Metabolism of the putative antifertility agents 3-36chloro-1-hydroxypropanone and its dimethyl ketal in the male rat

International Journal of Andrology

Volumn 23, Issue 4, 2000, Pages 243-247

  Cooper, T G ^b   Jones, A R ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

^b INST OF REPRO MED OF THE UNIV   (Germany)

Author keywords

Male antifertility (S) chlorohydrin; Male contraception; Metabolism

Indexed keywords

ACETAL; ALPHA CHLOROHYDRIN; CONTRACEPTIVE AGENT; LACTALDEHYDE;

ANIMAL EXPERIMENT; ARTICLE; CONTRACEPTION; DRUG METABOLISM; DRUG STRUCTURE; GLYCOLYSIS; ISOTOPE LABELING; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; SPERM; THIN LAYER CHROMATOGRAPHY;

ACETONE; ANIMALS; CONTRACEPTIVE AGENTS, MALE; CONTRACEPTIVES, ORAL, SYNTHETIC; FERTILITY; KIDNEY; MALE; MOLECULAR STRUCTURE; PROPANOLS; RATS; RATS, WISTAR;

EID: 0033925959     PISSN: 01056263     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1365-2605.2000.00238.x     Document Type: Article

References (18)

1. Beutler, H. O. (1984) D-fructose. In: Methods of Enzymatic Analysis, (ed. H. U. Bergmeyer), pp. 321-327. Verlag Chemie, Weinheim.
2. Cavanagh, J. B., Nolan, C. C. & Seville, M. P. (1993) The neurotoxicity of α-chlorohydrin in rats and mice: I. Evolution of the cellular changes. Neuropathology and Applied Neurobiology 19, 240-252.
3. Cooper, E. R. A., Jones, A. R. & Jackson, H. (1974) Effects of α-chlorohydrin and related compounds on the reproductive organs and fertility of the male rat. Journal of Reproduction and Fertility 38, 379-386.
4. Ford, W. C. L. (1980) The contraceptive effect of 6-chloro-6-deoxysugars in the male. In: Regulation of Male Fertility (eds G. R. Cunningham, W.-B. Schill & E. S. E. Hafez), pp. 123-126. Martinus-Nijhoff The Hague.
5. Ford, W. C. L. & Waites, G. M. H. (1982) Activities of various 6-chloro-6-deoxysugars and (S)-α-chlorohydrin in producing spermatocoeles in rats and paralysis in mice and in inhibiting glucose metabolism in bull spermatozoa in vitro. Journal of Reproduction and Fertility 65, 177-183.
6. Hirschbein, B. L. & Whitesides, G. M. (1982) Laboratory-scale enzymatic/chemical synthesis of D-and L-α-chlorolactic acid and D-and L-potassium glycidate. Journal of the American Chemical Society 104, 4458-4460.
7. Jones, A. R. (1978) The antifertility actions of α-chlorohydrin in the male. Life Sciences 23, 1625-1646.
8. Jones, A. R. (1983) Antifertility actions of α-chlorohydrin in the male. Australian Journal of Biological Science 36, 333-350.
9. Jones, A. R., Bubb, W. A., Murdoch, S. R. & Stevenson, D. A. (1986) Inhibition of fructolytic enzymes in boar spermatozoa by (S)-α-chlorohydrin and 1-chloro-3-hydroxypropanone. Australian Journal of Biological Science 39, 395-406.
10. 36Clornidazole after oral application to the male rat in relation to its antifertility activity. Xenobiotica 27, 711-721.
11. Jones, A. R. & Cooper, T. G. (1999) A re-appraisal of the post-testicular antifertility action and toxicity of chlorinated antifertility compounds. International Journal of Andrology 22, 130-138.
12. Koelsch, C. F. (1930) A sulfur analog of glyceric acid. Beta-thioglyceric acid. Journal of the American Chemical Society 52, 1105-1108.
13. Mudge, G. H. & Welt, L. G. (1970) Agents affecting volume and composition of body fluids. In: The Pharmacological Basis of Therapeutics (eds L. S. Goodman & A. Gilman), pp. 753-781. Macmillan, New York.
14. Porter, K. E. & Jones, A. R. (1982) The effect of the isomers of α-chlorohydrin and racemic α-chlorolactate on the rat kidney. Chemico-Biological Interactions 41, 95-104.
15. Porter, K. E. & Jones, A. R. (1987) The renal toxicity of (R)-3-chlorolactate in the rat. Chemico-Biological Interactions 62, 157-166.
16. Seiler, H. & Kaffenberger, T. (1961) Anorganische Dünnsicht-Chromatographie. Trennung von Anionen: Halogenide. Helvetica Chimica Acta 44, 1282-1283.
17. Stevenson, D. & Jones, A. R. (1985) Production of (S)-3-chlorolacaldehyde from (S)-α-chlorohydrin by boar spermatozoa and the inhibition of glyceraldehyde 3-phosphate dehydrogenase in vitro. Journal of Reproduction and Fertility 74, 157-165.
18. Williams, P. H., Payne, G. B., Sullivan, W. J. & Van Ess, P. R. (1960) Chemistry of glycidaldehyde. Journal of the American Chemical Society 82, 4883-4888.