1. Chapter 08
Drug Metabolism

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Figure 8.1 Effects of lipophilicity on direct renal clearance and on metabolism
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Scheme 8.1 Biosynthesis of penicillins
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Scheme 8.2 Chemical synthesis of linezolid
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Scheme 8.3 Cytochrome P450 oxidation of naphthalene
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Scheme 8.4 Addition–rearrangement mechanism for arene oxide formation
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Scheme 8.5 Possible fates of arene oxides
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Scheme 8.6 Rearrangement of arene oxides to arenols (NIH shift)
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Scheme 8.7 Competing pathway for NIH shift
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Scheme 8.8 NIH shift of chloride ion
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Scheme 8.9 NIH shift of nitro group
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Scheme 8.10 Metabolic formation and oxidation of catechols
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Scheme 8.11 Formation of glutathione adducts from naphthalene oxides
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Scheme 8.12 Deoxyribonucleic acid adduct with benzo[a]pyrene metabolite
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Scheme 8.13 Metabolism of carbamazepine
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Scheme 8.14 Metabolic reactions of aflatoxin B1
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Scheme 8.15 C-demethylation of a flutamide metabolite
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Scheme 8.16 Oxidative deamination of primary amines
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Scheme 8.17 N-Oxidation pathways of amphetamine
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Scheme 8.18 Amphetamine imine formation via the carbinolamine
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Scheme 8.19 Oxidative N-dealkylation of secondary amines
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Scheme 8.20 Oxidative metabolism of propranolol
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Scheme 8.21 N-Oxidation of fenfluramine
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Scheme 8.22 Metabolism of selegiline (deprenyl)
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Scheme 8.23 Oxidative metabolism of nicotine leading to C–N bond cleavage.
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Scheme 8.24 Metabolism of lidocaine
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Scheme 8.25 Mechanism of cytochrome P450-catalyzed N-oxidation of tertiary aromatic amines
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Scheme 8.26 Possible mechanism for N-oxidation of primary arylamines
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Scheme 8.27 Two pathways to N-demethylation of tertiary aromatic amines
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Scheme 8.28 Mechanism of carbinolamine formation during oxidation of tertiary aromatic amines
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Scheme 8.29 Metabolic activation of primary and secondary aromatic amines
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Scheme 8.30 Arylhydroxamic acid N,O-acyltransferase-catalyzed activation of N-hydroxy-2-acetylaminoarenes
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Scheme 8.31 Initial proposals for bioactivation of acetaminophen
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Scheme 8.32 Bioactivation of acetaminophen via a radical intermediate
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Scheme 8.33 Proposed bioactivation of acetaminophen by prostaglandin H synthase
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Scheme 8.34 Metabolic hydroxylation of rofecoxib
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Scheme 8.35 Cytochrome P450-catalyzed oxidation of sulfides
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Scheme 8.36 S-Oxidation of tienilic acid
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Scheme 8.37 Oxidative dehalogenation of halothane
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Scheme 8.38 Reactions catalyzed by alcohol dehydrogenase
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Figure
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Scheme 8.39 Nitro group reduction
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Scheme 8.40 Reductive metabolism of nitrofurazone
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Scheme 8.41 Azo group reduction
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Scheme 8.42 Reductive metabolism of sulfasalazine
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Scheme 8.43 Reductive dehalogenation of halothane
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Scheme 8.44 Competitive metabolism of R- and S-etomidate
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Scheme 8.45 Biosynthesis and reactions of UDP glucuronic acid
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Scheme 8.46 Sulfate conjugation
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Scheme 8.47 Bioactivation of phenacetin
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Scheme 8.48 Amino acid conjugation
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Scheme 8.49 Metabolism of brompheniramine
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Scheme 8.50 Examples of glutathione conjugation
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Scheme 8.51 Metabolism of glutathione conjugates to mercapturic acid conjugates
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Scheme 8.52 N-Acetylation of amines
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Scheme 8.53 Methylation of xenobiotics
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Scheme 8.55 Metabolism of lumiracoxib to a reactive quinone-imine
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Table 8.1
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Table 8.8
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