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N-Hydroxylation of 2-Acetylaminofluorene in the Rabbit^*

( Radioisotope Service, Veterans Administration Medical Teaching Group Hospital and Division of Biochemistry, The University of Tennessee Medical Units, Memphis, Tennessee)

The major urinary metabolites of 2-acetylaminofluorene (AAF) in the rabbit were N-hydroxy-2-acetylaminofluorene and 7-hydroxy-2-acetylaminofluorene. By the third day of AAF feeding (70 mg AAF/day), N-hydroxy-2-acetylaminofluorene was the predominant urinary metabolite, and its excretion accounted for 22–30 per cent of the daily dose of ingested AAF during the first 4 weeks of feeding. During this same time interval, 12–28 per cent of the dose of AAF per day was excreted as 7-hydroxy-2-acetylaminofluorene.

Only small (0.5–1.5 per cent of dose) or trace (0.1–0.5 per cent of dose) amounts of 3-hydroxy-2-acetylaminofluorene and 5-hydroxy-2-acetylaminofluorene were excreted. The rabbits did not excrete detectable quantities (more than 0.1 per cent of dose) of 1-hydroxy-2-acetylaminofluorene.

N-Hydroxy-2-acetylaminofluorene was excreted entirely as a conjugate which was hydrolyzed by bacterial ß-glucuronidase. 7-Hydroxy-2-acetylaminofluorene was excreted mainly as a conjugate cleaved by ß-glucuronidase; in addition, however, small amounts of the unconjugated form or the ethereal sulfate were excreted.

^* This investigation was supported in part by a research grant (C5490) from the National Cancer Institute, U.S. Public Health Service, and was presented in part at the 53d Annual Meeting of the American Association for Cancer Research, Atlantic City, New Jersey, April, 1962. The author is grateful to Mrs. Virginia Layton for her excellent technical assistance.

The nomenclature used in this paper is given below, followed in each case by the Chemical Abstracts nomenclature in brackets.

2-acetylaminofluorene [N-2-fluorenylacetamide]

N-hydroxy-2-acetylaminofluorene [N-hydroxy-N-2-fluorenylacetamide]

x-hydroxy-2-acetylaminofluorene [N-(x-hydroxy-2-fluorenyl)acetamide]

2-aminofluorene [2-fluorenamine]

Received 4/ 2/62.