Estriol succinate

Chemical compound

Not to be confused with Estradiol hemisuccinate.

Pharmaceutical compound

Estriol succinate

Clinical data
Trade names| Synapause, others
Other names| Oestriol succinate; Estriol disuccinate; Estriol hemisuccinate; Succinylestriol; Estriol 16α,17β-di(hydrogen succinate)
Routes of
administration| By mouth, vaginal[1]
Drug class| Estrogen; Estrogen ester
Identifiers

IUPAC name

* 4-{[(8R,9S,13S,14S,16R,17R)-17-(3-carboxypropanoyloxy)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]oxy}-4-oxobutanoic acid

CAS Number|

* 514-68-1

PubChem CID|

* 10577

ChemSpider|

* 10133

UNII|

* AS13K2DY03

KEGG|

* D07920

ChEBI|

* CHEBI:135790

CompTox Dashboard (EPA)|

* DTXSID401023693

ECHA InfoCard| 100.007.442
Chemical and physical data
Formula| C26H32O9
Molar mass| 488.533 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* C[C@]12CC[C@H]3[C@@H](CCc4cc(O)ccc34)[C@@H]1C[C@@H](OC(=O)CCC(O)=O)[C@@H]2OC(=O)CCC(O)=O

InChI

* InChI=1S/C26H32O9/c1-26-11-10-17-16-5-3-15(27)12-14(16)2-4-18(17)19(26)13-20(34-23(32)8-6-21(28)29)25(26)35-24(33)9-7-22(30)31/h3,5,12,17-20,25,27H,2,4,6-11,13H2,1H3,(H,28,29)(H,30,31)/t17-,18-,19+,20-,25+,26+/m1/s1

* Key:VBRVDDFOBZNCPF-BRSFZVHSSA-N

Estriol succinate, sold under the brand name Synapause among others, is an estrogen medication which is used in the treatment of menopausal symptoms.[1] It is taken by mouth, in through the vagina, and by injection.[1][2][3]

## Medical uses

[edit]

Estriol succinate is used in menopausal hormone therapy in the treatment and prevention of menopausal symptoms such as hot flashes, vaginal atrophy, and osteoporosis.[1] Unlike other estrogens, depending on how it is used (i.e., how often it is taken and at what dosage), estriol succinate may not require concomitant therapy with a progestogen to prevent endometrial hyperplasia and endometrial cancer in women with intact uteruses.[1]

The clinical effects of estriol succinate in the treatment of menopausal symptoms have been characterized in a large 5-year clinical trial of 911 menopausal women.[4][5][6]

### Available forms

[edit]

Estriol succinate is and has been available in the form of 2 and 4 mg oral tablets, as a 0.1% vaginal cream, and as a 20 mg vial for use by injection.[2][3]

## Side effects

[edit]

See also: Estriol (medication) § Side effects

## Pharmacology

[edit]

See also: Estriol (medication) § Pharmacology

Estriol succinate is an estrogen ester, specifically, an ester of estriol, and acts as a prodrug of estriol in the body.[7][1] It is described as a weak estrogen in comparison to estradiol valerate.[1][8] Estriol succinate is used medically via oral and vaginal routes similarly.[1] In estriol succinate, two of the hydroxyl groups of estriol, those at the C16α and C17β positions, are esterified with succinic acid.[1] As such, when adjusted for differences in molecular weight, a dose of 2 mg estriol succinate is equivalent to 1.18 mg unconjugated estriol.[1] Unlike other estrogen esters, such as estradiol valerate, estriol succinate is hydrolyzed almost not at all in the intestinal mucosa when taken orally, and in relation to this, is absorbed more slowly than is estriol.[1] Consequently, oral estriol succinate is a longer-acting form of estriol than oral estriol.[9] Instead of in the gastrointestinal tract, oral estriol succinate is cleaved into estriol mainly in the liver.[1] After a single 8 mg oral dose of estriol succinate, maximum levels of circulating estriol of 40 pg/mL are attained within 12 hours, and this increases up to 80 pg/mL with continued daily administration.[1]

