Adrenosterone
 | |
| 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  | |
| ChEMBL | ChEMBL485683  |
| ChemSpider | 194597 |
| Jmol 3D model | Interactive image |
| MeSH | Adrenosterone |
| PubChem | 223997 |
| UNII | AE4E9102GY |
| |
| |
| Properties | |
| C19H24O3 | |
| Molar mass | 300.39 g/mol |
| Melting point | 222 °C (432 °F; 495 K) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| 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]
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
- Fluoxymesterone (Adrenosterone used as precursor to make this drug molecule)
- 1-Dehydroandrenosterone is the precursor used to prepare Methynodiol Diacetate.
References
- ↑ 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.
- ↑ 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.
- ↑ http://www3.interscience.wiley.com/journal/123264350/abstract?CRETRY=1&SRETRY=0