Norgestimate
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Clinical data |
AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
MedlinePlus |
a601050 |
ATC code |
- G03AA11 (WHO) G03FA13 (WHO) (only combinations with estrogens)
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Legal status |
Legal status |
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Pharmacokinetic data |
Biological half-life |
12–30 hours |
Identifiers |
IUPAC name
- (13-Ethyl-17-ethynyl-3-hydroxyimino- 1,2,6,7,8,9,10,11,12,14,15,16- dodecahydrocyclopenta[a]phenanthren-17-yl) acetate
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Synonyms |
ORF-10131 |
CAS Number |
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PubChem CID |
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IUPHAR/BPS |
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DrugBank |
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ChemSpider |
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UNII |
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KEGG |
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ChEBI |
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ChEMBL |
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Chemical and physical data |
Formula |
C23H31NO3 |
Molar mass |
369.497 g/mol |
3D model (Jmol) |
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SMILES
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O=C(O[C@@]2(C#C)CC[C@H]1[C@H]4[C@H](CC[C@@]12CC)[C@@H]3/C(=C\C(=N\O)CC3)CC4)C
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InChI
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InChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1 Y
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Key:KIQQMECNKUGGKA-NMYWJIRASA-N Y
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NY (what is this?) (verify) |
Not to be confused with norgestomet.
Norgestimate (INN, USAN, BAN) (brand names Ortho-Cyclen, Ortho Tri-Cyclen, Previfem, Sprintec, Prefest, others) is a steroidal progestin of the 19-nortestosterone group that is used in combination with ethinylestradiol as an oral contraceptive and in combination with estradiol in menopausal hormone replacement therapy.[1] It is a prodrug, mainly of norelgestromin, but also of levonorgestrel in small amounts.[1][2]
Contents
- 1 Pharmacology
- 2 Pharmacokinetics
- 3 Chemistry
- 4 History
- 5 See also
- 6 References
Pharmacology
Norgestimate, unlike other 19-nortestosterone derivatives such as levonorgestrel, shows high selectivity for the progesterone receptor (PR) and low androgenic activity.[1][3] Moreover, norgestimate and its main active metabolite norelgestromin do not bind to or occupy sex hormone-binding globulin (SHBG).[1] In accordance, clinical trials of norgestimate have observed minimal androgenic side effects.[3]
Androgenic activity
The relative binding affinity of norgestimate and its metabolite norelgestromin for the rat prostatic androgen receptor (AR) are 0.3% and 1.3% of those of dihydrotestosterone (DHT), respectively, whereas the respective values for levonorgestrel and gestodene are 22.0% and 15.4%.[4] Moreover, the ratios of AR to PR binding are 219 for norgestimate and 48 for its metabolite norelgestromin, whereas the ratios of progesterone, levonorgestrel, and gestodene are 93, 11, and 28, respectively.[4]
Estrogens elevate and androgens suppress hepatic production of SHBG and by extension circulating SHBG levels.[4] Clinical studies have found that norgestimate does not appreciably inhibit the increase in SHBG levels produced by ethinylestradiol, and this is in accordance with preclinical research and the notion that norgestimate is minimally androgenic.[4]
Norgestimate and norelgestromin show virtually no affinity for SHBG, unlike levonorgestrel and gestodene (which have 87% and 202% of the relative binding affinity of testosterone for SHBG, respectively) but similarly to progesterone.[4]
Pharmacokinetics
Norgestimate acts as a prodrug to norelgestromin (17β-deacetylnorgestimate or levonorgestrel 3-oxime), the primary active metabolite, and to a lesser extent to levonorgestrel (~22% of an administered dose; deacetylation of norgestimate occurs in the intestines and the liver), as well as to levonorgestrel 17β-acetate in very small quantities.[1][5][6]
Chemistry
Norgestimate is also known as norgestrel 17β-acetate 3-oxime (or simply norgestrel acetate oxime) or as 17α-ethynyl-18-methyl-19-nortestosterone 3-oxime 17β-acetate, and is the 3-oxime, 17β-acetate ester of norgestrel.
