Chapter 5. The Hydrolysis of Lactams

  1. Prof. Bernard Testa and
  2. Dr. Joachim M. Mayer

Published Online: 9 NOV 2006

DOI: 10.1002/9783906390444.ch5

Hydrolysis in Drug and Prodrug Metabolism: Chemistry, Biochemistry, and Enzymology

Hydrolysis in Drug and Prodrug Metabolism: Chemistry, Biochemistry, and Enzymology

How to Cite

Testa, B. and Mayer, J. M. (2003) The Hydrolysis of Lactams, in Hydrolysis in Drug and Prodrug Metabolism: Chemistry, Biochemistry, and Enzymology, Verlag Helvetica Chimica Acta, Zürich. doi: 10.1002/9783906390444.ch5

Author Information

  1. Institute of Medicinal Chemistry, School of Pharmacy, University of Lausanne, CH-1015 Lausanne, Switzerland

Publication History

  1. Published Online: 9 NOV 2006
  2. Published Print: 17 JUN 2003

ISBN Information

Print ISBN: 9783906390253

Online ISBN: 9783906390444

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Keywords:

  • hydrolysis;
  • drug metabolism;
  • prodrug metabolism;
  • hydrolysis of lactams;
  • β-lactam antibiotics;
  • simple lactam derivatives;
  • complex lactam derivatives;
  • lactam metabolites

Summary

This chapter contains sections titled:

  • Introduction

  • β-Lactam Antibiotics

    • Structural Diversity

    • Reactivity of the β-Lactam Ring

      • Antibacterial Activity

      • Enzymatic Hydrolysis by β-Lactamases

      • Mechanism-Based Inactivators of β-Lactamases

      • Chemical Hydrolysis – Reactivity of the Nucleus

      • Chemical Hydrolysis – Substituent Effects

    • Relationship between Chemical Hydrolysis and Antibacterial Activity

    • Stereoselectivity of Hydrolysis

    • Intermolecular Reactions

    • External Factors Influencing Stability

      • Buffer-Catalyzed Hydrolysis

      • Metal Ion Catalyzed Hydrolysis

      • Micelle-Catalyzed Hydrolysis

      • Interaction with Serum Albumin

    • Metabolism in Mammals

  • Simple Lactam Derivatives

  • Complex Lactam Derivatives

  • Lactam Metabolites

    • Formation of Lactam Metabolites

    • Hydrolysis of Lactam Metabolites