Adrenosterone

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Adrenosterone
Adrenosterone.png
Names
IUPAC names
(8S,9S,10R,13S,14S)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-
decahydrocyclopenta[a]phenanthrene-3,11,17-trione
Other names
Reichstein's substance G
Identifiers
382-45-6 N
ChEMBL ChEMBL485683 YesY
ChemSpider 194597 YesY
Jmol-3D images Image
MeSH Adrenosterone
PubChem 223997
UNII AE4E9102GY YesY
Properties
C19H24O3
Molar mass 300.39 g/mol
Melting point 222 °C (432 °F; 495 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Adrenosterone is a steroid hormone with weak androgenic effect. It was first isolated in 1936 from the adrenal cortex by Tadeus Reichstein at the Pharmaceutical Institute in the University of Basel. 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, 11-ketotestosterone.[1]

Adrenosterone has shown to be converted into 11-ketotestosterone by the Scenedesmus algae. It is thought that a similar metabolism pathway occurs in humans, which contributes to adrenosterone's androgenic effects.[2]

Adrenosterone is sold as a dietary supplement since 2007 as a fat loss and muscle gaining supplement. It is thought to be a competitive selective 11βHSD1 inhibitor, which is responsible for activation of cortisol from cortisone.[3][dead link]

11-Keto-androstenedione or 11-keto-androstenetrione are also trade names for this hormone, while the correct name would be androst-4-ene-3,11,17-trione.

See also[edit]

  • Fluoxymesterone (Adrenosterone used as precursor to make this drug molecule)

References[edit]

  1. ^ Blasco, M. N.; Carriquiriborde, P.; Marino, D. N.; Ronco, A. E.; Somoza, G. M. (2009). "A quantitative HPLC–MS method for the simultaneous determination of testosterone, 11-ketotestosterone and 11-β hydroxyandrostenedione in fish serum". Journal of Chromatography B 877 (14–15): 1509–1515. doi:10.1016/j.jchromb.2009.03.028. PMID 19369122.  edit
  2. ^ Greca, M. D.; Fiorentino, A.; Guerriero, I.; Pinto, G.; Pollio, A.; Previtera, L. (1997). "Biotransformation of adrenosterone into 11-ketotestosterone by Scenedesmus quadricauda grown in myxotrophic conditions". Biotechnology Letters 19 (11): 1123–1124. doi:10.1023/A:1018448828758.  edit
  3. ^ http://www3.interscience.wiley.com/journal/123264350/abstract?CRETRY=1&SRETRY=0

See also[edit]