Steroid ester

Short description: Class of chemical compounds

Estradiol valerate, an ester of estradiol and one of the most widely used estrogen esters. It has increased oral bioavailability and a longer duration with intramuscular injection relative to estradiol.

A steroid ester is an ester of a steroid.[1][2] They include androgen esters, estrogen esters, progestogen esters, and corticosteroid esters.[1] Steroid esters may be naturally occurring/endogenous like DHEA sulfate or synthetic like estradiol valerate.[1][2] Esterification is useful because it is often able to render the parent steroid into a prodrug of itself with altered chemical properties such as improved metabolic stability, water solubility, and/or lipophilicity.[2] This, in turn, can enhance pharmacokinetics, for instance by improving the steroid's bioavailability and/or conferring depot activity and hence an extended duration with intramuscular or subcutaneous injection.[1][3]

Esterification of steroids with fatty acids was developed to prolong the duration of effect of steroid hormones.[4] By 1957, more than 500 steroid esters had been synthesized, most frequently of androgens.[4] The longer the fatty acid chain, up to a certain optimal length, the longer the duration when prepared as an oil solution and injected.[4] Across a chain length range of 6 to 12 carbon atoms, a length of 9 or 10 carbon atoms (nonanoate or decanoate ester) was found to be optimal in rodents in the case of testosterone esters.[4] Fatty acid esters increase the lipophilicity of steroids, with longer fatty acids resulting in greater lipophilicity.[4] The greater solubility in oil allows the steroid esters to be dissolved in a smaller oil volume, thereby allowing for larger doses with intramuscular injection.[4] In addition, the greater the lipophilicity of the steroid, as measured by the octanol/water partition coefficient (logP), the slower its release from the oily depot at the injection site and the longer its duration.[5]

Steroid esters can also be prepared as crystalline aqueous suspensions.[4] Aqueous suspensions of steroid crystals result in prolongation of duration with intramuscular injection similarly to oil solutions.[4] The duration is longer than that of oil solutions, intermediate between oil solutions and subcutaneous pellet implants.[4] The sizes of crystals in suspensions varies and can range from 0.1 μm to some hundreds of μm.[6] The duration of crystalline steroid suspensions increases directly with the size of the crystals.[4][6] However, crystalline suspensions have an irritating effect in the body, and intramuscular injections of crystalline steroid suspensions result in painful local reactions.[4][6] These reactions worsen with larger crystals, and for this reason, crystal sizes must be limited to minimize local reactions.[4][6] Particle sizes of more than 300 μg in the case of estradiol benzoate by intramuscular injection have been found to be too painful for use.[6]

In some cases, crystalline steroid suspensions are used not for prolongation of effect, but because the solubility of the steroid result in this preparation being the only practical way to deliver the steroid in a reasonable injection volume.[4][6] Examples include cortisone acetate and hydrocortisone and its esters.[6] A requirement of long-lasting crystalline steroid administration is that the steroid be sufficiently water-insoluble, so that it dissolves slowly and thereby attains a prolonged therapeutic effect.[4] The crystals in suspensions can sometimes clump together or aggregate and grow in size.[6][4] This can be avoided by careful formulation.[6][4] Crystalline suspensions of steroids are prepared either by precipitation or by dispersing finely divided material in an aqueous suspension medium.[6] Desired particle size can be achieved by grinding, for instance through the use of an atomizer.[6]

Adolf Butenandt reported in 1932 that estrone benzoate in oil solution had a prolonged duration with injection in animals.[7][8][9] No such prolongation of action occurred if it was given by intravenous injection.[8] Estradiol benzoate was synthesized in 1933 and was marketed for use the same year.[10][11][12]

## Contents

* 1 Sulfur-based esters
* 2 See also
* 3 References
* 4 Further reading

## Sulfur-based esters

Certain sulfur-based steroid esters have a sulfamate or sulfonamide moiety as the ester, typically at the C3 and/or C17β positions. Like many other steroid esters, they are prodrugs. Unlike other steroid esters however, they bypass first-pass metabolism with oral administration and have high oral bioavailability and potency, abolished first-pass hepatic impact, and long elimination half-lives and durations of action. They are under development for potential clinical use. Examples include the estradiol esters estradiol sulfamate (E2MATE; also a potent steroid sulfatase inhibitor) and EC508 (estradiol 17β-(1-(4-(aminosulfonyl)benzoyl)-L-proline)),[13][14] the testosterone ester EC586 (testosterone 17β-(1-((5-(aminosulfonyl)-2-pyridinyl)carbonyl)-L-proline)),[14] and sulfonamide esters of levonorgestrel and etonogestrel.[15]

