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Chemical compound
ICI-164384![](https://upload.wikimedia.org/wikipedia/commons/thumb/a/a1/ICI-164384.svg/250px-ICI-164384.svg.png) |
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Other names | N-n-Butyl-N-methyl-11-(3,17β-dihydroxyestra-1,3,5(10)-trien-7α-yl)undecanamide |
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N-butyl-11-[(7R,8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-yl]-N-methylundecanamide
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Formula | C34H55NO3 |
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Molar mass | 525.818g·mol−1 |
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3D model (JSmol) | |
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CCCCN(C)C(=O)CCCCCCCCCC[C@@H]1CC2=C(C=CC(=C2)O)[C@@H]3[C@@H]1[C@@H]4CC[C@@H]([C@]4(CC3)C)O
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InChI=1S/C34H55NO3/c1-4-5-22-35(3)32(38)15-13-11-9-7-6-8-10-12-14-25-23-26-24-27(36)16-17-28(26)29-20-21-34(2)30(33(25)29)18-19-31(34)37/h16-17,24-25,29-31,33,36-37H,4-15,18-23H2,1-3H3/t25-,29-,30+,31+,33-,34+/m1/s1 Key:BVVFOLSZMQVDKV-KXQIQQEYSA-N
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ICI-164384,also known asN-n-butyl-N-methyl-11-(3,17β-dihydroxyestra-1,3,5(10)-trien-7α-yl)undecanamide,is asteroidalantiestrogenand asyntheticderivativeofestradiolwhich is closely related tofulvestrantand was never marketed.[1][2]It is asilent antagonistof theestrogen receptor(ER) with no intrinsicestrogenicactivity and hence is a pure antiestrogen, unlikeselective estrogen receptor modulators(SERMs) liketamoxifen.[1][2]The drug was under development byAstraZenecafor the treatment ofbreast cancerbut was discontinued in favor offulvestrant,[3]which is very similar to ICI-164384 but is more potent in comparison.[4]
See also[edit]
References[edit]
External links[edit]
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ERTooltip 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.,testosteroneandesters,methyltestosterone,metandienone (methandrostenolone),nandroloneandesters,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)
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Mixed (SERMsTooltip Selective estrogen receptor modulators) | |
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Antagonists |
- Coregulator-binding modulators:ERX-11
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GPERTooltip G protein-coupled estrogen receptor | Agonists | |
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Antagonists | |
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Unknown | |
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