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Stilbestrol, or stilboestrol, also known as 4,4'-dihydroxystilbene or 4,4'-stilbenediol, is a stilbenoid and the parent compound of a group of non-steroidal estrogens that includes, most notably, diethylstilbestrol.[1][2]
The stilbestrol estrogens include diethylstilbestrol, diethylstilbestrol dipropionate, benzestrol, dienestrol, dienestrol acetate, dimestrol (dimethoxydiethylstilbene), fosfestrol (diethylstilbestrol diphosphate), furostilbestrol, hexestrol (dihydrodiethylstilbestrol), hexestrol diacetate, hexestrol dicaprylate, hexestrol diphosphate, hexestrol dipropionate, mestilbol (diethylstilbestrol monomethyl ether), methestrol (promethestrol; dimethylhexestrol), methestrol dipropionate (promethestrol dipropionate), among others. The stilbestrol estrogens bind with high affinity to both ERα and ERβ.[3]
Resveratrol is a stilbenoid with estrogenic properties that is not a silbestrol derivative (it is 3,4',5-stilbenetriol).[4]
The term "stilbestrol" is very often used incorrectly to refer to diethylstilbestrol.[1]
See also
References
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Receptor
(ligands) |
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Agonists
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- (R)-DPN
- (S)-DPN
- (R,R)-THC
- (S,S)-THC
- 2,8-DHHHC
- 3α-Androstanediol
- 3β-Androstanediol
- 3α-Hydroxytibolone
- 3β-Hydroxytibolone
- 7-Oxo-DHEA
- 7α-Hydroxy-DHEA
- 7β-Hydroxyepiandrosterone
- 8β-VE2
- 16α-Hydroxy-DHEA
- 16α-Hydroxyestrone
- 16α-IE2
- 16α-LE2 (Cpd1471)
- Δ4-Androstenedione
- Δ5-Androstenediol
- 17α-Estradiol (alfatradiol)
- 17β-Estradiol (estradiol)
- Alestramustine
- Almestrone
- Anabolic steroids (prodrugs; e.g., testosterone, metandienone (methandrostenolone), others)
- Anethole
- Anol
- Atrimustine
- Benzestrol
- Bifluranol
- Bisdehydrodoisynolic acid
- Cadmium
- Carbestrol
- Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
- Cloxestradiol
- Conjugated equine estrogens (e.g., sodium equilin sulfate, sodium equilenin sulfate)
- Coumestans (e.g., coumestrol, psoralidin)
- DHEA
- DHEA-S
- Deoxymiroestrol
- Dianethole
- Dianol
- Diarylpropionitrile
- Dieldrin
- Dienestrol
- Dienestrol acetate
- Diethylstilbestrol
- Diethylstilbestrol dipropionate
- Diosgenin
- Doisynoestrol (fenocycline)
- Doisynolic acid
- DY-131 (GSK-9089)
- Endosulfan
- Epiestriol
- Epimestrol
- ERB-196 (WAY-202196)
- Esterified estrogens (e.g., estrone sulfate, equilin sulfate, equilenin sulfate)
- Estetrol
- Estradiol benzoate
- Estradiol butyrylacetate
- Estradiol cypionate
- Estradiol dienanthate
- Estradiol dipropionate
- Estradiol diundecylate
- Estradiol diundecylenate
- Estradiol enanthate
- Estradiol furoate
- Estradiol hemihydrate
- Estradiol hemisuccinate
- Estradiol hexahydrobenzoate
- Estradiol monopropionate
- Estradiol palmitate
- Estradiol pivalate
- Estradiol propoxyphenylpropionate
- Estradiol stearate
- Estradiol succinate
- Estradiol undecylate
- Estradiol valerate
- Estramustine
- Estramustine phosphate
- Estrapronicate
- Estrazinol
- Estriol
- Estriol succinate
- Estriol tripropionate
- Estrobin (DBE)
- Estrofurate
- Estromustine
- Estrone
- Estrone acetate
- Estrone cyanate
- Estrone sulfate
- Estrone tetraacetylglucoside
- Estropipate
- Estropronicate
- Etamestrol (eptamestrol)
- Ethinyl estradiol
- Ethinyl estradiol 3-isopropylsulfonate
- Etynodiol diacetate
- Fenarimol
- Fenestrel
- FERb 033
- Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
- Fosfestrol
- Furostilbestrol
- GSK-4716
- Hexestrol
- Hexestrol diacetate
- Hexestrol dicaprylate
- Hexestrol diphosphate
- Hexestrol dipropionate
- Hydroxyestrone diacetate
- Lavender oil
- Lignans (e.g., enterodiol, enterolactone)
- Mestranol
- Metalloestrogens (e.g., cadmium)
- Methallenestril
- Methestrol
- Methestrol dipropionate
- Methiocarb
- Methylestradiol
- Miroestrol
- Moxestrol
- Nilestriol
- Noretynodrel
- Orestrate
- Paroxypropione
- Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
- Polyestradiol phosphate
- Prinaberel (ERB-041, WAY-202041)
- Propylpyrazoletriol
- Promestriene
- Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranal (zearalanol))
- Quadrosilan
- Quinestradol
- Quinestrol
- SKF-82,958
- Stilbenoids (e.g., resveratrol)
- Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
- WAY-166818
- WAY-200070
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Antagonists
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Enzyme |
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Others |
Precursors
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Indirect
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- Antigonadotropins (e.g., androgens, estrogens, progestogens, prolactin)
- Calcitriol (vitamin D)
- GnRH agonists (e,g, GnRH, leuprorelin)
- GnRH antagonists (e.g., cetrorelix)
- Gonadotropins (e.g., FSH, hCG, LH)
- Kisspeptin
- Plasma proteins (ABP, albumin, SHBG)
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Dihydroxylated |
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Trihydroxylated |
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Tetrahydroxylated |
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O-methylated |
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carboxylated |
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other acylations |
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Glycosides |
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of resveratrol
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of rhapontigenin
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Oligomeric forms |
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