Estramustine
Chemical compound
- L01XX11 (WHO)
- [(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] N,N-bis(2-chloroethyl)carbamate
- 2998-57-4
Y
- 259331
- 227635 Y
- 35LT29625A
- D04066 Y
- CHEBI:4868 Y
- ChEMBL1575 Y
- DTXSID8046458
- Interactive image
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl
InChI
- InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1Y
- Key:FRPJXPJMRWBBIH-RBRWEJTLSA-NY
Estramustine (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name) 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 (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
- Estradiol mustard
- List of hormonal cytostatic antineoplastic agents
- List of estrogen esters § Estradiol esters
References
- ^ a b c Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 502–. ISBN 978-1-4757-2085-3.
- ^ a b c Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 406–. ISBN 978-3-88763-075-1.
- ^ Niculescu-Duvăz I, Cambanis A, Tărnăuceanu E (March 1967). "Potential anticancer agents. II. Urethan-type nitrogen mustards of some natural sex hormones". Journal of Medicinal Chemistry. 10 (2): 172–174. doi:10.1021/jm00314a009. PMID 6034059.
- ^ Sk UH, Dixit D, Sen E (October 2013). "Comparative study of microtubule inhibitors--estramustine and natural podophyllotoxin conjugated PAMAM dendrimer on glioma cell proliferation". European Journal of Medicinal Chemistry. 68: 47–57. doi:10.1016/j.ejmech.2013.07.007. PMID 23954240.
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(M phase)
| Block microtubule assembly | |
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| Block microtubule disassembly |
inhibitor
| DNA precursors/ antimetabolites (S phase) |
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| Topoisomerase inhibitors (S phase) |
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| Crosslinking of DNA (CCNS) |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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