Biomaterial Database

Metabolism of three active analogues of the male antifertility agent alpha-chlorohydrin in the rat. 1980

A R Jones, and R W O'Brien

1. Two ketal derivatives of alpha-chlorohydrin, which possess male antifertility activity, have been synthesized labelled with 36Cl. Both are metabolized by the rat to beta-chloroacetic acid. 2. Neither derivative inhibited the glycolytic enzymes glyceraldehyde 3-phosphate dehydrogenase and triosephosphate isomerase. 3. The epoxide glycidol is metabolized to beta-chlorolactic acid, presumably by first being converted to alpha-chlorohydrin. 4. It is proposed that the male antifertility actions of these three analogues is due to their biotransformation to alpha-chlorohydrin, which is then metabolized within mature sperm to a compound which is an inhibitor of glycolysis.

UI	MeSH Term	Description	Entries
D008297	Male		Males
D002728	Chlorohydrins	Any of the compounds derived from a group of glycols or polyhydroxy alcohols by chlorine substitution for part of the hydroxyl groups. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Chlorhydrins
D000517	alpha-Chlorohydrin	A chlorinated PROPANEDIOL with antifertility activity in males used as a chemosterilant in rodents.	alpha-Chlorhydrin,3-Chloro-1,2-propanediol,3-Chloropropanediol,3-MCPD,3-Monochloropropane-1,2-diol,Glycerol alpha-Monochlorohydrin,U-5897,3 Chloro 1,2 propanediol,3 Chloropropanediol,3 Monochloropropane 1,2 diol,Glycerol alpha Monochlorohydrin,U 5897,U5897,alpha Chlorhydrin,alpha Chlorohydrin,alpha-Monochlorohydrin, Glycerol
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D001711	Biotransformation	The chemical alteration of an exogenous substance by or in a biological system. The alteration may inactivate the compound or it may result in the production of an active metabolite of an inactive parent compound. The alterations may be divided into METABOLIC DETOXICATION, PHASE I and METABOLIC DETOXICATION, PHASE II.
D051381	Rats	The common name for the genus Rattus.	Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus