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Chemical compound
D-15414 is a nonsteroidal weak estrogen of the 2-phenylindole group which was never marketed.[ 1] [ 2] It is the major metabolite of the selective estrogen receptor modulator (SERM) zindoxifene (D-16726).[ 3] D-15414 has high affinity for the estrogen receptor (ER) and inhibits the growth of ER-positive MCF-7 breast cancer cells in vitro .[ 3] However, contradictorily, subsequent research found that the drug produced fully estrogenic effects in vitro similarly to but less actively than estradiol , with no antiestrogenic activity observed.[ 1] [ 2] The reason for the discrepancy between the findings is unclear, though may be due to methodology .[ 2] The unexpected estrogenic activity of D-15414 may be responsible for the failure of zindoxifene in clinical trials as a treatment for breast cancer .[ 1] [ 4]
^ a b c Jordan VC, Tormey DC (1988). "Antiestrogen Therapy for Breast Cancer". Endocrine Therapies in Breast and Prostate Cancer . Cancer Treatment and Research. Vol. 39. pp. 97–110. doi :10.1007/978-1-4613-1731-9_7 . ISBN 978-1-4612-8974-6 . PMID 2908611 .
^ a b c Robinson SP, Koch R, Jordan VC (February 1988). "In vitro estrogenic actions in rat and human cells of hydroxylated derivatives of D16726 (zindoxifene), an agent with known antimammary cancer activity in vivo". Cancer Research . 48 (4): 784–787. PMID 3338076 .
^ a b von Angerer E, Prekajac J, Berger M (April 1985). "The inhibitory effect of 5-acetoxy-2-(4-acetoxyphenyl)-1-ethyl-3-methylindole (D 16726) on estrogen-dependent mammary tumors". European Journal of Cancer & Clinical Oncology . 21 (4): 531–537. doi :10.1016/0277-5379(85)90048-3 . PMID 3924626 .
^ Maximov PY, McDaniel RE, Jordan VC (23 July 2013). Tamoxifen: Pioneering Medicine in Breast Cancer . Springer Science & Business Media. pp. 170–. ISBN 978-3-0348-0664-0 .
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β べーた -ol
3α あるふぁ -Androstanediol
3α あるふぁ ,5α あるふぁ -Dihydrolevonorgestrel
3β べーた ,5α あるふぁ -Dihydrolevonorgestrel
3α あるふぁ -Hydroxytibolone
3β べーた -Hydroxytibolone
3β べーた -Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α あるふぁ -Hydroxy-DHEA
7α あるふぁ -Methylestradiol
7β べーた -Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β べーた -VE2
10β べーた ,17β べーた -Dihydroxyestra-1,4-dien-3-one (DHED)
11β べーた -Chloromethylestradiol
11β べーた -Methoxyestradiol
15α あるふぁ -Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α あるふぁ -Fluoroestradiol
16α あるふぁ -Hydroxy-DHEA
16α あるふぁ -Hydroxyestrone
16α あるふぁ -Iodoestradiol
16α あるふぁ -LE2
16β べーた -Hydroxyestrone
16β べーた ,17α あるふぁ -Epiestriol (16β べーた -hydroxy-17α あるふぁ -estradiol)
17α あるふぁ -Estradiol (alfatradiol )
17α あるふぁ -Dihydroequilenin
17α あるふぁ -Dihydroequilin
17α あるふぁ -Epiestriol (16α あるふぁ -hydroxy-17α あるふぁ -estradiol)
17α あるふぁ -Ethynyl-3α あるふぁ -androstanediol
17α あるふぁ -Ethynyl-3β べーた -androstanediol
17β べーた -Dihydroequilenin
17β べーた -Dihydroequilin
17β べーた -Methyl-17α あるふぁ -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 べーた -epiestriol, 16β べーた -hydroxy-17β べーた -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 べーた -sitosterol , campesterol , stigmasterol )
Resorcylic acid lactones (e.g., zearalanone , α あるふぁ -zearalenol , β べーた -zearalenol , zearalenone , zeranol (α あるふぁ -zearalanol) , taleranol (teranol, β べーた -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