View source for Template:Structural aspects of androgens and anabolic steroids

{| class="wikitable sortable mw-collapsible {{{state<includeonly>|mw-collapsed</includeonly>}}}" style="font-size:small; text-align:left; margin-left:auto; margin-right:auto; border:none;"
|+ class="nowrap" | {{Navbar|Structural aspects of androgens and anabolic steroids|mini=y}} {{Resize|108%|Structural aspects of <noinclude>{{No selflink|androgen}}s and {{No selflink|anabolic steroid}}s</noinclude><includeonly>androgens and anabolic steroids</includeonly>}}
|-
! Classes !! Androgen !! class="unsortable" | Structure !! class="unsortable" | Chemical name !! Features
|-
| rowspan="11" | Testosterone
| [[4-Hydroxytestosterone]]<sup>a</sup>
| [[File:4-hydroxytestosterone.png|center|30px]]
| 4-Hydroxytestosterone
| –
|-
| [[Androstenediol]]<sup>a</sup>
| [[File:Androstendiol.svg|center|30px]]
| 5-Androstenediol (androst-5-ene-3β,17β-diol)
| Prohormone
|-
| [[Androstenedione]]<sup>a</sup>
| [[File:Androstendion.svg|center|30px]]
| 4-Androstenedione (androst-4-ene-3,17-dione)
| Prohormone
|-
| [[Boldenone]]
| [[File:Boldenone.svg|center|30px]]
| 1-Dehydrotestosterone
| –
|-
| [[Boldione]]<sup>a</sup>
| [[File:Boldione.png|center|30px]]
| 1-Dehydro-4-androstenedione
| Prohormone
|-
| [[Clostebol]]
| [[File:Clostebol.svg|center|30px]]
| 4-Chlorotestosterone
| –
|-
| [[Cloxotestosterone]]
| [[File:Cloxotestosterone.svg|center|30px]]
| Testosterone 17-chloral hemiacetal ether
| Ether
|-
| [[Prasterone]]
| [[File:Dehydroepiandrosteron.svg|center|30px]]
| 5-Dehydroepiandrosterone (androst-5-en-3β-ol-17-one)
| Prohormone
|-
| [[Quinbolone]]
| [[File:Quinbolone.png|center|30px]]
| 1-Dehydrotestosterone 17β-cyclopentenyl enol ether
| Ether
|-
| [[Silandrone]]<sup>a</sup>
| [[File:Silandrone.png|center|30px]]
| Testosterone 17β-trimethylsilyl ether
| Ether
|-
| [[Testosterone (medication)|Testosterone]]
| [[File:Testosteron.svg|center|30px]]
| Androst-4-en-17β-ol-3-one
| –
|-
| rowspan="18" | 17α-Alkylated testosterone
| [[Bolasterone]]
| [[File:Bolasterone.png|center|30px]]
| 7α,17α-Dimethyltestosterone
| –
|-
| [[Calusterone]]
| [[File:Calusterone.svg|center|30px]]
| 7β,17α-Dimethyltestosterone
| –
|-
| [[Chlorodehydromethylandrostenediol]]<sup>a</sup>
| [[File:Halodrol.svg|center|30px]]
| 1-Dehydro-4-chloro-17α-methyl-4-androstenediol
| Prohormone
|-
| [[Chlorodehydromethyltestosterone]]
| [[File:4-Chlorodehydromethyltestosterone.png|center|30px]]
| 1-Dehydro-4-chloro-17α-methyltestosterone
| –
|-
| [[Chloromethylandrostenediol]]<sup>a</sup>
| [[File:Chloromethylandrostenediol.svg|center|30px]]
| 4-Chloro-17α-methyl-4-androstenediol
| –
|-
| [[Enestebol]]<sup>a</sup>
| [[File:Enestebol.png|center|30px]]
| 1-Dehydro-4-hydroxy-17α-methyltestosterone
| –
|-
| [[Ethyltestosterone]]<sup>a</sup>
| [[File:Ethyltestosterone structure.png|center|30px]]
| 17α-Ethyltestosterone
| –
|-
| [[Fluoxymesterone]]
| [[File:Fluoxymesterone structure.svg|center|30px]]
| 9α-Fluoro-11β-hydroxy-17α-methyltestosterone
| –
|-
| [[Formebolone]]
| [[File:Formebolone.png|center|30px]]
| 1-Dehydro-2-formyl-11α-hydroxy-17α-methyltestosterone
| –
|-
