Estramustine Explained

Estramustine 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. 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.

Synthesis

Estramustine is a carbamate derivative of the natural hormone, estradiol. The amine 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

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

Notes and References

1. Book: Elks J . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3. 502–.
2. Book: Index Nominum 2000: International Drug Directory. January 2000. Taylor & Francis. 978-3-88763-075-1. 406–.
3. Niculescu-Duvăz I, Cambanis A, Tărnăuceanu E . Potential anticancer agents. II. Urethan-type nitrogen mustards of some natural sex hormones . Journal of Medicinal Chemistry . 10 . 2 . 172–174 . March 1967 . 6034059 . 10.1021/jm00314a009 .
4. Sk UH, Dixit D, Sen E . 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 . 23954240 . 10.1016/j.ejmech.2013.07.007 .