Metabolism of N-acyl-chloroanilines@@@Stoffwechsel von N-Acyl-Chloranilinen

Rabbits excrete certain para-substituted acetanilides as the corresponding glycolanilides and oxanilic acids [2]. The hydroxylation of acetic acid to glycolic acid in acetanilides is carried out by microsomal oxygenases. We isolated 4-chloro-glycolanilide from suspensions of rabbit liver and kidney microsomes incubated with 4-chloro-acetanilide. The importance of the 4-position being substituted is shown by 3-chloro-acetanilide being excreted to only 0.1% of the dose and 2-chloro-acetanilide in untraceable amounts as glycolanilide. None of the acetanilides, a large portion of which was excreted as a glycolanilide, were found in the urine as hydroxamic acid. On the other hand, N-(2-fluorenyl)-acetanilide, of which up to 30% is found in the urine as the N-hydroxy derivative [1], was excreted to only about 0.1% as N-(2-fluorenyl)-glycolamide.