List of androgens and anabolic steroids

Last updated

Testosterone. Testosteron.svg
Testosterone.
Steroid ring system. Trimethyl steroid-nomenclature.svg
Steroid ring system.

This is a list of androgens/anabolic steroids (AAS) or testosterone derivatives. Androgen esters are mostly not included in this list. The major classes of testosterone derivatives include the following (as well as combinations thereof):

Contents

The last group consists of progestins with mostly only very weak androgenic/anabolic activity.

This article pertains to steroidal androgens; nonsteroidal androgens like the selective androgen receptor modulators (SARMs) andarine and enobosarm (ostarine) are not included here.

Testosterone derivatives

CompoundChemical nameStructureMarketed
Testosterone Androst-4-en-17β-ol-3-one Testosteron.svg
4-Hydroxytestosterone 4-Hydroxytestosterone 4-hydroxytestosterone.png
11-Ketotestosterone 11-Ketotestosterone 11-Ketotestosterone.svg
Boldenone Δ1-Testosterone Boldenone.svg
Clostebol 4-Chlorotestosterone Clostebol.svg

Prohormone-like

CompoundChemical nameStructureMarketed
4-Androstenediol 4-Androstenediol 4-Androstenediol.svg
4-Dehydroepiandrosterone (4-DHEA) 4-Dehydroepiandrosterone 3beta-Hydroxyandrost-4-en-17-one.png
5-Androstenedione 5-Androstenedione 5-Androstenedione.svg
5-Dehydroandrosterone (5-DHA) 5-Dehydroandrosterone Dehydroandrosterone.svg
11β-Hydroxyandrostenedione (11β-OHA4) 11β-Hydroxy-4-androstenedione 11b-Hydroxyandrostenedione.svg
Adrenosterone (11-ketoandrostenedione, 11-KA4) 11-Keto-4-androstenedione Adrenosterone.png
Androstenediol (5-androstenediol, A5) 5-Androstenediol 5-Androstenediol.png
Androstenedione (4-androstenedione, A4) 4-Androstenedione Androstendion.svg
Atamestane 1-Methyl-δ1-4-androstenedione Atamestane.svg
Boldione (1,4-androstadienedione) δ1-4-Androstenedione Boldione.png
Dehydroepiandrosterone (DHEA, 5-DHEA; prasterone, androstenolone) 5-Dehydroepiandrosterone Dehydroepiandrosteron.svg
Exemestane 6-Methylidene-δ1-4-androstenedione Exemestane.svg
Formestane 4-Hydroxy-4-androstenedione Formestane.svg
Plomestane 10-Propargyl-4-androstenedione Plomestane.svg

Prodrugs

Ethers

CompoundChemical nameStructureMarketed
Cloxotestosterone Testosterone 17-chloral hemiacetal ether Cloxotestosterone.svg
Quinbolone Δ1-Testosterone 17β-cyclopentenyl enol ether Quinbolone.png
Silandrone Testosterone 17β-trimethylsilyl ether Silandrone.png

Dihydrotestosterone derivatives

CompoundChemical nameStructureMarketed
Dihydrotestosterone (DHT); androstanolone, stanolone) 4,5α-Dihydrotestosterone Androstanolone.svg
1-Testosterone (dihydro-1-testosterone, dihydroboldenone) 4,5α-Dihydro-δ1-testosterone 1-testosterone.png
11-Ketodihydrotestosterone (11-KDHT) 11-Keto-4,5α-dihydrotestosterone 11-Ketodihydrotestosterone.svg
Drostanolone 2α-Methyl-4,5α-dihydrotestosterone Drostanolone.svg
Epitiostanol (epithioandrostanol) 2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone Epitiostanol.png
Mesterolone 1α-Methyl-4,5α-dihydrotestosterone Mesterolone.svg
Metenolone (methenolone, methylandrostenolone) 1-Methyl-4,5α-dihydro-δ1-testosterone Metenolone.svg
Nisterime 2α-Chloro-4,5α-dihydrotestosterone 3-O-(p-nitrophenyl)oxime Nisterime.svg
Stenbolone 2-Methyl-4,5α-dihydro-δ1-testosterone Stenbolone.svg

