PED2001: Drug Disposition and Pharmacokinetics - Non-P450 Mediated Phase I Metabolism

Non-P450 Mediated Phase I Metabolism: Overview

Non-P450 Phase I Metabolism

Flavin-Linked Monooxygenases (FMO)

FMO Reaction Mechanism

FMO Properties

N-hydroxylation of N-deacetyl ketoconazole

Metabolic Pathways of Tamoxifen

FMOs-Species and Tissue Variations

Peroxidase-Dependent Cooxidation

Prostaglandin H-Synthase (PGHS)

Co-oxidation of Xenobiotics by Prostaglandin H Synthase

Amine Oxidases

Monoamine Oxidase

Monoamine Oxidase (MAO)

Propranolol: MAOA

Oxidoreductases (Dehydrogenases)

Alcohol and Aldehyde Dehydrogenases

Alcohol Dehydrogenase

Aldehyde Dehydrogenase

Role of ALDH in Cyclophosphamide Metabolism

Carbonyl Reductase

Reduction of Doxorubicin

NAD(P)H: Quinone Oxidoreductase 1

Two Electron Versus Single Electron Reduction of Quinone

Esterases

Carboxylesterases

Butyrylcholinesterase

hCE1 Reactions

hCE-2 Reactions

Epoxide Hydrolases (EPH)

Importance of Epoxide Hydrolase on BaP Genotoxicity

Importance of Epoxide Hydrolase on BaP Genotoxicity

Paroxonase (PON) 1

PON1 and Paraoxon

  • PON1 hydrolyzes paraoxon to diethyl phosphate and p-nitrophenol.

PON3 and Statins

  • Lovastatin and simvastatin are prodrugs that are hydrolyzed to the active hydroxy acid by PON3 and hCE1.

Summary

  • There is more to Phase I metabolism than just CYPs.

  • Other Phase I enzymes such as oxidoreductases and hydrolases have received less attention but can be just as important for pharmacokinetics and toxicology.

  • The importance of non-CYP mediated phase I metabolism is now better understood.

Non-P450 Mediated Phase I Metabolism: Overview

Non-P450 Phase I Metabolism
Flavin-Linked Monooxygenases (FMO)
FMO Reaction Mechanism
FMO Properties
N-hydroxylation of N-deacetyl ketoconazole
Metabolic Pathways of Tamoxifen
FMOs-Species and Tissue Variations
Peroxidase-Dependent Cooxidation
Prostaglandin H-Synthase (PGHS)
Co-oxidation of Xenobiotics by Prostaglandin H Synthase
Amine Oxidases
Monoamine Oxidase
Monoamine Oxidase (MAO)
Propranolol: MAOA
Oxidoreductases (Dehydrogenases)
Alcohol and Aldehyde Dehydrogenases
Aldehyde Dehydrogenase
Role of ALDH in Cyclophosphamide Metabolism
Carbonyl Reductase
Reduction of Doxorubicin
NAD(P)H: Quinone Oxidoreductase 1
Two Electron Versus Single Electron Reduction of Quinone
Esterases
Carboxylesterases
Butyrylcholinesterase

hCE1 Reactions

hCE-2 Reactions
Epoxide Hydrolases (EPH)
Importance of Epoxide Hydrolase on BaP Genotoxicity
Importance of Epoxide Hydrolase on BaP Genotoxicity
Paroxonase (PON) 1
  • Multifunctional enzyme with arylesterase, lactonase and paroxonase activities (also hydrolyses other organophosphorus compounds).

  • Synthesised mainly in the liver, also found in plasma.

  • Has a role in degradation of oxidised lipids (protects LDL and HDL from lipid peroxidation).

  • Also do recently discovered PON2 and PON3.

PON1 and Paraoxon
  • PON1 hydrolyzes paraoxon to diethyl phosphate and p-nitrophenol.

PON3 and Statins
  • Lovastatin and simvastatin are prodrugs that are hydrolyzed to the active hydroxy acid by PON3 and hCE1.

Summary
  • There is more to Phase I metabolism than just CYPs.

  • Other Phase I enzymes such as oxidoreductases