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  • Title: Studies on the action of nitroimidazole drugs. The products of nitroimidazole reduction.
    Author: Knox RJ, Knight RC, Edwards DI.
    Journal: Biochem Pharmacol; 1983 Jul 15; 32(14):2149-56. PubMed ID: 6870942.
    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.
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