Identification of BVT.2938 metabolites by LC/MS and LC/MS/MS after in vitro incubations with liver microsomes and hepatocytes

J Pharm Biomed Anal. 2004 Mar 10;34(5):1079-90. doi: 10.1016/j.jpba.2003.12.010.

Abstract

The metabolism of the 5HT2c agonist BVT.2938, 1-(3-[2-[(2-ethoxy-3-pyridinyl)oxy]ethoxy]-2-pyrazinyl)-2(R)-methylpiperazine, was studied in vitro by incubation with rat, monkey and human liver microsomes as well as cryopreserved hepatocytes, followed by liquid chromatography/mass spectrometry (LC/MS) and LC/MS/MS analysis on a quadrupole-time of flight mass spectrometer for structural elucidation. Deuterium exchange on column was used to differentiate between hydroxylation and N-oxidation. Liver microsomes were incubated in two different buffer systems with optimum conditions for cytochrome P450 activity or UDP-glucuronosyltransferase activity. The major phase I metabolites of BVT.2938 originated from O-deethylation of the pyridine ring, O-dealkylation of the ethylene bridge, pyrazine ring hydroxylation, hydroxylation of pyridine ring and piperazine ring N-hydroxylation. When a hydrogen carbonate buffer system was supplemented with UDPGA, the piperazine carbamoyl-glucuronide from the parent compound was identified together with several glucuronides of the phase I metabolites. The metabolite pattern in hepatocytes was similar to microsomes except that the sulphate at the N-position of the piperazine ring of BVT.2938 was identified, while the carbamoyl-glucuronide was missing. Excellent correlation was obtained between radioactivity detection and the chemiluminescent nitrogen detector when the nitrogen content of the analytes was taken into account.

MeSH terms

  • Animals
  • Chromatography, Liquid / methods
  • Hepatocytes / chemistry
  • Hepatocytes / metabolism*
  • Humans
  • Macaca fascicularis
  • Male
  • Mass Spectrometry / methods
  • Microsomes, Liver / chemistry
  • Microsomes, Liver / metabolism*
  • Rats
  • Rats, Sprague-Dawley
  • Serotonin Receptor Agonists / analysis*
  • Serotonin Receptor Agonists / metabolism*

Substances

  • Serotonin Receptor Agonists