Reference

The action of (R)- and (S)-a-chlorohydrin and their metabolites on the metabolism of boar sperm

The action of (R)- and (S)-a-chlorohydrin and their metabolites on the metabolism of boar sperm. Stevenson, D.; Jones, A. R. (Dep. Biochem., Univ. Sydney, Sydney, Australia). Int. J. Androl., 7(1), 79-86 (English) 1984. CODEN: IJANDP. ISSN: 0105-6263. DOCUMENT TYPE: Journal CA Section: 2 (Mammalian Hormones) (S)-a-Chlorohydrin [60827-45-4] (0.1 or 0.2 mM), but not (R)-a-chlorohydrin [57090-45-6] (0.1 or 0.2 mM), inhibited the oxidn. of 14C-labeled D-fructose [57-48-7] to 14CO2 by boar sperm. At 50 mM, neither chlorohydrin isomer had any inhibitory effect on the oxidn. of pyruvate [127-17-3] or lactate [50-21-5] to CO2. (R,S)-3-Chlorolactaldehyde [84709-24-0], (R,S)-3-chlorolactate [50906-02-0], or 3--chloropyruvate [3681-17-2] incubated with boar sperm inhibited the oxidative metab. of fructose, pyruvate, or lactate to CO2. The action of a-chlorohydrin in inhibiting glycolysis in boar sperm is apparently due to the (S)-isomer, whereas the toxic action of (R)-a-chlorohydrin on sperm motility may be due to metabolites such as 3-chloroacetaldehyde, 3-chlorolactate, or 3-chloropyruvate.

Characterization and antifertility activity in rats of S(+)-a-chlorohydrin

Characterization and antifertility activity in rats of S(+)-a-chlorohydrin. Jackson, H.; Rooney, F. R.; Fitzpatrick, R. W.; Gibson, K. H. (Unit Reprod. Pharmacol., Univ. Manchester, Manchester, Engl.). Chem.-Biol. Interact., 17(1), 117-20 (English) 1977. CODEN: CBINA8. DOCUMENT TYPE: Journal CA Section: 2 (Hormone Pharmacology) In male rats, a single oral dose of S(+)a-chlorohydrin (I) [60827-45-4] (12.5 mg/kg) produced temporary infertility following pairing with females from matings between days 2 and 6 after the I dose. A similar dose of the racemic mixt. [52340-46-2] was ineffective and the antifertility effect of the active isomer was comparable to that produced by a mixt. of similar amts. of the S(+)- and R(-) [57090-45-6]-isomer or the corresponding dose of the racemate (25 mg/kg). However, the latter dose of the S(+)-isomer induced sterility during week 1, some degree of recovery of fertility in weeks 2-3 followed by permanent sterility. The S(+) isomer also maintained the reversible antifertility effect on epididymal spermatozoa at a daily oral dose of 5-10 mg/kg. Prepn. of derivs. of I may provide compds. with high antifertility potency and low toxicity.