The metabolism of 3-amino-1-chloropropan-2-ol in relation to its antifertility activity in male rats.
1. The metabolism of 3-amino[36Cl]chloropropan-2-ol (III) was studied in male rats. Three urinary metabolites were isolated and identified as alpha-chlorohydrin (I), beta-chlorolactic acid (V) and oxalic acid (VI). Much of the administered aminochloropropanol was excreted unchanged in the urine; 63% within 72 h, 75% over 250 h. 2. Monoamine oxidase is capable of converting aminochloropropanol to beta-chlorolactaldehyde (IV) which, by processes of either reduction or oxidation, suggests that the metabolic pathway is IV leads to I and IV leads to V leads to VI. 3. As assessed by the diuretic activities of the isomers of aminochloropropanol, oxalate appears to be produced by the (+)-isomer but not by the (-)-isomer. A difference in metabolic rate or route of the isomers may account for their differing physiological activities. 4. (+)- and (-)-aminochloropropanol exhibited identical in vitro inhibitory activities on the glycolytic enzymes glyceraldehyde-3-phosphate dehydrogenase and triosephosphate isomerase, and were substrates for monoamine oxidase to equivalent extents.
D000818:Animals; D002728:Chlorohydrins; D003272:Contraceptive Agents, Male / Q000378:metabolism* / Q000494:pharmacology; D004231:Diuresis / Q000187:drug effects; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases / Q000037:antagonists & inhibitors; D007700:Kinetics; D008297:Male; D011412:Propanolamines / Q000378:metabolism* / Q000494:pharmacology; D051381:Rats; D013237:Stereoisomerism; D013997:Time Factors; D014305:Triose-Phosphate Isomerase / Q000037:antagonists & inhibitors
D002728:Chlorohydrins; D003272:Contraceptive Agents, Male; D011412:Propanolamines; C009721:CL 88236; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases; D014305:Triose-Phosphate Isomerase