| [[Hydroxystenozole]]<sup>a</sup>
| [[File:Hydroxystenozole.png|center|30px]]
| 17α-Methyl-2'H-androsta-2,4-dieno[3,2-c]pyrazol-17β-ol
| Ring-fused
|-
| [[Metandienone]]
| [[File:Metandienone.svg|center|30px]]
| 1-Dehydro-17α-methyltestosterone
| –
|-
| [[Methandriol]]
| [[File:Methandriol.svg|center|30px]]
| 17α-Methyl-5-androstenediol
| Prohormone
|-
| [[Methylclostebol]]<sup>a</sup>
| [[File:Methylclostebol.svg|center|30px]]
| 4-Chloro-17α-methyltestosterone
| –
|-
| [[Methyltestosterone]]
| [[File:Methyltestosterone.svg|center|30px]]
| 17α-Methyltestosterone
| –
|-
| [[Methyltestosterone hexyl ether]]
| [[File:Methyltestosterone 3-hexyl ether.svg|center|30px]]
| 17α-Methyltestosterone 3-hexyl enol ether
| Ether
|-
| [[Oxymesterone]]
| [[File:Oxymesterone.png|center|30px]]
| 4-Hydroxy-17α-methyltestosterone
| –
|-
| [[Penmesterol]]
| [[File:Penmesterol.svg|center|30px]]
| 17α-Methyltestosterone 3-cyclopentyl enol ether
| Ether
|-
| [[Tiomesterone]]
| [[File:Tiomesterone structure.svg|center|30px]]
| 1α,7α-Diacetylthio-17α-methyltestosterone
| –
|-
| rowspan="1" | Other 17α-substituted testosterone
| [[Danazol]]
| [[File:Danazol.svg|center|30px]]
| 2,3-Isoxazol-17α-ethynyltestosterone
| Ring-fused
|-
| rowspan="11" | Dihydrotestosterone
| [[1-Testosterone]]<sup>a</sup>
| [[File:1-testosterone.png|center|30px]]
| 1-Dehydro-4,5α-dihydrotestosterone
| –
|-
| [[Androstanolone]]
| [[File:Androstanolone.svg|center|30px]]
| 4,5α-Dihydrotestosterone
| –
|-
| [[Bolazine]]
| [[File:Bolazine.png|center|30px]]
| C3 azine dimer of drostanolone
| Dimer
|-
| [[Drostanolone]]
| [[File:Drostanolone.svg|center|30px]]
| 2α-Methyl-4,5α-dihydrotestosterone
| –
|-
| [[Epitiostanol]]
| [[File:Epitiostanol.png|center|30px]]
| 2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone
| Ring-fused
|-
| [[Mepitiostane]]
| [[File:Mepitiostane.svg|center|30px]]
| 2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone 17β-(1-methoxycyclopentane) ether
| Ring-fused; Ether
|-
| [[Mesabolone]]<sup>a</sup>
| [[File:Mesabolone.png|center|30px]]
| 1-Dehydro-4,5α-Dihydrotestosterone 17β-(1-methoxycyclohexane) ether
| Ether
|-
| [[Mesterolone]]
| [[File:Mesterolone.svg|center|30px]]
| 1α-Methyl-4,5α-dihydrotestosterone
| –
|-
| [[Metenolone]]
| [[File:Metenolone.svg|center|30px]]
| 1-Dehydro-1-methyl-4,5α-dihydrotestosterone
| –
|-
| [[Prostanozol]]<sup>a</sup>
| [[File:Prostanozol.png|center|30px]]
| 2<nowiki>'</nowiki>''H''-5α-Androst-2-eno[3,2-''c'']pyrazol-17β-ol 17β-tetrahydropyran ether
| Ether
|-
| [[Stenbolone]]
| [[File:Stenbolone.svg|center|30px]]
| 1-Dehydro-2-methyl-4,5α-dihydrotestosterone
| –
|-
| rowspan="13" | 17α-Alkylated dihydrotestosterone
| [[Androisoxazole]]
| [[File:Androisoxazole.png|center|30px]]
| 17α-Methyl-5α-androstano[3,2-''c'']isoxazol-17β-ol
| Ring-fused
|-
| [[Desoxymethyltestosterone]]<sup>a</sup>
| [[File:Desoxymethyltestosterone.svg|center|30px]]
| 2-Dehydro-3-deketo-4,5α-dihydro-17α-methyltestosterone
| –
|-
| [[Furazabol]]
| [[File:Furazabol.png|center|30px]]
| 17α-Methyl-5α-androstano[2,3-''c''][1,2,5]oxadiazol-17β-ol
| Ring-fused
|-
| [[Mebolazine]]
| [[File:Mebolazine.png|center|30px]]
| C3 azine dimer of methasterone