History
Norgestimate was introduced in 1986.[7]
See also
- Desogestrel
- Norethisterone acetate oxime
References
- ^ a b c d e Thomas L. Lemke; David A. Williams (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1316–. ISBN 978-0-7817-6879-5.
- ^ Tommaso Falcone; William W. Hurd (2007). Clinical Reproductive Medicine and Surgery. Elsevier Health Sciences. pp. 389–. ISBN 0-323-03309-1.
- ^ a b Chapdelaine A, Desmarais JL, Derman RJ (1989). "Clinical evidence of the minimal androgenic activity of norgestimate". Int. J. Fertil. 34 (5): 347–52. PMID 2571595.
- ^ a b c d e Phillips A, Hahn DW, McGuire JL (1992). "Preclinical evaluation of norgestimate, a progestin with minimal androgenic activity". Am. J. Obstet. Gynecol. 167 (4 Pt 2): 1191–6. PMID 1415445.
- ^ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. World Health Organization. pp. 150–151. ISBN 978-92-832-1291-1.
- ^ Stanczyk FZ (2002). "Pharmacokinetics and potency of progestins used for hormone replacement therapy and contraception". Rev Endocr Metab Disord. 3 (3): 211–24. doi:10.1023/A:1020072325818. PMID 12215716.
- ^ Benno Clemens Runnebaum; Thomas Rabe; Ludwig Kiesel (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 13–. ISBN 978-3-642-73790-9.
Progestogens and antiprogestogens
|
|
Progestogens
(and progestins) |
Progesterone |
- Progesterone
- Quingestrone
|
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Retroprogesterone |
- Dydrogesterone
- Trengestone
|
|
17α-Hydroxyprogesterone
(and closely related) |
- Acetomepregenol (mepregenol diacetate)
- Algestone
- Algestone acetophenide (dihydroxyprogesterone acetophenide)
- Anagestone acetate
- Chlormadinone acetate
- Cyproterone acetate
- Delmadinone acetate
- Flugestone acetate (flurogestone acetate)
- Flumedroxone acetate
- Hydroxyprogesterone
- Hydroxyprogesterone acetate
- Hydroxyprogesterone caproate
- Hydroxyprogesterone heptanoate
- Medroxyprogesterone
- Medroxyprogesterone acetate#
- Megestrol acetate
- Melengestrol acetate
- Osaterone acetate
- Pentagestrone acetate
- Other 17α-substitutions: Haloprogesterone
- Medrogestone
- Proligestone
|
|
19-Norprogesterone
(including 17α-substituted) |
- Demegestone
- Gestonorone caproate (gestronol hexanoate)
- Nomegestrol acetate
- Norgestomet
- Promegestone
- Segesterone acetate (nestorone)
- Trimegestone
|
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17α-Ethynyltestosterone |
- Danazol
- Dimethisterone
- Ethisterone
|
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19-Nortestosterone
(including 17α-substituted) |
- Estranes: Etynodiol diacetate
- Gestrinone
- Lynestrenol
- Norethisterone (norethindrone)#
- Norethisterone acetate
- Norethisterone enanthate
- Noretynodrel
- Norgestrienone
- Quingestanol acetate
- Tibolone
- Gonanes: Desogestrel
- Dienogest
- Etonogestrel
- Gestodene
- Levonorgestrel#
- Norelgestromin
- Norgestimate
- Norgestrel
- Others: Allylestrenol
- Altrenogest
- Norgesterone
- Normethandrone (methylestrenolone)
- Norvinisterone
- Oxendolone
|
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17α-Spirolactosteroid |
- Canrenone
- Drospirenone
- Potassium canrenoate
- Spironolactone
|
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Others |
- Anabolic steroids (e.g., nandrolone esters, trenbolone esters, norethandrolone, normethandrone, propetandrol, others)
|
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SPRMs |
- Asoprisnil†
- Telapristone§
- Ulipristal acetate
|
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Antiprogestogens |
- Aglepristone
- Mifepristone
- Valproic acid
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
See also: Androgens and antiandrogens • Estrogens and antiestrogens • Glucocorticoids and antiglucocorticoids • Mineralocorticoids and antimineralocorticoids • Gonadotropins and GnRH
