Androstanoloneのソースを表示

{{Short description|Androgenic and anabolic steroid medication}}
{{cs1 config|name-list-style=vanc}}
{{Use dmy dates|date=December 2023}}
{{About|dihydrotestosterone as a medication|the natural hormone|Dihydrotestosterone}}
{{Infobox drug
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 459443200
| IUPAC_name = (5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[''a'']phenanthren-3-one
| image = Androstanolone.svg
| image_class = skin-invert-image
| width = 225px
| image2 = Dihydrotestosterone molecule ball.png
| width2 = 225px

<!--Clinical data-->
| tradename = Andractim, others
| pregnancy_category = X
| routes_of_administration = [[Transdermal]] ([[gel]]), [[buccal administration|in the cheek]], [[sublingual administration|under the tongue]], [[intramuscular injection]] (as [[Androgen ester#Dihydrotestosterone esters|ester]]s)
| class = [[Androgen]]; [[Anabolic steroid]]

<!-- Legal status -->
| legal_BR = C5
| legal_BR_comment = <ref>{{cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=31 March 2023 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=3 August 2023 |access-date=15 August 2023 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=4 April 2023}}</ref>

<!--Pharmacokinetic data-->
| bioavailability = [[Oral administration|Oral]]: Very low<ref name="Llewellyn2011" /><br />[[Transdermal administration|Transdermal]]: 10%<ref name="Llewellyn2011" /><ref name="pmid9365393" /><br />[[Intramuscular injection|{{Abbr|IM|Intramuscular injection}} injection]]: 100%<ref name="pmid9365393">{{cite journal | vauthors = Coutts SB, Kicman AT, Hurst DT, Cowan DA | title = Intramuscular administration of 5 alpha-dihydrotestosterone heptanoate: changes in urinary hormone profile | journal = Clinical Chemistry | volume = 43 | issue = 11 | pages = 2091–2098 | date = November 1997 | pmid = 9365393 | doi = 10.1093/clinchem/43.11.2091 | doi-access = free }}</ref>
| metabolism = [[Liver]]
| elimination_half-life = [[Transdermal administration|Transdermal]]: 2.8 hours<ref name="MozayaniRaymon2003" />
| excretion = [[Urine]]

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 521-18-6
| ATC_prefix = A14
| ATC_suffix = AA01
| PubChem = 10635
| IUPHAR_ligand = 2856
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB02901
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10189
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 08J2K08A3Y
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16330
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 27769
| synonyms = Stanolone; Dihydrotestosterone; DHT; 5α-Dihydrotestosterone; 5α-DHT

<!--Chemical data-->
| C=19 | H=30 | O=2
| SMILES = O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@]1(C)[C@@H](O)CC[C@H]12)[C@@]3(C)CC4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NVKAWKQGWWIWPM-ABEVXSGRSA-N
}}
<!-- Definition and medical uses -->
'''Androstanolone''', or '''stanolone''', also known as '''dihydrotestosterone''' ('''DHT''') and sold under the brand name '''Andractim''' among others, is an [[androgen]] and [[anabolic steroid]] (AAS) medication and [[sex hormone|hormone]] which is used mainly in the treatment of [[hypogonadism|low testosterone levels]] in men.<ref name="Llewellyn2011">{{cite book| vauthors = Llewellyn W |title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT353|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=8,23–25,353–359}}</ref> It is also used to treat [[gynecomastia|breast development]] and [[micropenis|small penis]] in males.<ref name="Llewellyn2011" /> 
Compared to [[testosterone]], androstanolone (DHT) is less likely to [[aromatase|aromatize]] into [[estrogen]], and therefore it shows less pronounced [[estrogen (medication)|estrogen]]ic side effects, such as [[gynecomastia]] and [[Water retention (medicine)|water retention]]. On the other hand, androstanolone (DHT) show more significant [[androgenic]] side effects, such as [[acne]], [[hair loss]] and [[prostate enlargement]]. 

It has strong [[androgen]]ic effects and  [[myotrophy|muscle-building]] effects, as well as relatively weak [[estrogen (medication)|estrogen]]ic effects.<ref name="Llewellyn2011" />

It is typically given as a [[gel]] for [[topical medication|application to the skin]], but can also be used as an [[dihydrotestosterone ester|ester]] by [[intramuscular injection|injection into muscle]].<ref name="Llewellyn2011" /><ref name="HydeGengenbach2007" />

<!-- Side effects and mechanism of action -->
[[Side effect]]s of androstanolone include [[symptom]]s of [[virilization|masculinization]] like [[acne]], [[hirsutism|increased hair growth]], [[voice deepening|voice changes]], and increased [[libido|sexual desire]].<ref name="Llewellyn2011" /> The medication is a [[natural product|naturally occurring]] androgen and anabolic steroid and hence is an [[agonist]] of the [[androgen receptor]] (AR), the [[biological target]] of androgens like [[testosterone]] and DHT.<ref name="Llewellyn2011" /><ref name="pmid18500378">{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–521 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}</ref> 

<!-- History, society, and culture -->
Androstanolone was discovered in 1935 and was introduced for medical use in 1953.<ref name="Llewellyn2011" /><ref name="Schnitzer1967" /><ref name="Krüskemper2013" /><ref name="Publishing2007" /> It is used mostly in [[France]] and [[Belgium]].<ref name="Llewellyn2011" /><ref name="Drugs.com" /><ref name="GoorenBunck2004" /> The drug has been used by weightlifters to increase performance due to its powerful androgenic properties.<ref>{{cite web | url=https://www.iwf.net/2018/05/30/public-disclosure-104/ |title = Public Disclosure|date = 30 May 2018}}</ref><ref>{{cite web | url=http://www.chicagotribune.com/news/ct-xpm-1994-12-10-9412100116-story.html |title = Steroid Use by Chinese Hints at Systematic Doping| website=[[Chicago Tribune]] | date=10 December 1994 }}</ref> The medication is a [[controlled substance]] in many countries and so non-medical use is generally illicit.<ref name="Llewellyn2011" />

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