* v
* t
* e

Potencies of oral estrogens[data sources 1] Compound  | Dosage for specific uses (mg usually)[a]

|

ETD[b] | EPD[b] | MSD[b] | MSD[c] | OID[c] | TSD[c]
Estradiol (non-micronized) | 30 | ≥120–300 | 120 | 6 | - | \-
Estradiol (micronized) | 6–12 | 60–80 | 14–42 | 1–2 | >5 | >8
Estradiol valerate | 6–12 | 60–80 | 14–42 | 1–2 | - | >8
Estradiol benzoate | - | 60–140 | - | - | - | \-
Estriol | ≥20 | 120–150[d] | 28–126 | 1–6 | >5 | \-
Estriol succinate  | - | 140–150[d] | 28–126 | 2–6 | - | \-
Estrone sulfate | 12 | 60 | 42 | 2 | - | \-
Conjugated estrogens | 5–12 | 60–80 | 8.4–25 | 0.625–1.25 | >3.75 | 7.5
Ethinylestradiol | 200 μg | 1–2 | 280 μg | 20–40 μg | 100 μg | 100 μg
Mestranol | 300 μg | 1.5–3.0 | 300–600 μg | 25–30 μg | >80 μg | \-
Quinestrol | 300 μg | 2–4 | 500 μg | 25–50 μg | - | \-
Methylestradiol | - | 2 | - | - | - | \-
Diethylstilbestrol | 2.5 | 20–30 | 11 | 0.5–2.0 | >5 | 3
DES dipropionate | - | 15–30 | - | - | - | \-
Dienestrol | 5 | 30–40 | 42 | 0.5–4.0 | - | \-
Dienestrol diacetate | 3–5 | 30–60 | - | - | - | \-
Hexestrol | - | 70–110 | - | - | - | \-
Chlorotrianisene | - | >100 | - | - | >48 | \-
Methallenestril | - | 400 | - | - | - | \-

Sources and footnotes:

1. ^ [10][11][12][13][14][15] [16][17][18][19] [20][21][22][23][24][25][26][27][28]

1. ^ Dosages are given in milligrams unless otherwise noted.
2. ^ a b c Dosed every 2 to 3 weeks
3. ^ a b c Dosed daily
4. ^ a b In divided doses, 3x/day; irregular and atypical proliferation.

## Chemistry

[edit]

See also: List of estrogen esters § Estriol esters

Estriol succinate, also known as estriol disuccinate or as estriol 16α,17β-di(hydrogen succinate), is a synthetic estrane steroid and a derivative of estriol.[7][29][30] It is specifically the C16α and C17β disuccinate ester of estriol.[7][29][30][1] The medication is provided both as estriol succinate and as estriol sodium succinate, the sodium salt.[7][29] Other marketed estriol esters besides estriol succinate include estriol acetate benzoate and estriol tripropionate, whereas estriol dihexanoate, estriol dipropionate, and estriol triacetate are estriol esters that were never marketed.[7][29] Quinestradol is an estriol ether and has also been marketed.[7][29] Polyestriol phosphate is an ester of estriol in the form of a polymer, and was previously marketed.[31][32][33][34]

## History

[edit]

Estriol succinate was introduced for medical use in 1966.[35]

## Society and culture

[edit]

### Generic names

[edit]

Estriol succinate is the generic name of the drug and its INNTooltip International Nonproprietary Name and BANTooltip British Approved Name.[7][29][36][30][35] Other synonyms include oestriol succinate, estriol disuccinate, and estriol hemisuccinate.[7][29][36][30] When provided as the sodium salt, estriol succinate is known as estriol sodium succinate (BANTooltip British Approved Name) or as oestriol sodium succinate.[7][29]

### Brand names

[edit]

Estriol succinate has been marketed under brand names including Blissel, Evalon, Gelistrol, Hemostyptanon, Orgastyptin, Ovestin, Sinapause, Styptanon, Synapsa, Synapasa, Synapausa, and Synapause, among others.[7][29][36][30] Estriol sodium succinate has been marketed specifically under the brand names Pausan and Styptanon.[7][29]

### Availability

[edit]

Estriol succinate is or has been marketed in Europe, Hong Kong, and Mexico.[29][30]

## Research

[edit]

Estriol succinate was under development for the treatment of multiple sclerosis in the United States and worldwide, and reached phase II clinical trials for this indication, but development was discontinued due to insufficient effectiveness.[37] It had the tentative brand name Trimesta.[37]

## References

[edit]