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Androgens and antiandrogens
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Androgens
(incl. AAS) |
AR agonists |
- Testosterone derivatives: Androstenediol dipropionate
- Boldenone undecylenate
- Clostebol
- Clostebol acetate
- Clostebol caproate
- Clostebol propionate
- Cloxotestosterone acetate
- Dehydroepiandrosterone (DHEA) (androstenolone, prasterone)
- DHEA enanthate (prasterone enanthate)
- Quinbolone
- Testosterone#
- Testosterone acetate
- Testosterone capropate
- Testosterone cyclohexylpropionate
- Testosterone cypionate
- Testosterone decanoate
- Testosterone enanthate
- Testosterone ester mixtures (Deposterona, Omnadren, Sustanon)
- Testosterone furoate
- Testosterone hexahydrobenzoate
- Testosterone hexahydrobenzylcarbonate
- Testosterone hexyloxyphenylpropionate
- Testosterone isobutyrate
- Testosterone isocaproate
- Testosterone ketolaurate
- Testosterone nicotinate
- Testosterone phenylacetate
- Testosterone phenylpropionate
- Testosterone phosphate
- Testosterone propionate
- Testosterone undecanoate
- Testosterone valerate
- Dihydrotestosterone derivatives: Bolazine capronate
- Dihydrotestosterone (DHT) (androstanolone, stanolone)
- Dihydrotestosterone acetate
- Dihydrotestosterone benzoate
- Dihydrotestosterone butyrate
- Dihydrotestosterone enanthate
- Dihydrotestosterone formate
- Dihydrotestosterone propionate
- Dihydrotestosterone valerate
- Drostanolone propionate (dromostanolone propionate)
- Epitiostanol
- Mepitiostane
- Mesterolone
- Metenolone acetate (methenolone acetate)
- Metenolone enanthate (methenolone enanthate)
- Stenbolone acetate
- 19-Nortestosterone derivatives: Bolandiol dipropionate
- Nandrolone caproate
- Nandrolone cypionate
- Nandrolone cyclohexanecarboxylate
- Nandrolone cyclohexylpropionate
- Nandrolone decanoate
- Nandrolone furylpropionate
- Nandrolone hexyloxyphenylpropionate
- Nandrolone hydrogen succinate
- Nandrolone laurate
- Nandrolone phenylpropionate
- Nandrolone propionate
- Nandrolone sulfate sodium
- Nandrolone undecanoate
- 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
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Progonadotropins |
- Antiestrogens (e.g., tamoxifen, clomifene)
- GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
- Gonadotropins (e.g., LH, hCG)
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|
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Antiandrogens |
AR antagonists |
- Steroidal: Abiraterone acetate
- Canrenone
- Chlormadinone acetate
- Cyproterone acetate
- Dienogest
- Drospirenone
- Medrogestone
- Megestrol acetate
- Nomegestrol acetate
- Osaterone acetate
- Oxendolone
- Potassium canrenoate
- Spironolactone
- Non-steroidal: Apalutamide†
- Bicalutamide
- Cimetidine
- Darolutamide†
- Enzalutamide
- Flutamide
- Ketoconazole
- Nilutamide
- Seviteronel†
- Topilutamide (fluridil)
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Steroidogenesis
inhibitors |
5α-Reductase |
- Alfatradiol
- Dutasteride
- Epristeride
- Finasteride
- Saw palmetto extract
|
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Others |
- Abiraterone acetate
- Aminoglutethimide
- Bifluranol
- Cyproterone acetate
- Flutamide
- Ketoconazole
- Nilutamide
- Seviteronel†
- Spironolactone
|
|
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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)
|
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Others |
- Androstenedione immunogens: Androvax (androstenedione albumin)
- Ovandrotone albumin (Fecundin)
|
|
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
See also: Estrogens and antiestrogens • Progestogens and antiprogestogens • Glucocorticoids and antiglucocorticoids • Mineralocorticoids and antimineralocorticoids • Gonadotropins and GnRH