Prohormone-like

CompoundChemical nameStructureMarketed
1-Androsterone (1-Andro, 1-DHEA) 1-Dehydroepiandrosterone 1-Androsterone.svg
1-Androstenediol (dihydro-1-androstenediol) 1-Androstenediol (4,5α-dihydro-δ1-4-androstenediol) 1-Androstenediol.svg
1-Androstenedione (dihydro-1-androstenedione) 1-Androstenedione (4,5α-dihydro-δ1-4-androstenedione) 1-Androstenedione.svg
5α-Androst-2-en-17-one 3-Deketo-2-androstenedione (3-deketo-4,5α-dihydro-δ2-4-androstenedione) 5alpha-androst-2-ene-17-one.svg
Androsterone Androsterone Androsteron.svg
Epiandrosterone Epiandrosterone Epiandrosterone.png

Prodrugs

Ethers

CompoundChemical nameStructureMarketed
Mepitiostane 2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone 17β-(1-methoxycyclopentane) ether Mepitiostane.svg
Mesabolone 4,5α-Dihydro-δ1-testosterone 17β-(1-methoxycyclohexane) ether Mesabolone.png
Prostanozol 2'H-5α-Androst-2-eno[3,2-c]pyrazol-17β-ol 17β-tetrahydropyran ether Prostanozol.png

Azine dimers

CompoundChemical nameStructureMarketed
Bolazine (di(drostanolone) azine) 3,3-[(1E,2E)-1,2-Hydrazinediylidene]di(2α-methyl-5α-androstan-17β-ol)? Bolazine.png

19-Nortestosterone (nandrolone) derivatives

CompoundChemical nameStructureMarketed
Nandrolone (nortestosterone) 19-Nortestosterone Nandrolone.svg
11β-Methyl-19-nortestosterone (11β-MNT) 11β-Methyl-19-nortestosterone 11b-Methyl-19-nortestosterone.svg
Dienolone 19-Nor-δ9-testosterone Dienolone structure.png
Dimethandrolone 7α,11β-Dimethyl-19-nortestosterone Dimethandrolone structure.svg
Norclostebol 4-Chloro-19-nortestosterone Norclostebol.svg
Oxabolone 4-Hydroxy-19-nortestosterone Oxabolone.svg
Trenbolone (trienolone) 19-Nor-δ9,11-testosterone Trenbolone.svg
Trestolone (MENT) 7α-Methyl-19-nortestosterone Trestolone structure.svg

Prohormone-like

CompoundChemical nameStructureMarketed
7α-Methyl-19-nor-4-androstenedione (MENT dione, trestione) 7α-Methyl-19-nor-4-androstenedione 7a-Methyl-19-norandrostenedione.svg
19-Nor-5-androstenediol 19-Nor-5-androstenediol 19-Nor-5-androstenediol.svg
19-Nor-5-androstenedione 19-Nor-5-androstenedione 19-Nor-5-androstenedione.svg
19-Nordehydroepiandrosterone 19-Nor-5-dehydroepiandrosterone 19-Nordehydroepiandrosterone.svg
Bolandiol (nor-4-androstenediol) 19-Nor-4-androstenediol Bolandiol.svg
Bolandione (nor-4-androstenedione) 19-Nor-4-androstenedione 19-norandrostenedione.png
Dienedione (nor-4,9-androstadienedione) 19-Nor-δ9-4-androstenedione Dienedione.svg
Methoxydienone (methoxygonadiene) 18-Methyl-19-nor-δ2,5(10)-epiandrosterone 3-methyl ether Methoxydienone.svg
Trendione (nor-4,9,11-androstatrienedione) 19-Nor-δ9,11-4-androstenedione Trendione.svg

Prodrugs

Esters

CompoundChemical nameStructureMarketed
Bolmantalate (nandrolone adamantoate) 19-Nortestosterone 17β-adamantoate Bolmantalate.svg

