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Drug Metabolism. Where? First-Pass Effect More than 1 metabolite! Varies depending on species, age, gender, genetic variation, disease. Phase I Oxidations Reductions Hydrolysis. Phase II Synthetic/Conjugation. Phases of Drug Metabolism. Phase I Oxidations.

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drug metabolism
Drug Metabolism
  • Where?
  • First-Pass Effect
  • More than 1 metabolite!
  • Varies depending on species, age, gender, genetic variation, disease
phases of drug metabolism
Phase I

Oxidations

Reductions

Hydrolysis

Phase II

Synthetic/Conjugation

Phases of Drug Metabolism
phase i oxidations
Phase I Oxidations
  • Hydroxylations of N, C, S atoms
  • N-, O-, and S- dealkylations
  • Oxidative Deaminations
  • ROH RCHO RCOOH
phase i oxidations the enzymes
Phase I Oxidations: The Enzymes
  • Mixed Function Oxygenases found in smooth ER, e.g. Cytochrome P-450
  • Microsomal Flavin Monoxygenase (FMO)
  • Alcohol Dehydrogenase
  • Xanthine Oxidase
  • Monoamine Oxidase (mitochondria)
oxidative deamination dealkylations
Oxidative Deamination/Dealkylations
  • Can occur on N-, O-, S-, or X- systems
  • Begins with hydroxylation, followed by elimination
  • Cytochrome P450 & MAO
other types of oxidative reactions
Other types of oxidative Reactions
  • ROH  RCHORCOOH
  • RSHRSSR
  • Desulfuration (C=S C=O)
hydrolysis
Hydrolysis
  • Nonspecific esterases, amidases
  • Amides hydrolyze more slowly than esters
  • May be stereospecific
  • Occurs in cytosol of cells (liver, kidney, intestine) and in plasma
reductions
Reductions
  • Less common than oxidations
  • Usually specific enzymes, e.g. aldo-keto reductases, nitro reductases
  • C=O  alcohols
  • NO2  NH2
  • N=N  2 NH2
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