Estradiol mustard

Estradiol mustard
Clinical data
Other names	NSC-112259; Estradiol 3,17β-bis(4-(bis(2-chloroethyl)amino)phenyl)acetate
Drug class	Chemotherapeutic agent; Estrogen; Estrogen ester
Identifiers
	IUPAC name [(8R,9S,13S,14S,17S)-3-[2-[4-[Bis(2-chloroethyl)amino]phenyl]acetyl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] 2-[4-[bis(2-chloroethyl)amino]phenyl]acetate;
CAS Number	22966-79-6;
PubChem CID	31586;
ChemSpider	29294;
UNII	GEO3F3A4K1;
ChEBI	CHEBI:82520;
ChEMBL	ChEMBL1697793;
CompTox Dashboard (EPA)	DTXSID5020574 ;
Chemical and physical data
Formula	C42H50Cl4N2O4
Molar mass	788.67 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CC4=CC=C(C=C4)N(CCCl)CCCl)CCC5=C3C=CC(=C5)OC(=O)CC6=CC=C(C=C6)N(CCCl)CCCl;
	InChI InChI=1S/C42H50Cl4N2O4/c1-42-17-16-36-35-13-11-34(51-40(49)26-29-2-7-32(8-3-29)47(22-18-43)23-19-44)28-31(35)6-12-37(36)38(42)14-15-39(42)52-41(50)27-30-4-9-33(10-5-30)48(24-20-45)25-21-46/h2-5,7-11,13,28,36-39H,6,12,14-27H2,1H3/t36-,37-,38+,39+,42+/m1/s1; Key:LRSFXIJGHRPOQQ-VZRQQIPSSA-N;

Estradiol mustard, also known as estradiol 3,17β-bis(4-(bis(2-chloroethyl)amino)phenyl)acetate, is a semisynthetic, steroidal estrogen and cytostatic antineoplastic agent and a phenylacetic acid nitrogen mustard-coupled estrogen ester that was never marketed.^[1] It is selectively distributed into estrogen receptor (ER)-positive tissues such as ER-expressing tumors like those seen in breast and prostate cancers.^[2] For this reason, estradiol mustard and other cytostatic-linked estrogens like estramustine phosphate have reduced toxicity relative to non-linked nitrogen mustard cytostatic antineoplastic agents.^[2] However, they may stimulate breast tumor growth due to their inherent estrogenic activity and are said to be devoid of major therapeutic efficacy in breast cancer,^[3] although estramustine phosphate has been approved for and is used (almost exclusively) in the treatment of prostate cancer.^[4]