Not to be confused with Diethylstilbestrol .
Stilbestrol
Names
Preferred IUPAC name
4,4′-[(E )-Ethene-1,2-diyl]diphenol
Other names
Dihydroxystilbene; 4,4'-Dihydroxystilbene, 4,4'-stilbenediol
Identifiers
CAS Number
659-22-3 Y
3D model (JSmol )
ChemSpider
UNII
show
InChI=1S/C14H12O2/c15-13-7-3-11(4-8-13)1-2-12-5-9-14(16)10-6-12/h1-10,15-16H/b2-1+
Key: XLAIWHIOIFKLEO-OWOJBTEDSA-N
show
C1=CC(=CC=C1C=CC2=CC=C(C=C2)O)O
c1cc(ccc1/C=C/c2ccc(cc2)O)O
Properties
Chemical formula
C14 H12 O2
Molar mass
212.24388 g/mol
Magnetic susceptibility (χ)
-130·10−6 cm3 /mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Stilbestrol , or stilboestrol , also known as 4,4'-dihydroxystilbene or 4,4'-stilbenediol , is a stilbenoid nonsteroidal estrogen [1] and the parent compound of a group of more potent nonsteroidal estrogen derivatives that includes, most notably, diethylstilbestrol (DES).[1] [2] [3] The term "stilbestrol" is often used incorrectly to refer to DES, but they are not the same compound.[2]
Stilbestrol itself is an active estrogen but is less potent than DES and other derivatives.[1]
Stilbestrol derivatives [ ]
The stilbestrol estrogenic drugs include the following:
Of the stilbestrol estrogens, diethylstilbestrol, hexestrol, and benzestrol are the most well-known.[4]
Mechanism of action [ ]
The stilbestrol estrogens bind with high affinity to both ERα and ERβ .[5]
Affinities of estrogen receptor ligands for the ERα and ERβ
show
Other names
Relative binding affinities (RBA, %)a
Absolute binding affinities (Ki , nM)a
Estradiol
E2; 17β-Estradiol
100
100
0.115 (0.04–0.24)
0.15 (0.10–2.08)
Estrogen
Estrone
E1; 17-Ketoestradiol
16.39 (0.7–60)
6.5 (1.36–52)
0.445 (0.3–1.01)
1.75 (0.35–9.24)
Estrogen
Estriol
E3; 16α-OH-17β-E2
12.65 (4.03–56)
26 (14.0–44.6)
0.45 (0.35–1.4)
0.7 (0.63–0.7)
Estrogen
Estetrol
E4; 15α,16α-Di-OH-17β-E2
4.0
3.0
4.9
19
Estrogen
Alfatradiol
17α-Estradiol
20.5 (7–80.1)
8.195 (2–42)
0.2–0.52
0.43–1.2
Metabolite
16-Epiestriol
16β-Hydroxy-17β-estradiol
7.795 (4.94–63)
50
?
?
Metabolite
17-Epiestriol
16α-Hydroxy-17α-estradiol
55.45 (29–103)
79–80
?
?
Metabolite
16,17-Epiestriol
16β-Hydroxy-17α-estradiol
1.0
13
?
?
Metabolite
2-Hydroxyestradiol
2-OH-E2
22 (7–81)
11–35
2.5
1.3
Metabolite
2-Methoxyestradiol
2-MeO-E2
0.0027–2.0
1.0
?
?
Metabolite
4-Hydroxyestradiol
4-OH-E2
13 (8–70)
7–56
1.0
1.9
Metabolite
4-Methoxyestradiol
4-MeO-E2
2.0
1.0
?
?
Metabolite
2-Hydroxyestrone
2-OH-E1
2.0–4.0
0.2–0.4
?
?
Metabolite
2-Methoxyestrone
2-MeO-E1
<0.001–<1
<1
?
?
Metabolite
4-Hydroxyestrone
4-OH-E1
1.0–2.0
1.0
?
?
Metabolite
4-Methoxyestrone
4-MeO-E1
<1
<1
?
?
Metabolite
16α-Hydroxyestrone
16α-OH-E1; 17-Ketoestriol
2.0–6.5
35
?
?
Metabolite
2-Hydroxyestriol
2-OH-E3
2.0
1.0
?
?
Metabolite
4-Methoxyestriol
4-MeO-E3
1.0
1.0
?
?
Metabolite
Estradiol sulfate
E2S; Estradiol 3-sulfate
<1
<1
?
?
Metabolite
Estradiol disulfate
Estradiol 3,17β-disulfate
0.0004
?
