The oxidative metabolism of alpha-chlorohydrin in the male rat and the formation of spermatocoeles.
1. The oxidative metabolism of [3-36C]chloropropan-1,2-diol (alpha-chlorohydrin, I) was studied in male rats. Two metabolites were isolated and identified as beta-chlorolactic acid (IV) and oxalic acid (V). 2. Neither alpha-chlorohydrin nor beta-chlorolactate was concentrated in any tissue. Traces of an intermediate metabolite, beta-chlorolactaldehyde (III) were detected in the urine within 4 h of administration. Studies in vitro indicated that the metabolic pathway is: alpha-chlorohydrin leads to beta-chlorolactaldehyde leads to beta-chlorolactic acid. 3. A comparative study of the metabolism of 36Cl- and 14C-beta-chlorolactate showed that oxalate was produced slowly and, as calcium oxalate, caused a type of renal glomerular nephritis. This pathological condition is responsible for the diuretic action of both alpha-chlorohydrin and beta-chlorolactate and, in higher doses, for their toxicities. 4. The role of oxalate, as a metabolite of alpha-chlorohydrin and of a number of related compounds, in inducing the formation of spermatocoeles in the male rat reproductive tract is discussed.
D000818:Animals; D001711:Biotransformation; D002728:Chlorohydrins / Q000378:metabolism*; D004231:Diuresis / Q000187:drug effects; D066298:In Vitro Techniques; D007773:Lactates / Q000378:metabolism; D008099:Liver / Q000378:metabolism; D008297:Male; D010070:Oxalates / Q000378:metabolism; D010084:Oxidation-Reduction; D051381:Rats; D013088:Spermatocele / Q000139:chemically induced*; D014018:Tissue Distribution; D000517:alpha-Chlorohydrin / Q000378:metabolism* / Q000494:pharmacology
D002728:Chlorohydrins; D007773:Lactates; D010070:Oxalates; D000517:alpha-Chlorohydrin