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  • Title: Synthesis and antifertility activity of some oximinoandrostenes.
    Author: Shroff AP, Harper CH, Allen GO, Blye RP.
    Journal: J Med Chem; 1973 Feb; 16(2):113-5. PubMed ID: 4683105.
    Abstract:
    3-aza-A-homo steroids have been of interest to these authors in their efforts to develop novel progestational agents. Because it exhibits antifertility activity both in humans and animals, 17alpha-ethynyl-19-nortestosterone (norethindrone) was chosen to undergo molecular modification. The syntheses of a number of oximino and 3-aza-A-homoandrostenes are described in the experimental section of the article. The progestational responses of the compounds were tested through the observation of rabbit uteri. The capacity of a compound to inhibit fertility in rate was noted from the minimum effective dose, i.e., the amount of compound in mg/kg per day which completely suppressed litter production (compound given to both male and female). Because of the suspicion that the oximino steroids were acting postcoitally, 17-beta-acetoxy-19-norandrost-4-en-3-one oxime was studied for its postcoital activity in rats. The postcoital antifertility action of the compound appears to be due to lytic degeneration of zygotes and/or their rapid expulsion from the reproductive tract. Some structure-function observations are made concerning the various compounds.
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