?
?
Metabolite
Estradiol 3-glucuronide
E2-3G
0.0079
?
?
?
Metabolite
Estradiol 17β-glucuronide
E2-17G
0.0015
?
?
?
Metabolite
Estradiol 3-gluc. 17β-sulfate
E2-3G-17S
0.0001
?
?
?
Metabolite
Estrone sulfate
E1S; Estrone 3-sulfate
<1
<1
>10
>10
Metabolite
Estradiol benzoate
EB; Estradiol 3-benzoate
10
?
?
?
Estrogen
Estradiol 17β-benzoate
E2-17B
11.3
32.6
?
?
Estrogen
Estrone methyl ether
Estrone 3-methyl ether
0.145
?
?
?
Estrogen
ent -Estradiol
1-Estradiol
1.31–12.34
9.44–80.07
?
?
Estrogen
Equilin
7-Dehydroestrone
13 (4.0–28.9)
13.0–49
0.79
0.36
Estrogen
Equilenin
6,8-Didehydroestrone
2.0–15
7.0–20
0.64
0.62
Estrogen
17β-Dihydroequilin
7-Dehydro-17β-estradiol
7.9–113
7.9–108
0.09
0.17
Estrogen
17α-Dihydroequilin
7-Dehydro-17α-estradiol
18.6 (18–41)
14–32
0.24
0.57
Estrogen
17β-Dihydroequilenin
6,8-Didehydro-17β-estradiol
35–68
90–100
0.15
0.20
Estrogen
17α-Dihydroequilenin
6,8-Didehydro-17α-estradiol
20
49
0.50
0.37
Estrogen
Δ8 -Estradiol
8,9-Dehydro-17β-estradiol
68
72
0.15
0.25
Estrogen
Δ8 -Estrone
8,9-Dehydroestrone
19
32
0.52
0.57
Estrogen
Ethinylestradiol
EE; 17α-Ethynyl-17β-E2
120.9 (68.8–480)
44.4 (2.0–144)
0.02–0.05
0.29–0.81
Estrogen
Mestranol
EE 3-methyl ether
?
2.5
?
?
Estrogen
Moxestrol
RU-2858; 11β-Methoxy-EE
35–43
5–20
0.5
2.6
Estrogen
Methylestradiol
17α-Methyl-17β-estradiol
70
44
?
?
Estrogen
Diethylstilbestrol
DES; Stilbestrol
129.5 (89.1–468)
219.63 (61.2–295)
0.04
0.05
Estrogen
Hexestrol
Dihydrodiethylstilbestrol
153.6 (31–302)
60–234
0.06
0.06
Estrogen
Dienestrol
Dehydrostilbestrol
37 (20.4–223)
56–404
0.05
0.03
Estrogen
Benzestrol (B2)
–
114
?
?
?
Estrogen
Chlorotrianisene
TACE
1.74
?
15.30
?
Estrogen
Triphenylethylene
TPE
0.074
?
?
?
Estrogen
Triphenylbromoethylene
TPBE
2.69
?
?
?
Estrogen
Tamoxifen
ICI-46,474
3 (0.1–47)
3.33 (0.28–6)
3.4–9.69
2.5
SERM
Afimoxifene
4-Hydroxytamoxifen; 4-OHT
100.1 (1.7–257)
10 (0.98–339)
2.3 (0.1–3.61)
0.04–4.8
SERM
Toremifene
4-Chlorotamoxifen; 4-CT
?
?
7.14–20.3
15.4
SERM
Clomifene
MRL-41
25 (19.2–37.2)
12
0.9
1.2
SERM
Cyclofenil
F-6066; Sexovid
151–152
243
?
?
SERM
Nafoxidine
U-11,000A
30.9–44
16
0.3
0.8
SERM
Raloxifene
–
41.2 (7.8–69)
5.34 (0.54–16)
0.188–0.52
20.2
SERM
Arzoxifene
LY-353,381
?
?
0.179
?
SERM
Lasofoxifene
CP-336,156
10.2–166
19.0
0.229
?
SERM
Ormeloxifene
Centchroman
?
?
0.313
?
SERM
Levormeloxifene
6720-CDRI; NNC-460,020
1.55
1.88
?
?
SERM
Ospemifene
Deaminohydroxytoremifene
0.82–2.63
0.59–1.22
?
?
SERM
Bazedoxifene
–
?
?
0.053
?
SERM
Etacstil
GW-5638
4.30
11.5
?
?
