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Estradiol benzoate/estradiol dienanthate/testosterone enanthate benzilic acid hydrazone

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(Redirected fromClimacteron)

Combination drug

Not to be confused withClimacteric orLactinex.

Pharmaceutical compound

EB/EDE/TEBH
Combination of
Estradiol benzoate	Estrogen
Estradiol dienanthate	Estrogen
Testosterone enanthate benzilic acid hydrazone	Androgen;Anabolic steroid
Clinical data
Trade names	Climacteron, Lactimex, Lactostat, Amenose
Other names	EB/EDE/TEBH
Routes of administration	Intramuscular injection
Identifiers
CAS Number	8063-58-9
PubChemCID	9577491

Estradiol benzoate/estradiol dienanthate/testosterone enanthate benzilic acid hydrazone (EB/EDE/TEBH), sold under the brand namesClimacteron,Lactimex,Lactostat, andAmenose, is aninjectable combination medication ofestradiol benzoate (EB), anestrogen,estradiol dienanthate (EDE), an estrogen, andtestosterone enanthate benzilic acid hydrazone (TEBH), anandrogen/anabolic steroid, which is used inmenopausal hormone therapy forperi- andpostmenopausal women and to suppresslactation inpostpartum women.^[1]^[2]^[3]^[4]^[5]^[6]^[7] Clinical studies have assessed this formulation.^[8]^[9]^[10]^[11]^[12]^[13]^[14]^[15]^[16]^[17]^[18]^[19]^[1]

Climacteron and Amenose contained 1.0 mg EB, 7.5 mg EDE, and 150 mg TEBH (69 mg freetestosterone) and was used to treatmenopausal symptoms.^[20]^[17]^[21] They were administered byintramuscular injection typically once every 6 weeks but with a range of every 4 to 8 weeks or less frequently.^[20] Climacteron was marketed inCanada in 1961 but waswithdrawn in this country in October 2005 due to risk ofendometrial hyperplasia andcancer from unopposed estrogen exposure (i.e., no concomitantprogestogen) as well as induction of supraphysiologicaltestosterone levels.^[1]^[22]^[23]

Lactimex and Lactostat contained 6 mg EB, 15 mg EDE, and 300 mg TEBH in 2 mL ofcorn oil and were used to suppress lactation.^[2]^[3]^[24]^[25] They were administered as a single intramuscular injection afterchildbirth or duringbreastfeeding.^[2] They were previously available inGermany and Canada.^[2]^[25]

Estradiol andtestosterone levels following a single intramuscular injection of EB/EDE/TEBH versus 10 mgestradiol valerate have been studied over 28 days.^[14]^[16]

v
t
e
Androgen replacement therapy formulations and dosages used in women
Route	Medication	Major brand names	Form	Dosage
Oral	Testosterone undecanoate	Andriol, Jatenzo	Capsule	40–80 mg 1x/1–2 days
	Methyltestosterone	Metandren, Estratest	Tablet	0.5–10 mg/day
	Fluoxymesterone	Halotestin	Tablet	1–2.5 mg 1x/1–2 days
	Normethandrone^a	Ginecoside	Tablet	5 mg/day
	Tibolone	Livial	Tablet	1.25–2.5 mg/day
	Prasterone (DHEA)^b	–	Tablet	10–100 mg/day
Sublingual	Methyltestosterone	Metandren	Tablet	0.25 mg/day
Transdermal	Testosterone	Intrinsa	Patch	150–300 μg/day
Transdermal	Testosterone	AndroGel	Gel, cream	1–10 mg/day
Vaginal	Prasterone (DHEA)	Intrarosa	Insert	6.5 mg/day
Injection	Testosterone propionate^a	Testoviron	Oil solution	25 mg 1x/1–2 weeks
	Testosterone enanthate	Delatestryl, Primodian Depot	Oil solution	25–100 mg 1x/4–6 weeks
	Testosterone cypionate	Depo-Testosterone, Depo-Testadiol	Oil solution	25–100 mg 1x/4–6 weeks
	Testosterone isobutyrate^a	Femandren M, Folivirin	Aqueous suspension	25–50 mg 1x/4–6 weeks
	Mixed testosterone esters	Climacteron^a	Oil solution	150 mg 1x/4–8 weeks
	Mixed testosterone esters	Omnadren, Sustanon	Oil solution	50–100 mg 1x/4–6 weeks
	Nandrolone decanoate	Deca-Durabolin	Oil solution	25–50 mg 1x/6–12 weeks
	Prasterone enanthate^a	Gynodian Depot	Oil solution	200 mg 1x/4–6 weeks
Implant	Testosterone	Testopel	Pellet	50–100 mg 1x/3–6 months
Notes:Premenopausal women produce about 230 ± 70 μgtestosterone per day (6.4 ± 2.0 mg testosterone per 4 weeks), with a range of 130 to 330 μg per day (3.6–9.2 mg per 4 weeks).Footnotes:^a = Mostly discontinued or unavailable.^b =Over-the-counter.Sources: See template.

