title: Studies on the action of nitroimidazole drugs. The products of nitroimidazole reduction.
abstract: The electron requirements for the electrolytic reduction of misonidazole, metronidazole and 4(5)-nitroimidazole have been measured using high-resolution coulometry. Eleven of the labelled final reduction products of metronidazole (a 5-nitroimidazole) have been separated by high-performance liquid chromatography and identified. These appear to be formed without the prior generation of a stable intermediate. In contrast, the reduction products of misonidazole (a 2-nitroimidazole) show little similarity to those of metronidazole but are likely to be formed via the four-electron hydroxylamine derivative. None of the final reduction products show toxicity towards Clostridium bifermentans or Escherichia coli suggesting that the short-lived cytotoxic agent of nitroimidazoles is a reduction product formed by the addition of not more than three electrons.
mesh_terms: D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D004572:Electrolysis; D008795:Metronidazole; D008920:Misonidazole; D009573:Nitrites / Q000032:analysis; D009593:Nitroimidazoles / Q000302:isolation & purification*; D010084:Oxidation-Reduction; D013053:Spectrophotometry
chemical_list: D009573:Nitrites; D009593:Nitroimidazoles; D008795:Metronidazole; D008920:Misonidazole