Etiocholanedioneのソースを表示

{{Chembox
<!-- Images -->
| ImageFile = 5beta-Androstanedione.svg
| ImageSize = 215px
| ImageAlt =
<!-- Names -->
| IUPACName = 5β-Androstane-3,17-dione
| SystematicName = (3a''S'',3b''R'',5a''R'',9a''S'',9b''S'',11a''S'')-9a,11a-Dimethyltetradecahydro-1''H''-cyclopenta[''a'']phenanthrene-1,7(3b''H'')-dione
| OtherNames = Etiocholane-3,17-dione; 5β-Androstanedione
<!-- Sections -->
| Section1 = {{Chembox Identifiers
| CASNo = 1229-12-5
| ChEBI = 16985
| ChEMBL = 1230988
| ChemSpiderID = 389114
| DrugBank = DB07375
| KEGG = C03772
| PubChem = 440114
| 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+/m1/s1
| StdInChIKey = RAJWOBJTTGJROA-QJISAEMRSA-N
| UNII = 213MVW2TZD
  }}
| 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 =
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}}

'''Etiocholanedione''', also known as '''5β-androstanedione''' or as '''etiocholane-3,17-dione''', is a [[natural product|naturally occurring]] [[etiocholane]] (5β-androstane) [[steroid]] and an [[endogenous]] [[metabolite]] of [[androgen]]s like [[testosterone]], [[dihydrotestosterone]], [[dehydroepiandrosterone]] (DHEA), and [[androstenedione]].<ref name="HMDB">{{cite web|url=http://www.hmdb.ca/metabolites/HMDB0003769|website=hmdb.ca|title=Human Metabolome Database: Showing metabocard for Etiocholanedione (HMDB0003769)|access-date=2018-07-13}}</ref> It is the C5 [[epimer]] of [[androstanedione]] (5α-androstanedione).<ref name="HMDB" /> Although devoid of androgenic activity like other [[5β-reductase|5β-reduced]] steroids, etiocholanedione has some [[biological activity]] of its own.<ref name="pmid10415598">{{cite journal | vauthors = Bradlow HL, Murphy J, Byrne JJ | title = Immunological properties of dehydroepiandrosterone, its conjugates, and metabolites | journal = Ann. N. Y. Acad. Sci. | volume = 876 | pages = 91–101 | date = June 1999 | issue = 1 | pmid = 10415598 | doi = 10.1111/j.1749-6632.1999.tb07627.x | bibcode = 1999NYASA.876...91B | s2cid = 46148045 }}</ref><ref name="McKeagMoeller2007">{{cite book|author1=Douglas McKeag|author2=James L. Moeller|title=ACSM's Primary Care Sports Medicine|url=https://books.google.com/books?id=KoeRrA_-td0C&pg=PA616|year=2007|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-7028-6|pages=616–}}</ref> The compound has been found to possess [[potency (pharmacology)|potent]] [[haematopoietic]] effects in a variety of models.<ref name="pmid10415598" /> In addition, it has been found to promote [[weight loss]] in animals and in a [[double-blind]], [[placebo-controlled]] clinical study in humans conducted in 1993.<ref name="McKeagMoeller2007" /><ref name="Rippe2013">{{cite book|author=James M. Rippe|title=Lifestyle Medicine, Second Edition|url=https://books.google.com/books?id=9ibOBQAAQBAJ&pg=PA559|date=15 March 2013|publisher=CRC Press|isbn=978-1-4398-4544-8|pages=559–}}</ref> These effects are said to be similar to those of DHEA.<ref name="pmid8697065">{{cite journal | vauthors = Clore JN | title = Dehydroepiandrosterone and body fat | journal = Obes. Res. | volume = 3 | pages = 613S–616S | date = November 1995 | issue = Suppl 4 | pmid = 8697065 | doi = 10.1002/j.1550-8528.1995.tb00234.x | doi-access = free }}</ref> Unlike DHEA however, etiocholanedione cannot be [[metabolism|metabolized]] further into [[steroid hormone]]s like androgens and [[estrogen]]s.<ref name="pmid8697065" />

==References==
{{Reflist}}

==External links==
* [http://www.hmdb.ca/metabolites/HMDB0003769 Etiocholanedione (HMDB0003769) - Human Metabolome Database]

{{Steroid hormones}}

[[Category:Experimental anti-obesity drugs]]
[[Category:Diketones]]
[[Category:Etiocholanes]]
[[Category:Steroid hormones]]


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