7-Keto-DHEA

7-Keto-DHEA
	; 7-Keto-DHEA
	; 7-Keto-DHEA acetate
Names
	IUPAC name (3β)-3-Hydroxyandrost-5-ene-7,17-dione
	Other names 7-Oxo-DHEA; 7-Ketodehydroepiandrosterone; 7-Oxodehydroepiandrosterone; 3β-Hydroxyandrost-5-ene-7,17-dione; Androst-5-en-3β-ol-7,17-dione
Identifiers
CAS Number	566-19-8 ; 1449-61-2 (acetate) ;
3D model (JSmol)	Interactive image;
ChemSpider	167751;
PubChem CID	193313;
UNII	2334LJD2E9 ; 84RQ0XOM11 (acetate) ;
	InChI InChI=1S/C19H26O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-14,17,20H,3-9H2,1-2H3/t12-,13-,14-,17-,18-,19-/m0/s1 Key: KPRGOTLNGIBVFL-GINZOMEDSA-N; InChI=1/C19H26O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-14,17,20H,3-9H2,1-2H3/t12-,13-,14-,17-,18-,19-/m0/s1 Key: KPRGOTLNGIBVFL-GINZOMEDBE;
	SMILES O=C2\C=C4/[C@]([C@H]3CC[C@@]1(C(=O)CC[C@H]1[C@H]23)C)(C)CC[C@H](O)C4;
Properties
Chemical formula	C19H26O3
Molar mass	302.414 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

7-Ketodehydroepiandrosterone (7-keto-DHEA), also known as 7-oxoprasterone, is a prohormone produced by metabolism of the prohormone dehydroepiandrosterone (DHEA).[1] 7-Keto-DHEA is not directly converted to testosterone or estrogen, and has thus been investigated as a potentially more useful relative of DHEA.[2][3] Researchers have raised concern that supplements may trigger positive tests for performance-enhancing drugs.[4][5]

The World Anti-Doping Agency lists 7-keto-DHEA as a prohibited anabolic agent.[6] The FDA has proposed that it be banned from used in compounded drugs.[7]

Chemistry

7-Keto-DHEA has a number of chemical names, including:

7-Ketodehydroepiandrosterone (7-keto-DHEA)
7-Oxodehydroepiandrosterone (7-oxo-DHEA)
7-Ketoprasterone
7-Oxoprasterone
3β-Hydroxyandrost-5-ene-7,17-dione
Androst-5-en-3β-ol-7,17-dione

For the acetate ester:

3β-Acetoxyandrost-5-ene-7,17-dione
7-Oxo-dehydroepiandrosterone acetate (7-oxo-DHEA acetate)
3-Acetyl-7-oxo-dehydroepiandrosterone (3-acetyl-7-oxo-DHEA)
DHEA acetate-7-one
Δ₅-Androstene-3β-acetoxy-7,17-dione

Note: "Keto" can be substituted for "oxo" in the above names.

History

7-Keto-DHEA has been marketed for treatment of the fake disease Adrenal fatigue.[7]

Regulation

The FDA has proposed that 7-Keto-DHEA be included among substances banned from use in compounded drugs.[7]

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References

Worrel ME; Gurkovskaya OV; Leonard ST; Lewis PB; Winsauer PJ (June 2011). "Effects of 7-keto dehydroepiandrosterone on voluntary ethanol intake in male rats". Alcohol. 45 (4): 349–54. doi:10.1016/j.alcohol.2010.08.020. PMC 3095668. PMID 21051179.
Lardy, H; Kneer N; Wei Y; Partridge B; Marwah P (1998). "Ergosteroids II: Biologically Active Metabolites and Synthetic Derivatives of Dehydroepiandrosterone". Steroids. 63 (3): 158–165. doi:10.1016/S0039-128X(97)00159-1. PMID 9558717.
Davidson, M; Marwah A; Sawchuk RJ; Maki K; Marwah P; Weeks C; Lardy H (2000). "Safety and Pharmacokinetic Study with Escalating Doses of 3-acetyl-7-oxo-dehydroepiandrosterone in Healthy Male Volunteers". Clin. Invest. Med. 23 (5): 300–310. PMID 11055323.
Delbeke FT; Van Eenoo P; Van Thuyne W; Desmet N (December 2002). "Prohormones and sport". J. Steroid Biochem. Mol. Biol. 83 (1–5): 245–51. doi:10.1016/S0960-0760(02)00274-1. PMID 12650722.
"7-Keto DHEA". Martindale: The Complete Drug Reference. Thomson Healthcare. July 10, 2011. 7-Keto-DHEA is reported to be an anabolic androgenic steroid that may be subject to abuse in sport.
"The World Anti-Doping Code International Standard Prohibited List January 2018" (PDF). World Anti-Doping Agency. Retrieved October 21, 2017.
Jann Bellamy (26 September 2019). "FDA proposes ban on curcumin and other naturopathic favorites in compounded drugs". Science-Based Medicine.

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[alcohol-rats-1] Worrel ME; Gurkovskaya OV; Leonard ST; Lewis PB; Winsauer PJ (June 2011). "Effects of 7-keto dehydroepiandrosterone on voluntary ethanol intake in male rats". Alcohol. 45 (4): 349–54. doi:10.1016/j.alcohol.2010.08.020. PMC 3095668. PMID 21051179.

[three-2] Lardy, H; Kneer N; Wei Y; Partridge B; Marwah P (1998). "Ergosteroids II: Biologically Active Metabolites and Synthetic Derivatives of Dehydroepiandrosterone". Steroids. 63 (3): 158–165. doi:10.1016/S0039-128X(97)00159-1. PMID 9558717.

[four-3] Davidson, M; Marwah A; Sawchuk RJ; Maki K; Marwah P; Weeks C; Lardy H (2000). "Safety and Pharmacokinetic Study with Escalating Doses of 3-acetyl-7-oxo-dehydroepiandrosterone in Healthy Male Volunteers". Clin. Invest. Med. 23 (5): 300–310. PMID 11055323.

[sport-4] Delbeke FT; Van Eenoo P; Van Thuyne W; Desmet N (December 2002). "Prohormones and sport". J. Steroid Biochem. Mol. Biol. 83 (1–5): 245–51. doi:10.1016/S0960-0760(02)00274-1. PMID 12650722.

[micromedex-5] "7-Keto DHEA". Martindale: The Complete Drug Reference. Thomson Healthcare. July 10, 2011. 7-Keto-DHEA is reported to be an anabolic androgenic steroid that may be subject to abuse in sport.

[wada-6] "The World Anti-Doping Code International Standard Prohibited List January 2018" (PDF). World Anti-Doping Agency. Retrieved October 21, 2017.

[sbm-7] Jann Bellamy (26 September 2019). "FDA proposes ban on curcumin and other naturopathic favorites in compounded drugs". Science-Based Medicine.

7-Keto-DHEA

Chemistry

History

Regulation

See also

References