PT  - JOURNAL ARTICLE
AU  - M S Rashed
AU  - A J Streeter
AU  - S D Nelson
TI  - Investigations of the N-hydroxylation of 3'-hydroxyacetanilide, a non-hepatotoxic positional isomer of acetaminophen.
DP  - 1989 Jul 01
TA  - Drug Metabolism and Disposition
PG  - 355--359
VI  - 17
IP  - 4
4099  - http://dmd.aspetjournals.org/content/17/4/355.short
4100  - http://dmd.aspetjournals.org/content/17/4/355.full
SO  - Drug Metab Dispos1989 Jul 01; 17
AB  - The hydroxamic acid of 3'-hydroxyacetanilide (AMAP) was synthesized to test the hypothesis that different reactive metabolites of AMAP and acetaminophen account for similarities in covalent binding of the two positional isomers to hepatic proteins, but for differences in their ability to cause hepatotoxicity. N-OH-AMAP was found to be a relatively stable hydroxamic acid, but it was not detected as a metabolite of AMAP formed in vitro by mouse liver microsomes or in urine of mice administered AMAP. Therefore, metabolites other than N-OH-AMAP must be responsible for covalent binding observed with AMAP to mouse liver proteins.