The anaerobic metabolism of metronidazole forms N-(2-hydroxyethyl)-oxamic acid

N-(2-hydroxyethyl)-oxamic acid is formed when metronidazole is reduced either chemically or by the action of the intestinal bacteria. When metronidazole, labeled with carbon-14 in the hydroxyethyl side chain, is administered by gavage to rats in doses of 200 mg/kg, an average of 1.4% of the administered radioactivity is recovered in the urine in the form of N-(2-hydroxyethyl)-oxamic acid. The presence of conjugated N-(2-hydroxyethyl)-oxamic acid in some samples was suggested by the detection of small additional amounts of the free acid after treatment of the urine with beta-glucuronidase. The metabolite is not found in the feces. In contrast N-(2-hydroxyethyl)-oxamic acid is not found in the urine or feces of germfree rats which receive metronidazole. Thus, the finding of N-(2-hydroxyethyl)-oxamic acid in the urine of rats which receive metronidazole appears to depend on the activity of the bacterial flora.