Androstanedioneのソースを表示

{{Distinguish|androstanediol|androstenedione|androstenediol|androstadienol}}
{{Chembox
<!-- Images -->
| ImageFile = 5alpha-Androstanedione.svg
| ImageSize = 225px
| ImageAlt = 
| ImageClass = skin-invert-image
<!-- Names -->
| IUPACName = (5''S'',8''R'',9''S'',10''S'',13''S'',14S)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1''H''-cyclopenta[''a'']phenanthrene-3,17-dione
| OtherNames = Dihydroandrostenedione; 5α-Androstanedione; 5α-Androstane-3,17-dione
<!-- Sections -->
| Section1 = {{Chembox Identifiers
| CASNo = 846-46-8
| ChEBI = 15994
| ChEMBL = 1230438
| ChemSpiderID = 193520
| DrugBank = DB01561
| PubChem = 222865
| SMILES = C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C
| StdInChI = 1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1
| StdInChIKey = RAJWOBJTTGJROA-WZNAKSSCSA-N
| UNII = 2KR72RNR8Z
  }}
| Section2 = {{Chembox Properties
| C=19 | H=28 | O=2
| MolarMass = 288.431 g/mol
| Appearance = 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility = 
  }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
  }}
}}

'''Androstanedione''', also known as '''5α-androstanedione''' or as '''5α-androstane-3,17-dione''', is a [[natural product|naturally occurring]] [[androstane]] (5α-androstane) [[steroid]] and an [[endogenous]] [[metabolite]] of [[androgen]]s like [[testosterone]], [[dihydrotestosterone]] (DHT), [[dehydroepiandrosterone]] (DHEA), and [[androstenedione]].<ref name="HMDB">{{Cite web|url=http://www.hmdb.ca/metabolites/HMDB0000899|title=Human Metabolome Database: Showing metabocard for Androstanedione (HMDB0000899)}}</ref> It is the C5 [[epimer]] of [[etiocholanedione]] (5β-androstanedione).<ref name="HMDB" /> Androstanedione is formed from androstenedione by [[5α-reductase]] and from DHT by [[17β-hydroxysteroid dehydrogenase]].<ref name="Becker2001">{{cite book|author=Kenneth L. Becker|title=Principles and Practice of Endocrinology and Metabolism|url=https://books.google.com/books?id=FVfzRvaucq8C&pg=PA994|year=2001|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-1750-2|pages=994–}}</ref><ref name="OrwollBilezikian2009">{{cite book|author1=Eric S. Orwoll|author2=John P. Bilezikian|author3=Dirk Vanderschueren|title=Osteoporosis in Men: The Effects of Gender on Skeletal Health|url=https://books.google.com/books?id=nfWNYFdOsCsC&pg=PA296|date=30 November 2009|publisher=Academic Press|isbn=978-0-08-092346-8|pages=296–}}</ref> It has some [[androgen]]ic activity.<ref name="Kochakian2012">{{cite book|author=Charles D. Kochakian|title=Anabolic-Androgenic Steroids|url=https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA171|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-66353-6|pages=171–}}</ref>

In female genital skin, the conversion of androstenedione into DHT through 5α-androstanedione appears to be more important than the direct conversion of testosterone into DHT.<ref name="pmid16772150">{{cite journal | vauthors = Stanczyk FZ | title = Diagnosis of hyperandrogenism: biochemical criteria | journal = Best Pract Res Clin Endocrinol Metab | volume = 20 | issue = 2 | pages = 177–91 | date = June 2006 | pmid = 16772150 | doi = 10.1016/j.beem.2006.03.007 | url = }}</ref>

==References==
{{Reflist}}

==External links==
* [http://www.hmdb.ca/metabolites/HMDB0000899 Androstanedione (HMDB0000899) - Human Metabolome Database]

{{Endogenous steroids}}
{{Androgen receptor modulators}}

[[Category:5α-Reduced steroid metabolites]]
[[Category:Anabolic–androgenic steroids]]
[[Category:Androstanes]]
[[Category:Diketones]]
[[Category:Steroid hormones]]


{{Steroid-stub}}
{{Biochemistry-stub}}