## See also

* List of steroid esters
* Steroid sulfate

## References

1. ↑ 1.0 1.1 1.2 1.3 "Longacting steroid preparations". Acta Clin Belg 30 (1): 48–55. 1975. doi:10.1080/17843286.1975.11716973. PMID 1231448.
2. ↑ 2.0 2.1 2.2 Valentino Stella; Ronald Borchardt; Michael Hageman; Reza Oliyai, Hans Maag, Jefferson Tilley (12 March 2007). Prodrugs: Challenges and Rewards. Springer Science & Business Media. pp. 220–. ISBN 978-0-387-49782-2. https://books.google.com/books?id=qkjHxX5TgHEC&pg=PA220.
3. ↑ William N. Taylor, M.D. (16 January 2002). Anabolic Steroids and the Athlete, 2d ed.. McFarland. pp. 39–. ISBN 978-0-7864-1128-3. https://books.google.com/books?id=OGcQ0Tp2AFcC&pg=PA39.
4. ↑ 4.00 4.01 4.02 4.03 4.04 4.05 4.06 4.07 4.08 4.09 4.10 4.11 4.12 4.13 4.14 4.15 Edkins, Robert Patrick (1959). "The Modification of the Duration of Drug Action". Journal of Pharmacy and Pharmacology 11 (S1): 54T–66T. doi:10.1111/j.2042-7158.1959.tb10412.x. ISSN 0022-3573.
5. ↑ Florence, Alexander T. (2011). "A Short History of Controlled Drug Release and an Introduction". Controlled Release in Oral Drug Delivery. pp. 1–26. doi:10.1007/978-1-4614-1004-1_1. ISBN 978-1-4614-1003-4.
6. ↑ 6.00 6.01 6.02 6.03 6.04 6.05 6.06 6.07 6.08 6.09 6.10 "Suspensions in pharmaceutical practice". Boll Chim Farm 101 (12): 105–22. February 1962. doi:10.1093/ajhp/19.12.611. PMID 14487508.
7. ↑ A. Labhart (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 512–. ISBN 978-3-642-96158-8. https://books.google.com/books?id=DAgJCAAAQBAJ&pg=PA512.
8. ↑ 8.0 8.1 "Effective Absorption of Hormones". Br Med J 1 (4024): 371–3. February 1938. doi:10.1136/bmj.1.4024.371. PMID 20781252.
9. ↑ Butenandt, Adolf; Störmer, Inge (1932). "Über isomere Follikelhormone. Untersuchungen über das weibliche Sexualhormon, 7. Mitteilung.". Hoppe-Seyler's Zeitschrift für physiologische Chemie 208 (4): 129–148. doi:10.1515/bchm2.1932.208.4.129. ISSN 0018-4888.
10. ↑ Michael Oettel; Ekkehard Schillinger (6 December 2012). Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens. Springer Science & Business Media. pp. 8–. ISBN 978-3-642-58616-3. https://books.google.com/books?id=0BfrCAAAQBAJ&pg=PA8.
11. ↑ "The activation of female sex hormones: Mono-esters of alpha-oestradiol". Biochem. J. 32 (8): 1273–80. 1938. doi:10.1042/bj0321273b. PMID 16746750.
12. ↑ Kaufman, C. (1933). "Die Behandlung der Amenorrhöe mit Hohen Dosen der Ovarialhormone". Klinische Wochenschrift 12 (40): 1557–1562. doi:10.1007/BF01765673. ISSN 0023-2173.
13. ↑ "Estradiol prodrugs (EP) for efficient oral estrogen treatment and abolished effects on estrogen modulated liver functions". J. Steroid Biochem. Mol. Biol. 165 (Pt B): 305–311. January 2017. doi:10.1016/j.jsbmb.2016.07.008. PMID 27449818.
14. ↑ 14.0 14.1 "A prodrug design for improved oral absorption and reduced hepatic interaction". Bioorg. Med. Chem. 25 (20): 5569–5575. October 2017. doi:10.1016/j.bmc.2017.08.027. PMID 28886996.
15. ↑ "Esters of levonorgestrel and etonogestrel intended as single, subcutaneous-injection, long-lasting contraceptives". Steroids 137: 47–56. September 2018. doi:10.1016/j.steroids.2018.07.010. PMID 30086356.

## Further reading

* "Longacting steroid preparations". Acta Clin Belg 30 (1): 48–55. 1975. doi:10.1080/17843286.1975.11716973. PMID 1231448.

Steroid receptor modulators

* v
* t
* e

Androgen receptor modulators

AR|

| Agonists|

* Testosterone derivatives: 4-Androstenediol
* 4-Dehydroepiandrosterone (4-DHEA)
* 4-Hydroxytestosterone
* 4,17α-Dimethyltestosterone
* 5-Androstenedione
* 11-Ketotestosterone
* 11β-Hydroxyandrostenedione
* Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
* Androstenediol (5-androstenediol)
* Androstenediol 3β-acetate
* Androstenediol 17β-acetate
* Androstenediol diacetate
* Androstenediol dipropionate
* Androstenedione (4-androstenedione)
* Atamestane
* Boldenone
* Boldenone undecylenate
* Boldione (1,4-androstadienedione)
* Clostebol
* Clostebol acetate
* Clostebol caproate
* Clostebol propionate
* Cloxotestosterone
* Cloxotestosterone acetate
* Dehydroandrosterone
* DHEA (androstenolone, prasterone; 5-DHEA)
* DHEA enanthate (prasterone enanthate)
* DHEA sulfate
* Exemestane
* Formestane
* Plomestane
* Quinbolone
* Silandrone
* Testosterone# (+dutasteride)
* Testosterone esters
* Polytestosterone phloretin phosphate

