Estramustine phosphate

Estramustine phosphate
Clinical data
Trade names	Emcyt, Estracyt
Other names	EMP; Leo 299; NSC-89199; Ro 21-8837/001; Estradiol normustine phosphate; Estradiol 3-normustine 17β-phosphate; Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(dihydrogen phosphate)
AHFS/Drugs.com	Monograph
MedlinePlus	a608046
License data	US FDA: Estramustine;
Pregnancy; category	AU: D;
Routes of; administration	By mouth, IV
Drug class	Chemotherapeutic agent; Estrogen; Estrogen ester
ATC code	L01XX11 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	44–75% (as estramustine and estromustine)
Protein binding	• Estradiol: 98%; • Estrone: 96%
Metabolism	Liver, intestines
Metabolites	• Estramustine; • Estromustine; • Estradiol; • Estrone; • Phosphoric acid; • Normustine
Elimination half-life	• EMP: 1.27 hours; • Estromustine: 10–14 hrs; • Estrone: 15–17 hours
Excretion	Bile, 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;
CAS Number	4891-15-0 ; 52205-73-9 (sodium); 325726-21-4 (meglumine);
PubChem CID	259329;
IUPHAR/BPS	9076;
DrugBank	DB01196;
ChemSpider	227633;
UNII	MUZ9585Y7B;
KEGG	D02398+D06397;
ChEBI	CHEBI:68643;
ChEMBL	ChEMBL1756;
CompTox Dashboard (EPA)	DTXSID7048667 ;
ECHA InfoCard	100.023.193
Chemical and physical data
Formula	C23H32Cl2NO6P
Molar mass	520.38 g·mol−1
3D model (JSmol)	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 (EMP), also known as estradiol normustine phosphate and sold under the brand names Emcyt and Estracyt, is a dual estrogen and chemotherapy medication which is used in the treatment of prostate cancer in men. It is taken multiple times a day by mouth or by injection into a vein.

Side effects of EMP include nausea, vomiting, gynecomastia, feminization, demasculinization, sexual dysfunction, blood clots, and cardiovascular complications. EMP is a dual cytostatic and hence chemotherapeutic agent and a hormonal anticancer agent of the estrogen type. It is a prodrug of estramustine and estromustine in terms of its cytostatic effects and a prodrug of estradiol in relation to its estrogenic effects. EMP has strong estrogenic effects at typical clinical dosages, and consequently has marked antigonadotropic and functional antiandrogenic effects.

EMP was introduced for medical use in the early 1970s. It is available in the United States, Canada, the United Kingdom, other European countries, and elsewhere in the world.

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