7-Keto-DHEA: Difference between revisions

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Created page with "<languages /> <translate> {{Pathnav|Dietary supplement|Prohormone|frame=1}} {{Chembox | ImageFile = 7-Keto-DHEA.svg | ImageSize = 200px | ImageCaption = 7-Keto-DHEA | ImageFile1 = 7-Keto-DHEA acetate.svg | ImageSize1 = 200px | ImageCaption1 = 7-Keto-DHEA acetate | IUPACName = 3β-Hydroxyandrost-5-ene-7,17-dione | SystematicName = (3a''S'',3b''R'',7''S'',9a''R'',9b''S'',11a''S'')-9a,11a-Dimethyl-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1''H''-cyclopenta[''a'']phenanthre..."
 
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'''7-Ketodehydroepiandrosterone''' ('''7-keto-DHEA''', '''7-oxo-DHEA'''), also known as '''7-oxoprasterone''', is a steroid [[prohormone]] produced by metabolism of the [[prohormone]] [[dehydroepiandrosterone]] (DHEA).
'''7-Ketodehydroepiandrosterone''' ('''7-keto-DHEA''', '''7-oxo-DHEA'''), also known as '''7-oxoprasterone''', is a steroid [[prohormone]] produced by metabolism of the [[prohormone]] [[dehydroepiandrosterone]] (DHEA).


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==Pharmacodynamics==
==Pharmacodynamics==
7-Keto-DHEA is not directly converted to [[testosterone]] or [[estrogen]] by the human body. Due to this fact, the suppliers of supplements have investigated it as a potentially more useful relative of the DHEA [[steroid]] when used as a supplementation, but the results are inconclusive.
7-Keto-DHEA is not directly converted to [[testosterone]] or [[estrogen]] by the human body. Due to this fact, the suppliers of supplements have investigated it as a potentially more useful relative of the DHEA [[steroid]] when used as a supplementation, but the results are inconclusive.


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==Unsubstantiated health claims==
==Unsubstantiated health claims==
The benefits of 7-keto-DHEA supplementation are not definitively established. The health claims on potential weight loss benefits are not supported by solid evidence. The current evidence is mixed and limited by factors such as small sample sizes, short study durations, and a lack of diversity in the study populations. The safety profile of 7-keto-DHEA appears to be generally well-tolerated with a low side-effect profile, but changes in blood hormone parameters have been reported. Given these uncertainties, the potential benefits and safety of 7-keto-DHEA, particularly with long-term use, are not established. The US Food and Drug Administration (FDA) has not added 7-keto-DHEA to the list of bulk drug substances due to a lack of clinical evidence regarding its safety and efficacy.
The benefits of 7-keto-DHEA supplementation are not definitively established. The health claims on potential weight loss benefits are not supported by solid evidence. The current evidence is mixed and limited by factors such as small sample sizes, short study durations, and a lack of diversity in the study populations. The safety profile of 7-keto-DHEA appears to be generally well-tolerated with a low side-effect profile, but changes in blood hormone parameters have been reported. Given these uncertainties, the potential benefits and safety of 7-keto-DHEA, particularly with long-term use, are not established. The US Food and Drug Administration (FDA) has not added 7-keto-DHEA to the list of bulk drug substances due to a lack of clinical evidence regarding its safety and efficacy.


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In particular, 7-Keto-DHEA is marketed (also as 7-oxo-DHEA) to be more effective than DHEA for inducing heat production ([[thermogenesis]]) to be used in weight loss: because [[dieting]] is usually accompanied by reduced [[resting metabolic rate]], obese persons may benefit from using 7-keto-DHEA when dieting due to increased metabolic rate. Still, these claimed benefits are not supported by solid evidence.
In particular, 7-Keto-DHEA is marketed (also as 7-oxo-DHEA) to be more effective than DHEA for inducing heat production ([[thermogenesis]]) to be used in weight loss: because [[dieting]] is usually accompanied by reduced [[resting metabolic rate]], obese persons may benefit from using 7-keto-DHEA when dieting due to increased metabolic rate. Still, these claimed benefits are not supported by solid evidence.


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7-Keto-DHEA has also been marketed by [[alternative medicine]] providers as a treatment of [[adrenal fatigue]], a [[Pseudoscience|pseudo-scientific]] term with no scholarly basis.
7-Keto-DHEA has also been marketed by [[alternative medicine]] providers as a treatment of [[adrenal fatigue]], a [[Pseudoscience|pseudo-scientific]] term with no scholarly basis.