* Dihydrotestosterone derivatives: 1-Androstenediol
* 1-Androstenedione
* 1-Androsterone (1-andro, 1-DHEA)
* 1-Testosterone
* 3α-Androstanediol
* 5α-Androst-2-en-17-one
* 7β-Hydroxyepiandrosterone
* 11-Ketodihydrotestosterone
* Androsterone
* Bolazine
* Bolazine capronate
* Dihydroethisterone
* Dihydroethyltestosterone
* Dihydrofluoxymesterone
* Dihydromethylandrostenediol
* Dihydrotestosterone (DHT) (androstanolone, stanolone)
* Dihydrotestosterone esters
* Drostanolone
* Drostanolone propionate
* Epiandrosterone
* Epitiostanol
* Mepitiostane
* Mesabolone
* Mesterolone
* Mesterolone cipionate
* Methyldiazinol
* Nisterime
* Nisterime acetate
* Prostanozol
* Stenbolone
* Stenbolone acetate
* Testifenon (testiphenon, testiphenone)

* 19-Nortestosterone derivatives: 7α-Methyl-19-norandrostenedione (MENT dione, trestione)
* 11β-Methyl-19-nortestosterone
* 11β-Methyl-19-nortestosterone dodecylcarbonate
* 19-Nor-5-androstenediol
* 19-Nor-5-androstenedione
* 19-Nordehydroepiandrosterone
* Bolandiol
* Bolandiol dipropionate
* Bolandione (19-nor-4-androstenedione)
* Bolmantalate (nandrolone adamantoate)
* Dienedione
* Dienolone
* Dimethandrolone
* Dimethandrolone buciclate
* Dimethandrolone dodecylcarbonate
* Dimethandrolone undecanoate
* LS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate)
* Methoxydienone (methoxygonadiene)
* Nandrolone
* Nandrolone esters
* Norclostebol
* Norclostebol acetate
* Normethandrone (methylestrenolone, normethisterone)
* Oxabolone
* Oxabolone cipionate (oxabolone cypionate)
* Trenbolone
* Trenbolone acetate
* Trenbolone enanthate
* Trenbolone hexahydrobenzylcarbonate
* Trenbolone undecanoate
* Trendione
* Trestolone (MENT)
* Trestolone acetate
* Trestolone enanthate

* Dihydrotestosterone and 19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
* 5α-Dihydronandrolone
* 5α-Dihydronorethandrolone
* 5α-Dihydronorethisterone
* 5α-Dihydronormethandrone
* 5α-Dihydrotrestolone
* 19-Norandrosterone

* 17α-Alkylated testosterone derivatives: Bolasterone
* Calusterone
* Chlorodehydromethylandrostenediol (CDMA)
* Chlorodehydromethyltestosterone (CDMT)
* Chloromethylandrostenediol (CMA)
* Enestebol
* Ethyltestosterone
* Fluoxymesterone
* Formebolone
* Hydroxystenozole
* Metandienone (methandrostenolone)
* Methandriol (methylandrostenediol)
* Methandriol bisenanthoyl acetate
* Methandriol diacetate
* Methandriol dipropionate
* Methandriol propionate
* Methylclostebol (chloromethyltestosterone)
* Methyltestosterone (+esterified estrogens)
* Methyltestosterone 3-hexyl ether
* Oxymesterone
* Penmesterol
* Tiomesterone

* 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
* Desoxymethyltestosterone
* Furazabol
* Mebolazine (dimethazine)
* Mestanolone
* Metenolone
* Metenolone acetate
* Metenolone enanthate
* Methasterone
* Methyl-1-testosterone
* Methylepitiostanol
* Methylstenbolone
* Oxandrolone
* Oxymetholone
* Stanozolol

* 17α-Alkylated 19-nortestosterone derivatives: Bolenol
* Dimethyldienolone
* Dimethyltrienolone
* Ethyldienolone
* Ethylestrenol
* Methyldienolone
* Methylhydroxynandrolone (MOHN, MHN)
* Metribolone
* Mibolerone
* Norboletone
* Norethandrolone
* Propetandrol
* RU-2309
* Tetrahydrogestrinone