SERM
ICI-164,384
–
63.5 (3.70–97.7)
166
0.2
0.08
Antiestrogen
Fulvestrant
ICI-182,780
43.5 (9.4–325)
21.65 (2.05–40.5)
0.42
1.3
Antiestrogen
Propylpyrazoletriol
PPT
49 (10.0–89.1)
0.12
0.40
92.8
ERα agonist
16α-LE2
16α-Lactone-17β-estradiol
14.6–57
0.089
0.27
131
ERα agonist
16α-Iodo-E2
16α-Iodo-17β-estradiol
30.2
2.30
?
?
ERα agonist
Methylpiperidinopyrazole
MPP
11
0.05
?
?
ERα antagonist
Diarylpropionitrile
DPN
0.12–0.25
6.6–18
32.4
1.7
ERβ agonist
8β-VE2
8β-Vinyl-17β-estradiol
0.35
22.0–83
12.9
0.50
ERβ agonist
Prinaberel
ERB-041; WAY-202,041
0.27
67–72
?
?
ERβ agonist
ERB-196
WAY-202,196
?
180
?
?
ERβ agonist
Erteberel
SERBA-1; LY-500,307
?
?
2.68
0.19
ERβ agonist
SERBA-2
–
?
?
14.5
1.54
ERβ agonist
Coumestrol
–
9.225 (0.0117–94)
64.125 (0.41–185)
0.14–80.0
0.07–27.0
Xenoestrogen
Genistein
–
0.445 (0.0012–16)
33.42 (0.86–87)
2.6–126
0.3–12.8
Xenoestrogen
Equol
–
0.2–0.287
0.85 (0.10–2.85)
?
?
Xenoestrogen
Daidzein
–
0.07 (0.0018–9.3)
0.7865 (0.04–17.1)
2.0
85.3
Xenoestrogen
Biochanin A
–
0.04 (0.022–0.15)
0.6225 (0.010–1.2)
174
8.9
Xenoestrogen
Kaempferol
–
0.07 (0.029–0.10)
2.2 (0.002–3.00)
?
?
Xenoestrogen
Naringenin
–
0.0054 (<0.001–0.01)
0.15 (0.11–0.33)
?
?
Xenoestrogen
8-Prenylnaringenin
8-PN
4.4
?
?
?
Xenoestrogen
Quercetin
–
<0.001–0.01
0.002–0.040
?
?
Xenoestrogen
Ipriflavone
–
<0.01
<0.01
?
?
Xenoestrogen
Miroestrol
–
0.39
?
?
?
Xenoestrogen
Deoxymiroestrol
–
2.0
?
?
?
Xenoestrogen
β-Sitosterol
–
<0.001–0.0875
<0.001–0.016
?
?
Xenoestrogen
Resveratrol
–
<0.001–0.0032
?
?
?
Xenoestrogen
α-Zearalenol
–
48 (13–52.5)
?
?
?
Xenoestrogen
β-Zearalenol
–
0.6 (0.032–13)
?
?
?
Xenoestrogen
Zeranol
α-Zearalanol
48–111
?
?
?
Xenoestrogen
Taleranol
β-Zearalanol
16 (13–17.8)
14
0.8
0.9
Xenoestrogen
Zearalenone
ZEN
7.68 (2.04–28)
9.45 (2.43–31.5)
?
?
Xenoestrogen
Zearalanone
ZAN
0.51
?
?
?
Xenoestrogen
Bisphenol A
BPA
0.0315 (0.008–1.0)
0.135 (0.002–4.23)
195
35
Xenoestrogen
Endosulfan
EDS
<0.001–<0.01
<0.01
?
?
Xenoestrogen
Kepone
Chlordecone
0.0069–0.2
?
?
?
Xenoestrogen
o,p' -DDT
–
0.0073–0.4
?
?
?
Xenoestrogen
p,p' -DDT
–
0.03
?
?
?
Xenoestrogen
Methoxychlor
p,p' -Dimethoxy-DDT
0.01 (<0.001–0.02)
0.01–0.13
?
?
Xenoestrogen
HPTE
Hydroxychlor; p,p' -OH-DDT
1.2–1.7
?
?
?
