Estradiol mustard

Estramustine is used to treat prostate cancer. It is a derivative of estradiol with an nitrogen mustard-carbamate ester moiety. 

This resonance-stabilized, mustard-like antineoplastic agent utilizes an estradiol carrier (Fig. 42.3) to selectively deliver drug to steroid-dependent prostate tissue, and its use is limited to the palliative treatment of progressive prostate cancer. The essential 17P-OH group has been esterified with phosphoric acid, and the C3-phenol has been carbamylated. The body still, however, transports the basic steroidal pharmacophore into cells. The ionized sodium phosphate ester of the active 17P-OH group makes the compound water soluble and able to distribute in the blood. The ester is readily cleaved during absorption to provide the active 17(3-OH. 

Inhibitory effect on intestinal vitamin K synthesis, VI, 41 7,12-DiketochoIanic acid, configuration, VIII, 261 Dimenformon, see Estradiol benzoate 2,3-Dimercaptopropanol (BAL), as antidote against lewisite, VII, 106 mercury, VII, 106 mustard gas, VII, 106... 

The idea of using molecules with alEnity for the estrogen receptors as vectors for cytotoxic agents arose in the 1970s. It was applied in the first instance to nitrogen mustards (N-mustard) [56], and then to cisplatin. Several inorganic complexes derived from estradiol, estrone or the synthetic estrogen hexestrol were prepared in this way (Scheme 3.5) [57-63]. 

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