Chemistry:Estramustine

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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

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

References

  1. ↑ 1.0 1.1 1.2 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 502–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA502. 
  2. ↑ 2.0 2.1 2.2 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 406–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA406. 
  3. ↑ "Potential anticancer agents. II. Urethan-type nitrogen mustards of some natural sex hormones". Journal of Medicinal Chemistry 10 (2): 172–174. March 1967. 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 68: 47–57. October 2013. doi:10.1016/j.ejmech.2013.07.007. PMID 23954240. 



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