Chemistry:7-Keto-DHEA
 7-Keto-DHEA
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 7-Keto-DHEA acetate
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| Names | |
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| IUPAC name
3β-Hydroxyandrost-5-ene-7,17-dione
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| Systematic 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
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| 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,7-oxo-DHEA), also known as 7-oxoprasterone, is a prohormone produced by metabolism of the prohormone dehydroepiandrosterone (DHEA).[1]
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
- List of investigational anxiolytics
- 7α-Hydroxy-DHEA
- 7β-Hydroxy-DHEA
- 7α-Hydroxyepiandrosterone
- 7β-Hydroxyepiandrosterone
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. PMID 21051179.
- ↑ "Steroids and thermogenesis". Physiological Research 55 (2): 123–131. 2006. doi:10.33549/physiolres.930758. PMID 15910167. http://www.biomed.cas.cz/physiolres/pdf/55/55_123.pdf.
- ↑ "HUM5007, a novel combination of thermogenic compounds, and 3-acetyl-7-oxo-dehydroepiandrosterone: each increases the resting metabolic rate of overweight adults". Journal of Nutritional Biochemistry 18 (9): 629–634. 2007. doi:10.1016/j.jnutbio.2006.11.008. PMID 17418559. http://drkrygier.com/uploads/3/0/9/5/3095100/7-ketostudy.pdf.
- ↑ 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". World Anti-Doping Agency. https://www.wada-ama.org/sites/default/files/prohibited_list_2018_en.pdf.
- ↑ 9.0 9.1 9.2 Jann Bellamy (26 September 2019). "FDA proposes ban on curcumin and other naturopathic favorites in compounded drugs". Science-Based Medicine. https://sciencebasedmedicine.org/fda-proposes-ban-on-curcumin-and-other-naturopathic-favorites-in-compounded-drugs/.
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