Estramustine

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]

Trade namesEmcyt, Estracyt

Other namesEM; 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 classChemotherapeutic agent; Estrogen; Estrogen ester

ATC code

• L01XX11 (WHO)

Quick facts Clinical data, Trade names ...

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

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