Estramustine phosphate
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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.[7][5][8][9][10][3][1][11][6][12] It is taken multiple times a day by mouth or by injection into a vein.[7][8][3][1][6][12]
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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 |
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Routes of administration | By mouth, IV |
Drug class | Chemotherapeutic agent; Estrogen; Estrogen ester |
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Bioavailability | 44–75% (as estramustine and estromustine)[1] |
Protein binding | • Estradiol: 98%[2] • Estrone: 96%[2] |
Metabolism | Liver, intestines[3][1][4] |
Metabolites | • Estramustine[3][1] • Estromustine[3][1] • Estradiol[3][1] • Estrone[3][1] • Phosphoric acid[3][1] • Normustine[5] |
Elimination half-life | • EMP: 1.27 hours[6] • Estromustine: 10–14 hrs[1] • Estrone: 15–17 hours[1] |
Excretion | Bile, feces (2.9–4.8%)[1][4] |
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ECHA InfoCard | 100.023.193 |
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Formula | C23H32Cl2NO6P |
Molar mass | 520.38 g·mol−1 |
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Side effects of EMP include nausea, vomiting, gynecomastia, feminization, demasculinization, sexual dysfunction, blood clots, and cardiovascular complications.[3][9][13] EMP is a dual cytostatic and hence chemotherapeutic agent and a hormonal anticancer agent of the estrogen type.[1][3][14][6] 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.[1][3] EMP has strong estrogenic effects at typical clinical dosages, and consequently has marked antigonadotropic and functional antiandrogenic effects.[5][1][3][14]
EMP was introduced for medical use in the early 1970s.[3] It is available in the United States, Canada, the United Kingdom, other European countries, and elsewhere in the world.[15][16]