Metabolism of the putative antifertility agents 3-(36)chloro-1-hydroxypropanone and its dimethyl ketal in the male rat.
3-(36)Chloro-1-hydroxypropanone (CHOP), a specific inhibitor of sperm glycolysis in vitro, is rapidly metabolized by the male rat to alpha-chlorohydrin, 3-chlorolactate and the inhibitory sperm metabolite, 3-chlorolactaldehyde, presumably all being of the (S)-configuration. The dimethyl ketal of (36)Cl-CHOP [3-(36)Cl-dimethyl-CHOP] is rapidly metabolized producing identical metabolites and excreted radioactivity in urine at a similar rate. As neither compound produced diuresis, glucosuria or induced the formation of spermatocoeles, conditions associated with related male antifertility and antiglycolytic agents, they could represent an alternative means of producing (S)-3-chlorolactaldehyde within spermatozoa in vivo.
Cooper
T G
TG
Institute of Reproductive Medicine of the University, Münster, Germany. cooper@uni-muenster.de
Jones
A R
AR
D000096:Acetone / Q000031:analogs & derivatives; D000818:Animals; D003272:Contraceptive Agents, Male / Q000008:administration & dosage / Q000378:metabolism*; D003280:Contraceptives, Oral, Synthetic / Q000008:administration & dosage / Q000378:metabolism*; D005298:Fertility; D007668:Kidney / Q000187:drug effects / Q000378:metabolism / Q000502:physiology; D008297:Male; D015394:Molecular Structure; D020005:Propanols / Q000008:administration & dosage / Q000378:metabolism*; D051381:Rats; D017208:Rats, Wistar
D003272:Contraceptive Agents, Male; D003280:Contraceptives, Oral, Synthetic; D020005:Propanols; D000096:Acetone; C110397:3-chloro-1-propanol; C027160:1-hydroxy-3-chloroacetone