{{위키데이터 속성 추적}}
{{Drugbox
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| IUPAC_name = (3''S'',8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-13-methyl-1,2,3,6,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[''a'']phenanthrene-3,17-diol
| image = Bolandiol.svg
| width = 250

<!--Clinical data-->
| tradename = 
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = 
| legal_UK = 
| legal_US = 
| legal_status = 
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion =

<!--Identifiers-->
| CAS_number_Ref = 
| CAS_number = 19793-20-5
| CAS_supplemental = 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 49SD6G16U5
| ATC_prefix = 
| ATC_suffix = 
| PubChem = 9835303
| DrugBank_Ref = 
| DrugBank = 
| ChemSpiderID_Ref = 
| ChemSpiderID = 8011024
| ChEBI = 145661
| ChEMBL = 2106664

<!--Chemical data-->
| C=18 | H=28 | O=2
| molecular_weight = 
| smiles = O[C@@H]4/C=C2\[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4
| StdInChI_Ref = 
| StdInChI = 1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,12-17,19-20H,2-9H2,1H3/t12-,13-,14+,15+,16-,17-,18-/m0/s1
| StdInChIKey_Ref = 
| StdInChIKey = CMXKUJNZWYTFJN-XFUVECHXSA-N
| synonyms = 19-Norandrostenediol; 19-Nor-4-androstene-3β,17β-diol; Estr-4-ene-3β,17β-diol; 3β-Dihydronandrolone
}}
'''볼란디올'''(Bolandiol)은 시장에 도입된 적이 없는 [[단백동화 스테로이드]](AAS)이다.<ref name="Elks2014">{{서적 인용| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA899|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=899–}}</ref> 그러나 [[프로피온산|디프로피온산]] [[에스터]] [[유도체]] [[볼란디올 디프로피온산]]은 시장에 도입되었다.<ref name="Elks2014" /><ref name="HydeGengenbach2007">{{서적 인용| first1 = Thomas E. | last1 = Hyde | first2 =Marianne S. | last2 = Gengenbach | name-list-style = vanc |title=Conservative Management of Sports Injuries|url=https://books.google.com/books?id=uzPwfNYyjjUC&pg=PA1100|year=2007|publisher=Jones & Bartlett Learning|isbn=978-0-7637-3252-3|pages=1100–}}</ref> 볼란디올과 볼란디올의 디프로피온산 에스터는 [[에스트로겐]]과 [[프로게스타겐]] 기전을 갖고 있는 것으로 보고되어 AAC 중에서는 독특하다.<ref>{{서적 인용|title=Hormones: Advances in Research and Application | edition = 2011 |url=https://books.google.com/books?id=zhzrlLrsI4AC&pg=PT59|date=9 January 2012|publisher=ScholarlyEditions|isbn=978-1-4649-2242-8 |pages=59–}}</ref><ref>{{저널 인용| vauthors = Attardi BJ, Page ST, Hild SA, Coss CC, Matsumoto AM | title = Mechanism of action of bolandiol (19-nortestosterone-3beta,17beta-diol), a unique anabolic steroid with androgenic, estrogenic, and progestational activities | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 118 | issue = 3 | pages = 151–61 | date = February 2010 | pmid = 19941958 | pmc = 2831543 | doi = 10.1016/j.jsbmb.2009.11.008 }}</ref>

볼란디올은 [[세계 반도핑 기구]]의 금지 약물로 등재되어 있으므로<ref>{{웹 인용| url=http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf | title=The World Anti-Doping Code: The 2012 Prohibited List | publisher=[[World Anti-Doping Agency]] | access-date=2012-07-17 | url-status=dead | archive-url=https://web.archive.org/web/20120513020202/http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf | archive-date=2012-05-13 }}</ref> 주요 스포츠 대부분에서 복용이 금지되어 있다.

== 각주 ==
{{각주}}

[[분류:안드로겐과 단백동화 스테로이드]]
[[분류:에스트란]]
[[분류:에스트로겐]]
[[분류:전구약물]]
[[분류:프로게스토겐]]
[[분류:세계 반도핑 기구 금지 약물]]
[[분류:사이클로펜탄올]]
[[분류:개발이 중지된 약]]
[[분류:사이클로헥센올]]