A novel metabolite of tinidazole involving nitro-group migration.
After oral doses to dogs of 14C-tinidazole, a 5-nitroimidazolyl antiprotozoal compound, a major and previously unidentified radioactive metabolite was isolated from urine and shown by FAB mass spectrometry and n.m.r. spectroscopy to be ring-hydroxylated. The exact identity of this metabolite was established by X-ray diffraction analysis as ethyl 2-(5-hydroxy-2-methyl-4-nitro-1-imidazolyl)ethyl sulphone. The apparent migration of the nitro group from the 5 position in the parent drug to the 4 position in the metabolite is a novel metabolic route.
D000818:Animals; D001711:Biotransformation; D004285:Dogs; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D008958:Models, Molecular; D009593:Nitroimidazoles / Q000378:metabolism*; D013056:Spectrophotometry, Ultraviolet; D014011:Tinidazole / Q000031:analogs & derivatives* / Q000378:metabolism* / Q000652:urine; D014961:X-Ray Diffraction
D009593:Nitroimidazoles; D014011:Tinidazole; C045438:ethyl 2-(5-hydroxy-2-methyl-4-nitro-1-imidazolyl)ethylsulfone