title: Synthesis and use of affinity-labeling steroids for interceptive purposes.
abstract: Synthesis of 17 beta-bromoacetoxy-19-nortestosterone was carried out by reaction of 19-nortestosterone with bromoacetic acid in the presence of dicyclohexycarbodiimide. The steroid was capable of alkylating cysteine, methionine, and histidine under physiologic conditions, indicating its potential as an affinity-labeling steroid. 17beta-Bromoacetoxy-19-nortestosterone interrupted postimplantation pregnancy in the rat when administered into the lumen of the uterus at low doses or subcutaneously at higher doses. Exogenous gonadotropins or steroids in dosages sufficient to maintain pregnancy do not prevent the interceptive action of this steroid. Animals whose first pregnancies were interrupted by this steroid had a subsequent normal pregnancy. The mode of action may be via covalent bonding to the progesterone receptor resulting in exclusion of endogenous progesterone.
mesh_terms: D000019:Abortifacient Agents / Q000138:chemical synthesis*; D000028:Abortion, Induced; D000085:Acetates / Q000494:pharmacology; D000818:Animals; D001665:Binding Sites; D001966:Bromine / Q000494:pharmacology; D004024:Dicyclohexylcarbodiimide / Q000494:pharmacology; D004958:Estradiol / Q000494:pharmacology; D005260:Female; D005313:Fetal Death / Q000139:chemically induced*; D005333:Fetus / Q000187:drug effects*; D005640:Follicle Stimulating Hormone / Q000494:pharmacology; D007016:Hypophysectomy; D007279:Injections, Subcutaneous; D009277:Nandrolone / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000494:pharmacology; D011247:Pregnancy; D011374:Progesterone / Q000031:analogs & derivatives / Q000494:pharmacology; D011388:Prolactin / Q000494:pharmacology; D051381:Rats; D011919:Rats, Inbred Strains; D012826:Silicone Elastomers / Q000494:pharmacology; D013997:Time Factors; D014599:Uterus
chemical_list: D000019:Abortifacient Agents; D000085:Acetates; D012826:Silicone Elastomers; D011374:Progesterone; D004958:Estradiol; D004024:Dicyclohexylcarbodiimide; C009859:17 beta-bromoacetoxy-19-nortestosterone; D009277:Nandrolone; D011388:Prolactin; D005640:Follicle Stimulating Hormone; D001966:Bromine