Chromatographic and spectroscopic characterization of sulphur-bound dimetridazole and ranidazole derivatives

J Pharm Biomed Anal. 1991;9(2):151-7. doi: 10.1016/0731-7085(91)80138-y.

Abstract

The 5-nitroimidazoles, dimetridazole and ronidazole, two important veterinary drugs, were reacted under reductive conditions with the sulfhydryl-containing substrates cysteine and glutathione to yield 5-amino-4-S-substituted imidazoles. After purification by reversed-phase liquid chromatography (RP-LC), the four adducts were characterized by RP-LC with photodiode array detection using conditions where their parent drugs were not eluted from the column. Structural identification was conducted by spectroscopic techniques, mainly 1-dimensional and 2-dimensional NMR. While the dimetridazole adducts were found to be monosubstituted at the C-4 position, the two ronidazole products contained two units of the sulfhydryl substrate, located at the C-4 and C-6 positions.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Chromatography, Liquid
  • Cysteine / analysis
  • Dimetridazole / analogs & derivatives
  • Dimetridazole / analysis*
  • Glutathione / analysis
  • Magnetic Resonance Spectroscopy
  • Ronidazole / analogs & derivatives
  • Ronidazole / analysis*
  • Spectrophotometry, Ultraviolet
  • Sulfhydryl Compounds / analysis

Substances

  • Sulfhydryl Compounds
  • Ronidazole
  • Glutathione
  • Dimetridazole
  • Cysteine