7-Keto-DHEA

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7-Keto-DHEA
7-Keto-DHEA.svg
7-Keto-DHEA
7-Keto-DHEA acetate.svg
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
PubChem CID
UNII
  • 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
  • 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
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).

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). [1] [2]

Contents

Pharmacodynamics

7-Keto-DHEA is not directly converted to testosterone or estrogen by the human body. [3] 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. [1] [3]

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. [3] [4] 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. [3]

In particular, 7-Keto-DHEA is marketed (also as 7-oxo-DHEA) to be more effective than DHEA for inducing heat production (thermogenesis) [5] 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. [6] Still, these claimed benefits are not supported by solid evidence. [3]

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. [7]

Chemistry

7-keto-DHEA is a prohormone produced by metabolism of the prohormone dehydroepiandrosterone (DHEA). [1]

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

For the acetate ester:

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]

7-Keto-DHEA may trigger positive tests for performance-enhancing drugs. [8] [9]

The World Anti-Doping Agency (WADA) lists 7-keto-DHEA as a prohibited anabolic agent. [10]

See also

Related Research Articles

<span class="mw-page-title-main">Dehydroepiandrosterone</span> Chemical compound

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 functions as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids both in the gonads and in various other tissues. However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors, and acting as a neurosteroid and modulator of neurotrophic factor receptors.

An androgen prohormone, or proandrogen, is a prohormone of an anabolic-androgenic steroid (AAS). They can be prohormones of testosterone or of synthetic AAS, for example, nandrolone (19-nortestosterone). Dehydroepiandrosterone (DHEA), DHEA sulfate (DHEA-S), and androstenedione may all be considered proandrogens of testosterone.

<span class="mw-page-title-main">Androstenedione</span> Endogenous weak androgen

Androstenedione, or 4-androstenedione, also known as androst-4-ene-3,17-dione, is an endogenous weak androgen steroid hormone and intermediate in the biosynthesis of estrone and of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenediol (androst-5-ene-3β,17β-diol).

<span class="mw-page-title-main">Prasterone</span> Medical usage of the prasterone compound

Prasterone, also known as dehydroepiandrosterone (DHEA) and sold under the brand name Intrarosa among others, is a medication as well as over-the-counter dietary supplement which is used to correct DHEA deficiency due to adrenal insufficiency or old age, as a component of menopausal hormone therapy, to treat painful sexual intercourse due to vaginal atrophy, and to prepare the cervix for childbirth, among other uses. It is taken by mouth, by application to the skin, in through the vagina, or by injection into muscle.

<span class="mw-page-title-main">Androstenediol</span> Chemical compound

Androstenediol, or 5-androstenediol, also known as androst-5-ene-3β,17β-diol, is an endogenous weak androgen and estrogen steroid hormone and intermediate in the biosynthesis of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenedione (androst-4-ene-3,17-dione).

<span class="mw-page-title-main">4-Androstene-3,6,17-trione</span> Chemical compound

4-Androstene-3,6,17-trione is a drug or nutritional supplement that may increase the testosterone-estrogen ratio, but has no proven effect on body composition. Its use can be detected in urine.

<span class="mw-page-title-main">17α-Hydroxypregnenolone</span> Chemical compound

17α-Hydroxypregnenolone is a pregnane (C21) steroid that is obtained by hydroxylation of pregnenolone at the C17α position. This step is performed by the mitochondrial cytochrome P450 enzyme 17α-hydroxylase (CYP17A1) that is present in the adrenal and gonads. Peak levels are reached in humans at the end of puberty and then decline. High levels are also achieved during pregnancy. It is also a known neuromodulator.

3β-Hydroxysteroid dehydrogenase/Δ5-4 isomerase (3β-HSD) is an enzyme that catalyzes the biosynthesis of the steroid progesterone from pregnenolone, 17α-hydroxyprogesterone from 17α-hydroxypregnenolone, and androstenedione from dehydroepiandrosterone (DHEA) in the adrenal gland. It is the only enzyme in the adrenal pathway of corticosteroid synthesis that is not a member of the cytochrome P450 family. It is also present in other steroid-producing tissues, including the ovary, testis and placenta. In humans, there are two 3β-HSD isozymes encoded by the HSD3B1 and HSD3B2 genes.

<span class="mw-page-title-main">Epiandrosterone</span> Chemical compound

Epiandrosterone, or isoandrosterone, also known as 3β-androsterone, 3β-hydroxy-5α-androstan-17-one, or 5α-androstan-3β-ol-17-one, is a steroid hormone with weak androgenic activity. It is a metabolite of testosterone and dihydrotestosterone (DHT). It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystalline androsterone, which was sufficient to find that the chemical formula was very similar to estrone.

<span class="mw-page-title-main">7α-Methyl-19-norandrostenedione</span> Chemical compound

7α-Methyl-19-norandrostenedione, or 7α-methyl-19-norandrost-4-ene-3,17-dione, also known as trestione, as well as 7α-methylestr-4-ene-3,17-dione, is a synthetic anabolic-androgenic steroid (AAS) and a derivative of 19-nortestosterone (nandrolone). It may act as a prohormone of trestolone. MENT dione has been sold on the Internet under the name Mentabolan as a "dietary supplement".

<span class="mw-page-title-main">7β-Hydroxyepiandrosterone</span> Chemical compound

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, along with 7α-hydroxyepiandrosterone, may mediate the neuroprotective effects of DHEA. 7β-OH-EPIA may act as a highly potent antagonist of the G protein-coupled estrogen receptor (GPER).

