estradiol sulfate and estradiol valerate, but differs in the presence of its nitrogen mustard ester moiety. Antineoplastic agents related to EMP, although none of them were marketed, include alestramustine, atrimustine, cytestrol acetate, estradiol mustard, ICI-85966, and phenestrol. Due to its hydrophilic phosphate ester moiety, EMP is a readily water-soluble compound. This is in contrast to most other estradiol esters, which are fatty acid esters and lipophilic compounds that are not particularly soluble in water. Unlike EMP, estramustine is highly lipophilic, practically insoluble in water, and non-ionizable. The phosphate ester of EMP was incorporated into the molecule in order to increase its water solubility and allow for intravenous administration. The molecular weight of EMP sodium is 564.3 g/mol, of EMP meglumine is 715.6 g/mol, of EMP is 520.4 g/mol, of estramustine is 440.4 g/mol, and of estradiol is 272.4 g/mol. As a result of these differences in molecular weights, EMP contains about 52%, EMP sodium about 48%, and EMP meglumine about 38% of the amount of estradiol within their structures as does an equal-mass quantity of estradiol. History EMP was first synthesized in the mid-1960s and was patented in 1967. It was initially developed for the treatment of breast cancer. The idea for EMP was inspired by the uptake and accumulation of radiolabeled estrogens into breast cancer tissue. However, initial clinical findings of EMP in women with breast cancer were disappointing. Subsequently, radiolabeled EMP was found to be taken up into and accumulated rat prostate gland, and this finding culminated in the medication being repurposed for the treatment of prostate cancer. EMP was introduced for medical use in the treatment of this condition in the early 1970s, and was approved in the United States for this indication in 1981. EMP was originally introduced for use by intravenous injection. Subsequently, an oral formulation was introduced, and the intravenous preparation was almost abandoned in favor of the oral version. Society and culture Generic names EMP is provided as the sodium salt for oral administration, which has the generic names estramustine phosphate sodium () and estramustine sodium phosphate (, ), and as the meglumine salt for intravenous administration, which has the generic name estramustine phosphate meglumine. The is estramustine phosphate. The name estramustine phosphate is a contraction of estradiol normustine phosphate. EMP is also known by its former developmental code names Leo 299, Ro 21-8837, and Ro 21-8837/001. Brand names EMP is most commonly