Estramustine phosphate

Estramustine phosphate
Clinical data

Trade names	Emcyt, Estracyt
AHFS/Drugs.com	Monograph
MedlinePlus	a608046
License data	US FDA: Estramustine
Pregnancy category	AU: D US: X (Contraindicated)
Routes of administration	Oral
ATC code	L01XX11 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	75%
Metabolism	Hepatic
Metabolites	Estramustine, estromustine, normustine, estradiol, estrone, phosphoric acid
Biological half-life	15–24 hours
Excretion	Feces (2.9–4.8%)
Identifiers
IUPAC name [(8R,9S,13S,14S,17S)-13-methyl-17-phosphonooxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] N,N-bis(2-chloroethyl)carbamate
Synonyms	Leo 299; NSC-89199; Ro 21-8837/001; Estradiol 3-[bis(2-chloroethyl)carbamate] dihydrogen phosphate
CAS Number	4891-15-0 52205-73-9 (sodium)
PubChem CID	259329
DrugBank	DB01196
ChemSpider	227633
UNII	MUZ9585Y7B
ChEBI	CHEBI:68643
ChEMBL	CHEMBL1756
ECHA InfoCard	100.019.161
Chemical and physical data
Formula	C₂₃H₃₂Cl₂NO₆P
Molar mass	520.384 g/mol
3D model (Jmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OP(=O)(O)O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl
InChI InChI=1S/C23H32Cl2NO6P/c1-23-9-8-18-17-5-3-16(31-22(27)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)32-33(28,29)30/h3,5,14,18-21H,2,4,6-13H2,1H3,(H2,28,29,30)/t18-,19-,20+,21+,23+/m1/s1 Key:ADFOJJHRTBFFOF-RBRWEJTLSA-N

Estramustine phosphate, sold under the brand names Emcyt and Estracyt and provided as the sodium or meglumine salt, is a dual alkylating antineoplastic agent (i.e., a chemotherapy drug) of the nitrogen mustard type and hormonal antineoplastic agent of the estrogen type that is used in the treatment of prostate cancer.

Estramustine phosphate is indicated, in the United States, for the palliative treatment of metastatic and/or progressive prostate cancer, whereas in the United Kingdom it is indicated for the treatment of unresponsive or relapsing prostate cancer.

Estramustine phosphate is contraindicated when used in children, patients hypersensitive to estrogen or nitrogen mustards, those with peptic ulcer (an ulcer in the digestive tract), those with severely compromised liver function, those with weak heart muscle (also known as myocardial insufficiency) and those with thromboembolic disorders or complications related to fluid retention.