Estramustine

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

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]

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 Y
PubChem CID	259331
ChemSpider	227635 Y
UNII	35LT29625A
KEGG	D04066 Y
ChEBI	CHEBI:4868 Y
ChEMBL	ChEMBL1575 Y
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 Y Key:FRPJXPJMRWBBIH-RBRWEJTLSA-N Y

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