List of estrogens

Estradiol, the prototypical estrogen. Steroid ring system.

This is a list of steroidal estrogens or derivatives of estradiol, estrone, and estriol. Most esters of these estrogens are not included in this list; for esters, see here instead.

## Estradiol derivatives

[edit]

Compound  | Chemical name  | Structure  | Marketed

|
|
|

Estradiol (E2) | Estra-1,3,5(10)-triene-3,17β-diol  |  | ✓
2-Hydroxyestradiol | 2-Hydroxyestradiol  |  | –
4-Hydroxyestradiol | 4-Hydroxyestradiol  |  | –
4-Methoxyestradiol | 4-Methoxyestradiol  |  | –
8β-VE2 | 8β-Vinylestradiol  |  | –
16α-IE2 | 16α-Iodoestradiol  |  | –
16α-LE2 | Estradiol 21,16α-lactone? |  | –
Cloxestradiol | Estradiol 17β-chloral hemiacetal ether  |  | –
Cloxestradiol acetate | Estradiol 17β-chloral hemiacetal ether O,O-diacetate  |  | ✓
Estradiol sulfate | Estradiol 3-sulfate  |  | –
Estrapronicate | Estradiol 3-propionate 17β-nicotinate  |  | ✓
Orestrate | Estradiol 3-propionate 17β-(1-cyclohexenyl) ether  |  | –
Polyestradiol phosphate | Estradiol 17β-phosphate polymer  |  | ✓
Promestriene | Estradiol 3-propyl 17β-methyl diether  |  | ✓

### 17α-Substituted estradiol derivatives

[edit]

Compound  | Chemical name  | Structure  | Marketed

|
|
|

Cyclodiol | 14α,17α-Ethanoestradiol  |  | –
Estrazinol | 8-Aza-17α-ethynylestradiol 3-methyl ether  |  | –
Estrofurate | 17α-(3-Furyl)-δ7-estradiol 3-acetate  |  | –
Etamestrol (eptamestrol) | 1-Hydroxy-7α-methyl-17α-ethynylestradiol 1,3-dibenzoate  |  | –
Ethinylestradiol (EE) | 17α-Ethynylestradiol  |  | ✓
Ethinylestradiol sulfonate (EES) | 17α-Ethynylestradiol 3-isopropylsulfonate  |  | ✓
Ethylestradiol | 17α-Ethylestradiol  |  | –
Mestranol (EE3ME) | 17α-Ethynylestradiol 3-methyl ether  |  | ✓
Methylestradiol | 17α-Methylestradiol  |  | ✓
Moxestrol | 11β-Methoxy-17α-ethynylestradiol  |  | ✓
Quinestrol | 17α-Ethynylestradiol 3-cyclopentyl ether  |  | ✓
RU-16117 | 11α-Methoxy-17α-ethynylestradiol  |  | –

### Nitrogen mustard-coupled alkylating antineoplastic estradiol derivatives

[edit]

Compound  | Chemical name  | Structure  | Marketed

|
|
|

Alestramustine | Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(2β-aminopropanoate)  |  | –
Atrimustine | Estradiol 3-benzoate 17β-(4-(4-(bis(2-chloroethyl)amino)phenyl)-1-oxobutoxy)acetate  |  | –
Estramustine | Estradiol 3-(bis(2-chloroethyl)carbamate)  |  | –
Estramustine phosphate | Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-phosphate  |  | ✓

### 17β-Aminoestrogens

[edit]

See also: 17β-Aminoestrogen

Compound  | Chemical name  | Structure  | Marketed

|
|
|

Aminoestradiol | 17β-Aminoestradiol  |  | –
Butolame | 17β-((4-Hydroxybutyl)amino)estradiol  |  | –
Hexolame | 17β-((6-Hydroxyhexyl)amino)estradiol  |  | –
Pentolame | 17β-((5-Hydroxypentyl)amino)estradiol  |  | –
Prodiame | 17β-((3-Aminopropyl)amino)estradiol  |  | –
Prolame | 17β-((3-Hydroxypropyl)amino)estradiol  |  | –

## Estrone derivatives

[edit]

Compound  | Chemical name  | Structure  | Marketed

|
|
|

Estrone (E1) | Estra-1,3,5(10)-triene-3-ol-17-one  |  | ✓
2-Hydroxyestrone | 2-Hydroxyestrone  |  | –
4-Hydroxyestrone | 4-Hydroxyestrone  |  | –
4-Methoxyestrone | 4-Methoxyestrone  |  | –
16α-Hydroxyestrone | 16α-Hydroxyestrone  |  | –
Almestrone | 7α-Methylestrone  |  | ✓
Clomestrone | 16α-Chloroestrone 3-methyl ether  |  | ✓
Estrone sulfate | Estrone 3-sulfate  |  | ✓
Estropipate | Estrone 3-sulfate piperazine salt  |  | ✓
Hydroxyestrone diacetate | 16α-Hydroxyestrone 3,16α-diacetate  |  | ✓

### Nitrogen mustard-coupled alkylating antineoplastic estrone derivatives

[edit]

Compound  | Chemical name  | Structure  | Marketed

|
|
|

Estromustine | Estrone 3-(bis(2-chloroethyl)carbamate)  |  | –

## Estriol derivatives

[edit]

Compound  | Chemical name  | Structure  | Marketed

|
|
|

Estriol (E3) | 16α-Hydroxyestradiol  |  | ✓
Estetrol (E4) | 15α-Hydroxyestriol  |  | –
Quinestradol | Estriol 3-cyclopentyl ether  |  | ✓

### 17α-Substituted estriol derivatives

[edit]

