The metabolism of the male antifertility agent 1-amino-3-chloropropan-2-ol in the rat

Jones, A. R.; Murcott, Carole; Milton, D. H.; Flynn, J R

doi:10.1007/bf01951290

Cited by 8 publications

(1 citation statement)

References 17 publications

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“…4) into its (R)‐ and (S)‐isomers showed that the antifertility activity of the racemate was due to the (S)‐isomer ( Paul et al ., 1974 ). Metabolic studies with the 36 Cl‐labelled racemate revealed that it was `metabolized to α‐chlorohydrin and metabolites of α‐chlorohydrin' which indicates that the (S)‐isomer owes its antifertility activity, identical to that produced by (S)‐α‐chlorohydrin, to its metabolism to that compound ( Jones et al ., 1977 ).…”

Section: Introductionmentioning

confidence: 99%

A re‐appraisal of the post‐testicular action and toxicity of chlorinated antifertility compounds

Tg²

1999

Int J of Andrology

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Some 30 years ago, alpha-chlorohydrin and some analogues were considered as close to the ideal contraceptive which acted rapidly and reversibly on the post-testicular maturation of spermatozoa. Despite their early promise, research funding was withdrawn only 5 years later because of what were considered to be unacceptable side-effects in primates. The literature on the toxic effects of these contraceptive agents was reviewed and was found to be wanting in respect to the rigour of scientific methods applied (impure compounds were used, inappropriate target populations were studied, excessive doses were employed, abstracts were cited from which no full publications subsequently arose). These compounds remain the closest approach yet to non-hormonal contraceptives for males and have led to the synthesis of related compounds which have a similar antifertility action but with much diminished toxicity. If toxicity remains a problem, a range of other compounds now known to have a similar antifertility action, should be investigated.

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Section: Introductionmentioning

confidence: 99%

A re‐appraisal of the post‐testicular action and toxicity of chlorinated antifertility compounds

Tg²

1999

Int J of Andrology

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Antifertility Potential of Ornidazole Analogues in Rats

COOPER,

YEUNG,

SKUPIN

et al. 1997

Journal of Andrology

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In order to determine which part of the ornidazole molecule [1‐(3‐chloro‐2‐hydroxy)propyhl‐2‐methyl‐5‐nitroimidazole] is responsible for its antifertility action, structural analogues were fed to male rats of proven fertility at doses equivalent to the antifertility dose of ornidazole (1.82 mmol/kg/day). The fertility of the males was tested, before oral gavage (control mating) and after 10 and 14 days of feeding, by counting the number of fetuses and corpora lutea present in females 12 days after mating. The day after the last mating, the kinematic parameters of sperm from the cauda epididymldis were assessed objectively with a Hamilton‐Thome motility analyzer. Analogues bearing the 2‐nitro and 5‐methyl groups on the imidazole ring were inactive if the (chlorohydroxy)propyl group were substituted by proton or methyl, hydroxyethyl, chloroethyl, or (sulfonylethyl)ethyl groups, indicating that the three‐carbon side chain of ornidazole was necessary for the antifertility action. Only ornidazole and its acetate were effective antifertility agents, but a compound bearing the (chlorohydroxy)propyi side chain attached to a nitrogen atom of a heterocyclic phthalimide produced a partial but temporary reduction in fertility. Similarities of the action of ornidazole with the male antifertility agent, α‐chbrohydrin [3‐chloro‐1,2‐propanediol], are discussed.

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α-Chlorohydrin: Review of a Model Posttesticular Antifertility Agent

Lobl¹

1980

Regulation of Male Fertility

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The metabolism of the male antifertility agent 1-amino-3-chloropropan-2-ol in the rat

Cited by 8 publications

References 17 publications

A re‐appraisal of the post‐testicular action and toxicity of chlorinated antifertility compounds

A re‐appraisal of the post‐testicular action and toxicity of chlorinated antifertility compounds

Antifertility Potential of Ornidazole Analogues in Rats

α-Chlorohydrin: Review of a Model Posttesticular Antifertility Agent

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