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==Chemistry==
==Chemistry==
7-keto-DHEA is a [[prohormone]] produced by metabolism of the [[prohormone]] [[dehydroepiandrosterone]] (DHEA).
7-keto-DHEA is a [[prohormone]] produced by metabolism of the [[prohormone]] [[dehydroepiandrosterone]] (DHEA).


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7-Keto-DHEA has a number of chemical names, including:
7-Keto-DHEA has a number of chemical names, including:
* 7-Ketodehydroepiandrosterone (7-keto-DHEA)
* 7-Ketodehydroepiandrosterone (7-keto-DHEA)
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* Androst-5-en-3β-ol-7,17-dione
* Androst-5-en-3β-ol-7,17-dione


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For the acetate ester:
For the acetate ester:
* 3β-Acetoxyandrost-5-ene-7,17-dione
* 3β-Acetoxyandrost-5-ene-7,17-dione
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* Δ<sub>5</sub>-Androstene-3β-acetoxy-7,17-dione
* Δ<sub>5</sub>-Androstene-3β-acetoxy-7,17-dione


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


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


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7-Keto-DHEA may trigger positive tests for [[performance-enhancing drug]]s.
7-Keto-DHEA may trigger positive tests for [[performance-enhancing drug]]s.


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The [[World Anti-Doping Agency]] (WADA) lists 7-keto-DHEA as a prohibited anabolic agent.
The [[World Anti-Doping Agency]] (WADA) lists 7-keto-DHEA as a prohibited anabolic agent.


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==See also==
==See also==
* [[List of investigational anxiolytics]]
* [[List of investigational anxiolytics]]
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* [[7β-Hydroxyepiandrosterone]]
* [[7β-Hydroxyepiandrosterone]]


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{{Steroid hormones}}
{{Steroid hormones}}
{{Estrogen receptor modulators}}
{{Estrogen receptor modulators}}


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{{二次利用|date=1 April 2024}}
{{二次利用|date=1 April 2024}}
[[Category:Androstanes]]
[[Category:Androstanes]]

Latest revision as of 20:41, 23 April 2024

Other languages:
Dietary supplement > Prohormone > 7-Keto-DHEA
7-Keto-DHEA

7-Keto-DHEA

7-Keto-DHEA acetate
Names
IUPAC name
3β-Hydroxyandrost-5-ene-7,17-dione
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
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
Properties
C19H26O3
Molar mass 302.414 g·mol−1

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

Pharmacodynamics

7-Keto-DHEA is not directly converted to testosterone or estrogen by the human body. Due to this fact, the suppliers of supplements have investigated it as a potentially more useful relative of the DHEA steroid when used as a supplementation, but the results are inconclusive.

Unsubstantiated health claims

The benefits of 7-keto-DHEA supplementation are not definitively established. The health claims on potential weight loss benefits are not supported by solid evidence. The current evidence is mixed and limited by factors such as small sample sizes, short study durations, and a lack of diversity in the study populations. The safety profile of 7-keto-DHEA appears to be generally well-tolerated with a low side-effect profile, but changes in blood hormone parameters have been reported. Given these uncertainties, the potential benefits and safety of 7-keto-DHEA, particularly with long-term use, are not established. The US Food and Drug Administration (FDA) has not added 7-keto-DHEA to the list of bulk drug substances due to a lack of clinical evidence regarding its safety and efficacy.

In particular, 7-Keto-DHEA is marketed (also as 7-oxo-DHEA) to be more effective than DHEA for inducing heat production (thermogenesis) to be used in weight loss: because dieting is usually accompanied by reduced resting metabolic rate, obese persons may benefit from using 7-keto-DHEA when dieting due to increased metabolic rate. Still, these claimed benefits are not supported by solid evidence.

7-Keto-DHEA has also been marketed by alternative medicine providers as a treatment of adrenal fatigue, a pseudo-scientific term with no scholarly basis.

Chemistry

7-keto-DHEA is a prohormone produced by metabolism of the prohormone dehydroepiandrosterone (DHEA).

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.

Regulation

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

7-Keto-DHEA may trigger positive tests for performance-enhancing drugs.

The World Anti-Doping Agency (WADA) lists 7-keto-DHEA as a prohibited anabolic agent.

See also

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