Estramustine

Estramustine

Systematic (IUPAC) name
(17β)-17-Hydroxyestra-1(10),2,4-trien-3-yl bis(2-chloroethyl)carbamate
Clinical data
Trade names	Emcyt
AHFS/Drugs.com	monograph
MedlinePlus	a608046
Pregnancy cat.	X (US)
Legal status	℞ Prescription only
Pharmacokinetic data
Half-life	20 hours
Identifiers
CAS number	2998-57-4
ATC code	L01XX11
PubChem	CID 259331
DrugBank	DB01196
ChemSpider	227635 Y
UNII	35LT29625A Y
KEGG	D04066 Y
ChEBI	CHEBI:4868 Y
ChEMBL	CHEMBL1575 Y
Chemical data
Formula	C23H31Cl2NO3
Mol. mass	440.403 g/mol
SMILES ClCCN(C(=O)Oc1cc3c(cc1)[C@H]2CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]2CC3)C)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
Y (what is this?)  (verify)

Estramustine (Emcyt, Estracit) is a chemotherapy agent used to treat prostate cancer. It is a derivative of estrogen (specifically, estradiol) with a nitrogen mustard-carbamate ester moiety that makes it an alkylating antineoplastic agent similar to mechlorethamine, with estrogen-induced specificity.

Estramustine is marketed in the United States by Pharmacia (now a subsidiary of Pfizer)

• 

  Mechlorethamine

• 

  Estradiol

Clinical uses

Estramustine is indicated for the palliative treatment of metastatic and/or progressive carcinoma of the prostate.

Synthesis

Estramustine can be prepared directly from estradiol.

See also

• Estrogen ester
• Estradiol and estrogen

External links

• Emcyt prescribing information