17α-Alkylated testosterone derivatives

CompoundChemical nameStructureMarketed
Bolasterone 7α,17α-Dimethyltestosterone Bolasterone.png
Calusterone 7β,17α-Dimethyltestosterone Calusterone.svg
Chlorodehydromethyltestosterone (CDMT) 4-Chloro-17α-methyl-δ1-testosterone 4-Chlorodehydromethyltestosterone.png
Enestebol 4-Hydroxy-17α-methyl-δ1-testosterone Enestebol.png
Ethyltestosterone 17α-Ethyltestosterone Ethyltestosterone structure.png
Fluoxymesterone 9α-Fluoro-11β-hydroxy-17α-methyltestosterone Fluoxymesterone structure.svg
Formebolone 2-Formyl-11α-hydroxy-17α-methyl-δ1-testosterone Formebolone.png
Hydroxystenozole 17α-Methyl-2'H-androsta-2,4-dieno[3,2-c]pyrazol-17β-ol Hydroxystenozole.png
Metandienone (methandienone, methandrostenolone) 17α-Methyl-δ1-testosterone Metandienone.svg
Methylclostebol (chloromethyltestosterone) 4-Chloro-17α-methyltestosterone Methylclostebol.svg
Methyltestosterone 17α-Methyltestosterone Methyltestosterone.svg
Oxymesterone 4-Hydroxy-17α-methyltestosterone Oxymesterone.png
Tiomesterone (thiomesterone) 1α,7α-Diacetylthio-17α-methyltestosterone Tiomesterone structure.svg

Prohormone-like

CompoundChemical nameStructureMarketed
Chlorodehydromethylandrostenediol (CDMA) 4-Chloro-17α-methyl-δ1-4-androstenediol Halodrol.svg
Chloromethylandrostenediol (CMA) 4-Chloro-17α-methyl-4-androstenediol Chloromethylandrostenediol.svg
Methandriol (methylandrostenediol) 17α-Methyl-5-androstenediol Methandriol.svg

Prodrugs

Ethers

CompoundChemical nameStructureMarketed
Methyltestosterone 3-hexyl ether 17α-Methyl-4-hydro-δ3,5-testosterone 3-hexyl ether? Methyltestosterone 3-hexyl ether.svg
Penmesterol (penmestrol) 17α-Methyl-4-hydro-δ3,5-testosterone 3-cyclopentyl ether? Penmesterol.svg

17α-Alkylated dihydrotestosterone derivatives

CompoundChemical nameStructureMarketed
Androisoxazole 17α-Methyl-5α-androstano[3,2-c]isoxazol-17β-ol Androisoxazole.png
Desoxymethyltestosterone 3-Deketo-17α-methyl-4,5α-dihydro-δ2-testosterone Desoxymethyltestosterone.svg
Furazabol 17α-Methyl-5α-androstano[2,3-c][1,2,5]oxadiazol-17β-ol Furazabol.png
Mestanolone (methyl-DHT) 17α-Methyl-4,5α-dihydrotestosterone Mestanolone.png
Methasterone (methyldrostanolone) 2α,17α-Dimethyl-4,5α-dihydrotestosterone Methasterone.png
Methyl-1-testosterone (methyldihydro-1-testosterone) 17α-Methyl-4,5α-dihydro-δ1-testosterone Methyl-1-testosterone.svg
Methyldiazinol 3-Azi-17α-methyl-4,5α-dihydrotestosterone Methyldiazirinol.svg
Methylepitiostanol 2α,3α-Epithio-3-deketo-17α-methyl-4,5α-dihydrotestosterone Methylepitiostanol.svg
Methylstenbolone 2,17α-Dimethyl-4,5α-dihydro-δ1-testosterone Methylstenbolone.svg
Oxandrolone 2-Oxa-17α-methyl-4,5α-dihydrotestosterone Oxandrolone.svg
Oxymetholone 2-Hydroxymethylene-4,5α-dihydro-17α-methyltestosterone Oxymetholone.svg
Stanozolol 17α-Methyl-2'H-5α-androst-2-eno[3,2-c]pyrazol-17β-ol Stanozolol.svg

Prodrugs

Azine dimers

CompoundChemical nameStructureMarketed
Mebolazine (dimethazine, di(methasterone) azine) 3,3-[(1E,2E)-1,2-Hydrazinediylidene]di(2α,17α-dimethyl-5α-androstan-17β-ol)? Mebolazine.png