| Dimer
|-
| [[Mestanolone]]
| [[File:Mestanolone.png|center|30px]]
| 4,5α-Dihydro-17α-methyltestosterone
| –
|-
| [[Methasterone]]<sup>a</sup>
| [[File:Methasterone.png|center|30px]]
| 2α,17α-Dimethyl-4,5α-dihydrotestosterone
| –
|-
| [[Methyl-1-testosterone]]<sup>a</sup>
| [[File:Methyl-1-testosterone.svg|center|30px]]
| 1-Dehydro-4,5α-dihydro-17α-methyltestosterone
| –
|-
| [[Methyldiazinol]]<sup>a</sup>
| [[File:Methyldiazirinol.svg|center|30px]]
| 3-Deketo-3-azi-4,5α-dihydro-17α-methyltestosterone
| –
|-
| [[Methylepitiostanol]]<sup>a</sup>
| [[File:Methylepitiostanol.svg|center|30px]]
| 2α,3α-Epithio-3-deketo-4,5α-dihydro-17α-methyltestosterone
| –
|-
| [[Methylstenbolone]]<sup>a</sup>
| [[File:Methylstenbolone.svg|center|30px]]
| 1-Dehydro-2,17α-dimethyl-4,5α-dihydrotestosterone
| –
|-
| [[Oxandrolone]]
| [[File:Oxandrolone.svg|center|30px]]
| 2-Oxa-4,5α-dihydro-17α-methyltestosterone
| –
|-
| [[Oxymetholone]]
| [[File:Oxymetholone.svg|center|30px]]
| 2-Hydroxymethylene-4,5α-dihydro-17α-methyltestosterone
| –
|-
| [[Stanozolol]]
| [[File:Stanozolol.svg|center|30px]]
| 17α-Methyl-2<nowiki>'</nowiki>''H''-5α-androst-2-eno[3,2-''c'']pyrazol-17β-ol
| Ring-fused
|-
| rowspan="17" | 19-Nortestosterone
| [[11β-Methyl-19-nortestosterone]]<sup>a</sup>
| [[File:11β-Methyl-19-nortestosterone.svg|center|30px]]
| 11β-Methyl-19-nortestosterone
| –
|-
| [[19-Nor-5-androstenediol]]<sup>a</sup>
| [[File:19-Nor-5-androstenediol.svg|center|30px]]
| 19-Nor-5-androstenediol
| Prohormone
|-
| [[19-Nordehydroepiandrosterone]]<sup>a</sup>
| [[File:19-Nordehydroepiandrosterone.svg|center|30px]]
| 19-Nor-5-dehydroepiandrosterone
| Prohormone
|-
| [[Bolandiol]]<sup>a</sup>
| [[File:Bolandiol.svg|center|30px]]
| 19-Nor-4-androstenediol
| Prohormone
|-
| [[Bolandione]]<sup>a</sup>
| [[File:19-norandrostenedione.png|center|30px]]
| 19-Nor-4-androstenedione
| Prohormone
|-
| [[Bolmantalate]]<sup>a</sup>
| [[File:Bolmantalate.svg|center|30px]]
| 19-Nortestosterone 17β-adamantoate
| Ester
|-
| [[Dienedione]]<sup>a</sup>
| [[File:Dienedione.svg|center|30px]]
| 9-Dehydro-19-nor-4-androstenedione
| Prohormone
|-
| [[Dienolone]]<sup>a</sup>
| [[File:Dienolone structure.png|center|30px]]
| 9-Dehydro-19-nortestosterone
| –
|-
| [[Dimethandrolone]]<sup>a</sup>
| [[File:Dimethandrolone structure.svg|center|30px]]
| 7α,11β-Dimethyl-19-nortestosterone
| –
|-
| [[Methoxydienone]]<sup>a</sup>
| [[File:Methoxydienone.svg|center|30px]]
| 2,5(10)-Didehydro-18-methyl-19-norepiandrosterone 3-methyl ether
| Prohormone; Ether
|-
| [[Nandrolone]]
| [[File:Nandrolone.svg|center|30px]]
| 19-Nortestosterone
| –
|-
| [[Norclostebol]]
| [[File:Norclostebol.svg|center|30px]]
| 4-Chloro-19-nortestosterone
| –
|-
| [[Oxabolone]]
| [[File:Oxabolone.svg|center|30px]]
| 4-Hydroxy-19-nortestosterone
| –
|-
| [[Trestolone]]<sup>a</sup>
| [[File:Trestolone structure.svg|center|30px]]
| 7α-Methyl-19-nortestosterone
| –
|-
| [[Trenbolone]]
| [[File:Trenbolone.svg|center|30px]]
| 9,11-Didehydro-19-nortestosterone
| –
|-
| [[Trendione]]<sup>a</sup>
| [[File:Trendione.svg|center|30px]]
| 9,11-Didehydro-19-nor-4-androstenedione
| Prohormone
|-
