Chemistry:List of androgens and anabolic steroids

Short description: None

Testosterone.

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):

• Testosterone derivatives: direct derivatives of testosterone not falling into the groups below
• 4,5α-Reduced/dihydrogenated testosterone derivatives: dihydrotestosterone (DHT) derivatives
• 19-Demethylated testosterone derivatives: 19-nortestosterone (nandrolone) derivatives
• 17α-Alkylated testosterone derivatives: methyltestosterone and ethyltestosterone derivatives
• 17α-Ethynylated/vinylated testosterone derivatives: ethynyltestosterone (ethisterone) and vinyltestosterone derivatives

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

Compound	Chemical name	Structure	Marketed
Testosterone	Androst-4-en-17β-ol-3-one		✓
4-Hydroxytestosterone	4-Hydroxytestosterone		–
11-Ketotestosterone	11-Ketotestosterone		–
Boldenone	Δ1-Testosterone		✓
Clostebol	4-Chlorotestosterone		✓

Prohormone-like

Compound	Chemical name	Structure	Marketed
4-Androstenediol	4-Androstenediol		–
4-Dehydroepiandrosterone (4-DHEA)	4-Dehydroepiandrosterone		–
5-Androstenedione	5-Androstenedione		–
5-Dehydroandrosterone (5-DHA)	5-Dehydroandrosterone		–
11β-Hydroxyandrostenedione (11β-OHA4)	11β-Hydroxy-4-androstenedione		–
Adrenosterone (11-ketoandrostenedione, 11-KA4)	11-Keto-4-androstenedione		–
Androstenediol (5-androstenediol, A5)	5-Androstenediol		–
Androstenedione (4-androstenedione, A4)	4-Androstenedione		–
Atamestane	1-Methyl-δ1-4-androstenedione		–
Boldione (1,4-androstadienedione)	δ1-4-Androstenedione		–
Dehydroepiandrosterone (DHEA, 5-DHEA; prasterone, androstenolone)	5-Dehydroepiandrosterone		✓
Exemestane	6-Methylidene-δ1-4-androstenedione		✓
Formestane	4-Hydroxy-4-androstenedione		✓
Plomestane	10-Propargyl-4-androstenedione		–

Prodrugs

Ethers

Compound	Chemical name	Structure	Marketed
Cloxotestosterone	Testosterone 17-chloral hemiacetal ether		✓
Quinbolone	Δ1-Testosterone 17β-cyclopentenyl enol ether		✓
Silandrone	Testosterone 17β-trimethylsilyl ether		–

Dihydrotestosterone derivatives

Compound	Chemical name	Structure	Marketed
Dihydrotestosterone (DHT); androstanolone, stanolone)	4,5α-Dihydrotestosterone		✓
1-Testosterone (dihydro-1-testosterone, dihydroboldenone)	4,5α-Dihydro-δ1-testosterone		–
11-Ketodihydrotestosterone (11-KDHT)	11-Keto-4,5α-dihydrotestosterone		–
Drostanolone	2α-Methyl-4,5α-dihydrotestosterone		✓
Epitiostanol (epithioandrostanol)	2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone		✓
Mesterolone	1α-Methyl-4,5α-dihydrotestosterone		✓
Metenolone (methenolone, methylandrostenolone)	1-Methyl-4,5α-dihydro-δ1-testosterone		✓
Nisterime	2α-Chloro-4,5α-dihydrotestosterone 3-O-(p-nitrophenyl)oxime		–
Stenbolone	2-Methyl-4,5α-dihydro-δ1-testosterone		✓

Prohormone-like

Compound	Chemical name	Structure	Marketed
1-Androsterone (1-Andro, 1-DHEA)	1-Dehydroepiandrosterone		–
1-Androstenediol (dihydro-1-androstenediol)	1-Androstenediol (4,5α-dihydro-δ1-4-androstenediol)		–
1-Androstenedione (dihydro-1-androstenedione)	1-Androstenedione (4,5α-dihydro-δ1-4-androstenedione)		–
5α-Androst-2-en-17-one	3-Deketo-2-androstenedione (3-deketo-4,5α-dihydro-δ2-4-androstenedione)		–
Androsterone	Androsterone		–
Epiandrosterone	Epiandrosterone		–

Prodrugs

Ethers

Compound	Chemical name	Structure	Marketed
Mepitiostane	2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone 17β-(1-methoxycyclopentane) ether		✓
Mesabolone	4,5α-Dihydro-δ1-testosterone 17β-(1-methoxycyclohexane) ether		–
Prostanozol	2'H-5α-Androst-2-eno[3,2-c]pyrazol-17β-ol 17β-tetrahydropyran ether		–

Azine dimers

Compound	Chemical name	Structure	Marketed
Bolazine (di(drostanolone) azine)	3,3-[(1E,2E)-1,2-Hydrazinediylidene]di(2α-methyl-5α-androstan-17β-ol)?		✓

