Estramustine

Estramustine
Clinical data
Trade names	Emcyt, Estracyt
Other names	EM; EaM; Leo 275; Ro 21-8837; Estradiol 3-(bis(2-chloroethyl)carbamate) ester; Estra-1,3,5(10)-triene-3,17β-diol 3-(bis(2-chloroethyl)carbamate) ester
Drug class	Chemotherapeutic agent; Estrogen; Estrogen ester
ATC code	L01XX11 (WHO) ;
Identifiers
	IUPAC name [(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;
CAS Number	2998-57-4 ;
PubChem CID	259331;
ChemSpider	227635 ;
UNII	35LT29625A;
KEGG	D04066 ;
ChEBI	CHEBI:4868 ;
ChEMBL	ChEMBL1575 ;
CompTox Dashboard (EPA)	DTXSID8046458 ;
ECHA InfoCard	100.019.161
Chemical and physical data
Formula	C23H31Cl2NO3
Molar mass	440.41 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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/s1 ; Key:FRPJXPJMRWBBIH-RBRWEJTLSA-N ;

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]

^ ^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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