Estramustine

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Chemical compound 


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


Template:Cs1 config

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.[1][2] It is a carbamate derivative of estradiol and acts in part as a prodrug of estradiol in the body.[1][2] 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.[1][2]

Synthesis[edit | edit source]

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.[3][4]

See also[edit | edit source]

References[edit | edit source]

  1. ↑ 1.0 1.1 1.2 , The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. online version, Springer, ISBN 978-1-4757-2085-3, Pages: 502–,
  2. ↑ 2.0 2.1 2.2 , Index Nominum 2000: International Drug Directory. online version, Taylor & Francis, ISBN 978-3-88763-075-1, Pages: 406–,
  3. ↑ , 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,
  4. ↑ , 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,




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Contributors: Prab R. Tumpati, MD