v
t
e
Potencies and durations of natural estrogens by intramuscular injection
Estrogen	Form	Dose (mg)		Duration by dose (mg)
Estrogen	Form	EPD	CICD	Duration by dose (mg)
Estradiol	Aq. soln.	?	–	<1 d
	Oil soln.	40–60	–	1–2 ≈ 1–2 d
	Aq. susp.	?	3.5	0.5–2 ≈ 2–7 d; 3.5 ≈ >5 d
	Microsph.	?	–	1 ≈ 30 d
Estradiol benzoate	Oil soln.	25–35	–	1.66 ≈ 2–3 d; 5 ≈ 3–6 d
	Aq. susp.	20	–	10 ≈ 16–21 d
	Emulsion	?	–	10 ≈ 14–21 d
Estradiol dipropionate	Oil soln.	25–30	–	5 ≈ 5–8 d
Estradiol valerate	Oil soln.	20–30	5	5 ≈ 7–8 d; 10 ≈ 10–14 d; 40 ≈ 14–21 d; 100 ≈ 21–28 d
Estradiol benz. butyrate	Oil soln.	?	10	10 ≈ 21 d
Estradiol cypionate	Oil soln.	20–30	–	5 ≈ 11–14 d
Estradiol cypionate	Aq. susp.	?	5	5 ≈ 14–24 d
Estradiol enanthate	Oil soln.	?	5–10	10 ≈ 20–30 d
Estradiol dienanthate	Oil soln.	?	–	7.5 ≈ >40 d
Estradiol undecylate	Oil soln.	?	–	10–20 ≈ 40–60 d; 25–50 ≈ 60–120 d
Polyestradiol phosphate	Aq. soln.	40–60	–	40 ≈ 30 d; 80 ≈ 60 d; 160 ≈ 120 d
Estrone	Oil soln.	?	–	1–2 ≈ 2–3 d
Estrone	Aq. susp.	?	–	0.1–2 ≈ 2–7 d
Estriol	Oil soln.	?	–	1–2 ≈ 1–4 d
Polyestriol phosphate	Aq. soln.	?	–	50 ≈ 30 d; 80 ≈ 60 d
Notes and sources Notes: Allaqueous suspensions are ofmicrocrystalline particle size.Estradiol production during themenstrual cycle is 30–640 µg/d (6.4–8.6 mg total per month or cycle). Thevaginal epithelium maturation dosage ofestradiol benzoate orestradiol valerate has been reported as 5 to 7 mg/week. An effectiveovulation-inhibiting dose ofestradiol undecylate is 20–30 mg/month.Sources: See template.

Hormone levels with estradiol benzoate/estradiol dienanthate/testosterone enanthate benzilic acid hydrazone by intramuscular injection

Estradiol and testosterone levels after an intramuscular injection of 1 mgestradiol benzoate, 7.5 mgestradiol dienanthate, and 150 mgtestosterone enanthate benzilic acid hydrazone in oil (brand name Climacteron) in ovariectomized women.^[15] Assays were performed usingimmunoassays.^[15] Source was Sherwin (1987).^[15]
Estradiol levels after an intramuscular injection of 10 mg estradiol valerate in oil orClimacteron (1 mgestradiol benzoate, 7.5 mgestradiol dienanthate in oil) in ovariectomized women.^[14] Assays were performed usingRIA.^[14] Source was Sherwin et al. (1987).^[14]

References

[edit]

