Comparison of estrogens

Estradiol, a major estrogen and both a hormone and a medication.

This is a comparison of estrogens, or agonists of the estrogen receptor (ER). Estrogens include both natural estrogens like estradiol and synthetic estrogens like ethinylestradiol and diethylstilbestrol.

## Contents

* 1 Pharmacodynamics
* 1.1 Affinities and efficacies
* 2 See also
* 3 References

## Pharmacodynamics

### Affinities and efficacies

Relative binding affinities of estrogens[1][2] Estrogen | ERα (%) | ERβ (%)

|
|

Estradiol | 100 | 100
Estrone | 60 | 37
Estriol | 14 | 21
Ethinylestradiol | 190 | 11[3]
17α-Estradiol | 58 | 11
4-Hydroxyestradiol | 13 | 7
2-Hydroxyestradiol | 7 | 11
Estrone 3-sulfate | <1 | <1
Moxestrol | 43 | 5
Diethylstilbestrol | 468 | 295
Hexestrol | 302 | 234
Dienestrol | 223 | 404
Tamoxifen | 7 | 6
4-Hydroxytamoxifen | 178 | 339
Clomifene | 25 | 12
Nafoxidine | 44 | 16
ICI-164384 | 85 | 166
5-Androstenediol | 6 | 17
4-Androstenediol | 0.5 | 0.6
3β-Androstanediol | 3 | 7
3α-Androstanediol | 0.07 | 0.3
Dehydroepiandrosterone | 0.04 | 0.07
4-Androstenedione | <0.01 | <0.01
Coumestrol | 94 | 185
Genistein | 5 | 36
β-Zearalanol | 16 | 14
Bisphenol A | 0.05 | 0.33
Relative binding affinities + transactivation capacities of estrogens[4] | RBA | RTC

|
|

Estrogen | ERα (%) | ERβ (%) | ERα (%) | ERβ (%)
Estradiol | 100 | 100 | 100 | 100
Estrone | 4.0 | 3.5 | 2.6 | 4.3
Estriol | 11.3 | 17.6 | 10.6 | 16.6
Ethinylestradiol | 233 | 37.8 | 213 | 27.2
Propylpyrazoletriol | 10.0 | 0.12 | 20.0 | ND
16α-LE2 | 14.6 | 0.089 | 18.9 | 0.07
Diarylpropionitrile | 0.12 | 6.6 | 0.063 | 3.0
8β-VE2 | 0.35 | 22.0 | 0.11 | 34.0
Fulvestrant | 9.4 | 8.3 | ND | ND
4-Hydroxytamoxifen | 1.7 | 2.3 | ND | ND
Raloxifene | 7.8 | 0.54 | ND | ND
Genistein | 0.032 | 0.86 | 0.045 | 1.2
Biochanin A | 0.022 | 1.2 | 0.021 | 1.0
Coumestrol | 0.05 | 0.41 | 0.11 | 1.0
Daidzein | 0.015 | 0.13 | 0.011 | 0.12
ER (rat uterine cytosol) RBA \+ estrogenicity (change in rat uterine wet weight) of estrogen metabolites[5] Compound | RBA | Uterine weight (%)

|
|

Control | – | 100
Estradiol | 100 | 506
Estriol | 10 | 468
2-Hydroxyestradiol | 24 | 285
2-Methoxyestradiol | 0.05 | 101
4-Hydroxyestradiol | 45 | ?
4-Methoxyestradiol | 13 | 260
2-Hydroxyestrone | 2 | 130
2-Methoxyestrone | 0.01 | ?
4-Hydroxyestrone | 11 | 351
4-Methoxyestrone | 0.13 | 338

## See also

* List of estrogens
* Estrogen ester

## References

1. ↑ "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric 8 Suppl 1: 3–63. 2005. doi:10.1080/13697130500148875. PMID 16112947. http://hormonebalance.org/images/documents/Kuhl 05 Pharm Estro Progest Climacteric_1313155660.pdf.
2. ↑ "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology 138 (3): 863–70. 1997. doi:10.1210/endo.138.3.4979. PMID 9048584.
3. ↑ "Differential Response of Estrogen Receptor α and Estrogen Receptor β to Partial Estrogen Agonists/Antagonists". Molecular Pharmacology 54 (1): 105-112. 1998. doi:10.1124/mol.54.1.105. PMID 9658195. http://molpharm.aspetjournals.org/content/54/1/105.long.
4. ↑ "Evaluation of ligand selectivity using reporter cell lines stably expressing estrogen receptor alpha or beta". Biochem. Pharmacol. 71 (10): 1459–69. 2006. doi:10.1016/j.bcp.2006.02.002. PMID 16554039.
5. ↑ "Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women". J. Soc. Gynecol. Investig. 7 (3): 175–83. 2000. doi:10.1016/s1071-5576(00)00049-6. PMID 10865186.