17α-Alkylated 19-nortestosterone derivatives

CompoundChemical nameStructureMarketed
Dimethyltrienolone (7α,17α-dimethyltrenbolone) 7α,17α-Dimethyl-19-nor-δ9,11-testosterone 7a17a-dimethyltrenbolone.png
Dimethyldienolone (7α,17α-dimethyldienolone) 7α,17α-Dimethyl-19-nor-δ9-testosterone Dimethyldienolone.svg
Ethyldienolone 17α-Ethyl-19-nor-δ9-testosterone Ethyldienolone.png
Ethylestrenol (ethylnandrol) 17α-Ethyl-3-deketo-19-nortestosterone Ethylestrenol.svg
Methyldienolone 17α-Methyl-19-nor-δ9-testosterone Methyldienolone.svg
Methylhydroxynandrolone (MOHN, MHN) 4-Hydroxy-17α-methyl-19-nortestosterone Methylhydroxynandrolone.svg
Metribolone (methyltrienolone, R-1881) 17α-Methyl-19-nor-δ9,11-testosterone Methyltrienolone.svg
Mibolerone 7α,17α-Dimethyl-19-nortestosterone Mibolerone structure.png
Norboletone 17α-Ethyl-18-methyl-19-nortestosterone Norboletone.svg
Norethandrolone (ethylnandrolone, ethylestrenolone) 17α-Ethyl-19-nortestosterone Norethandrolone structure.png
Normethandrone (methylestrenolone, normethisterone) 17α-Methyl-19-nortestosterone Methylestrenolone.png
RU-2309 (18-methymetribolone, 17α-methyl-THG) 17α,18-Dimethyl-19-nor-δ9,11-testosterone RU-2309.svg
Tetrahydrogestrinone (THG) 17α-Ethyl-18-methyl-19-nor-δ9,11-testosterone Tetrahydrogestrinone Structural Formula V1.svg

Prohormone-like

CompoundChemical nameStructureMarketed
Bolenol (ethylnorandrostenol) 3-Deketo-17α-ethyl-19-nor-5-androstenediol Bolenol.png

Prodrugs

Esters

CompoundChemical nameStructureMarketed
Propetandrol 17α-Ethyl-19-nortestosterone 3-propionate Propetandrol.png

17α-Vinylated testosterone derivatives

CompoundChemical nameStructureMarketed
Vinyltestosterone 17α-Ethenyltestosterone 17a-vinyltestosterone structure.png

17α-Vinylated 19-nortestosterone derivatives

CompoundChemical nameStructureMarketed
Norvinisterone (vinylnortestosterone) 17α-Ethenyl-19-nortestosterone Norvinisterone.svg

Commentary

The 17α-ethenylated (vinylated) testosterone derivative norvinisterone (vinylnortestosterone) is much more potent as an AAS than the 17α-ethynylated testosterone derivatives and is intermediate in potency between the 17α-ethynylated progestins and conventional AAS, with approximately one-third and one-fifth of the respective androgenic and anabolic activity of nandrolone in animal bioassays. [1]

Vinyltestosterone has been described as a weak AAS, though stronger than its 17α-ethynylated analogue ethisterone. [2]

17α-Ethynylated testosterone derivatives

CompoundChemical nameStructureMarketed
Ethisterone (ethinyltestosterone) 17α-Ethynyltestosterone Ethisterone.svg
Danazol (2,3-isoxazolethisterone) 2,3-Isoxazol-17α-ethynyltestosterone Danazol.svg

17α-Ethynylated 19-nortestosterone derivatives

CompoundChemical nameStructureMarketed
Norethisterone (norethindrone) 17α-Ethynyl-19-nortestosterone Norethisterone.svg
Etynodiol (ethynodiol, 3β-hydroxynorethisterone) 17α-Ethynyl-3-deketo-3β-hydroxy-19-nortestosterone Etynodiol.svg
Gestrinone (ethylnorgestrienone, R-2323) 17α-Ethynyl-18-methyl-19-nor-δ9,11-testosterone Gestrinone.svg
Levonorgestrel ((−)-norgestrel) (−)-17α-Ethynyl-18-methyl-19-nortestosterone Levonorgestrel.svg
Lynestrenol (3-deketonorethisterone) 17α-Ethynyl-3-deketo-19-nortestosterone Lynestrenol.svg
Norgestrel (18-methylnorethisterone) 17α-Ethynyl-18-methyl-19-nortestosterone Levonorgestrel.svg Dextronorgestrel.svg
Norgestrienone (ethynyltrenbolone) 17α-Ethynyl-19-nor-δ9,11-testosterone Norgestrienone.svg
Tibolone (7α-methylnoretynodrel) 7α-Methyl-17α-ethynyl-19-nor-δ5(10)-testosterone Tibolone.svg

Prodrugs

Ethers

CompoundChemical nameStructureMarketed
Quingestanol 4-Hydro-19-nor-δ3,5-testosterone 3-cyclopentyl ether? Quingestanol structure.svg