19-Nortestosterone (nandrolone) derivatives

Compound	Chemical name	Structure	Marketed
Nandrolone (nortestosterone)	19-Nortestosterone		✓
11β-Methyl-19-nortestosterone (11β-MNT)	11β-Methyl-19-nortestosterone		–
Dienolone	19-Nor-δ9-testosterone		–
Dimethandrolone	7α,11β-Dimethyl-19-nortestosterone		–
Norclostebol	4-Chloro-19-nortestosterone		✓
Oxabolone	4-Hydroxy-19-nortestosterone		✓
Trenbolone (trienolone)	19-Nor-δ9,11-testosterone		✓
Trestolone (MENT)	7α-Methyl-19-nortestosterone		–

Prohormone-like

Compound	Chemical name	Structure	Marketed
7α-Methyl-19-nor-4-androstenedione (MENT dione, trestione)	7α-Methyl-19-nor-4-androstenedione		–
19-Nor-5-androstenediol	19-Nor-5-androstenediol		–
19-Nor-5-androstenedione	19-Nor-5-androstenedione		–
19-Nordehydroepiandrosterone	19-Nor-5-dehydroepiandrosterone		–
Bolandiol (nor-4-androstenediol)	19-Nor-4-androstenediol		✓
Bolandione (nor-4-androstenedione)	19-Nor-4-androstenedione		–
Dienedione (nor-4,9-androstadienedione)	19-Nor-δ9-4-androstenedione		–
Methoxydienone (methoxygonadiene)	18-Methyl-19-nor-δ2,5(10)-epiandrosterone 3-methyl ether		–
Trendione (nor-4,9,11-androstatrienedione)	19-Nor-δ9,11-4-androstenedione		–

Prodrugs

Esters

Compound	Chemical name	Structure	Marketed
Bolmantalate (nandrolone adamantoate)	19-Nortestosterone 17β-adamantoate		✓

17α-Alkylated testosterone derivatives

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

Prohormone-like

Compound	Chemical name	Structure	Marketed
Chlorodehydromethylandrostenediol (CDMA)	4-Chloro-17α-methyl-δ1-4-androstenediol		–
Chloromethylandrostenediol (CMA)	4-Chloro-17α-methyl-4-androstenediol		–
Methandriol (methylandrostenediol)	17α-Methyl-5-androstenediol		✓

Prodrugs

Ethers

Compound	Chemical name	Structure	Marketed
Methyltestosterone 3-hexyl ether	17α-Methyl-4-hydro-δ3,5-testosterone 3-hexyl ether?		✓
Penmesterol (penmestrol)	17α-Methyl-4-hydro-δ3,5-testosterone 3-cyclopentyl ether?		✓

17α-Alkylated dihydrotestosterone derivatives

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

Prodrugs

Azine dimers

Compound	Chemical name	Structure	Marketed
Mebolazine (dimethazine, di(methasterone) azine)	3,3-[(1E,2E)-1,2-Hydrazinediylidene]di(2α,17α-dimethyl-5α-androstan-17β-ol)?		✓

17α-Alkylated 19-nortestosterone derivatives

Compound	Chemical name	Structure	Marketed
Dimethyltrienolone (7α,17α-dimethyltrenbolone)	7α,17α-Dimethyl-19-nor-δ9,11-testosterone		–
Dimethyldienolone (7α,17α-dimethyldienolone)	7α,17α-Dimethyl-19-nor-δ9-testosterone		–
Ethyldienolone	17α-Ethyl-19-nor-δ9-testosterone		–
Ethylestrenol (ethylnandrol)	17α-Ethyl-3-deketo-19-nortestosterone		✓
Methyldienolone	17α-Methyl-19-nor-δ9-testosterone		–
Methylhydroxynandrolone (MOHN, MHN)	4-Hydroxy-17α-methyl-19-nortestosterone		–
Metribolone (methyltrienolone, R-1881)	17α-Methyl-19-nor-δ9,11-testosterone		–
Mibolerone	7α,17α-Dimethyl-19-nortestosterone		✓
Norboletone	17α-Ethyl-18-methyl-19-nortestosterone		–
Norethandrolone (ethylnandrolone, ethylestrenolone)	17α-Ethyl-19-nortestosterone		✓
Normethandrone (methylestrenolone, normethisterone)	17α-Methyl-19-nortestosterone		✓
RU-2309 (18-methymetribolone, 17α-methyl-THG)	17α,18-Dimethyl-19-nor-δ9,11-testosterone		–
Tetrahydrogestrinone (THG)	17α-Ethyl-18-methyl-19-nor-δ9,11-testosterone		–

Prohormone-like

Compound	Chemical name	Structure	Marketed
Bolenol (ethylnorandrostenol)	3-Deketo-17α-ethyl-19-nor-5-androstenediol		–

Prodrugs

Esters

Compound	Chemical name	Structure	Marketed
Propetandrol	17α-Ethyl-19-nortestosterone 3-propionate		✓

17α-Vinylated testosterone derivatives

Compound	Chemical name	Structure	Marketed
Vinyltestosterone	17α-Ethenyltestosterone		–

17α-Vinylated 19-nortestosterone derivatives

Compound	Chemical name	Structure	Marketed
Norvinisterone (vinylnortestosterone)	17α-Ethenyl-19-nortestosterone		✓

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.

