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Chemical compound
Cytestrol acetate 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)
(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
ChemSpider Formula C 29 H 35 Cl 2 N O 6 Molar mass 564.50 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 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]
^ a b c d Oborotov 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 .
^ a b c d Smirnova 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 .
^ a b c d Smirnova ZS (2003). "[Experimental Study of Hormonocytostatics for Treatment of Breast Cancer.]" [Russian biotherapeutic journal]. Российский биотерапевтический журнал (in Russian). 2 (2).
^ a b c Smirnova 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.
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
17β-Dihydroequilenin
17β-Dihydroequilin
17β-Methyl-17α-dihydroequilenin
Abiraterone
Abiraterone acetate
Alestramustine
Almestrone
Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)
Atrimustine
Bolandiol
Bolandiol dipropionate
Butolame
Clomestrone
Cloxestradiol
Conjugated estriol
Conjugated estrogens
Cyclodiol
Cyclotriol
DHEA
DHEA-S
ent -Estradiol
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
Estriol
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol
Ethylestradiol
Etynodiol
Etynodiol diacetate
Hexolame
Hippulin
Hydroxyestrone diacetate
Lynestrenol
Lynestrenol phenylpropionate
Mestranol
Methylestradiol
Moxestrol
Mytatrienediol
Nilestriol
Norethisterone
Noretynodrel
Orestrate
Pentolame
Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
Quinestrol
Tibolone
Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol , photoanethole )
Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )
Coumestans (e.g., coumestrol , psoralidin )
Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , epicatechin , equol , formononetin , glabrene , glabridin , genistein , genistin , glycitein , kaempferol , liquiritigenin , mirificin , myricetin , naringenin , penduletin , pinocembrin , prunetin , puerarin , quercetin , tectoridin , tectorigenin )
Lavender oil
Lignans (e.g., enterodiol , enterolactone , nyasol (cis -hinokiresinol) )
Metalloestrogens (e.g., cadmium )
Pesticides (e.g., alternariol , dieldrin , endosulfan , fenarimol , HPTE , methiocarb , methoxychlor , triclocarban , triclosan )
Phytosteroids (e.g., digitoxin (digitalis ), diosgenin , guggulsterone )
Phytosterols (e.g., β-sitosterol , campesterol , stigmasterol )
Resorcylic acid lactones (e.g., zearalanone , α-zearalenol , β-zearalenol , zearalenone , zeranol (α-zearalanol) , taleranol (teranol, β-zearalanol) )
Steroid -like (e.g., deoxymiroestrol , miroestrol )
Stilbenoids (e.g., resveratrol , rhaponticin )
Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )
Others (e.g., agnuside , rotundifuran )
Mixed (SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
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