Methyltestosteroneのソースを表示

{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
<nowiki></nowiki>{{Redirect|Android (drug)|the drug used in the treatment of anemia|Androyd}}
{{Infobox drug
| Verifiedfields     = verified
| Watchedfields      = verified
| verifiedrevid      = 434903709
| IUPAC_name         = (8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1''H''-cyclopenta[''a'']phenanthren-3-one
| image              = Methyltestosterone.svg
| image_class        = skin-invert-image
| width              = 225px
| image2             = Methyltestosterone molecule ball.png
| width2             = 235px

<!--Clinical data-->| tradename          = Agoviron, Android, Metandren, Oraviron, Oreton, Testovis, Testred, Virilon, others
| Drugs.com          = {{drugs.com|monograph|methyltestosterone}}
| pregnancy_AU       = D
| pregnancy_US       = X
| pregnancy_category = 
| legal_BR = C5
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |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=2023-08-03 |access-date=2023-08-15 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA           = Schedule IV
| legal_US           = Schedule III
| legal_AU           = Schedule 4
| legal_status       = Rx-only
| routes_of_administration = [[Oral administration|By mouth]], [[buccal administration|buccal]], [[sublingual administration|sublingual]]<ref name="Llewellyn2009" /><ref name="Ebadi2007" /><ref name="Hohl2017" />
| class              = [[Androgen]]; [[Anabolic steroid]]

<!--Pharmacokinetic data-->| protein_bound      = 98%<ref name="WooRobinson2015" />
| bioavailability    = ~70%<ref name="LemkeWilliams2012" />
| metabolism         = [[Liver]]
| elimination_half-life = 150 minutes (~2.5–3 hours)<ref name="LemkeWilliams2012" /><ref name="BehreWang2004">{{cite book| vauthors = Behre HM, Wang C, Handelsman DJ, Nieschlag E |title=Testosterone |chapter=Pharmacology of testosterone preparations|year=2004|pages=405–444|doi=10.1017/CBO9780511545221.015|isbn=978-0-511-54522-1}}</ref>
| duration_of_action = 1–3 days<ref name="WooRobinson2015" />
| excretion          = [[Urine]]: 90%<ref name="WooRobinson2015" /><br />[[Feces]]: 6%<ref name="WooRobinson2015" /><ref name="Saeb-Parsy1999" />

<!--Identifiers-->| IUPHAR_ligand      = 6945
| CAS_number_Ref     = {{cascite|correct|CAS}}
| CAS_number         = 58-18-4
| ATC_prefix         = G03
| ATC_suffix         = BA02
| ATC_supplemental   = {{ATC|G03|EK01}}
| PubChem            = 6010
| DrugBank_Ref       = {{drugbankcite|correct|drugbank}}
| DrugBank           = DB06710
| ChemSpiderID_Ref   = {{chemspidercite|correct|chemspider}}
| ChemSpiderID       = 5788
| UNII_Ref           = {{fdacite|correct|FDA}}
| UNII               = V9EFU16ZIF
| ChEBI_Ref          = {{ebicite|correct|EBI}}
| ChEBI              = 6892
| ChEMBL_Ref         = {{ebicite|correct|EBI}}
| ChEMBL             = 1395
| KEGG_Ref           = {{keggcite|correct|kegg}}
| KEGG               = D00408
| synonyms           = RU-24400; NSC-9701; 17α-Methyltestosterone; 17α-Methylandrost-4-en-17β-ol-3-one<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Drugs.com" />