1. ^ a b c d e f g h i j k l m n Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63\. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.3-63&rft.date=2005-08&rft_id=https://api.semanticscholar.org/CorpusID:24616324#id-name=S2CID&rft_id=info:pmid/16112947&rft_id=info:doi/10.1080/13697130500148875&rft.aulast=Kuhl&rft.aufirst=H&rfr_id=info:sid/en.wikipedia.org:Estriol+succinate" class="Z3988">
2. ^ a b Satoskar RS, Bhandarkar SD, Rege NN (1973). "Gonadotropins, Estrogens, and Progestins". Pharmacology and Pharmacotherapeutics. Popular Prakashan. pp. 934–. ISBN 978-81-7991-527-1.
3. ^ a b Kleemann A, Engel J (2001). Pharmaceutical substances: syntheses, patents, applications. Thieme. p. 786\. ISBN 978-3-13-558404-1.
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5. ^ Ali ES, Mangold C, Peiris AN (September 2017). "Estriol: emerging clinical benefits". Menopause. 24 (9): 1081–1085\. doi:10.1097/GME.0000000000000855. PMID 28375935. S2CID 41137736.1081-1085&rft.date=2017-09&rft_id=https://api.semanticscholar.org/CorpusID:41137736#id-name=S2CID&rft_id=info:pmid/28375935&rft_id=info:doi/10.1097/GME.0000000000000855&rft.aulast=Ali&rft.aufirst=ES&rft.au=Mangold,+C&rft.au=Peiris,+AN&rfr_id=info:sid/en.wikipedia.org:Estriol+succinate" class="Z3988">
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10. ^ Lauritzen C (September 1990). "Clinical use of oestrogens and progestogens". Maturitas. 12 (3): 199–214\. doi:10.1016/0378-5122(90)90004-P. PMID 2215269.199-214&rft.date=1990-09&rft_id=info:doi/10.1016/0378-5122(90)90004-P&rft_id=info:pmid/2215269&rft.aulast=Lauritzen&rft.aufirst=C&rfr_id=info:sid/en.wikipedia.org:Estriol+succinate" class="Z3988">
11. ^ Lauritzen C (June 1977). "[Estrogen thearpy in practice. 3. Estrogen preparations and combination preparations]" [Estrogen therapy in practice. 3. Estrogen preparations and combination preparations]. Fortschritte Der Medizin (in German). 95 (21): 1388–92\. PMID 559617.1388-92&rft.date=1977-06&rft_id=info:pmid/559617&rft.aulast=Lauritzen&rft.aufirst=C&rfr_id=info:sid/en.wikipedia.org:Estriol+succinate" class="Z3988">
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16. ^ Pschyrembel W (1968). Praktische Gynäkologie: für Studierende und Ärzte. Walter de Gruyter. pp. 598–599\. ISBN 978-3-11-150424-7.598-599&rft.pub=Walter+de+Gruyter&rft.date=1968&rft.isbn=978-3-11-150424-7&rft.aulast=Pschyrembel&rft.aufirst=W&rft_id=https://books.google.com/books-id=vVaTnHDFzZ0C&pg;=PA598&rfr_id=info:sid/en.wikipedia.org:Estriol+succinate" class="Z3988">
17. ^ Lauritzen CH (January 1976). "The female climacteric syndrome: significance, problems, treatment". Acta Obstetricia Et Gynecologica Scandinavica. Supplement. 51: 47–61\. doi:10.3109/00016347509156433. PMID 779393.47-61&rft.date=1976-01&rft_id=info:doi/10.3109/00016347509156433&rft_id=info:pmid/779393&rft.aulast=Lauritzen&rft.aufirst=CH&rfr_id=info:sid/en.wikipedia.org:Estriol+succinate" class="Z3988">
18. ^ Lauritzen C (1975). "The Female Climacteric Syndrome: Significance, Problems, Treatment". Acta Obstetricia et Gynecologica Scandinavica. 54 (s51): 48–61\. doi:10.3109/00016347509156433. ISSN 0001-6349.48-61&rft.date=1975&rft_id=info:doi/10.3109/00016347509156433&rft.issn=0001-6349&rft.aulast=Lauritzen&rft.aufirst=C&rfr_id=info:sid/en.wikipedia.org:Estriol+succinate" class="Z3988">
19. ^ Kopera H (1991). "Hormone der Gonaden". Hormonelle Therapie für die Frau. Kliniktaschenbücher. pp. 59–124\. doi:10.1007/978-3-642-95670-6_6. ISBN 978-3-540-54554-5. ISSN 0172-777X.59-124&rft.date=1991&rft.issn=0172-777X&rft_id=info:doi/10.1007/978-3-642-95670-6_6&rft.isbn=978-3-540-54554-5&rft.aulast=Kopera&rft.aufirst=H&rfr_id=info:sid/en.wikipedia.org:Estriol+succinate" class="Z3988">
20. ^ Scott WW, Menon M, Walsh PC (April 1980). "Hormonal Therapy of Prostatic Cancer". Cancer. 45 (Suppl 7): 1929–1936\. doi:10.1002/cncr.1980.45.s7.1929. PMID 29603164.1929-1936&rft.date=1980-04&rft_id=info:doi/10.1002/cncr.1980.45.s7.1929&rft_id=info:pmid/29603164&rft.aulast=Scott&rft.aufirst=WW&rft.au=Menon,+M&rft.au=Walsh,+PC&rfr_id=info:sid/en.wikipedia.org:Estriol+succinate" class="Z3988">