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

17α-Ethynylated testosterone derivatives

Compound	Chemical name	Structure	Marketed
Ethisterone (ethinyltestosterone)	17α-Ethynyltestosterone		✓
Danazol (2,3-isoxazolethisterone)	2,3-Isoxazol-17α-ethynyltestosterone		✓

17α-Ethynylated 19-nortestosterone derivatives

Compound	Chemical name	Structure	Marketed
Norethisterone (norethindrone)	17α-Ethynyl-19-nortestosterone		✓
Etynodiol (ethynodiol, 3β-hydroxynorethisterone)	17α-Ethynyl-3-deketo-3β-hydroxy-19-nortestosterone		–
Gestrinone (ethylnorgestrienone, R-2323)	17α-Ethynyl-18-methyl-19-nor-δ9,11-testosterone		✓
Levonorgestrel ((−)-norgestrel)	(−)-17α-Ethynyl-18-methyl-19-nortestosterone		✓
Lynestrenol (3-deketonorethisterone)	17α-Ethynyl-3-deketo-19-nortestosterone		✓
Norgestrel (18-methylnorethisterone)	17α-Ethynyl-18-methyl-19-nortestosterone		✓
Norgestrienone (ethynyltrenbolone)	17α-Ethynyl-19-nor-δ9,11-testosterone		✓
Tibolone (7α-methylnoretynodrel)	7α-Methyl-17α-ethynyl-19-nor-δ5(10)-testosterone		✓

Prodrugs

Ethers

Compound	Chemical name	Structure	Marketed
Quingestanol	4-Hydro-19-nor-δ3,5-testosterone 3-cyclopentyl ether?		–

Esters

Compound	Chemical name	Structure	Marketed
Etynodiol diacetate (ethynodiol diacetate)	17α-Ethynyl-3-deketo-3β-hydroxy-19-nortestosterone 3β,17β-diacetate		✓
Norethisterone acetate (norethindrone acetate)	17α-Ethynyl-19-nortestosterone 17β-acetate		✓
Norethisterone enanthate (norethindrone enanthate)	17α-Ethynyl-19-nortestosterone 17β-enanthate		✓

Ethers and esters

Compound	Chemical name	Structure	Marketed
Quingestanol acetate	4-Hydro-17α-ethynyl-19-nor-δ3,5-testosterone 3-cyclopentyl ether 17β-acetate?		✓

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.

See also

• List of steroids
• List of designer drugs § Androgens
• List of androgens/anabolic steroids available in the United States

Notes

^? = Chemical names that are unverified.

Further reading

• Kicman, A T (2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology 154 (3): 502–521. doi:10.1038/bjp.2008.165. ISSN 0007-1188. PMID 18500378. 
• "Structural characteristics of anabolic androgenic steroids contributing to binding to the androgen receptor and to their anabolic and androgenic activities. Applied modifications in the steroidal structure". Steroids 74 (2): 172–97. 2009. doi:10.1016/j.steroids.2008.10.016. PMID 19028512. 
• "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". J. Steroid Biochem. Mol. Biol. 110 (1–2): 39–47. 2008. doi:10.1016/j.jsbmb.2007.10.008. PMID 18395441. 

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| name = Androgens and antiandrogens
| title = Androgens and antiandrogens
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| listclass = hlist
| groupstyle = text-align:center;

| group1 = Androgens
(incl. AAS)

| list1 =

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 mixture]]s (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), [[Chemistry:Lynestrlynestrenol, Norgestrienone|norgestrienone]]) Tibolone Progesterone derivatives: Medroxyprogesterone acetate

Progonadotropins

Antiestrogens (e.g., tamoxifen, Chemistry:Clomifene

| group2 = Antiandrogens
| list2 = {{Navbox|child
| groupstyle = text-align:center;
| groupwidth = 9em;

  | group1 = AR antagonists
  | list1 =

• Steroidal: Abiraterone acetate
• Canrenone
• Chlormadinone acetate
• Cyproterone acetate
• Delmadinone acetate
• Dienogest
• Drospirenone
• Medrogestone
• Megestrol acetate
• Nomegestrol acetate
• Osaterone acetate
• Oxendolone
• Potassium canrenoate
• Spironolactone

• Nonsteroidal: Apalutamide
• Bicalutamide
• Cimetidine
• Darolutamide
• Enzalutamide
• Flutamide
• Ketoconazole
• Nilutamide
• Seviteronel^†
• Topilutamide (fluridil)

  | group2 = Steroidogenesis
inhibitors

| list2 =

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

  | group3 = Antigonadotropins
  | list3 =

• 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, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])

  | group4 = Others
  | list4 =

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

}}

| liststyle = background:#DDDDFF;

| list3 =

• ^#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

}}