7-Ketodehydroepiandrosterone (7-keto-DHEA,7-oxo-DHEA), also known as 7-oxoprasterone, is a
prohormone
A prohormone is a committed precursor of a hormone consisting of peptide hormones synthesized together that has a minimal hormonal effect by itself because of its expression-suppressing structure, often created by protein folding and binding additi ...
produced by metabolism of the
prohormone
A prohormone is a committed precursor of a hormone consisting of peptide hormones synthesized together that has a minimal hormonal effect by itself because of its expression-suppressing structure, often created by protein folding and binding additi ...
dehydroepiandrosterone
Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. It is one of the most abundant circulating steroids in humans. DHEA is produced in the adrenal glands, the gonads, and the brain. It fun ...
(DHEA).
7-oxo-DHEA is even more effective than DHEA for inducing heat production (
thermogenesis
Thermogenesis is the process of heat production in organisms. It occurs in all warm-blooded animals, and also in a few species of thermogenic plants such as the Eastern skunk cabbage, the Voodoo lily ('' Sauromatum venosum''), and the giant w ...
).
Because
dieting is usually accompanied by reduced
resting metabolic rate Resting metabolic rate (RMR) is whole-body mammal (and other vertebrate) metabolism during a time period of strict and steady ''resting conditions'' that are defined by a combination of assumptions of physiological homeostasis and biological equili ...
, obese persons may benefit from using 7-oxo-DHEA when dieting due to increased metabolic rate.
7-Keto-DHEA is not directly converted to
testosterone
Testosterone is the primary sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteristi ...
or
estrogen
Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal ac ...
, and has thus been investigated as a potentially more useful relative of DHEA.
Researchers have raised concern that supplements may trigger positive tests for
performance-enhancing drug
Performance-enhancing substances, also known as performance-enhancing drugs (PEDs), are substances that are used to improve any form of activity performance in humans. A well-known example of cheating in sports involves doping in sport, where bann ...
s.
The
World Anti-Doping Agency
The World Anti-Doping Agency (WADA; french: Agence mondiale antidopage, AMA) is a foundation initiated by the International Olympic Committee based in Canada to promote, coordinate, and monitor the fight against drugs in sports. The agency's key ...
lists 7-keto-DHEA as a prohibited anabolic agent.
The FDA has proposed that it be banned from use in
compounded drugs.
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
* Δ
5-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
Adrenal fatigue or hypoadrenia is a pseudo-scientific term used by alternative medicine providers to suggest that the adrenal glands are exhausted and unable to produce adequate quantities of hormones, primarily cortisol, due to chronic stress o ...
, a
pseudo-scientific
Pseudoscience consists of statements, beliefs, or practices that claim to be both scientific and factual but are incompatible with the scientific method. Pseudoscience is often characterized by contradictory, exaggerated or unfalsifiable claim ...
term with no scientific basis.
Regulation
The FDA has proposed that 7-Keto-DHEA be included among substances banned from use in
compounded drugs.
[
]
See also
* List of investigational anxiolytics
This is a list of investigational anxiolytics, or anxiolytics that are currently under development for clinical use but are not yet approved. Chemical/generic names are listed first, with developmental code names, synonyms, and brand names in paren ...
* 7α-Hydroxy-DHEA
7α-Hydroxydehydroepiandrosterone (7α-hydroxy-DHEA; 7α-OH-DHEA), also known as 3β,7α-dihydroxyandrost-5-ene-17-one, is an endogenous, naturally occurring steroid and a major metabolite of dehydroepiandrosterone (DHEA) that is formed by CYP7B1 ...
* 7β-Hydroxy-DHEA
7β-Hydroxydehydroepiandrosterone (7β-hydroxy-DHEA; 7β-OH-DHEA), also known as 3β,7β-dihydroxyandrost-5-ene-17-one, is an endogenous, naturally occurring steroid and a metabolite of dehydroepiandrosterone (DHEA). The major metabolic pathway o ...
* 7α-Hydroxyepiandrosterone
7α-Hydroxyepiandrosterone (7α-OH-EPIA), also known as 3β,7α-dihydroxy-5α-androstan-17-one, is an endogenous, naturally occurring metabolite of epiandrosterone and dehydroepiandrosterone (DHEA) that is formed by the enzyme CYP7B1 in tissues ...
* 7β-Hydroxyepiandrosterone
7β-Hydroxyepiandrosterone (7β-OH-EPIA), also known as 5α-androstan-3β,7β-diol-17-one, is an endogenous androgen, estrogen, and neurosteroid that is produced from dehydroepiandrosterone and epiandrosterone. It has neuroprotective effects and, ...
References
{{Estrogen receptor modulators
Androstanes
Estrogens
World Anti-Doping Agency prohibited substances