* 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
* Vinyltestosterone

* 17α-Ethynyltestosterone derivatives: Δ4-Tibolone
* Danazol
* Desogestrel
* Ethisterone (ethynyltestosterone)
* Etonogestrel
* Etynodiol
* Etynodiol diacetate
* Gestodene
* Gestrinone
* Levonorgestrel
* Levonorgestrel esters (e.g., levonorgestrel butanoate)
* Lynestrenol
* Lynestrenol phenylpropionate
* Norethisterone
* Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate)
* Norgestrel
* Norgestrienone
* Quingestanol
* Quingestanol acetate
* Tibolone

* Progesterone derivatives: Medroxyprogesterone acetate
* Megestrol acetate

* Others/unsorted: 3-Keto-5α-abiraterone
* 5α-Androstane
* Alternariol
* Cl-4AS-1
* Drupanol
* ZM-182345

|

Mixed
(SARMs)|

* Nonsteroidal: 198RL26
* ACP-105
* AC-262536
* Acetothiolutamide
* Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
* BMS-564929
* DTIB
* Enobosarm (ostarine, MK-2866, GTx-024, S-22)
* FTBU-1
* GSK-4336A
* GSK-8698
* LG-121071 (LGD-121071)
* LGD-2226
* LGD-2941 (LGD-122941)
* LGD-3303
* LGD-4033
* JNJ-26146900
* JNJ-28330835
* JNJ-37654032
* ORM-11984
* R-1
* RAD140
* RU-59063
* S-1
* S-23
* S-40503
* S-101479
* Triclosan

* Steroidal: EM-9017
* MK-0773
* TFM-4AS-1
* YK-11

Antagonists|

* Steroidal: 7α-Thioprogesterone
* 7α-Thiospironolactone
* 7α-Thiomethylspironolactone
* 11α-Hydroxyprogesterone
* 15β-Hydroxycyproterone acetate
* Abiraterone
* Abiraterone acetate
* Allyltestosterone
* Benorterone
* BOMT
* Canrenoic acid
* Canrenone
* Chlormadinone acetate
* Clascoterone
* Clometerone
* Cyproheptadine
* Cyproterone
* Cyproterone acetate
* Delanterone
* Delmadinone acetate
* Dicirenone
* Dienogest
* Drospirenone
* DU-41165
* Edogestrone
* EM-4350
* EM-5854
* EM-5855
* EM-6537
* Epitestosterone
* Galeterone
* Guggulsterone
* Medrogestone
* Megestrol acetate
* Mespirenone
* Metogest
* Mexrenone
* Mifepristone
* Nomegestrol acetate
* Nordinone
* Osaterone
* Osaterone acetate
* Oxendolone
* Potassium canrenoate
* Promegestone
* Prorenone
* Rosterolone
* RU-15328
* SC-5233 (spirolactone)
* Spironolactone
* Spirorenone
* Spiroxasone
* Topterone
* Trimegestone
* Trimethyltrienolone (R-2956)
* Zanoterone

* Nonsteroidal: 5N-Bicalutamide
* AA560
* Antarlides
* Arabilin
* Apalutamide
* Atraric acid
* AZD-3514
* Bakuchiol
* BAY-1024767
* Bicalutamide
* Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S)
* BMS-501949
* BMS-570511
* BMS-641988
* CH5137291
* Cimetidine
* Cioteronel
* Cyanonilutamide
* Darolutamide
* DDT (via metabolite p,p’-DDE)
* Dieldrin
* DIMP
* Endosulfan
* Enzalutamide
* EPI-001
* Fenarimol
* Flutamide
* Hydroxyflutamide
* Inocoterone
* Inocoterone acetate
* Ketoconazole
* Ketodarolutamide
* Lavender oil
* LG-105
* LG-120907
* LGD-1331
* Linuron
* Methiocarb
* N-Butylbenzenesulfonamide
* N-Desmethylapalutamide
* N-Desmethylenzalutamide
* Nilutamide
* ONC1-13B
* Pentomone
* PF-998425
* Phenothrin
* Prochloraz
* Procymidone
* Proxalutamide
* Ralaniten (EPI-002)
* Ralaniten acetate (EPI-506)
* RD-162
* Ro 2-7239
* Ro 5-2537
* RU-22930
* RU-56187
* RU-57073
* RU-58642
* RU-58841
* Seviteronel
* Thalidomide
* Topilutamide (fluridil)
* Valproic acid
* Vinclozolin
* YM-580
* YM-92088
* YM-175735

GPRC6A|

| Agonists|

* Cations (incl. aluminum, calcium, Gadolinium

|

See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens/anabolic steroids

* 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

* v
* t
* e

Glucocorticoid receptor modulators

GR|

| Agonists|

* Cortisol-like and related (16-unsubstituted): 3α,5α-Tetrahydrocorticosterone
* 5α-Dihydrocorticosterone
* 9α-Fluorocortisone (alfluorone)
* 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
* 11-Dehydrocorticosterone acetate
* 11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)
* Desoxycortone esters
* 11-Deoxycortisol (cortodoxone, cortexolone)
* Cortifen (cortiphen, kortifen)
* Cortodoxone acetate
* 21-Deoxycortisol
* Δ7-Prednisolone
* Δ7-Prednisolone 21-acetate
* Amebucort
* Chloroprednisone
* Chloroprednisone acetate
* Cloprednol
* Cloprednol acetate
* Corticosterone
* Corticosterone acetate
* Corticosterone benzoate
* Cortisol (hydrocortisone)
* Benzodrocortisone (hydrocortisone benzoate)
* Hydrocortamate (hydrocortisone diethylaminoacetate)
* Hydrocortisone esters
* Cortisone
* Cortisone acetate
* Deprodone
* Deprodone propionate
* Dichlorisone
* Dichlorisone acetate
* Dichlorisone diacetate
* Difluprednate
* Endrisone (endrysone)
* Etiprednol
* Etiprednol dicloacetate (etiprednol dichloroacetate)
* Fludrocortisone (fludrocortone)
* Fludrocortisone acetate
* Fluorometholone
* Fluorometholone acetate
* Fluperolone
* Fluperolone acetate
* Fluprednisolone
* Fluprednisolone esters
* Halopredone
* Halopredone acetate (halopredone diacetate)
* Isoflupredone (9α-fluoroprednisolone)
* Isoflupredone acetate
* Loteprednol
* Mazipredone (depersolone)
* Medrysone
* Methylprednisolone
* Methylprednisolone esters
* Prebediolone
* Prebediolone acetate
* Prednisolone
* Prednazate
* Prednazoline
* Prednicarbate (prednisolone ethylcarbonate propionate)
* Prednimustine
* Prednisolamate (prednisolone diethylaminoacetate)
* Prednisolone esters
* Prednisone
* Prednisone esters
* Pregnenolone
* Pregnenolone acetate
* Pregnenolone succinate (pregnenolone hemisuccinate)
* Resocortol
* Tipredane
* Tixocortol
* Butixocort (tixocortol butyrate)
* Butixocort propionate
* Tixocortol pivalate

* Methasones and related (16-substituted): 16α-Methyl-11-oxoprednisolone
* Alclometasone
* Alclometasone dipropionate
* Amelometasone
* Beclometasone (beclomethasone)
* Beclometasone esters
* Betamethasone (betametasone)
* Betamethasone esters
* Cortobenzolone (betamethasone salicylate)
* Ciclometasone (ciclomethasone, cyclomethasone)
* Clobetasol
* Clobetasol propionate
* Clobetasone
* Clobetasone butyrate
* Clocortolone
* Clocortolone esters
* Cloticasone
* Cloticasone propionate
* Cormetasone (cormethasone)
* Cormetasone acetate
* Descinolone
* Desoximetasone (desoxymethasone)
* Dexamethasone (dexametasone)
* Dexamethasone esters
* Diflorasone
* Diflorasone diacetate
* Diflucortolone
* Diflucortolone pivalate
* Diflucortolone valerate
* Dimesone
* Dimesone acetate
* Doxibetasol (doxybetasol)
* Fluclorolone
* Flumetasone (flumethasone)
* Flumetasone acetate
* Flumetasone pivalate
* Fluocinolone
* Fluocortin
* Fluocortin butyl (fluocortin butylate)
* Fluocortolone
* Fluocortolone esters
* Fluprednidene (fluprednylidene)
* Fluprednidene acetate
* Fluticasone
* Fluticasone furoate
* Fluticasone propionate
* Halocortolone
* Halometasone
* Icometasone
* Icometasone enbutate (icometasone butyrate acetate)
* Isoprednidene
* Locicortolone (locicortone)
* Locicortolone dicibate (locicortone dicibate)
* Meclorisone
* Meclorisone dibutyrate
* Meprednisone (methylprednisone)
* Meprednisone acetate
* Meprednisone hydrogen succinate (methylprednisone hemisuccinate)
* Mometasone
* Mometasone furoate
* Paramethasone
* Paramethasone acetate
* Paramethasone disodium phosphate
* Paramethasone phosphate
* Prednylidene
* Prednylidene diethylaminoacetate
* Rimexolone
* Ticabesone
* Ticabesone propionate
* Timobesone
* Timobesone acetate
* Triamcinolone
* Triamcinolone diacetate
* Ulobetasol (halobetasol)
* Ulobetasol propionate
* Vamorolone

* Cyclic ketals (16,17-cyclized): Acrocinonide (triamcinolone acroleinide)
* Amcinafal (triamcinolone pentanonide)
* Amcinafide (triamcinolone acetophenide)
* Amcinonide (triamcinolone acetate cyclopentanonide)
* Budesonide
* Ciclesonide
* Cicortonide
* Deflazacort (azacort)
* Descinolone acetonide
* Desonide (hydroxyprednisolone acetonide)
* Desonide disodium phosphate
* Desonide pivalate
* Dexbudesonide
* Drocinonide
* Drocinonide phosphate
* Fluazacort
* Fluclorolone acetonide (flucloronide)
* Fludroxycortide (flurandrenolone, flurandrenolide)
* Flumoxonide
* Flunisolide
* Flunisolide acetate
* Fluocinolone acetonide
* Ciprocinonide (fluocinolone acetonide cyclopropylcarboxylate)
* Fluocinonide (fluocinolide, fluocinolone acetonide acetate)
* Procinonide (fluocinolone acetonide propionate)
* Formocortal
* Halcinonide
* Itrocinonide
* Rofleponide
* Rofleponide palmitate
* Tralonide
* Triamcinolone acetonide
* Flupamesone (triamcinolone acetonide metembonate)
* Triamcinolone acetonide esters
* Triamcinolone aminobenzal benzamidoisobutyrate (TBI-PAB)
* Triclonide

* Others/atypical (other expanded steroid ring systems, homosteroids, and non-pregnane steroids): Cortisuzol
* Cortivazol
* Domoprednate
* Naflocort
* Nicocortonide
* Nicocortonide acetate
* Nivacortol (nivazol)
* Oxisopred
* RU-26988
* RU-28362

* Non-corticosteroids with some glucocorticoid activity: 15β-Hydroxycyproterone acetate
* 17α-Hydroxyprogesterone
* Bromoketoprogesterone
* Chlormadinone acetate
* Cyproterone
* Cyproterone acetate
* Danazol
* Delmadinone acetate
* Desogestrel
* DU-41165
* Etonogestrel
* Flugestone
* Flugestone acetate (flurogestone acetate)
* Fluoromedroxyprogesterone acetate
* Fluoxymesterone
* Gestodene
* Medrogestone
* Medroxyprogesterone acetate
* Megestrol acetate
* Metribolone
* Norgestomet
* Osaterone acetate
* Progesterone
* Promegestone
* RU-2309
* Quingestrone
* Segesterone acetate (nestorone)
* Tetrahydrogestrinone

* Nonsteroidal glucocorticoids: AZD-5423
* GSK-9027

|

Mixed
(SEGRMs)|

* Dagrocorat
* Fosdagrocorat
* Mapracorat

Antagonists|

* 7α-Hydroxy-DHEA
* 17α-Methylprogesterone
* Aglepristone
* Asoprisnil
* Asoprisnil ecamate
* C108297
* C113176
* CORT-108297
* Cyproterone acetate
* Exicorilant (CORT-125281)
* Guggulsterone
* Ketoconazole
* Lilopristone
* LLY-2707
* Metapristone (RU-42633)
* Miconazole
* Mifepristone (RU-486)
* Miricorilant (CORT-118335)
* Onapristone
* ORG-34116
* ORG-34517 (SCH-900636)
* ORG-34850
* Pregnenolone 16α-carbonitrile
* Relacorilant (CORT-125134)
* RTI 3021–012
* RTI 3021–022
* Telapristone
* Tibolone
* Toripristone
* Ulipristal acetate

Others|

* Antisense oligonucleotides: IONIS-GCCRRx (ISIS-426115)

See also
Receptor/signaling modulators
Glucocorticoids and antiglucocorticoids
Mineralocorticoid receptor modulators
List of corticosteroids

* v
* t
* e

Mineralocorticoid receptor modulators

MR|

| Agonists|

* 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
* 11-Dehydrocorticosterone acetate
* 11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)
* Desoxycortone esters
* 11-Deoxycortisol (cortodoxone, cortexolone)
* Cortifen (cortiphen, kortifen)
* Cortodoxone acetate
* 11β-Hydroxyprogesterone
* 16α,18-Dihydroxy-11-deoxycorticosterone
* 17α-Hydroxyaldosterone
* 18-Hydroxy-11-deoxycorticosterone
* 19-Norprogesterone
* Aldosterone
* Corticosterone
* Corticosterone acetate
* Corticosterone benzoate
* Cortisol (hydrocortisone)
* Benzodrocortisone (hydrocortisone benzoate)
* Hydrocortamate (hydrocortisone diethylaminoacetate)
* Hydrocortisone esters
* Cortisone
* Cortisone acetate
* Fludrocortisone (fludrocortone)
* Fludrocortisone acetate
* Mometasone
* Mometasone furoate
* Prednisolone
* Prednazate
* Prednazoline
* Prednicarbate (prednisolone ethylcarbonate propionate)
* Prednimustine
* Prednisolamate (prednisolone diethylaminoacetate)
* Prednisolone esters
* Prednisone
* Prednisone esters

