Estramustine

Chemical compound

 This article is about a non-clinically used compound.
   For the pharmaceutical drug, see Estramustine phosphate.

Estramustine
Skeletal formula of estramustine
INN
Drug class	Chemotherapeutic agent; Estrogen; Estrogen ester
Routes of administration
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status
CAS Number	2998-57-4
PubChem	259331
DrugBank
ChemSpider	227635
KEGG	D04066

Estramustine (INN

, USAN

, BAN

) is an estrogen and cytostatic antineoplastic agent which was never marketed.<ref name="Elks2014">,

 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. online version, 
  
 Springer, 
  
  
  
 ISBN 978-1-4757-2085-3, 
  
  
  
 Pages: 502–,</ref><ref name="IndexNominum2000">, 
  
 Index Nominum 2000: International Drug Directory. online version, 
  
 Taylor & Francis, 
  
  
  
 ISBN 978-3-88763-075-1, 
  
  
  
 Pages: 406–,</ref> It is a carbamate derivative of estradiol and acts in part as a prodrug of estradiol in the body.<ref name="Elks2014" /><ref name="IndexNominum2000" /> Estramustine phosphate, the C17β phosphate ester of estramustine and a prodrug of estramustine, estromustine, estradiol, and estrone, is marketed and used in the treatment of prostate cancer.<ref name="Elks2014" /><ref name="IndexNominum2000" />

Synthesis

Estramustine is a carbamate derivative of the natural hormone, estradiol. The amine (ClCH₂CH₂)₂NH

is treated with phosgene to give the acid chloride of normustine. This reacts with the phenolic hydroxyl group of estradiol in the presence of a base to give estramustine.<ref>, 
 Potential anticancer agents. II. Urethan-type nitrogen mustards of some natural sex hormones, 
 Journal of Medicinal Chemistry, 
 
 Vol. 10(Issue: 2),
 pp. 172–174,
 DOI: 10.1021/jm00314a009,
 PMID: 6034059,</ref><ref>, 
 Comparative study of microtubule inhibitors--estramustine and natural podophyllotoxin conjugated PAMAM dendrimer on glioma cell proliferation, 
 European Journal of Medicinal Chemistry, 
 
 Vol. 68,
 pp. 47–57,
 DOI: 10.1016/j.ejmech.2013.07.007,
 PMID: 23954240,</ref>

See also

• Estradiol mustard
• List of hormonal cytostatic antineoplastic agents
• List of estrogen esters § Estradiol esters

References

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