Document Detail

Synthesis and use of affinity-labeling steroids for interceptive purposes.
MedLine Citation:
PMID:  1119494     Owner:  NLM     Status:  MEDLINE    
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.
S W Clark; F Sweet; J C Warren
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  American journal of obstetrics and gynecology     Volume:  121     ISSN:  0002-9378     ISO Abbreviation:  Am. J. Obstet. Gynecol.     Publication Date:  1975 Mar 
Date Detail:
Created Date:  1975-06-06     Completed Date:  1975-06-06     Revised Date:  2003-11-14    
Medline Journal Info:
Nlm Unique ID:  0370476     Medline TA:  Am J Obstet Gynecol     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  864-73     Citation Subset:  AIM; IM    
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MeSH Terms
Abortifacient Agents / chemical synthesis*
Abortion, Induced*
Acetic Acids / pharmacology
Binding Sites
Bromine / pharmacology
Dicyclohexylcarbodiimide / pharmacology
Estradiol / pharmacology
Fetal Death / chemically induced*
Fetus / drug effects*
Follicle Stimulating Hormone / pharmacology
Injections, Subcutaneous
Nandrolone / administration & dosage,  analogs & derivatives*,  pharmacology
Progesterone / analogs & derivatives,  pharmacology
Prolactin / pharmacology
Rats, Inbred Strains
Silicone Elastomers / pharmacology
Time Factors
Reg. No./Substance:
0/Abortifacient Agents; 0/Acetic Acids; 0/Silicone Elastomers; 434-22-0/Nandrolone; 50-28-2/Estradiol; 538-75-0/Dicyclohexylcarbodiimide; 57-83-0/Progesterone; 7726-95-6/Bromine; 9002-62-4/Prolactin; 9002-68-0/Follicle Stimulating Hormone

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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