Compound  | Chemical name  | Structure  | Marketed

|
|
|

Cyclotriol | 14α,17α-Ethanoestriol  |  | –
Ethinylestriol | 17α-Ethynylestriol  |  | –
Nilestriol | 17α-Ethynylestriol 3-cyclopentyl ether  |  | ✓

## Other estrogen derivatives

[edit]

### Epimers

[edit]

Compound  | Chemical name  | Structure  | Marketed

|
|
|

17α-Estradiol (alfatradiol)  | 17α-Estradiol  |  | ✓
16β-Epiestriol (epiestriol) | 16β-Hydroxy-17β-estradiol  |  | ✓
17α-Epiestriol | 16α-Hydroxy-17α-estradiol  |  | –
16β,17α-Epiestriol | 16β-Hydroxy-17α-estradiol  |  | –
Epimestrol | 17α-Epiestriol 3-methyl ether  |  | ✓
Mytatrienediol | 16α-Methyl-16β-epiestriol 3-methyl ether  |  | –

### Equine estrogens

[edit]

See also: Conjugated estrogens and Esterified estrogens

Compound  | Chemical name  | Structure  | Marketed

|
|
|

Equilin | Δ7-Estrone  |  | ✓
Equilenin | Δ6,8-Estrone  |  | ✓
17α-Dihydroequilin | Δ7-17α-Estradiol  |  | ✓
17β-Dihydroequilin | Δ7-17β-Estradiol  |  | ✓
17α-Dihydroequilenin | Δ6,8-17α-Estradiol  |  | ✓
17β-Dihydroequilenin | Δ6,8-17β-Estradiol  |  | ✓
8,9-Dehydroestrone | Δ8-Estrone  |  | ✓
8,9-Dehydroestradiol | Δ8-17β-Estradiol  |  | ✓
Hippulin | Δ8-14-Isoestrone  |  | ✓

## See also

[edit]

* List of steroids

## Notes

[edit]

? = Chemical names that are unverified.

## References

[edit]

* v
* t
* e

Estrogens and antiestrogens

Estrogens|

| ERTooltip Estrogen receptor 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
* 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 (promethestrol)
* Methestrol dipropionate (promethestrol dipropionate)
* Paroxypropione
* Quadrosilan
* Triphenylbromoethylene
* Triphenylchloroethylene
* Zeranol

|

Progonadotropins|

* Antiandrogens (e.g., bicalutamide)
* GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
* Gonadotropins (e.g., FSHTooltip follicle-stimulating hormone, LHTooltip luteinizing hormone)

Antiestrogens|

| ERTooltip Estrogen receptor antagonists
(incl. SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)|

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

* Exclusively antagonistic: Elacestrant
* Fulvestrant

* Noncompetitive inhibitors: Trilostane

|

Aromatase inhibitors|

* First-generation: Aminoglutethimide
* Testolactone

* Second-generation: Fadrozole
* Formestane

* 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

* 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

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., 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
* ent-Estradiol
* 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
* Estrogenic substances
* Estromustine
* Estrone
* Estrone esters
* Estrone methyl ether
* Estropipate
* Etamestrol (eptamestrol)
* Ethinylandrostenediol
* Ethandrostate
* 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
* Butestrol
* Carbestrol
* D-15414
* DCW234
* Diarylpropionitrile
* Dienestrol
* Dienestrol diacetate
* Diethylstilbestrol
* Diethylstilbestrol esters
* Dimestrol (dianisylhexene)
* Dimethylstilbestrol
* Doisynoestrol (fenocycline)
* Doisynolic acid
* Efavirenz
* Elacestrant
* 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)
* M2613
* meso-Butestrol
* meso-Hexestrol
* Mestilbol
* Methallenestril
* Methestrol
* Methestrol dipropionate
* Paroxypropione
* Pentafluranol
* Phenestrol
* Prinaberel (ERB-041, WAY-202041)
* Propylpyrazoletriol
* Quadrosilan
* SC-3296
* 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, 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)

|

Mixed
(SERMsTooltip Selective estrogen receptor modulators)|

* 2-Phenylbenzofuran
* 2-Phenylbenzothiophene
* 4'-Hydroxynorendoxifen
* 27-Hydroxycholesterol
* Acefluranol
* Acolbifene
* Afimoxifene
* Anordiol
* Anordrin
* Arzoxifene
* Bazedoxifene
* Brilanestrant
* Broparestrol
* Camizestrant
* Chlorotrianisene
* Clomifene
* Clomifenoxide
* CN-55945-27
* Cyclofenil
* D-15413
* Desmethylchlorotrianisene
* Droloxifene
* 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
* MRL-37
* 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
* U-11555A
* U-11634
* Y-134
* Zindoxifene
* Zuclomifene

Antagonists|

* (R,R)-THC
* 7β-Hydroxy-DHEA
* Chloroindazole
* Cytestrol acetate
* EM-800 (SCH-57050)
* Epitiostanol
* ERA-90
* ERB-88
* Fulvestrant (ICI-182780)
* Glyceollins (I, II, III, IV)
* ICI-164384
* MDL-101906
* Mepitiostane
* Methylepitiostanol
* Methylpiperidinopyrazole
* MIBE
* Oxabicycloheptene sulfonate
* Phenytoin
* PHTPP
* Prochloraz
* RU-39411
* RU-58668
* SS1020
* TAS-108 (SR-16234)
* ZB716
* ZK-164015
* ZK-191703

* Coregulator-binding modulators: ERX-11

* Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor|

| Agonists|

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

|

Antagonists|

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

Unknown|

* Diethylstilbestrol
* Zearalenone

See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[ER]: Estrogen receptor
*[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