| [[Trestione]]<sup>a</sup>
| [[File:7α-Methyl-19-norandrostenedione.svg|center|30px]]
| 7α-Methyl-19-nor-4-androstenedione
| Prohormone
|-
| rowspan="14" | 17α-Alkylated 19-nortestosterone
| [[Dimethyltrienolone]]<sup>a</sup>
| [[File:7a17a-dimethyltrenbolone.png|center|30px]]
| 7α,17α-Dimethyl-9,11-didehydro-19-nortestosterone
| –
|-
| [[Dimethyldienolone]]<sup>a</sup>
| [[File:Dimethyldienolone.svg|center|30px]]
| 7α,17α-Dimethyl-9-dehydro-19-nortestosterone
| –
|-
| [[Ethyldienolone]]<sup>a</sup>
| [[File:Ethyldienolone.png|center|30px]]
| 9-Dehydro-17α-ethyl-19-nortestosterone
| –
|-
| [[Ethylestrenol]]
| [[File:Ethylestrenol.svg|center|30px]]
| 17α-Ethyl-3-deketo-19-nortestosterone
| –
|-
| [[Methyldienolone]]<sup>a</sup>
| [[File:Methyldienolone.svg|center|30px]]
| 9-Dehydro-17α-methyl-19-nortestosterone
| –
|-
| [[Methylhydroxynandrolone]]<sup>a</sup>
| [[File:Methylhydroxynandrolone.svg|center|30px]]
| 4-Hydroxy-17α-methyl-19-nortestosterone
| –
|-
| [[Metribolone]]<sup>a</sup>
| [[File:Methyltrienolone.svg|center|30px]]
| 9,11-Didehydro-17α-methyl-19-nortestosterone
| –
|-
| [[Mibolerone]]
| [[File:Mibolerone structure.png|center|30px]]
| 7α,17α-Dimethyl-19-nortestosterone
| –
|-
| [[Norboletone]]<sup>a</sup>
| [[File:Norboletone.svg|center|30px]]
| 17α-Ethyl-18-methyl-19-nortestosterone
| –
|-
| [[Norethandrolone]]
| [[File:Norethandrolone structure.png|center|30px]]
| 17α-Ethyl-19-nortestosterone
| –
|-
| [[Normethandrone]]
| [[File:Methylestrenolone.png|center|30px]]
| 17α-Methyl-19-nortestosterone
| –
|-
| [[Propetandrol]]
| [[File:Propetandrol.png|center|30px]]
| 17α-Ethyl-19-nortestosterone 3-propionate
| Ester
|-
| [[RU-2309]]<sup>a</sup>
| [[File:RU-2309.svg|center|30px]]
| 9,11-Didehydro-17α,18-dimethyl-19-nortestosterone
| –
|-
| [[Tetrahydrogestrinone]]<sup>a</sup>
| [[File:Tetrahydrogestrinone Structural Formula V1.svg|center|30px]]
| 9,11-Didehydro-17α-ethyl-18-methyl-19-nortestosterone
| –
|-
| rowspan="3" | Other 17α-substituted 19-nortestosterone
| [[Gestrinone]]
| [[File:Gestrinone.svg|center|30px]]
| 9,11-Didehydro-17α-ethynyl-18-methyl-19-nortestosterone
| –
|-
| [[Tibolone]]
| [[File:Tibolone.svg|center|30px]]
| 5(10)-Dehydro-7α-methyl-17α-ethynyl-19-nortestosterone
| –
|-
| [[Vinyltestosterone]]<sup>a</sup>
| [[File:Norvinisterone.svg|center|30px]]
| 17α-Ethenyltestosterone
| –
|- class="sortbottom"
| colspan="5" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' Esters of androgens and anabolic steroids are mostly not included in this table; see [[List of androgen esters|here]] instead. Weakly androgenic progestins are mostly not included in this table; see [[Template:Structural aspects of marketed progestogens|here]] instead. '''Footnotes:''' <sup>a</sup> = Never marketed.
|}<noinclude>{{Documentation|content=
==See also==
* [[Template:Structural aspects of marketed progestogens]]
* [[List of androgen esters]]
* [[List of androgens/anabolic steroids]]
* [[List of androgens/anabolic steroids (alternate)]]
* [[Structure–activity relationships of anabolic steroids]]
==References==
{{Reflist}}
}}
[[Category:Anabolic–androgenic steroids]]
[[Category:Medication templates]]
</noinclude>