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Cytestrol acetate

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Cytestrol acetate
Clinical data
Other names11α-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)
Identifiers
  • (1S,10S,11S,14R,15S,17R)-17-(Acetyloxy)-5-{[bis(2-chloroethyl)carbamoyl]oxy}-14-ethynyl-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-14-yl acetate
PubChemCID
ChemSpider
Chemical and physical data
FormulaC29H35Cl2NO6
Molar mass564.50 g·mol−1
3D model (JSmol)
  • [H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(C)C[C@@H](OC(C)=O)[C@]1([H])C3=CC=C(OC(=O)N(CCCl)CCCl)C=C3CC[C@@]21[H]
  • InChI=1S/C29H35Cl2NO6/c1-5-29(38-19(3)34)11-10-24-23-8-6-20-16-21(37-27(35)32(14-12-30)15-13-31)7-9-22(20)26(23)25(36-18(2)33)17-28(24,29)4/h1,7,9,16,23-26H,6,8,10-15,17H2,2-4H3/t23-,24-,25+,26+,28-,29-/m0/s1
  • Key:RRJRVDYYFLBGSE-UPRLNUCLSA-N

Cytestrol acetate is asteroidalantiestrogen and acytostaticantineoplastic agent (i.e.,chemotherapeutic) which was developed for the treatment ofbreast cancer but was never marketed.[1][2][3][4]

It is an 11α-hydroxylatedderivative ofethinylestradiol in which abis(2-chloroethyl)aminenitrogen mustardmoiety has been attached as anester at the C3 position andacetate esters have been attached at the C11α and C17β positions.[1][2][3][4] Themechanism of action of cytestrol acetate in breast cancer is two-fold: (1) acting as an antiestrogen similarly tofulvestrant orICI-164384; and (2) havingcytostatic actions via the carbamate–nitrogen mustard moiety analogously toestramustine phosphate.[1][2][3][4] The drug shows potentefficacy against breast cancer superior to that oftamoxifen inin vitro models.[1][2][3]

See also

[edit]

References

[edit]
  1. ^abcdOborotov AV, Smirnova ZS, Osetrova IP, Polozkova AP, Rzheznikov VM (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.S2CID 5550495.
  2. ^abcdSmirnova ZS, Rzheznikov VM, Tolkachev VN, Borisova LM, Kiseleva MP, Semeĭkin AV, et al. (2014). "[Antitumor and antiproliferative action of the steroidal cytostatic antiestrogen cytestrol acetate on hormone-dependent tumor models]".Eksperimental'naia i Klinicheskaia Farmakologiia (in Russian).77 (10):31–35.PMID 25518525.
  3. ^abcdSmirnova ZS (2003). "[Experimental Study of Hormonocytostatics for Treatment of Breast Cancer.]" [Russian biotherapeutic journal].Российский биотерапевтический журнал (in Russian).2 (2).
  4. ^abcSmirnova ZS, Rzheznikov VM, Tolkachev VN, Borisova LM, Kiseleva MP, Semeykin AV, Fedocheva TA, Shirokikh KE, Banin VV, Shimanovsky NL (November 2014). "Противоопухолевое и антипролиферативное действие стероидного антиэстрогена цитэстрола ацетата на моделях гормонозависимых опухолей" [Antitumor and antiproliferative effects of the steroid antiestrogen citestrol acetate in models of hormone-dependent tumors.].Экспериментальная и клиническая фармакология [Experimental and clinical pharmacology.] (in Russian).77 (10):31–35.
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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