^^a ^b ^cAl-Imari L, Wolfman WL (September 2012). "The safety of testosterone therapy in women".Journal of Obstetrics and Gynaecology Canada.34 (9):859–865.doi:10.1016/S1701-2163(16)35385-3.PMID 22971455.
^^a ^b ^c ^dGeburtshilfe und Frauenheilkunde: Ergebnisse der Forschung für die Praxis. Georg Thieme Verlag. 1969. p. 387,390.[Kelly and Primose and Dodek found the following androgen-estrogen combination to be particularly effective and well-tolerated: 300 mg 3-benzilic acid hydrazone-testosterone-17-enanthate, 15 mg estradiol di-enanthate, 6 mg estradiol benzoate in 2 ml corn oil. This product is sold in Germany under the name Lactimex and has been clinically examined by us.] [...] Of 1200 postpartum patients one quarter stopped breast feeding for a variety of reasons and received an injection of Lactimex (Protina: Benzil acid hydrazon-testosteron-oenanthat 300 mg, Oestradiol-di-oenanthat 15 mg and Oestradiol-benzoate 6 mg in 1.0 ml of oil). In 76% of cases one injection was sufficient and the remaining 24% required a second injection. A second injection was required rarer if the first injection had been longer after delivery. A higher dosage of Lactimex was not necessary in cases with a preceding medical induction with intraveinous Oxytocin (Orasthin). Mothers who had been treated postpartum with methylergobasin did not as often require a second injection. No localized or generalized adverse reaction to the drug was noticed.
^^a ^bZentralblatt für Gynäkologie. J. A. Barth. 1971.The preparation Lactimex (300 mg 3-benzyl hydrazone-testosterone-17-enanthate + 15 mg estradiol-dienanthate + 6 mg estradiol benzoate in 2 ml corn oil) was injected. [...]
^Ginsburg ES (1999). "Androgen Replacement in Postmenopausal Women". In Seifer DB, Kennard EA (eds.).Menopause. Contemporary Endocrinology. Vol. 18. Humana Press. pp. 209–219.doi:10.1007/978-1-59259-246-3_13.ISBN 978-1-61737-129-5.
^Greenblatt RB, Barfield WE, Jungck EC (January 1962)."The treatment of the menopause".Canadian Medical Association Journal.86 (3):113–114.PMC 1848811.PMID 13901504.
^Seifer DB (27 July 1999). Seifer DB, Kennard EA (eds.).Menopause: Endocrinology and Management. Springer Science & Business Media. pp. 183–.doi:10.1007/978-1-59259-246-3.ISBN 978-1-59259-246-3.
^Hager HH, Kern W, Heinz P, Roth HJ (29 July 2013).Hagers Handbuch der Pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Ärzte und Medizinalbeamte: Wirkstoffgruppen II Chemikalien und Drogen (A-AL). Springer-Verlag. pp. 157–.ISBN 978-3-662-25655-8.
^Kelly MJ, Primrose T (December 1960)."Evaluation of a new preparation for the suppression of lactation".Canadian Medical Association Journal.83 (24):1240–1242.PMC 1938994.PMID 13752392.
^Schneider J, Macarthur JL, Patrick JW, Burton GV (August 1964)."The Suppression of Lactation: An Objective Study".Obstetrics and Gynecology.24 (2):294–297.PMID 14199544.
^Sherwin BB, Gelfand MM (March 1984). "Effects of parenteral administration of estrogen and androgen on plasma hormone levels and hot flushes in the surgical menopause".American Journal of Obstetrics and Gynecology.148 (5):552–557.doi:10.1016/0002-9378(84)90746-4.PMID 6367474.
^Sherwin BB, Gelfand MM (January 1985). "Differential symptom response to parenteral estrogen and/or androgen administration in the surgical menopause".American Journal of Obstetrics and Gynecology.151 (2):153–160.doi:10.1016/0002-9378(85)90001-8.PMID 3881960.
^Sherwin BB (September 1985). "Changes in sexual behavior as a function of plasma sex steroid levels in post-menopausal women".Maturitas.7 (3):225–233.doi:10.1016/0378-5122(85)90044-1.PMID 4079822.
^Sherwin BB, Gelfand MM (1985). "Sex steroids and affect in the surgical menopause: a double-blind, cross-over study".Psychoneuroendocrinology.10 (3):325–335.doi:10.1016/0306-4530(85)90009-5.PMID 3903822.S2CID 40861936.
^^a ^b ^c ^d ^eSherwin BB, Gelfand MM, Schucher R, Gabor J (February 1987). "Postmenopausal estrogen and androgen replacement and lipoprotein lipid concentrations".American Journal of Obstetrics and Gynecology.156 (2):414–419.doi:10.1016/0002-9378(87)90295-X.PMID 3826177.