21. ^ Leinung MC, Feustel PJ, Joseph J (2018). "Hormonal Treatment of Transgender Women with Oral Estradiol". Transgender Health. 3 (1): 74–81\. doi:10.1089/trgh.2017.0035. PMC 5944393. PMID 29756046.74-81&rft.date=2018&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5944393#id-name=PMC&rft_id=info:pmid/29756046&rft_id=info:doi/10.1089/trgh.2017.0035&rft.aulast=Leinung&rft.aufirst=MC&rft.au=Feustel,+PJ&rft.au=Joseph,+J&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5944393&rfr_id=info:sid/en.wikipedia.org:Estriol+succinate" class="Z3988">
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32. ^ Bachmann FF (January 1971). "[Treatment of menopausal complants with polyoestriol-phosphate. Experiences with Gynäsan injections]" [Treatment of menopausal complaints with polyoestriol-phosphate. Experiences with Gynäsan injections]. Munchener Medizinische Wochenschrift (in German). 113 (5): 166–169\. PMID 5107471.166-169&rft.date=1971-01&rft_id=info:pmid/5107471&rft.aulast=Bachmann&rft.aufirst=FF&rfr_id=info:sid/en.wikipedia.org:Estriol+succinate" class="Z3988">
33. ^ Labhart A (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 548, 551. ISBN 978-3-642-96158-8. "The polymer of estradiol or estriol and phosphoric acid has an excellent depot action when given intramuscularly (polyestriol phosphate or polyestradiol phosphate) (Table 16). Phosphoric acid combines with the estrogen molecule at C3 and C17 to form a macromolecule. The compound is stored in the liver and spleen where the estrogen is steadily released by splitting off of the phosphate portion due to the action of alkaline phosphatase. [...] Conjugated estrogens and polyestriol and estradiol phosphate can also be given intravenously in an aqueous solution. Intravenous administration of ovarian hormones offers no advantages, however, and therefore has no practical significance. [...] The following duarations of action have been obtained with a single administration (WlED, 1954; LAURITZEN, 1968): [...] 50 mg polyestradiol phosphate ~ 1 month; 50 mg polyestriol phosphate ~ 1 month; 80 mg polyestriol phosphate ~ 2 months."
34. ^ Campbell S (6 December 2012). The Management of the Menopause & Post-Menopausal Years: The Proceedings of the International Symposium held in London 24–26 November 1975 Arranged by the Institute of Obstetrics and Gynaecology, The University of London. Springer Science & Business Media. pp. 395–. ISBN 978-94-011-6165-7. "In the Federal Republic of Germany between 10 and 20% of all climacteric women are on estrogen treatment. We have the following oral estrogens for a treatment. (t) Conjugated estrogens, (2) estradiol valerate, (3) ethinyl-estradiol and its cyclopentyl-enol ether, (4) stilbestrol, (5) ethinyl-estradiol-methyltestosterone, (6) estriol and estriol succinate, most of them as coated tablets. Several long acting injectable preparations are available: several esters of combined estradiol-testosterone, one of estradiol-dehydroepiandrosterone enanthate and a prolonged polyestriol phosphate are also available. Lastly, depot injections of estradiol- and stilbestrol-esters are on the market."
35. ^ a b William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1481–. ISBN 978-0-8155-1856-3.
36. ^ a b c Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 114–. ISBN 978-94-011-4439-1.
37. ^ a b "Estriol succinate - Synthetic Biologics - AdisInsight".

* 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
*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[ETD]: Endometrial threshold dose
*[EPD]: Endometrial proliferation dose
*[MSD]: Menopausal substitution dose
*[OID]: Ovulation-inhibiting dose
*[TSD]: Testosterone suppression dose
*[INN]: International Nonproprietary Name
*[BAN]: British Approved Name
*[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