1-thiocarbamoyl-2-imidazolidinone, a metabolite of niridazole in Schistosoma mansoni.
Niridazole, a nitro heterocyclic antischistosomal drug, is extensively metabolized to unknown metabolites by Schistosoma mansoni. We report that 1-thiocarbamoyl-2-imidazolidinone was isolated by high pressure liquid chromatography and identified by high resolution electron impact mass spectroscopy as a niridazole metabolite in schistosomes. After a 20-h in vitro incubation in 30 ml of medium containing 10 micrograms ml-1 [14C]niridazole (5.2 Ci mol-1), 100 S. mansoni worm pairs contained approximately 275 ng of 1-thiocarbamoyl-2-imidazolidinone. This amount represented 4% of the total metabolized fraction of niridazole in the parasite. Incubation of schistosomes with 1-thiocarbamoyl-2-[2 14C]imidazolidinone (2.7 Ci mol-1) indicated that this metabolite was not taken up. However, schistosomes released an average of 44 ng ml-1 or 1% of the total 1-thiocarbamoyl-2-imidazolidinone found in the worm back into 1 ml of medium during incubation. No host oxidative metabolites of niridazole were found in the parasites.
D000818:Animals; D001692:Biological Transport; D007093:Imidazoles / Q000096:biosynthesis* / Q000378:metabolism; D009560:Niridazole / Q000378:metabolism*; D010084:Oxidation-Reduction; D012550:Schistosoma mansoni / Q000378:metabolism*; D013859:Thiocarbamates / Q000096:biosynthesis* / Q000378:metabolism
D007093:Imidazoles; D013859:Thiocarbamates; C026957:1-thiocarbamoyl-2-imidazolidinone; D009560:Niridazole