine Oxides

Reduction of Azo Compounds

Reduction of Aldehydes and Ketones

Reduction of Quinones

Reduction of Sulfoxides

Reduction of Disulfides and Other Oxidation States of Sulfur

Reduction of Peroxides

Reductive Dehalogenation

References

6 Hydrolytic Pathways

Hydrolysis Of Esters, Amides, And Thioesters

Esterases

Acetylcholinesterase

Pseudocholinesterase

Carboxylesterases

Paraoxonase

Amidases

Hydrolysis Of Epoxides

Hydrolysis Of Sulfates And Glucuronides

References

7 Conjugation Pathways

Glucuronidation

Glucuronosyl Transferases

Glucuronidation Characteristics

Sulfation

Acetylation

Methylation

Amino Acid Conjugation

Chiral Inversion Of 2-Arylpropionic Acids

Glutathione Conjugation

Conversion Of Glutathione Conjugates To Mercapturic Acids

Cysteine Conjugate β-Lyase

References

8 Reactive Metabolites

Good Leaving Groups

Ring Strain

Michael Acceptors

Isocyanates And Isothiocyanates

Carbenes

Free Radicals

Prediction Of Reactive Metabolite Formation

References

Practice Problems

Answers to Practice Problems

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