Cytestrol acetate
Cytestrol acetate is a steroidal antiestrogen and a cytostatic antineoplastic agent (i.e., chemotherapeutic) which was developed for the treatment of breast cancer but was never marketed.[1][2][3][4] It is an 11α-hydroxylated derivative of ethinylestradiol in which a bis(2-chloroethyl)amine nitrogen mustard moiety has been attached as an ester at the C3 position and acetate esters have been attached at the C11α and C17β positions.[1][2][3][4] The mechanism of action of cytestrol acetate in breast cancer is two-fold: (1) acting as an antiestrogen similarly to fulvestrant or ICI-164384; and (2) having cytostatic actions via the carbamate–nitrogen mustard moiety analogously to estramustine phosphate.[1][2][3][4] The drug shows potent efficacy against breast cancer superior to that of tamoxifen in in vitro models.[1][2][3]
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| Other names | 11α-Hydroxyethinylestradiol 3-(bis(2-chloroethyl)carbamate) 11α,17β-diacetate; 17α-Ethynylestra-1,3,5(10)-triene-3,11α,17β-triol 11α,17β-diacetate 3-(bis(2-chloroethyl)carbamate) |
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| Formula | C29H35Cl2NO6 |
| Molar mass | 564.50 g·mol−1 |
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References
- Oborotov, A. V.; Smirnova, Z. S.; Osetrova, I. P.; Polozkova, A. P.; Rzheznikov, V. M. (1999). "Antitumor activity of various medicinal forms of the new estrogenocytostatic drug cytestrol acetate". Pharmaceutical Chemistry Journal. 33 (10): 526–527. doi:10.1007/BF02508372. ISSN 0091-150X.
- Smirnova ZS, Rzheznikov VM, Tolkachev VN, Borisova LM, Kiseleva MP, Semeĭkin AV, Fedotcheva TA, Shirokikh KE, Banin VV, Shimanovskiĭ NL (2014). "[Antitumor and antiproliferative action of the steroidal cytostatic antiestrogen cytestrol acetate on hormone-dependent tumor models]". Eksp Klin Farmakol (in Russian). 77 (10): 31–5. PMID 25518525.
- Smirnova Z. S, (2003). [Experimental Study of Hormonocytostatics for Treatment of Breast Cancer.] Российский биотерапевтический журнал, 2(2).
- Смирнова, З. С., Ржезников, В. М., Толкачев, В. Н., Борисова, Л. М., Киселева, М. П., Семейкин, А. В., ... & Шимановский, Н. Л. (2014). Противоопухолевое и антипролиферативное действие стероидного антиэстрогена цитэстрола ацетата на моделях гормонозависимых опухолей. Экспериментальная и клиническая фармакология, 77(10), 31-35.