Adrenosterone

Adrenosterone
Names
IUPAC name
Androst-4-ene-3,11,17-trione
Systematic IUPAC name
(3aS,3bS,9aR,9bS,11aS)-9a,11a-Dimethyl-2,3,3a,3b,4,5,8,9,9a,9b,11,11a-dodecahydro-1H-cyclopenta[a]phenanthrene-1,7,10-trione
Other names
Reichstein's substance G
Identifiers
CAS Number
  • 382-45-6 ☒N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:2495
ChEMBL
  • ChEMBL485683 checkY
ChemSpider
  • 194597 checkY
ECHA InfoCard 100.006.222 Edit this at Wikidata
MeSH Adrenosterone
PubChem CID
  • 223997
UNII
  • AE4E9102GY checkY
InChI
  • InChI=1S/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 checkY
    Key: RZRPTBIGEANTGU-IRIMSJTPSA-N checkY
  • 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
    Key: RZRPTBIGEANTGU-IRIMSJTPBG
  • O=C4/C=C3/CC[C@@H]2[C@H](C(=O)C[C@@]1(C(=O)CC[C@H]12)C)[C@@]3(C)CC4
Properties
Chemical formula
 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).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

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 steroid hormone with an extremely weak androgenic effect, and an intermediate/prohormone of 11-ketotestosterone.[1] 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.[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] Thus preventing muscle breakdown, and contributing to a majority of its effects.

See also

References

  1. ^ Pretorius, Elzette; Arlt, Wiebke; Storbeck, Karl-Heinz (2016). "A new dawn for androgens: Novel lessons from 11-oxygenated C19 steroids" (PDF). Molecular and Cellular Endocrinology. 441: 76–85. doi:10.1016/j.mce.2016.08.014. ISSN 0303-7207. PMID 27519632. S2CID 4079662.
  2. ^ 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.
  3. ^ Brooker L, Parr MK, Cawley A, Flenker U, Howe C, Kazlauskas R, Schänzer W, George A (2009). "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". Drug Test Anal. 1 (11–12): 587–95. doi:10.1002/dta.108. PMID 20355175.
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Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids