Esterified estrogens/methyltestosterone

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Esterified estrogens /
methyltestosterone
Combination of

Estrone sulfate (top) and methyltestosterone (bottom)
Esterified estrogens	Estrogen
Methyltestosterone	Androgen; Anabolic steroid
Clinical data
Trade names	Covaryx, Essian, Estratest, Menogen, Syntest
Other names	EEs/MT
Routes of administration	By mouth
Drug class	Estrogen; Androgen
ATC code	G03EA01 (WHO)
Legal status
Legal status	US: WARNING^[1]
Identifiers
CAS Number	928330-97-6

Esterified estrogens/methyltestosterone (EEs/MT), sold under brand names such as Covaryx, Eemt, Essian, Estratest, Menogen, and Syntest, is a hormonal preparation that combines esterified estrogens (EEs) with methyltestosterone (MT) in one tablet and is used in menopausal hormone therapy.^[2]

Medical uses

EEs/MT is used to treat menopausal women who suffer from hot flashes, but do not get relief from estrogen-only therapy.

Available forms

EEs/MT is sold in tablet form, with either 1.25 mg EEs/2.5 mg MT or 0.625 mg EEs/1.25 mg MT available.

Pharmacology

The product is a combination of esterified estrogens, an estrogen, and low-dose methyltestosterone, an androgen/anabolic steroid, in a single tablet.

History

EEs/MT was first marketed in the United States in 1965 by Reid-Provident Laboratories, which as 100% of Reid-Rowell, Inc. stock was acquired by the Belgian pharmaceutical company Solvay in 1986. There has been some controversy surrounding the drug in recent years as to its status with the U.S. Food and Drug Administration.

Solvay sponsored a clinical trial of EEs/MT in the United States to determine whether the product is superior to treatment with esterified estrogens tablets.

EEs/MT was supplied by Solvay. In March 2009 Solvay announced that, based on a variety of business factors, it would discontinue supplying Estratest and Estratest HS tablets, and would stop accepting orders for the product on March 31, 2009.

References

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ "Esterified Estrogens And Methyltestosterone (Oral Route)". Mayo Clinic. Mayo Foundation for Medical Education and Research.

External links

The product's web site

Medical uses

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, 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

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

Androgens and antiandrogens

Androgens
(incl. AAS)

AR agonists

Testosterone derivatives: Androstenediol dipropionate
Boldenone undecylenate
Clostebol
Clostebol acetate
Clostebol caproate
Clostebol propionate
Cloxotestosterone acetate
Prasterone (dehydroepiandrosterone, DHEA)
Prasterone enanthate (DHEA enanthate)
Prasterone sulfate (DHEA sulfate)
Quinbolone
Testosterone^#
Testosterone esters (e.g., testosterone cypionate, testosterone enanthate, testosterone propionate, testosterone undecanoate, testosterone ester mixtures (Deposterona, Omnadren, Sustanon, Testoviron Depot))

Dihydrotestosterone derivatives: Androstanolone (stanolone, dihydrotestosterone, DHT)
Androstanolone esters
Bolazine capronate
Drostanolone propionate (dromostanolone propionate)
Epitiostanol
Mepitiostane
Mesterolone
Metenolone acetate (methenolone acetate)
Metenolone enanthate (methenolone enanthate)
Stenbolone acetate

19-Nortestosterone derivatives: Bolandiol dipropionate
Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate)
Norclostebol
Norclostebol acetate
Oxabolone cipionate (oxabolone cypionate)
Trenbolone acetate
Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)

17α-Alkylated testosterone derivatives: Bolasterone
Calusterone
Chlorodehydromethyltestosterone (CDMT)
Fluoxymesterone
Formebolone
Metandienone (methandienone, methandrostenolone)
Methandriol (methylandrostenediol)
Methandriol bisenanthoyl acetate
Methandriol dipropionate
Methandriol propionate
Methyltestosterone
Methyltestosterone 3-hexyl ether
Oxymesterone
Penmesterol
Tiomesterone (thiomesterone)

17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
Furazabol
Mebolazine (dimethazine)
Mestanolone
Oxandrolone
Oxymetholone
Stanozolol

17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol
Mibolerone
Norethandrolone
Normethandrone (methylestrenolone, normethisterone)
Propetandrol (propethandrol)

17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)

17α-Ethynyltestosterone derivatives: Danazol
Gestrinone
Progestins (e.g., ethisterone (ethynyltestosterone), levonorgestrel, norgestrel, norethisterone (norethindrone), lynestrenol, norgestrienone)
Tibolone

Progesterone derivatives: Medroxyprogesterone acetate

Progonadotropins

Antiestrogens (e.g., tamoxifen, clomifene)
GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
Gonadotropins (e.g., LHTooltip luteinizing hormone, hCGTooltip human chorionic gonadotropin)

Antiandrogens

AR antagonists

Steroidogenesis
inhibitors

5α-Reductase	Alfatradiol Dutasteride Epristeride Finasteride Saw palmetto extract
Others	Abiraterone acetate +niraparib Aminoglutethimide Bifluranol Cyproterone acetate Flutamide Ketoconazole Nilutamide Seviteronel^† Spironolactone

Antigonadotropins

D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
Estrogens (e.g., bifluranol, diethylstilbestrol, estradiol, estradiol esters, ethinylestradiol, ethinylestradiol sulfonate, paroxypropione)
GnRH agonists (e.g., leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Progestogens (incl., chlormadinone acetate, cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, medroxyprogesterone acetate, megestrol acetate)

Others

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

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Androgen receptor modulators; Estrogens and antiestrogens; Progestogens and antiprogestogens; List of androgens/anabolic steroids

Pharmacodynamics

Estrogen receptor modulators

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

GPER

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 Niacin Niacinamide 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

Androgen receptor modulators

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 5α-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 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 5α-Dihydro-19-nortestosterone derivatives: 5α-Dihydronandrolone 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 5α-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-Alkylated 5α-dihydro-19-nortestosterone derivatives: 5α-Dihydronorethandrolone 5α-Dihydronormethandrone 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone) 17α-Vinyl-19-nortestosterone derivatives: Vinyltestosterone 17α-Ethynyltestosterone derivatives: Danazol Ethinylandrostenediol Ethandrostate Ethisterone (ethynyltestosterone) 5α-Dihydro-17α-ethynyltestosterone derivatives: 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol Dihydroethisterone 17α-Ethynyl-19-nortestosterone derivatives: Δ⁴-Tibolone Desogestrel 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 5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel 5α-Dihydronorethisterone Progesterone derivatives: 6α-Methylprogesterone Medroxyprogesterone acetate Megestrol acetate Others/unsorted: 3-Keto-5α-abiraterone 5α-Androstane Alternariol Cl-4AS-1 Drupanol Trilostane ZM-182345
SARMsTooltip Selective androgen receptor modulator	Nonsteroidal: 198RL26 ACP-105 AC-262,536 Acetothiolutamide Acetoxolutamide Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4) BMS-564,929 DTIB Enobosarm (ostarine, MK-2866, GTx-024, S-22) FTBU-1 GLPG-0492 GSK2881078 GSK-4336A GSK-8698 LG121071 (LGD-121071) LGD-2226 LGD-2941 (LGD-122941) LGD-3303 LGD-4033 LY305 JNJ-26146900 JNJ-28330835 JNJ-37654032 OPK-88004 (LY-2452473, TT-701) ORM-11984 PF-06260414 R-1 RU-59063 S-1 S-23 S-40503 S-101479 Vosilasarm 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 Ludaterone 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 Bavdegalutamide 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 Masofaniten Methiocarb N-Butylbenzenesulfonamide N-Desmethylapalutamide N-Desmethylenzalutamide Nilutamide ONC1-13B Pentomone PF-998425 Phenothrin Prochloraz Procymidone Proxalutamide Pyrilutamide Ralaniten (EPI-002) Ralaniten acetate (EPI-506) RD-162 Rezvilutamide 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. aluminium, calcium, gadolinium, magnesium, strontium, zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin SHBGTooltip Sex hormone-binding globulin Testosterone

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

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