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Progesterone receptor modulators
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PR |
Agonists
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Mixed (SPRMs)
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- Apigenin
- Asoprisnil
- Asoprisnil ecamate
- Guggulsterone
- Kaempferol
- J1042
- LG-120838
- Naringenin
- PRA-910
- Syringic acid
- Telapristone
- Antagonistic: Mifepristone
- ORG-31710
- ORG-33628
- Ulipristal acetate
- ZK-137316
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Antagonists
|
- Aglepristone
- LG-100127
- LG-100128
- Lilopristone
- Lonaprisan
- Onapristone
- Toripristone
- Valproic acid
- Vilaprisan
- Zanoterone
- ZM-150271
- ZM-172406
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|
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mPRs
(PAQRs) |
Agonists
|
- 5α-Dihydroprogesterone
- 5β-Dihydroprogesterone
- 11-Deoxycortisone (21-hydroxyprogesterone)
- 11-Deoxycortisol (17α,21-dihydroxyprogesterone)
- 17α-Hydroxyprogesterone
- Allopregnanolone
- Mifepristone
- Pregnenolone
- Progesterone
|
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Antagonists
|
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See also: Receptor/signaling modulators • Androgenics • Estrogenics • Glucocorticoidics • Mineralocorticoidics • Steroid metabolism modulators • List of progestogens
|
Androgen receptor modulators
|
|
AR |
Agonists
|
- Testosterone derivatives: 4-Androstenediol
- 4-Dehydroepiandrosterone (4-DHEA)
- 4-Hydroxytestosterone
- 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
- 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#
- Testosterone acetate
- Testosterone acetate butyrate
- Testosterone acetate propionate
- Testosterone benzoate
- Testosterone butyrate
- Testosterone buciclate
- Testosterone capropate
- Testosterone cyclohexylpropionate
- Testosterone cypionate
- Testosterone decanoate
- Testosterone diacetate
- Testosterone dipropionate
- Testosterone enanthate
- Testosterone enanthate benziloylhydrazone
- Testosterone formate
- Testosterone furoate
- Testosterone hexahydrobenzoate
- Testosterone hexahydrobenzylcarbonate
- Testosterone hexyloxyphenylpropionate
- Testosterone isobutyrate
- Testosterone isocaproate
- Testosterone isovalerate
- Testosterone ketolaurate
- Testosterone nicotinate
- Testosterone palmitate
- Testosterone phenylacetate
- Testosterone phenylbutyrate
- Testosterone phenylpropionate
- Testosterone phosphate
- Testosterone propionate
- Testosterone stearate
- Testosterone sulfate
- Testosterone undecanoate
- Testosterone valerate
- 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
- Dihydrotestosterone (androstanolone, stanolone)
- Dihydrotestosterone acetate
- Dihydrotestosterone benzoate
- Dihydrotestosterone butyrate
- Dihydrotestosterone enanthate
- Dihydrotestosterone formate
- Dihydrotestosterone propionate
- Dihydrotestosterone valerate
- Drostanolone
- Epiandrosterone
- Epitiostanol
- Mepitiostane
- Mesabolone
- Mesterolone
- Nisterime
- Prostanozol
- Stenbolone
- 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
- Bolandiol
- 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 acetate
- Nandrolone caproate
- Nandrolone cypionate
- Nandrolone cyclohexanecarboxylate
- Nandrolone cyclohexylpropionate
- Nandrolone cyclotate
- Nandrolone decanoate
- Nandrolone formate
- Nandrolone furylpropionate
- Nandrolone hexyloxyphenylpropionate
- Nandrolone hydrogen succinate
- Nandrolone laurate
- Nandrolone phenylpropionate
- Nandrolone propionate
- Nandrolone sulfate
- Nandrolone sulfate sodium
- Nandrolone undecanoate
- Norclostebol
- Normethandrone (methylestrenolone, normethisterone)
- Oxabolone
