Chemical metabolite synthesis and profiling: Mimicking in vivo biotransformation reactions

Bioorg Chem. 2023 Oct:139:106722. doi: 10.1016/j.bioorg.2023.106722. Epub 2023 Jul 8.

Abstract

Biotransformation was previously viewed as merely the structural characterization of drug metabolites, and it was performed only when drug candidates entered clinical development. The synthesis of drug metabolites is crucial to the drug development process because it generates either pharmacologically active, inactive, or reactive molecules and hence their characterization and comprehensive pharmacological evaluation is necessary. The chemical metabolite synthesis is very challenging due to the complex structures of many drug molecules, presence of multiple stereocenters, poor reaction yields, and the formation of unwanted by-products. Drug metabolites and their chemical synthesis have immense significance in the drug discovery process. The chemical synthesis of metabolites facilitates on- or off-target pharmacological and toxicological evaluations at the easiest. In a broader view metabolite could be a target lead molecule for drug design, toxic reactive metabolites, pharmaceutical standards for bioanalytical methods, etc. Collectively these metabolite information dossiers will aid regulatory agencies such as the EMA and FDA in maintaining strict vigilance over drug manufacturers with regard to the safety of NCE's and their hidden metabolites. Herein, we are presenting a systematic compilation of chemical and biocatalytic strategies reported to date for pharmaceutical drug metabolite synthesis. This review report is very useful for the laboratory synthesis of new drug metabolites, and their preclinical biological evaluation could aid in the detection of early threats (alerts) in drug discovery, eliminate the toxicity profile, explore newer pharmacology, and delivering a promising and safe drug candidate to humankind.

Keywords: Biotransformation; Electrochemistry; Glucuronidation; Glutathione conjugation; Human drug metabolites; Metabolite synthesis; Phase I and phase II metabolism; Reactive metabolites.

Publication types

  • Review
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotransformation
  • Drug Design*
  • Drug Discovery* / methods
  • Pharmaceutical Preparations

Substances

  • Pharmaceutical Preparations