7-Keto-DHEA

7-Ketodehydroepiandrosterone (7-keto-DHEA,7-oxo-DHEA), also known as 7-oxoprasterone, is a prohormone produced by metabolism of the prohormone dehydroepiandrosterone (DHEA).[1]

7-Keto-DHEA

7-Keto-DHEA

7-Keto-DHEA acetate
Names
IUPAC name
(3β)-3-Hydroxyandrost-5-ene-7,17-dione
Preferred IUPAC name
(3aS,3bR,7S,9aR,9bS,11aS)-9a,11a-Dimethyl-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[a]phenanthrene-1,4(3bH)-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
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
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-oxo-DHEA is even more effective than DHEA for inducing heat production (thermogenesis).[2] Because dieting is usually accompanied by reduced resting metabolic rate, obese persons may benefit from using 7-oxo-DHEA when dieting due to increased metabolic rate.[3]

7-Keto-DHEA is not directly converted to testosterone or estrogen, and has thus been investigated as a potentially more useful relative of DHEA.[4][5] Researchers have raised concern that supplements may trigger positive tests for performance-enhancing drugs.[6][7]

The World Anti-Doping Agency lists 7-keto-DHEA as a prohibited anabolic agent.[8] The FDA has proposed that it be banned from use in compounded drugs.[9]

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 by alternative medicine providers as a treatment of Adrenal fatigue, a pseudo-scientific term with no scientific basis.[9]

Regulation

The FDA has proposed that 7-Keto-DHEA be included among substances banned from use in compounded drugs.[9]

See also

References
  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.
  2. Hamp R, Stárka L, Janský L (2006). "Steroids and thermogenesis" (PDF). Physiological Research. 55 (2): 123–131. doi:10.33549/physiolres.930758. PMID 15910167. S2CID 17390475.
  3. Zenk JL, Frestedt JL, Kuskowski MA (2007). "HUM5007, a novel combination of thermogenic compounds, and 3-acetyl-7-oxo-dehydroepiandrosterone: each increases the resting metabolic rate of overweight adults" (PDF). Journal of Nutritional Biochemistry. 18 (9): 629–634. doi:10.1016/j.jnutbio.2006.11.008. PMID 17418559.
  4. 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. S2CID 19894334.
  5. 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.
  6. 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. S2CID 46183096.
  7. "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.
  8. "The World Anti-Doping Code International Standard Prohibited List January 2018" (PDF). World Anti-Doping Agency. Retrieved October 21, 2017.
  9. Jann Bellamy (26 September 2019). "FDA proposes ban on curcumin and other naturopathic favorites in compounded drugs". Science-Based Medicine.
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