- Oxabolone cipionate (oxabolone cypionate)
- Trenbolone
- Trenbolone acetate
- Trenbolone enanthate
- Trenbolone hexahydrobenzylcarbonate
- Trestolone (MENT)
- Dihydrotestosterone and 19-nortestosterone derivatives: 5α-Dihydronandrolone
- 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
- 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
- Dimethyltrienolone (7α-methylmetribolone, 7α,17α-dimethyltrenbolone)
- Ethyldienolone
- Ethylestrenol
- Methyldienolone
- Methylhydroxynandrolone (MOHN, MHN)
- Metribolone
- Mibolerone
- Norboletone
- Norethandrolone
- Propetandrol
- Tetrahydrogestrinone
- 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
- Vinyltestosterone
- 17α-Ethynyltestosterone derivatives: Δ4-Tibolone
- Danazol
- Desogestrel
- Ethisterone (ethynyltestosterone)
- Etonogestrel
- Etynodiol
- Etynodiol diacetate
- Gestodene
- Gestrinone
- Levonorgestrel
- Levonorgestrel butanoate
- Lynestrenol
- Norethisterone
- Norethisterone acetate
- Norethisterone acetate oxime
- Norethisterone enanthate
- Norgestrel
- Norgestrienone
- Quingestanol
- Quingestanol acetate
- Tibolone
- Progesterone derivatives: Medroxyprogesterone acetate
- Others/unsorted: Cl-4AS-1
- Drupanol
- ZM-182345
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Mixed (SARMs)
|
- Non-steroidal: 198RL26
- ACP-105
- AC-262,356
- Acetothiolutamide
- Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
- BMS-564,929
- 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
- RAD140
- R-1
- R-2
- R-3
- S-1
- S-23
- S-40503
- S-101479
- Triclosan
- Steroidal: MK-0773
- TFM-4AS-1
- YK-11
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Antagonists
|
- Steroidal: 9,11-Dehydrocortexolone 17α-butyrate (CB-03-04)
- 11α-Hydroxyprogesterone
- 15β-Hydroxycyproterone acetate
- Abiraterone
- Abiraterone acetate
- Allyltestosterone
- Benorterone
- BOMT
- Canrenoic acid
- Canrenone
- Chlormadinone acetate
- Clometerone
- Cortexolone 17α-propionate (CB-03-01)
- Cyproterone
- Cyproterone acetate
- Delanterone
- Dienogest
- Drospirenone
- Edogestrone
- Epitestosterone
- Galeterone
- Guggulsterone
- Medrogestone
- Megestrol acetate
- Mespirenone
- Metogest
- Mexrenone
- Mifepristone
- Nomegestrol acetate
- Nordinone
- Osaterone
- Osaterone acetate
- Oxendolone
- Potassium canrenoate
- Prorenone
- Rosterolone
- SC-5233 (spirolactone)
- Spironolactone
- Spirorenone
- Topterone
- Trimethyltrienolone (R-2956)
- Zanoterone
- Non-steroidal: AA560
- Apalutamide
- Atraric acid
- AZD-3514
- Bakuchiol
- BAY-1024767
- Bicalutamide
- Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S)
- BMS-641,988
- Cimetidine
- Cioteronel
- Darolutamide
- DDT (via metabolite p,p’-DDE)
- Dieldrin
- DIMP
- Endosulfan
- Enzalutamide
- EPI-001
- EPI-506
- Fenarimol
- Flutamide
- Hydroxyflutamide
- Inocoterone
- Inocoterone acetate
- Ketoconazole
- Lavender oil
- LG-105
- LG-120907
- Linuron
- Methiocarb
- N-Butylbenzenesulfonamide
- N-Desmethylenzalutamide
- Nilutamide
- ONC1-13B
- ORM-15341
- Pentomone
- PF-998425
- Phenothrin
- Prochloraz
- Procymidone
- RU-22930
- RU-58642
- RU-58841
- Seviteronel
- Thalidomide
- Topilutamide (fluridil)
- Valproic acid
- Vinclozolin
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GPRC6A |
Agonists
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- Cations (incl. aluminum, calcium, gadolinium, magnesium, strontium)
- Dehydroandrosterone
- Dihydrotestosterone
- Estradiol
- L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine)
- Osteocalcin
- Testosterone
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See also: Receptor/signaling modulators • Estrogenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics • Steroid metabolism modulators • List of androgens/anabolic steroids
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