* v
* t
* e

Estrogens and antiestrogens

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, [[Chemistry:Estradiol estradiol valerate, Polyestradiol phosphate|polyestradiol phosphate]], estradiol ester mixtures (Climacteron))
* Estramustine phosphate
* Estriol
* Estriol esters (e.g., estriol succinate, polyestriol phosphate)
* Estrone
* Estrone esters
* Estrone sulfate
* Estropipate (piperazine estrone sulfate)
* Ethinylestradiol#
* Ethinylestradiol sulfonate
* Hydroxyestrone diacetate
* Mestranol
* Methylestradiol
* Moxestrol
* Nilestriol
* Prasterone (dehydroepiandrosterone; DHEA)
* Prasterone enanthate
* Prasterone sulfate
* Promestriene
* Quinestradol
* Quinestrol

* Nonsteroidal: Benzestrol
* Bifluranol
* Chlorotrianisene
* Dienestrol
* Dienestrol diacetate
* Diethylstilbestrol (stilbestrol)
* Diethylstilbestrol esters/ethers
* Dimestrol (diethylstilbestrol dimethyl ether)
* Fosfestrol (diethylstilbestrol diphosphate)
* Mestilbol (diethylstilbestrol monomethyl ether)
* Doisynoestrol (fenocycline)
* Hexestrol
* Hexestrol esters
* Methallenestril
* Methestrol dipropionate (promethestrol dipropionate)
* Paroxypropione
* Quadrosilan
* Triphenylbromoethylene
* Triphenylchloroethylene
* Zeranol

|

Progonadotropins|

* Antiandrogens (e.g., bicalutamide)
* GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
* Gonadotropins (e.g., FSH, LH)

Antiestrogens|

| ER antagonists
(incl. SERMs/SERDs)|

* Acolbifene†
* Anordrin
* Bazedoxifene
* Broparestrol
* Clomifene#
* Cyclofenil
* Enclomifene†
* Epitiostanol
* Lasofoxifene
* Mepitiostane
* Ormeloxifene
* Ospemifene
* Raloxifene
* Tamoxifen#
* Toremifene

* Exclusively antagonistic: Fulvestrant

|

Aromatase inhibitors|

* First-generation: Aminoglutethimide
* Testolactone

* Second-generation: Fadrozole
* Formestane

* Third-generation: Anastrozole
* Exemestane
* Letrozole

Antigonadotropins|

* Androgens/Anabolic steroid|Anabolic steroid|Anabolic steroid]]]]s (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, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])

Others|

* Mixed mechanism of action: Danazol
* Gestrinone

* Androstenedione immunogens: Androvax (androstenedione albumin)
* Ovandrotone albumin (Fecundin)

* #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

* v
* t
* e

Estrogen receptor modulators

ER|

| 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-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)
* 16α-Fluoroestradiol
* 16α-Hydroxy-DHEA
* 16α-Hydroxyestrone
* 16α-Iodoestradiol
* 16α-LE2
* 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
* 17α-Estradiol (alfatradiol)
* 17α-Dihydroequilenin
* 17α-Dihydroequilin
* 17α-Epiestriol (16α-hydroxy-17α-estradiol)
* 17β-Dihydroequilenin
* 17β-Dihydroequilin
* 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
* Cloxestradiol acetate
* Conjugated estriol
* Conjugated estrogens
* Cyclodiol
* Cyclotriol
* DHEA
* DHEA-S
* Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
* Epimestrol
* Equilenin
* Equilin
* ERA-63 (ORG-37663)
* Esterified estrogens
* Estetrol
* Estradiol
* Estradiol esters
* Lipoidal estradiol
* Polyestradiol phosphate
* Estramustine
* Estramustine phosphate
* Estrapronicate
* Estrazinol
* Estriol
* Estriol esters
* Polyestriol phosphate
* Estrofurate
* Estromustine
* Estrone
* Estrone esters
* Estrone methyl ether
* Estropipate
* Etamestrol (eptamestrol)
* Ethinylestradiol
* Ethinylestradiol 3-benzoate
* Ethinylestradiol sulfonate
* 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