Xenoestrogen
Testosterone
T; 4-Androstenolone
<0.0001–<0.01
<0.002–0.040
>5000
>5000
Androgen
Dihydrotestosterone
DHT; 5α-Androstanolone
0.01 (<0.001–0.05)
0.0059–0.17
221–>5000
73–1688
Androgen
Nandrolone
19-Nortestosterone; 19-NT
0.01
0.23
765
53
Androgen
Dehydroepiandrosterone
DHEA; Prasterone
0.038 (<0.001–0.04)
0.019–0.07
245–1053
163–515
Androgen
5-Androstenediol
A5; Androstenediol
6
17
3.6
0.9
Androgen
4-Androstenediol
–
0.5
0.6
23
19
Androgen
4-Androstenedione
A4; Androstenedione
<0.01
<0.01
>10000
>10000
Androgen
3α-Androstanediol
3α-Adiol
0.07
0.3
260
48
Androgen
3β-Androstanediol
3β-Adiol
3
7
6
2
Androgen
Androstanedione
5α-Androstanedione
<0.01
<0.01
>10000
>10000
Androgen
Etiocholanedione
5β-Androstanedione
<0.01
<0.01
>10000
>10000
Androgen
Methyltestosterone
17α-Methyltestosterone
<0.0001
?
?
?
Androgen
Ethinyl-3α-androstanediol
17α-Ethynyl-3α-adiol
4.0
<0.07
?
?
Estrogen
Ethinyl-3β-androstanediol
17α-Ethynyl-3β-adiol
50
5.6
?
?
Estrogen
Progesterone
P4; 4-Pregnenedione
<0.001–0.6
<0.001–0.010
?
?
Progestogen
Norethisterone
NET; 17α-Ethynyl-19-NT
0.085 (0.0015–<0.1)
0.1 (0.01–0.3)
152
1084
Progestogen
Norethynodrel
5(10)-Norethisterone
0.5 (0.3–0.7)
<0.1–0.22
14
53
Progestogen
Tibolone
7α-Methylnorethynodrel
0.5 (0.45–2.0)
0.2–0.076
?
?
Progestogen
Δ4 -Tibolone
7α-Methylnorethisterone
0.069–<0.1
0.027–<0.1
?
?
Progestogen
3α-Hydroxytibolone
–
2.5 (1.06–5.0)
0.6–0.8
?
?
Progestogen
3β-Hydroxytibolone
–
1.6 (0.75–1.9)
0.070–0.1
?
?
Progestogen
Footnotes: a = (1) Binding affinity values are of the format "median (range)" (# (#–#)), "range" (#–#), or "value" (#) depending on the values available. The full sets of values within the ranges can be found in the Wiki code. (2) Binding affinities were determined via displacement studies in a variety of in-vitro systems with labeled estradiol and human ERα and ERβ proteins (except the ERβ values from Kuiper et al. (1997), which are rat ERβ). Sources: See template page.
Closely related compounds [ ]
Estrogens closely related to the stilbestrols include paroxypropione (a metabolite of diethylstilbestrol) and the anise and fennel -derived compounds anol , dianol , anethole , dianethole , and photoanethole (from which the stilbestrol estrogens were actually originally derived). The triphenylethylene group of estrogenic drugs that includes triphenylethylene itself, estrobin , chlorotrianisene , broparestrol , ethamoxytriphetol , clomifene , tamoxifen , and more recently developed derivatives is also very closely related structurally to the stilbestrols.
Resveratrol is a stilbenoid with estrogenic properties that is not technically a silbestrol derivative (it is 3,4',5-stilbenetriol).[6]
Occupational exposure [ ]
Occupational exposure to stilbestrol has resulted in gynaecomastia in workers.[7]
See also [ ]
References [ ]
^ Jump up to: a b c Noller KL, Fish CR (July 1974). "Diethylstilbestrol usage: Its interesting past, important present, and questionable future". Med. Clin. North Am . 58 (4): 793–810. doi :10.1016/s0025-7125(16)32122-8 . PMID 4276416 .
^ Jump up to: a b VITAMINS AND HORMONES . Academic Press. 1 January 1945. pp. 233 –. ISBN 978-0-08-086600-0 .
^ William John Edward Jessop (12 May 2014). Fearon's Introduction to Biochemistry . Elsevier. pp. 408–. ISBN 978-1-4831-9556-8 .
^ Actions and Uses of Drugs . Stanford University Press. pp. 234–. ISBN 978-0-8047-1505-8 .
^ Kuiper, George G. J. M.; Carlsson, Bo; Grandien, Kaj; Enmark, Eva; Häggblad, Johan; Nilsson, Stefan; Gustafsson, Jan-Åke (1997). "Comparison of the Ligand Binding Specificity and Transcript Tissue Distribution of Estrogen Receptors α and β" . Endocrinology . 138 (3): 863–870. doi :10.1210/endo.138.3.4979 . ISSN 0013-7227 . PMID 9048584 .