^^a ^b ^c ^dSherwin BB, Gelfand MM (1987). "Individual differences in mood with menopausal replacement therapy: possible role of sex hormone-binding globulin".Journal of Psychosomatic Obstetrics & Gynecology.6 (2):121–131.doi:10.3109/01674828709016773.ISSN 0167-482X.
^^a ^bSherwin BB (1988). "Affective changes with estrogen and androgen replacement therapy in surgically menopausal women".Journal of Affective Disorders.14 (2):177–187.doi:10.1016/0165-0327(88)90061-4.PMID 2966832.
^^a ^bSherwin BB (1988). "Estrogen and/or androgen replacement therapy and cognitive functioning in surgically menopausal women".Psychoneuroendocrinology.13 (4):345–357.doi:10.1016/0306-4530(88)90060-1.PMID 3067252.S2CID 24695692.
^Sherwin BB (1994). "The Effect of Sex Steroids on Brain Mechanisms Relating to Mood and Sexuality".Comprehensive Management of Menopause. Clinical Perspectives in Obstetrics and Gynecology. Springer. pp. 327–333.doi:10.1007/978-1-4612-4330-4_31.ISBN 978-1-4612-8737-7.ISSN 0178-0328.
^Sherwin BB (April 2002)."Randomized clinical trials of combined estrogen-androgen preparations: effects on sexual functioning".Fertility and Sterility.77 (Suppl 4):S49 –S54.doi:10.1016/S0015-0282(02)03002-9.PMID 12007902.
^^a ^b"Climacteron Drug Information, Professional".Drugs.com. Archived fromthe original on 2 June 2019. Retrieved2 June 2019.
^Bundesverband der Pharmazeutischen Industrie (Germany) (1974).Rote Liste: Verzeichnis pharmazeutischer Spezialpräparate. Editio Cantor.ISBN 9783871930133.49035 В Amenose® Rp Ampullen Zus.: 1 Amp. 1 ml enth.: Benzilsäurehydrazid-N-testosteron-hydrazon-17-oenanthat 150 mg, Oestradiol-di-oenanthat 7.5 mg. Oestradiolbenzoat 1 mg in öl-Lösg. Ind.: Androgen-Oestrogen-Gemisch. Gegen Ausfallserscheinungen im Klimakterium und nach Ovarektomie. Osteoporose. Kontraind.: A 90, О 5 Dos.: Durchschnittl. alle 6 Wochen 1 Amp. im. 1 Amp. I ml 6.75 3 Amp 17.40 AP.: 10 Amp.
^Lexchin J (2010)."Drug safety and Health Canada".International Journal of Risk & Safety in Medicine.22 (1):41–53.doi:10.3233/JRS-2010-0490.
^"Discontinuation of CLIMACTERON® Injection (estradiol dienanthate ⁄ estradiol benzoate and testosterone enanthate benzilic acid hydrazone injection in corn oil)"(PDF).Sandoz Canada Inc. 23 November 2005. Archived fromthe original(PDF) on 2013-01-11. Retrieved2 June 2019.
^Vorherr H (2 December 2012).The Breast: Morphology, Physiology, and Lactation. Elsevier Science. pp. 201–.ISBN 978-0-323-15726-1.
^^a ^bCompendium of Pharmaceuticals and Specialties. Canadian Pharmaceutical Association. 1983.ISBN 978-0-919115-04-0.LACTOSTAT [...] Each 2 mL of injectable solution contains testosteorne enanthate benzilic acid hydrazone 300 mg, estradiol dienanthate 15 mg, estradiol benzoate 6 mg, benzyl alcohol 7.5% as preservative, benzyl benzoate 0.75 mg, corn oil q.s. Available in 2 mL ampuls, boxes of 25.

Estrogens andantiestrogens

Estrogens

ERTooltip Estrogen receptor agonists

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 Imlunestrant 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 andantiandrogens

Androgens
(incl.AASTooltip anabolic–androgenic steroid)

ARTooltip Androgen receptoragonists

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 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

ARTooltip Androgen receptorantagonists

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

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

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 andesters,methyltestosterone,metandienone (methandrostenolone),nandrolone andesters, 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-Phenyl-1-benzothiophene 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

Androgen receptor modulators

ARTooltip Androgen receptor

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 S42 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 metabolitep,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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