Adrenosterone

Adrenosterone
Names
	IUPAC name (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
CAS Number	382-45-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:2495;
ChEMBL	ChEMBL485683 ;
ChemSpider	194597 ;
ECHA InfoCard	100.006.222
MeSH	Adrenosterone
PubChem CID	223997;
UNII	AE4E9102GY ;
	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 Key: RZRPTBIGEANTGU-IRIMSJTPSA-N ; 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;
	SMILES 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).

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 a 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]

References

^ 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.
^ 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.
^ 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.

[PretoriusArlt2016-1] 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.

[pmid19369122-2] 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.

[pmid20355175-3] 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.

[1]

[2]

[3]

Names

IUPAC name (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
CAS Number	382-45-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:2495
ChEMBL	ChEMBL485683
ChemSpider	194597
ECHA InfoCard	100.006.222
MeSH	Adrenosterone
PubChem CID	223997
UNII	AE4E9102GY
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 Key: RZRPTBIGEANTGU-IRIMSJTPSA-N 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
SMILES 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).

Adrenosterone

See also

References