^ Bhat KP, Lantvit D, Christov K, Mehta RG, Moon RC, Pezzuto JM; Lantvit; Christov; Mehta; Moon; Pezzuto (October 2001). "Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models". Cancer Res . 61 (20): 7456–63. PMID 11606380 . CS1 maint: multiple names: authors list (link )
^ Fitzsimons, P.M. (October 1944). "Gynaecomastia in Stilboestrol Workers" . Br J Ind Med . 1 (4): 235–237. PMC 1035620 .
show Estrogens
ER agonists
Steroidal: Alfatradiol
Certain androgens /anabolic steroids (e.g., testosterone , testosterone esters , methyltestosterone , metandienone , nandrolone esters ) (via estrogenic metabolites)
Certain progestins (e.g., norethisterone , noretynodrel , etynodiol diacetate , tibolone )
Clomestrone
Cloxestradiol acetate
Conjugated estriol
Conjugated estrogens
Epiestriol
Epimestrol
Esterified estrogens
Estetrol †
Estradiol
Estradiol esters (e.g., estradiol acetate , estradiol benzoate , estradiol cypionate , estradiol enanthate , estradiol undecylate , estradiol valerate , polyestradiol phosphate , estradiol ester mixtures (Climacteron ))
Estramustine phosphate
Estriol
Estriol esters (e.g., estriol succinate , polyestriol phosphate )
Estrogenic substances
Estrone
Estrone esters
Ethinylestradiol #
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
Nilestriol
Prasterone (dehydroepiandrosterone; DHEA)
Promestriene
Quinestradol
Quinestrol
Progonadotropins
Antiandrogens (e.g., bicalutamide )
GnRH agonists (e.g., GnRH (gonadorelin) , leuprorelin )
Gonadotropins (e.g., FSH , LH )
Antiestrogens
ER antagonists (incl. SERMs /SERDs )
Exclusively antagonistic: Fulvestrant
Noncompetitive inhibitors: Trilostane
Aromatase inhibitors
Third-generation: Anastrozole
Exemestane
Letrozole
Antigonadotropins
Androgens /anabolic steroids (e.g., testosterone , testosterone esters , nandrolone esters , oxandrolone , fluoxymesterone )
D2 receptor antagonists (prolactin releasers) (e.g., domperidone , metoclopramide , risperidone , haloperidol , chlorpromazine , sulpiride )
GnRH agonists (e.g., leuprorelin , goserelin )
GnRH antagonists (e.g., cetrorelix , elagolix )
Progestogens (e.g., chlormadinone acetate , cyproterone acetate , gestonorone caproate , hydroxyprogesterone caproate , medroxyprogesterone acetate , megestrol acetate )
Others
Mixed mechanism of action: Danazol
Gestrinone
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
See also
Estrogen receptor modulators
Androgens and antiandrogens
Progestogens and antiprogestogens
List of estrogens
show ER
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
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 , , 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 , )
Mixed (SERMs ) Antagonists
Coregulator-binding modulators: ERX-11
Noncompetitive inhibitors: Trilostane
GPER
Agonists Antagonists Unknown
Diethylstilbestrol
Zearalenone
See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens
show Hydroxystilbenes and their glycosides (monomeric forms)
Dihydroxylated Trihydroxylated Tetrahydroxylated
Oxyresveratrol
Piceatannol
O-methylated
4-Methoxyresveratrol
Gnetucleistol D (2-methoxyoxyresveratrol)
Gnetucleistol E (3-methoxy-isorhapontigenin)
Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene)
Pinostilbene (3-methoxyresveratrol)
Pterostilbene (3',5'-dimethoxyresveratrol)
Rhapontigenin (piceatannol 4'-methyl ether)
Combretastatins
Combretastatin A-1
Combretastatin A-4
carboxylated other acylations
3,5-Dihydroxy-4-isopropyl-trans-stilbene
Glycosides
Astringin (Piceatannol 3-O-glucoside)
Isorhapontin (Isorhapontigenin glucoside)
Mulberroside A (Oxyresveratrol diglucoside)
of resveratrol
Piceid (trans-Resveratrol-3-O-glucoside)
trans-Resveratrol-3-O-glucuronide
Resveratroloside (trans-resveratrol-4'-O-beta-D-glucopyranoside)
of rhapontigenin
Rhaponticin (Rhapontigenin glucoside)
Oligomeric forms