Esters

CompoundChemical nameStructureMarketed
Etynodiol diacetate (ethynodiol diacetate) 17α-Ethynyl-3-deketo-3β-hydroxy-19-nortestosterone 3β,17β-diacetate Ethynodiol diacetate.svg
Norethisterone acetate (norethindrone acetate) 17α-Ethynyl-19-nortestosterone 17β-acetate Norethisterone acetate.svg
Norethisterone enanthate (norethindrone enanthate) 17α-Ethynyl-19-nortestosterone 17β-enanthate Norethindrone enanthate.svg

Ethers and esters

CompoundChemical nameStructureMarketed
Quingestanol acetate 4-Hydro-17α-ethynyl-19-nor-δ3,5-testosterone 3-cyclopentyl ether 17β-acetate? Quingestanol acetate.svg

Commentary

17α-Ethynylated testosterone derivatives are potent progestins with only very weak androgenic/anabolic activity and are used as oral contraceptives or for the treatment of gynecological conditions in women. They are invariably classified as progestins rather than as AAS. However, these progestins are testosterone derivatives and do have significant androgenic/anabolic activity, sometimes producing acne and other mild androgenic effects in women. Conversely, in men, these drugs may actually have functional antiandrogen effects due to their potent progestogenic and hence antigonadotropic activity and capacity to suppress gonadal testosterone production. [3]

See also

Notes

? = Chemical names that are unverified.

Related Research Articles

<span class="mw-page-title-main">Tetrahydrogestrinone</span> Synthetic and orally active anabolic–androgenic steroid (AAS)

Tetrahydrogestrinone (THG), known by the nickname The Clear, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was developed by Patrick Arnold and was used by a number of high-profile athletes such as Barry Bonds and Dwain Chambers.

<span class="mw-page-title-main">Nandrolone</span> Androgenic Anabolic steroid

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are now used by oral administration or instead are given by injection into muscle or fat.

<span class="mw-page-title-main">Ethylestrenol</span> Chemical compound

Ethylestrenol, also known as ethyloestrenol or ethylnandrol and sold under the brand names Maxibolin and Orabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used in the past for a variety of indications such as to promote weight gain and to treat anemia and osteoporosis but has been discontinued for use in humans. It is still available for veterinary use in Australia and New Zealand however. It is taken by mouth.

<span class="mw-page-title-main">Norethandrolone</span> Chemical compound

Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued. It is still available for use in France however. It is taken by mouth.

<span class="mw-page-title-main">Norethisterone</span> Progestin medication

Norethisterone, also known as norethindrone and sold under the brand name Norlutin among others, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen. It is used by mouth or, as norethisterone enanthate, by injection into muscle.

<span class="mw-page-title-main">Ethisterone</span> Chemical compound

Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecological disorders but is now no longer available. It was used alone and was not formulated in combination with an estrogen. The medication is taken by mouth.

<span class="mw-page-title-main">Trestolone</span> Chemical compound

Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.

<span class="mw-page-title-main">Metribolone</span> Chemical compound

Metribolone is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.

<span class="mw-page-title-main">Normethandrone</span> Chemical compound

Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. It is taken by mouth.

<span class="mw-page-title-main">Altrenogest</span> Chemical compound

Altrenogest, sold under the brand names Swinemate and Altren manufactured by Aurora Pharmaceutical and Regumate manufactured by Merck, is a progestin of the 19-nortestosterone group which is widely used in veterinary medicine to suppress or synchronize estrus in horses and pigs. It is available for veterinary use in both Europe and the United States.

<span class="mw-page-title-main">Norvinisterone</span> Chemical compound

Norvinisterone, sold under the brand names Neoprogestin and Nor-Progestelea, is a progestin and androgen/anabolic steroid (AAS) medication which was used in Europe but is now no longer marketed. It is taken by mouth.

<span class="mw-page-title-main">Dimethandrolone</span> Chemical compound

Dimethandrolone (DMA), also known by its developmental code name CDB-1321, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under investigation for potential clinical use.

A 17α-alkylated anabolic steroid is a synthetic anabolic–androgenic steroid (AAS) that features an alkyl group, specifically a methyl or ethyl group, at the C17α position. Unlike many other AAS, 17α-alkylated AAS are orally active and do not require intramuscular injection. However, they uniquely possess a high potential for hepatotoxicity, which simultaneously limits their use. In addition, some have a high risk of gynecomastia due to uniquely high estrogenic activity, although this does not apply to 17α-alkylated AAS that are also 4,5α-reduced or 19-demethylated. The prototypical example of a 17α-alkylated AAS is methyltestosterone (17α-methyltestosterone).