|

Antagonists|

* Steroidal: 6β-Hydroxy-7α-thiomethylspironolactone
* 7α-Acetylthio-17α-hydroxyprogesterone
* 7α-Thiomethylspironolactone (SC-26519)
* 7α-Thioprogesterone (SC-8365)
* 7α-Thiospironolactone (SC-24813)
* 16α-Hydroxyprogesterone
* 17α-Hydroxyprogesterone (hydroxyprogesterone)
* 18-Deoxyaldosterone
* 18,19-Dinorprogesterone
* Canrenoate potassium (potassium canrenoate)
* Canrenoic acid (canrenoate)
* Canrenone (canrenoate y-lactone)
* Dicirenone
* Dimethisterone
* Drospirenone
* Dydrogesterone
* Eplerenone
* Gestodene
* Guggulsterone
* Hydroxyprogesterone caproate
* Medrogestone
* Mespirenone
* Metribolone
* Mexrenoate potassium
* Mexrenoic acid (mexrenoate)
* Mexrenone
* Oxprenoic acid (oxprenoate)
* Oxprenoate potassium (RU-28318)
* Pregnenolone
* Progesterone
* Prorenoate potassium
* Prorenoic acid (prorenoate)
* Prorenone
* RO-14-9012
* RU-26752
* SC-5233 (spirolactone)
* SC-8109
* SC-11927 (CS-1)
* SC-19886
* SC-27169
* Spirorenone
* Spironolactone
* Spiroxasone
* Tibolone
* Trimegestone
* ZK-91587
* ZK-97894

* Nonsteroidal: Amlodipine
* Apararenone
* Benidipine
* BR-4628
* Esaxerenone
* Felodipine
* Finerenone
* Miricorilant (CORT-118335)
* Nifedipine
* Nimodipine
* Nitrendipine
* PF-03882845
* SM-368229

See also
Receptor/signaling modulators
Mineralocorticoids and antimineralocorticoids
Glucocorticoid receptor modulators
List of corticosteroids

* v
* t
* e

Progesterone receptor modulators

PR|

| Agonists|

* Progesterone derivatives: 3β-Dihydroprogesterone
* 5α-Dihydroprogesterone
* 9α-Bromo-11-ketoprogesterone
* 11-Dehydroprogesterone
* 11-Deoxycorticosterone
* 16α-Hydroxyprogesterone
* 20α-Dihydroprogesterone
* 20β-Dihydroprogesterone
* Dimepregnen
* Diosgenin
* P1-185
* Progesterone
* Progesterone 3-acetyl enol ether
* Quingestrone

* Retroprogesterone derivatives: 20α-Dihydrodydrogesterone
* 20α-Dihydrotrengestone
* DU-41164
* DU-41165
* Dydrogesterone
* Retroprogesterone
* Ro 6-3129
* Trengestone

* 17α-Substituted progesterone derivatives: 6α-Methyl-17α-bromoprogesterone
* 15β-Hydroxycyproterone acetate
* 16-Methylene-17α-hydroxyprogesterone acetate
* 17α-Bromoprogesterone
* 17α-Hydroxyprogesterone (hydroxyprogesterone)
* 17α-Methylprogesterone
* Acetomepregenol (mepregenol diacetate)
* Algestone
* Algestone acetonide
* Algestone acetophenide
* Anagestone
* Anagestone acetate
* Bromethenmadinone
* Bromethenmadinone acetate
* Butagest (buterol)
* Chlormadinone
* Chlormadinone acetate
* Chlormadinone caproate
* Chlormethenmadinone
* Chlormethenmadinone acetate
* Cismadinone
* Cismadinone acetate
* Clogestone
* Clogestone acetate
* Clomegestone
* Clomegestone acetate
* Cymegesolate
* Cyproterone acetate
* Delmadinone
* Delmadinone acetate
* Edogestrone
* Flugestone
* Flugestone acetate
* Fluorometholone
* Fluorometholone acetate
* Flumedroxone
* Flumedroxone acetate
* Fluoromedroxyprogesterone acetate
* Gestaclone
* Haloprogesterone
* Hydromadinone
* Hydromadinone acetate
* Hydroxyprogesterone acetate
* Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)
* Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)
* Hydroxyprogesterone heptanoate benzilic acid hydrazone
* Mecigestone (pentarane B)
* Medrogestone
* Medroxyprogesterone
* Medroxyprogesterone acetate
* Medroxyprogesterone caproate
* Megestrol
* Megestrol acetate
* Megestrol caproate
* Melengestrol
* Melengestrol acetate
* Methenmadinone
* Methenmadinone acetate
* Methenmadinone caproate
* Mometasone
* Mometasone furoate
* Osaterone
* Osaterone acetate
* Pentagestrone
* Pentagestrone acetate
* Pentarane A
* Proligestone

* 19-Norprogesterone derivatives: 17α-Methyl-19-norprogesterone
* 18-Methylsegesterone acetate
* 19-Norprogesterone
* Amadinone
* Amadinone acetate
* Demegestone
* Fluoro ethyl norprogesterone
* Fluoro furanyl norprogesterone
* Gestadienol
* Gestadienol acetate
* Gestonorone acetate (gestronol acetate)
* Gestonorone caproate (gestronol hexanoate)
* Gestronol (gestonorone)
* Nomegestrol
* Nomegestrol acetate
* Norgestomet
* ORG-2058
* Oxogestone
* Oxogestone phenpropionate (xinogestone)
* Promegestone
* Segesterone
* Segesterone acetate (nestorone)
* Trimegestone

* Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
* 6,6-Difluoronorethisterone acetate
* 17α-Allyl-19-nortestosterone
* Allylestrenol
* Altrenogest
* Chloroethynylnorgestrel
* Cingestol
* Danazol
* Desogestrel
* Dienogest
* Ethisterone
* Ethynerone
* Etonogestrel
* Etynodiol
* Etynodiol diacetate
* Gestodene
* Gestrinone
* Levonorgestrel
* Levonorgestrel esters (e.g., levonorgestrel butanoate)
* Lynestrenol
* Lynestrenol phenylpropionate
* Metynodiol
* Metynodiol diacetate
* Norelgestromin
* Norethisterone (norethindrone)
* Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate)
* Noretynodrel
* Norgesterone
* Norgestimate
* Norgestrel
* Norgestrienone
* Norvinisterone
* Oxendolone
* Quingestanol
* Quingestanol acetate
* Tibolone
* Tigestol
* Tosagestin; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
* 11β-Methyl-19-nortestosterone dodecylcarbonate
* 19-Nor-5-androstenediol
* 19-Nor-5-androstenedione
* 19-Nordehydroepiandrosterone
* Bolandiol
* Bolandiol dipropionate
* Bolandione
* Dimethisterone
* Dienedione
* Dienolone
* Dimethandrolone
* Dimethandrolone buciclate
* Dimethandrolone dodecylcarbonate
* Dimethandrolone undecanoate
* Dimethyldienolone
* Dimethyltrienolone
* Ethyldienolone
* Ethylestrenol (ethylnandrol)
* Methyldienolone
* Metribolone (R-1881)
* Methoxydienone (methoxygonadiene)
* Mibolerone
* Nandrolone
* Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate)
* Norethandrolone
* Normethandrone (methylestrenolone, normethandrolone, normethisterone)
* RU-2309
* Tetrahydrogestrinone
* Trenbolone (trienolone)
* Trenbolone esters (e.g., trenbolone acetate, trenbolone enanthate)
* Trendione
* Trestolone
* Trestolone acetate

* Spirolactone derivatives: Canrenoic acid
* Canrenone
* Drospirenone
* Mespirenone
* Potassium canrenoate
* Prorenone
* SC-5233 (spirolactone)
* SC-8109
* Spironolactone
* Spirorenone

* Nonsteroidal: 3,8-Dihydrodiligustilide
* LG-2527
* LG-100128
* Riligustilide
* RWJ-26819
* RWJ-49853
* RWJ-60130
* Tanaproget
* ZM-182345

* Unknown: ORG-47241
* ORG-201745

|

Mixed
(SPRMs)|

* Steroidal: Dihydroethisterone
* 5α-Dihydrolevonorgestrel
* 5α-Dihydronorethisterone
* Asoprisnil
* Asoprisnil ecamate
* Guggulsterone
* J1042
* LG-120838
* Metapristone (RU-42633)
* Mifepristone (RU-486)
* ORF-9371
* ORF-9326
* ORG-31710
* ORG-33628
* RMI-12936
* Telapristone
* Ulipristal acetate
* Vilaprisan
* ZK-137316

* Nonsteroidal: Apigenin
* Kaempferol
* LG-120920
* Naringenin
* PRA-910
* Syringic acid

Antagonists|

* Steroidal: Aglepristone
* Lilopristone
* Lonaprisan
* Onapristone
* ORG-31710
* ORG-31806
* ORG-33628
* RTI 3021–022
* Toripristone
* Zanoterone

* Nonsteroidal: Darolutamide
* LG-001447
* LG-100127
* LG-100128
* LG-120830
* LG-121046
* Valproic acid
* ZM-150271
* ZM-172406

mPR
(PAQR)|

| Agonists|

* 5α-Dihydroprogesterone
* 5β-Dihydroprogesterone
* 11-Deoxycortisone (21-hydroxyprogesterone)
* 11-Deoxycortisol (17α,21-dihydroxyprogesterone)
* 17α-Hydroxyprogesterone
* Allopregnanolone
* Mifepristone
* Pregnenolone
* Progesterone

|

Antagonists|

* Mifepristone

See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens

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*[v]: View this template
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*[AR]: Androgen receptor
*[SARMs]: Selective androgen receptor modulator
*[GPRC6A]: G protein-coupled receptor family C group 6 member A
*[ER]: Estrogen receptor
*[SERMs]: Selective estrogen receptor modulators
*[GPER]: G protein-coupled estrogen receptor
*[GR]: Glucocorticoid receptor
*[SEGRMs]: Selective glucocorticoid receptor agonists
*[MR]: Mineralocorticoid receptor
*[PR]: Progesterone receptor
*[SPRMs]: Selective progesterone receptor modulators
*[mPR]: Membrane progesterone receptor
*[PAQR]: Progestin and adipoQ receptor