A new orally active male antifertility agent

Coppola, J. A.; Saldarini, Ronald J.

doi:10.1016/0010-7824(74)90058-4

Cited by 37 publications

(5 citation statements)

References 12 publications

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“…Classical chemical syntheses of either compound, therefore, produces a racemic product containing equimolar amounts of the (R)and (S)-isomers. Due to the presence of the amino group, the amino analogue could be resolved into its (R)-and (S)-isomers and when the antifertility activity of these enantiomers was assessed (Coppola and Saldarini 1974), the (R)-isomer was found to be ineffective whereas the (S)-isomer possessed the antifertility activity. While the effects of (S)-1-amino-3-chloropropan-2-01 on male fertility have not been studied in detail, possibly because of an unfavourable report concerning its neurological toxicity in Rhesus monkeys (Heywood et al 1978), the stereospecificity for antifertility activity that this compound demonstrated prompted the synthesis of the individual isomers of oc-chlorohydrin.…”

Section: Structure-activity Studies With (X-chlorohydrinmentioning

confidence: 99%

Antifertility Actions of a-Chlorohydrin in the Male

Ar¹

1983

Aust. Jnl. Of Bio. Sci.

112

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Non-steroidal chemicals that affect male fertility have been known for over 25 years but only one compound, alpha-chlorohydrin, possesses most of the attributes of an ideal male contraceptive. In the male rat, for example, continuous daily oral administration of low doses produces an almost immediate and continuous antifertility response that ceases when treatment is withdrawn. Such a dose regime does not interfere with libido, is apparently not toxic and the action is specific towards mature sperm. Furthermore, the action of the compound is species-specific: it is effective in the rat, ram, boar, guinea pig, hamster, rhesus monkey and upon ejaculated human sperm but it is ineffective in the mouse and the rabbit. High doses of alpha-chlorohydrin can be neurotoxic, nephrotoxic and, in rats, lead to prolonged or permanent infertility. However, the antifertility response and the toxicity of racemic alpha-chlorohydrin may be due, respectively, to the separate enantiomers. No other antifertility chemical has been investigated to such an extent as alpha-chlorohydrin; this article reviews the progress that has been achieved with alpha-chlorohydrin during the past six years.

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Section: Structure-activity Studies With (X-chlorohydrinmentioning

confidence: 99%

Antifertility Actions of a-Chlorohydrin in the Male

Ar¹

1983

Aust. Jnl. Of Bio. Sci.

112

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“…In rats, (-)-amino chloropropanol is more effective as an antifertility agent and is much less toxic than the (+)-enantiomer (Paul, Williams & Cohen, 1974;Coppola & Saldarini, 1974 (-)-Amino chloropropanol is known to have the S absolute configuration (Robinson, 1976). Alphachlorohydrin (3-chloro-l,2-propanediol) induces reversible infertility in male rats, sheep, pigs hamsters and guinea-pigs when given in oral doses too low to produce toxic effects (Coppola, 1969;Ericsson & Youngdale, 1970;Ericsson & Baker, 1970;Johnson & Pursel, 1972;Brown & White, 1973;Lubicz-Nawrocki & Chang, 1974).…”

Section: Introductionmentioning

confidence: 98%

Effects of the optical isomers of -chlorohydrin on glycolysis by ram testicular spermatozoa and the fertility of male rats

Ford¹,

Harrison²,

Waites³

1977

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When 0-1 mM-S alpha-chlorohydrin was present in incubations, glycolysis by ram testicular spermatozoa was almost completely inhibited whereas 10 mM-R alpha-chlorohydrin had no effect. Male rats dosed orally with S alpha-chlorohydrin (3-25 mg/kg/day) became much less fertile than controls but those dosed with R alpha-chlorohydrin (13 mg/kg/day) did not. The loss of fertility was associated with a reduced ability of spermatozoa from the cauda epididymidis of these rats to oxidize glucose. It is concluded that the S enantiomer is responsible for both the inhibition of sperm glycolysis and the reduction in fertility caused by the racemic mixture of alpha-chlorohydrin.

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“…The demonstration that the antifertility effect of -chlorohydrin is specific to the S(+)isomer (Jackson & Robinson, 1976;Ford, Harrison & Waites, 1977;Jackson, Rooney & Fitzpatrick, 1977) is comparable with the differential antifertility action of the isomers of l,amino-3,chloro-2-propanol (Paul, Williams & Cohen, 1974;Coppola & Saldarmi, 1974) …”

Section: Discussionmentioning

confidence: 93%

The interaction of -chlorohydrin with glycerol kinase

De¹

1979

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A new orally active male antifertility agent

Cited by 37 publications

References 12 publications

Antifertility Actions of a-Chlorohydrin in the Male

Antifertility Actions of a-Chlorohydrin in the Male

Effects of the optical isomers of -chlorohydrin on glycolysis by ram testicular spermatozoa and the fertility of male rats

The interaction of -chlorohydrin with glycerol kinase

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