<span class="mw-page-title-main">19-Nor-5-androstenediol</span> Chemical compound

19-Nor-5-androstenediol, also known as estr-5-ene-3β,17β-diol, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a derivative of 19-nortestosterone (nandrolone) that was never introduced for medical use. It is an androgen prohormone of nandrolone and of other 19-norandrostanes.

<span class="mw-page-title-main">1-Androsterone</span> Chemical compound

1-Androsterone is a synthetic, orally active anabolic-androgenic steroid (AAS). It is an androgen prohormone of 1-testosterone (dihydroboldenone), 1-androstenedione, and other 1-dehydrogenated androstanes. The drug has been sold on the Internet as a designer steroid and "dietary supplement". It is a positional isomer of dehydroepiandrosterone.

<span class="mw-page-title-main">7α-Hydroxy-DHEA</span> Chemical compound

7α-Hydroxydehydroepiandrosterone, 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 in tissues such as the prostate gland and by CYP3A4 in the liver. The major metabolic pathway of DHEA outside the liver is via 7-hydroxylation into 7α-OH-DHEA and 7β-OH-DHEA. 7α-OH-DHEA has weak estrogenic activity, selectively activating the estrogen receptor ERβ. In addition, 7α-OH-DHEA may be responsible for the known antiglucocorticoid effects of DHEA.

7-Hydroxy-DHEA, or 7-hydroxydehydroepiandrosterone, may refer to:

<span class="mw-page-title-main">7β-Hydroxy-DHEA</span> Chemical compound

7β-Hydroxydehydroepiandrosterone, 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 of DHEA outside the liver is via 7-hydroxylation into 7α-OH-DHEA and 7β-OH-DHEA. 7β-OH-DHEA has weak antiestrogenic activity, selectively antagonizing the estrogen receptor ERβ.

<span class="mw-page-title-main">7α-Hydroxyepiandrosterone</span> Chemical compound

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 such as the liver and brain.

<span class="mw-page-title-main">19-Nordehydroepiandrosterone</span> Chemical compound

19-Nordehydroepiandrosterone (19-nor-DHEA), or 19-nor-5-dehydroepiandrosterone (19-nor-5-DHEA), is an estrane (19-norandrostane) steroid which was never marketed. It is the combined derivative of the androgen/anabolic steroid nandrolone (19-nortestosterone) and the androgen prohormone dehydroepiandrosterone. Related compounds include 19-nor-5-androstenediol, bolandiol (19-nor-4-androstenediol), and bolandione (nor-4-androstenedione), which are all known orally active prohormones of nandrolone. 19-Nor-DHEA may occur as a metabolite of bolandione and related steroids.

<span class="mw-page-title-main">Androstenetriol</span> Chemical compound

Androstenetriol is a steroid produced in the adrenal glands as a metabolite of DHEA. It is believed to have similar effects as DHEA and androstenediol. A study in rodents found that the compound was a weak androgen and estrogen, but did not attach to the androgen, estrogen, progesterone, or glucocorticoid receptors. Synthetic analogs of AET known as HE3286 and NE3107 have been developed.

References

  1. 1 2 3 Bonetti G, Herbst KL, Dhuli K, Kiani AK, Michelini S, Michelini S, Ceccarini MR, Michelini S, Ricci M, Cestari M, Codini M, Beccari T, Bellinato F, Gisondi P, Bertelli M (June 2022). "Dietary supplements for lipedema". J Prev Med Hyg. 63 (2 Suppl 3): E169–E173. doi:10.15167/2421-4248/jpmh2022.63.2S3.2758. PMC   9710418 . PMID   36479502.
  2. ↑ "7-Keto-dehydroepiandrosterone". PubChem . National Center for Biotechnology Information . Retrieved 1 April 2024.
  3. 1 2 3 4 5 Jeyaprakash N, Maeder S, Janka H, Stute P (September 2023). "A systematic review of the impact of 7-keto-DHEA on body weight". Arch Gynecol Obstet. 308 (3): 777–785. doi: 10.1007/s00404-022-06884-8 . PMC   10348924 . PMID   36566478. Creative Commons by small.svg  This article incorporates textfrom this source, which is available under the CC BY 4.0 license.
  4. ↑ Barber TM, Kabisch S, Pfeiffer AF, Weickert MO (June 2023). "Metabolic-Associated Fatty Liver Disease and Insulin Resistance: A Review of Complex Interlinks". Metabolites. 13 (6): 757. doi: 10.3390/metabo13060757 . PMC   10304744 . PMID   37367914.
  5. ↑ 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. Archived (PDF) from the original on 2023-01-09. Retrieved 2024-03-31.
  6. ↑ 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. Archived (PDF) from the original on 2022-08-12. Retrieved 2024-03-31.
  7. 1 2 Jann Bellamy (26 September 2019). "FDA proposes ban on curcumin and other naturopathic favorites in compounded drugs". Science-Based Medicine. Archived from the original on 28 March 2024. Retrieved 31 March 2024.
  8. ↑ 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.
  9. ↑ "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.
  10. ↑ "The World Anti-Doping Code International Standard Prohibited List January 2018" (PDF). World Anti-Doping Agency. Archived (PDF) from the original on October 22, 2017. Retrieved October 21, 2017.
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