<span class="mw-page-title-main">Ethyltestosterone</span> Synthetic anabolic steroid

Ethyltestosterone, or 17α-ethyltestosterone, also known as 17α-ethylandrost-4-en-17β-ol-3-one or 17α-pregn-4-en-17-ol-3-one, is a synthetic, orally active anabolic–androgenic steroid (AAS) of the 17α-alkylated group related to methyltestosterone which was never marketed. Like methyltestosterone, ethyltestosterone is the parent compound of many AAS. Derivatives of ethyltestosterone include norethandrolone, ethylestrenol (ethylnandrol), norboletone, ethyldienolone, tetrahydrogestrinone, bolenol (ethylnorandrostenol), and propetandrol.

<span class="mw-page-title-main">Dimethyltrienolone</span> Anabolic–androgenic steroid

Dimethyltrienolone is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and 17α-alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical use. It has among the highest known affinity of any AAS for the androgen receptors, and has been said to be perhaps the most potent AAS to have ever been developed.

<span class="mw-page-title-main">Vinyltestosterone</span> Chemical compound

Vinyltestosterone is a synthetic anabolic–androgenic steroid (AAS) that was never marketed. However, two 19-nortestosterone derivatives of vinyltestosterone, norvinisterone (17α-vinyl-19-nortestosterone) and norgesterone, have been marketed. They are used as progestins for female hormonal contraception, rather than as AAS.

<span class="mw-page-title-main">11β-Methyl-19-nortestosterone</span> Chemical compound

11β-Methyl-19-nortestosterone (11β-MNT) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time.

<span class="mw-page-title-main">5α-Dihydronorethisterone</span> Chemical compound

5α-Dihydronorethisterone is a major active metabolite of norethisterone (norethindrone). Norethisterone is a progestin with additional weak androgenic and estrogenic activity. 5α-DHNET is formed from norethisterone by 5α-reductase in the liver and other tissues.

<span class="mw-page-title-main">17α-Allyl-19-nortestosterone</span> Chemical compound

17α-Allyl-19-nortestosterone, also known as 3-ketoallylestrenol or as 17α-allylestr-4-en-17β-ol-3-one, is a progestin which was never marketed. It is a combined derivative of the anabolic–androgenic steroid and progestogen nandrolone (19-nortestosterone) and the antiandrogen allyltestosterone (17α-allyltestosterone). The drug is a major active metabolite of allylestrenol, which is thought to be a prodrug of 17α-allyl-19-nortestosterone.

References

  1. Saunders, Francis J.; Drill, Victor A. (1956). "The Myotrophic and Androgenic Effects of 17-Ethyl-19-Nortestosterone and Related Compounds". Endocrinology. 58 (5): 567–572. doi:10.1210/endo-58-5-567. ISSN   0013-7227. PMID   13317831.
  2. LEWIS RA, DeMAJO S, ROSEMBERG E (1949). "The effects of 17-vinyl testosterone upon the rat adrenal". Endocrinology. 45 (6): 564–70. doi:10.1210/endo-45-6-564. PMID   15402199.
  3. Paulsen, C. Alvin; Leach, Robert B.; Lanman, John; Goldston, Norman; Maddock, W. O.; Heller, Carl G. (1962). "Inherent Estrogenicity of Norethindrone and Norethynodrel: Comparison with Other Synthetic Progestins and Progesterone1". The Journal of Clinical Endocrinology & Metabolism. 22 (10): 1033–1039. doi:10.1210/jcem-22-10-1033. ISSN   0021-972X. PMID   13942007. Androgenic effects were absent for each of the compounds in the doses administered as judged by: (a) marked decrease in libido and sexual potentia in each of 21 normal male subjects receiving norethynodrel, norethindrone and norethandrolone; (b) failure to increase libido and sexual potentia in each of four hypogonadotrophic eunuchoidal men receiving norethandrolone (each had previously responded to testosterone administration); (c) no virilization of 14 of 15 postmenopausal women receiving the three progestins (one who was taking norethandrolone at the dose level of 30 mg daily noted lowering in the pitch of her voice during the second month of therapy).

Further reading