| Revision as of 20:12, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465327573 of page Adrenosterone for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 17:41, 11 November 2023 edit JJMC89 bot III (talk | contribs)Bots, Administrators3,665,934 editsm Moving Category:Androgens and anabolic steroids to Category:Anabolic–androgenic steroids per Misplaced Pages:Categories for discussion/Log/2023 October 29#Category:Androgens and anabolic steroids |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 456666971 |
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| verifiedrevid = 477243123 |
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|ImageFile=Adrenosterone.png |
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| ImageFile = Adrenosterone.png |
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|ImageSize= |
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| ImageSize = 250 |
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|IUPACName=(8S,9S,10R,13S,14S)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-<br>decahydrocyclopentaphenanthrene-3,11,17-trione |
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| IUPACName = Androst-4-ene-3,11,17-trione |
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| SystematicName = (3a''S'',3b''S'',9a''R'',9b''S'',11a''S'')-9a,11a-Dimethyl-2,3,3a,3b,4,5,8,9,9a,9b,11,11a-dodecahydro-1''H''-cyclopentaphenanthrene-1,7,10-trione |
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|OtherNames=Reichstein's substance G |
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| OtherNames =Reichstein's substance G |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 194597 |
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| ChemSpiderID = 194597 |
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| ChEBI = 2495 |
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| InChI = 1/C19H24O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1 |
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| InChI = 1/C19H24O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1 |
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| InChIKey = RZRPTBIGEANTGU-IRIMSJTPBG |
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| InChIKey = RZRPTBIGEANTGU-IRIMSJTPBG |
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| StdInChIKey = RZRPTBIGEANTGU-IRIMSJTPSA-N |
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| StdInChIKey = RZRPTBIGEANTGU-IRIMSJTPSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 382-45-6 --> |
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| CASNo =382-45-6 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 485683 |
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| ChEMBL = 485683 |
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| PubChem=223997 |
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| PubChem =223997 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = AE4E9102GY |
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| UNII = AE4E9102GY |
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| SMILES = O=C4/C=C3/CC2(C(=O)C1(C(=O)CC12)C)3(C)CC4 |
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| SMILES = O=C4/C=C3/CC2(C(=O)C1(C(=O)CC12)C)3(C)CC4 |
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| MeSHName=Adrenosterone |
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| MeSHName =Adrenosterone |
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|Section2= {{Chembox Properties |
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| C=19 | H=24 | O=3 |
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| Formula=C<sub>19</sub>H<sub>24</sub>O<sub>3</sub> |
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| MolarMass=300.39 g/mol |
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| MolarMass =300.39 g/mol |
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| MeltingPtC = 222 |
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| MeltingPt=222 °C |
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'''Adrenosterone''', also known as '''Reichstein's substance G ''', as well as '''11-ketoandrostenedione''' ('''11-KA4'''), '''11-oxoandrostenedione''' ('''11-OXO'''), and '''androst-4-ene-3,11,17-trione''', is a ] with an extremely weak ]ic effect, and an ]/] of ].<ref name="PretoriusArlt2016">{{cite journal|last1=Pretorius|first1=Elzette|last2=Arlt|first2=Wiebke|last3=Storbeck|first3=Karl-Heinz|title=A new dawn for androgens: Novel lessons from 11-oxygenated C19 steroids|journal=Molecular and Cellular Endocrinology|volume=441|pages=76–85|year=2016|issn=0303-7207|doi=10.1016/j.mce.2016.08.014|pmid=27519632|s2cid=4079662|url=http://pure-oai.bham.ac.uk/ws/files/30346231/Pretorius_et_al_manuscript.pdf}}</ref> It was first isolated in 1936 from the ] by ] at the Pharmaceutical Institute in the ]. Originally, adrenosterone was called Reichstein's substance G. Adrenosterone occurs in trace amounts in humans as well as most mammals and in larger amounts in fish, where it is a precursor to the primary androgen, ].<ref name="pmid19369122">{{Cite journal | last1 = Blasco | first1 = M. N. | last2 = Carriquiriborde | first2 = P. | last3 = Marino | first3 = D. N. | last4 = Ronco | first4 = A. E. | last5 = Somoza | first5 = G. M. | title = A quantitative HPLC–MS method for the simultaneous determination of testosterone, 11-ketotestosterone and 11-β hydroxyandrostenedione in fish serum | doi = 10.1016/j.jchromb.2009.03.028 | journal = Journal of Chromatography B | volume = 877 | issue = 14–15 | pages = 1509–1515 | year = 2009 | pmid = 19369122}}</ref> |
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Adrenosterone is sold as a ] since 2007 as a fat loss and muscle gaining supplement. It is thought to be a competitive selective ] inhibitor, which is responsible for activation of ] from ].<ref name="pmid20355175">{{cite journal | vauthors = Brooker L, Parr MK, Cawley A, Flenker U, Howe C, Kazlauskas R, Schänzer W, George A | title = Development of criteria for the detection of adrenosterone administration by gas chromatography-mass spectrometry and gas chromatography-combustion-isotope ratio mass spectrometry for doping control | journal = Drug Test Anal | volume = 1 | issue = 11–12 | pages = 587–95 | year = 2009 | pmid = 20355175 | doi = 10.1002/dta.108 }}</ref> Thus preventing muscle breakdown, and contributing to a majority of its effects. |
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==See also== |
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* ] |
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* ] |
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==References== |
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{{Reflist|2}} |
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{{Steroid hormones}} |
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{{Androgen receptor modulators}} |
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] |
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] |
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] |
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] |
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] |
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] |