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2026-04-12T09:17:45Z
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WikiSysop: 1版 をインポートしました
2025-03-18T10:31:49Z
<p>1版 をインポートしました</p>
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bsd>Maxim Masiutin: Alter: volume. Add: issue. | Use this bot. Report bugs.
2023-12-09T01:24:44Z
<p>Alter: volume. Add: issue. | <a href="https://en.wikipedia.org/wiki/WP:UCB" class="extiw" title="en:WP:UCB">Use this bot</a>. <a href="https://en.wikipedia.org/wiki/WP:DBUG" class="extiw" title="en:WP:DBUG">Report bugs</a>.</p>
<p><b>新規ページ</b></p><div>{{Chembox<br />
<!-- Images --><br />
| ImageFile = 5beta-Androstanedione.svg<br />
| ImageSize = 215px<br />
| ImageAlt =<br />
<!-- Names --><br />
| IUPACName = 5β-Androstane-3,17-dione<br />
| 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<br />
| OtherNames = Etiocholane-3,17-dione; 5β-Androstanedione<br />
<!-- Sections --><br />
| Section1 = {{Chembox Identifiers<br />
| CASNo = 1229-12-5<br />
| ChEBI = 16985<br />
| ChEMBL = 1230988<br />
| ChemSpiderID = 389114<br />
| DrugBank = DB07375<br />
| KEGG = C03772<br />
| PubChem = 440114<br />
| SMILES = C[C@]12CCC(=O)C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C<br />
| 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<br />
| StdInChIKey = RAJWOBJTTGJROA-QJISAEMRSA-N<br />
| UNII = 213MVW2TZD<br />
}}<br />
| Section2 = {{Chembox Properties<br />
| C=19 | H=28 | O=2<br />
| MolarMass = 288.431 g/mol<br />
| Appearance = <br />
| Density = <br />
| MeltingPt = <br />
| BoilingPt = <br />
| Solubility = <br />
}}<br />
| Section3 = {{Chembox Hazards<br />
| MainHazards =<br />
| FlashPt =<br />
| AutoignitionPt =<br />
}}<br />
}}<br />
<br />
'''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" /><br />
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==References==<br />
{{Reflist}}<br />
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==External links==<br />
* [http://www.hmdb.ca/metabolites/HMDB0003769 Etiocholanedione (HMDB0003769) - Human Metabolome Database]<br />
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{{Steroid hormones}}<br />
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[[Category:Experimental anti-obesity drugs]]<br />
[[Category:Diketones]]<br />
[[Category:Etiocholanes]]<br />
[[Category:Steroid hormones]]<br />
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{{Steroid-stub}}<br />
{{Biochemistry-stub}}</div>
bsd>Maxim Masiutin