* Nonsteroidal: (R,R)-THC
* (S,S)-THC
* 2,8-DHHHC
* β-LGND1
* β-LGND2 (GTx-878)
* AC-186
* Allenestrol
* Allenolic acid
* Benzestrol
* Bifluranol
* Bisdehydrodoisynolic acid
* Carbestrol
* D-15414
* DCW234
* Diarylpropionitrile
* Dienestrol
* Dienestrol diacetate
* Diethylstilbestrol
* Diethylstilbestrol esters
* Dimestrol (dianisylhexene)
* Doisynoestrol (fenocycline)
* Doisynolic acid
* Efavirenz
* ERB-196 (WAY-202196)
* Erteberel (SERBA-1, LY-500307)
* Estrobin (DBE)
* Fenestrel
* FERb 033
* Fosfestrol (diethylstilbestrol diphosphate)
* Furostilbestrol (diethylstilbestrol difuroate)
* GTx-758
* Hexestrol
* Hexestrol esters
* ICI-85966 (Stilbostat)
* Mestilbol
* Methallenestril
* Methestrol
* Methestrol dipropionate
* Paroxypropione
* Pentafluranol
* Phenestrol
* Prinaberel (ERB-041, WAY-202041)
* Propylpyrazoletriol
* Quadrosilan
* SC-4289
* SERBA-2
* SKF-82,958
* Terfluranol
* Triphenylbromoethylene
* Triphenylchloroethylene
* Triphenyliodoethylene
* Triphenylmethylethylene (triphenylpropene)
* WAY-166818
* WAY-169916
* WAY-200070
* WAY-204688 (SIM-688)
* WAY-214156

* Unknown/unsorted: ERB-26
* ERA-45
* ERB-79
* ZK-283197

* 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, [[Chemistry:Epicateepicatechin, Chemistry:Equol|equol]], formononetin, glabrene, glabridin, Genistein|genistein]], genistin, glycitein, kaempferol, Chemistry:Liquiritigenin

|

Mixed
(SERMs)|

* 2-Phenylbenzofuran
* 2-Phenylbenzothiophene
* 4'-Hydroxynorendoxifen
* 27-Hydroxycholesterol
* Acefluranol
* Acolbifene
* Afimoxifene
* Anordiol
* Anordrin
* Arzoxifene
* Bazedoxifene
* Brilanestrant
* Broparestrol
* Chlorotrianisene
* Clomifene
* Clomifenoxide
* Cyclofenil
* D-15413
* Droloxifene
* Elacestrant
* Enclomifene
* Endoxifen
* Etacstil (GW-5638, DPC-974)
* Ethamoxytriphetol (MER-25)
* Femarelle
* Fispemifene
* GW-7604
* ICI-55548
* Idoxifene
* Lasofoxifene
* Levormeloxifene
* LN-1643
* LN-2299
* LY-117018
* Menerba
* Miproxifene
* Miproxifene phosphate
* Nafoxidine
* Nitromifene
* NNC 45-0095
* NNC 45-0320
* NNC 45-0781
* NNC 45-1506
* Ormeloxifene
* Ospemifene
* Panomifene
* Pipendoxifene
* Promensil
* Raloxifene
* Rimostil (P-081)
* Spironolactone
* SS1010
* Tamoxifen
* TAS-108 (SR-16234)
* Toremifene
* Trioxifene
* TZE-5323
* Y-134
* Zindoxifene
* Zuclomifene

Antagonists|

* (R,R)-THC
* 7β-Hydroxy-DHEA
* Chloroindazole
* Cytestrol acetate
* EM-800
* Epitiostanol
* ERA-90
* ERB-88
* Fulvestrant (ICI-182780)
* Glyceollins (I, II, III, IV)
* ICI-164384
* Mepitiostane
* Methylepitiostanol
* Methylpiperidinopyrazole
* MIBE
* Oxabicycloheptene sulfonate
* Phenytoin
* PHTPP
* Prochloraz
* RU-58668
* SS1020
* TAS-108 (SR-16234)
* ZB716
* ZK-164015
* ZK-191703

* Coregulator-binding modulators: ERX-11

GPER|

| Agonists|

* 2-Methoxyestradiol
* 7β-Hydroxyepiandrosterone
* Afimoxifene (4-hydroxytamoxifen)
* Atrazine
* Bisphenol A
* Daidzein
* DDT (p,p'-DDT, o',p'-DDE)
* Equol
* Estradiol
* Ethinylestradiol
* Fulvestrant (ICI-182780)
* G-1
* Genistein
* GPER-L1
* GPER-L2
* Hydroxytyrosol
* Kepone
* Niacin
* Nicotinamide
* Nonylphenol
* Oleuropein
* PCBs (2,2',5'-PCB-4-OH)
* Propylpyrazoletriol
* Quercetin
* Raloxifene
* Resveratrol
* Tamoxifen
* Tectoridin
* Zearalanone
* Zearalenol
* Zearalenone
* Zeranol (zearalanol))

|

Antagonists|

* CCL18
* Estriol
* G-15
* G-36
* MIBE

See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Comparison_of_estrogens&oldid=287601"
*[RBA]: Relative binding affinity
*[RTC]: Relative transactivation capacity
*[ND]: No data
*[ER]: Estrogen receptor
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[GnRH]: gonadotropin-releasing hormone
*[FSH]: follicle-stimulating hormone
*[LH]: luteinizing hormone
*[SERMs]: Selective estrogen receptor modulators
*[SERDs]: selective estrogen receptor downregulators
*[GPER]: G protein-coupled estrogen receptor