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| Other names | MDL-18962; Propargylestrenedione; PED; 10-(2-Propyn-1-yl)estr-4-ene-3,17-dione; 10-Propargylestr-4-ene-3,17-dione |
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| Formula | C21H26O2 |
| Molar mass | 310.437 g·mol−1 |
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Plomestane (INNTooltip International Nonproprietary Name,USANTooltip United States Adopted Name; former developmental code nameMDL-18962; also known aspropargylestrenedione,PED) is asteroidal,irreversiblearomatase inhibitor which was under development byMarion Merrell Dow/Hoechst Marion Russell (nowHoechst AG) as anantineoplastic agent for the treatment ofbreast cancer.[1][2][3][4][5] It was found to be effective inpreclinical studies and was also found to produce fewadverse effects in humanclinical trials, significantly reducingestrogen levels with a single administration.[5] However, development of the drug for clinical use was halted due to "technical issues" and it was never marketed.[6]
In addition to its activity as an aromatase inhibitor, plomestane has weakandrogenic properties.[5]
The chemical synthesis was described:[7] Patent:[8]
Ketalization of Estr-5(10)-ene-3,17-dione [3962-66-1] (1) with two equivalents of ethylene glycol gives (2). Addition of NBS in water and hencehypobromous acid adds across the olefin to give (3). This rearranges to the oxirane in the presence of sodium methoxide base (4). TheGilman reagent was prepared from 1-(Trimethylsilyl)-1-propyne [6224-91-5] (6) and the reaction gave (7). Removal of the ketal protecting groups in acid, PC11784353 (8) and removal of the trimethyl silyl protecting group in base occurred with concomitant dehydration of the alcohol, completing the synthesis of plomestane (9).
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