<!--Chemical data-->| C                  = 20
| H                  = 30
| O                  = 2
| SMILES             = C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C)O)C
| StdInChI_Ref       = {{stdinchicite|correct|chemspider}}
| StdInChI           = 1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1
| StdInChIKey_Ref    = {{stdinchicite|correct|chemspider}}
| StdInChIKey        = GCKMFJBGXUYNAG-HLXURNFRSA-N
}}
<!-- Definition and medical uses -->
'''Methyltestosterone''', sold under the brand names '''Android''', '''Metandren''', and '''Testred''' among others, is an [[androgen]] and [[anabolic steroid]] (AAS) medication which is used in the treatment of [[hypogonadism|low testosterone levels]] in men, [[delayed puberty]] in boys, at low doses as a component of [[menopausal hormone therapy]] for [[menopause|menopausal]] [[symptom]]s like [[hot flash]]es, [[osteoporosis]], and [[hypoactive sexual desire disorder|low sexual desire]] in women, and to treat [[breast cancer]] in women.<ref name="Llewellyn2009">{{cite book| vauthors = Llewellyn W |title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC|year=2009|publisher=Molecular Nutrition Llc|isbn=978-0-9679304-7-3|pages=16,19,22,27,30,36,39,42,46,291–293}}</ref><ref name="Ebadi2007">{{cite book| vauthors = Ebadi M |title=Desk Reference of Clinical Pharmacology, Second Edition|url=https://books.google.com/books?id=ihxyHbnj3qYC&pg=PA434|date=31 October 2007|publisher=CRC Press|isbn=978-1-4200-4744-8|pages=434–}}</ref><ref name="YagielaDowd2010">{{cite book | vauthors = Yagiela JA, Dowd FJ, Johnson B, Mariotti A, Neidle EA |title= Pharmacology and Therapeutics for Dentistry - E-Book|url=https://books.google.com/books?id=utVOHYuhxioC&pg=PA569 |date= 19 March 2010 |publisher= Elsevier Health Sciences|isbn=978-0-323-07824-5|pages=569–}}</ref><ref name="Android-Label" /><ref name="EE-MT-Label" /> It is taken [[oral administration|by mouth]] or held [[buccal administration|in the cheek]] or [[sublingual administration|under the tongue]].<ref name="Llewellyn2009" /><ref name="Android-Label" /><ref name="EE-MT-Label" /><ref name="Hohl2017">{{cite book| vauthors = Kalinchenko S, Tyuzikov I, Mskhalaya G, Tishova Y | chapter = Testosterone Therapy: Oral Androgens | veditors = Hohl A |title=Testosterone: From Basic to Clinical Aspects|chapter-url=https://books.google.com/books?id=Et6TDgAAQBAJ&pg=PA205|date=30 March 2017|publisher=Springer|isbn=978-3-319-46086-4|pages=204–205}}</ref>

<!-- Side effects and mechanism of action -->
[[Side effect]]s of methyltestosterone include [[symptom]]s of [[virilization|masculinization]] like [[acne]], [[hirsutism|increased hair growth]], [[voice deepening|voice changes]], and increased [[libido|sexual desire]].<ref name="Llewellyn2009" /> It can also cause [[estrogen (medication)|estrogen]]ic effects like [[water retention (medicine)|fluid retention]], [[breast tenderness]], and [[gynecomastia|breast enlargement]] in men and [[hepatotoxicity|liver damage]].<ref name="Llewellyn2009" /> The drug is a [[synthetic compound|synthetic]] androgen and anabolic steroid and hence is an [[agonist]] of the [[androgen receptor]] (AR), the [[biological target]] of androgens like [[testosterone]] and [[dihydrotestosterone]] (DHT).<ref name="Llewellyn2009" /><ref name="pmid18500378">{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = Br. J. Pharmacol. | volume = 154 | issue = 3 | pages = 502–21 | year = 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}</ref> It has moderate [[androgen]]ic effects and moderate [[anabolic]] effects, which make it useful for producing masculinization.<ref name="Llewellyn2009" /><ref name="Kochakian2012">{{cite book| vauthors = Potts GO, Arnold A, Beyler AL | chapter = Dissociation of the androgenic and other hormonal activities from the protein anabolic effects of steroids | veditors = Kochakian CD |title=Anabolic-Androgenic Steroids| chapter-url=https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA401|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-66353-6 | doi = 10.1007/978-3-642-66353-6_11 |pages=13,401,454}}</ref>

<!-- History, society, and culture -->
Methyltestosterone was discovered in 1935 and was introduced for medical use in 1936.<ref name="Hohl2017" /><ref name="ThiemeHemmersbach2009">{{cite book | vauthors = Thieme D, Hemmersbach P |title=Doping in Sports |url= https://books.google.com/books?id=R-hIC-caIn8C&pg=PA101 |date=18 December 2009 |publisher=Springer Science & Business Media |isbn=978-3-540-79088-4 |pages=101, 470}}</ref><ref name="pmid11589254" /><ref name="NARD1956" /><ref name="Llewellyn2009" /> It was [[chemical synthesis|made]] shortly after the discovery of [[testosterone]] and was one of the first synthetic AAS to be developed.<ref name="Hohl2017" /><ref name="ThiemeHemmersbach2009" /><ref name="pmid11589254" /> In addition to its medical use, methyltestosterone is used to [[performance-enhancing substance|improve physique and performance]], although it is not as commonly used as other AAS for such purposes due to its androgenic effects, estrogenic effects, and risk of liver damage.<ref name="Llewellyn2009" /> The drug is a [[controlled substance]] in many countries and so non-medical use is generally illicit.<ref name="Llewellyn2009" />
{{TOC limit}}