Successful preparation of metabolite of troglitazone by in-flow electrochemical reaction on coulometric electrode

Kayoko Tahara, Yuka Yano, Kiyotada Kanagawa, Yoshihiro Abe, Junko Yamada, Shiro Iijima, Masataka Mochizuki, Takashi Nishikawa

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21 Citations (Scopus)

Abstract

A simple, rapid and efficient system utilizing a coulometric electrode was developed for the preparation of drug metabolites. Trace amounts of reactants are usually generated in electrochemical reactions, which are not suitable for the sufficient preparation of products to obtain NMR and other spectral data for chemical structure confirmation or to obtain data from pharmacological activity screening tests of products. In the developed system, called the "in-flow electrochemical reaction system," a drug, troglitazone, was dissolved in a volatile flow solvent, and pumped into a coulometric electrode under optimized conditions, and the effluent was evaporated. Without any further purification, milligram amounts of a pure oxidation product of troglitazone could be obtained within several hours. The amount obtained was enough for 1H- and 13C-NMR analysis by which the structure could be confirmed and was found to be identical to one of the metabolites of troglitazone detected in human plasma. This system will be useful to prepare standard compounds of the required amount for pharmacokinetic study and for toxicokinetic study.

Original languageEnglish
Pages (from-to)1207-1212
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume55
Issue number8
DOIs
Publication statusPublished - 2007 Aug 1

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Keywords

  • Drug metabolite
  • Electrochemical reaction
  • Preparation
  • Troglitazone

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

Cite this

Tahara, K., Yano, Y., Kanagawa, K., Abe, Y., Yamada, J., Iijima, S., Mochizuki, M., & Nishikawa, T. (2007). Successful preparation of metabolite of troglitazone by in-flow electrochemical reaction on coulometric electrode. Chemical and Pharmaceutical Bulletin, 55(8), 1207-1212. https://doi.org/10.1248/cpb.55.1207