In vitro metabolism of KBH-A40, a novel delta-lactam-based histone deacetylase (HDAC) inhibitor, in human liver microsomes and serum

Xenobiotica. 2008 Mar;38(3):281-93. doi: 10.1080/00498250701813222.

Abstract

1. The metabolism of KBH-A40, a novel delta-lactam-based histone deacetylase (HDAC) inhibitor, was investigated in vitro using human liver microsomes and serum. After 60-min incubation in human liver microsomes with beta-nicotinamide adenine dinucleotide phosphate (NADPH) or uridine diphosphate glucuronic acid (UDPGA), the residual KBH-A40 was 90.6% +/- 5.1% and 28.9% +/- 2.0% (t(1/2) = 26 min), respectively, suggesting that KBH-A40 is likely predominantly metabolized by glucuronidation, rather than by cytochrome P450 (CYP)-mediated oxidation. Consistently, KBH-A40 glucuronide was the only metabolite identified following incubations of KBH-A40 with human liver microsomes in the presence of both NADPH and UDPGA. 2. KBH-A40 was not notably degraded when incubated with human serum for 60 min. In contrast, KBH-A40 was rapidly hydrolysed to its carboxylic acid form in rat serum (t(1/2) = 13 min). 3. Taken collectively, the results suggest that KBH-A40 is likely metabolized in man predominantly by glucuronidation of its hydroxamic acid moiety, with negligible biotransformation elsewhere in the molecule.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biotransformation / drug effects
  • Chromatography, Liquid
  • Drug Stability
  • Enzyme Inhibitors / blood
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / metabolism*
  • Enzyme Inhibitors / pharmacology*
  • Histone Deacetylase Inhibitors*
  • Humans
  • Hydroxamic Acids / blood
  • Hydroxamic Acids / chemistry
  • Hydroxamic Acids / metabolism*
  • Hydroxamic Acids / pharmacology*
  • Lactams / blood*
  • Lactams / chemistry
  • Lactams / metabolism*
  • Lactams / pharmacology
  • Male
  • Mass Spectrometry
  • Microsomes, Liver / drug effects
  • Microsomes, Liver / metabolism*
  • Pyridones / blood
  • Pyridones / chemistry
  • Pyridones / metabolism*
  • Pyridones / pharmacology*
  • Rats
  • Rats, Sprague-Dawley
  • Time Factors

Substances

  • Enzyme Inhibitors
  • Histone Deacetylase Inhibitors
  • Hydroxamic Acids
  • Lactams
  • N-hydroxy-3-(2-oxo-1-phenethyl-1,2,5,6-tetrahydropyridin-3-yl)propanamide
  • Pyridones