Androgen prohormone

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An androgen prohormone, or proandrogen, is a prohormone (or prodrug) 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. [1]

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In the last two decades, prohormones have also been used by bodybuilders, athletes, and nonmedical users of AAS and other hormones to refer to substances that are expected to convert to active hormones in the body. The intent is to provide the benefits of taking an AAS without the legal risks, and to achieve the hoped-for benefits or advantages without use of AAS themselves. Many of these compounds are legal to manufacture, sell, possess and ingest eliminating the legal problems associated with schedule III AAS. This also enables chemists to further their legal research and get around the law (albeit for a short time). [2] The typical definition of "prohormone" includes a steroidal molecule that has the opposite molecular structure to testosterone on either the 3a/b position or the 17b position. Testosterone has a ketone group on the 3 carbon and a hydroxyl on the 17b carbon. A steroid with modifications away from testosterone in one or both of these areas is commonly referred to as a "prohormone". These enzymatic changes occur with the body's bidirectional enzymes. [3] [4]

On October 22, 2004, President Bush signed into law the Anabolic Steroid Control Act of 2004 (118 Stat. 1661). [5] The bill was written to become effective in 90 days, which was January 20, 2005. This legislation places both AAS and some androgen prohormones on a list of controlled substances (a new type of "regulatory control"). [5] Statutory definition of AAS: "The term 'anabolic steroid' means any drug or hormonal substance, chemically and pharmacologically related to testosterone (other than estrogens, progestins, corticosteroids and dehydroepiandrosterone)". The Act also lists substances called prohormones, qualifying them as AAS, yet these substances were mainly included in the list due to the generalization of the definition of AAS which makes it currently impossible to synthesize any further substances linked with testosterone for the needs of athlete supplementation. [6]

Prohormones added to the list of schedule III AAS

The 108th Congress amended the Controlled Substances Act to include AAS and to add in information about steroids and steroid precursors. This amendment is sometimes called the Anabolic Steroid Control Act of 2004.

The first thing this amendment did was insert a definition of AAS as follows: "The term 'anabolic steroid' means any drug or hormonal substance, chemically and pharmacologically related to testosterone (other than estrogens, progestins, corticosteroids and dehydroepiandrosterone)." [6]

Apart from the definition, the document enumerates the presently known prohormones:

Note that this list contains examples and it is not a closed list – any other compound, which affects testosterone, according to the definition is an AAS under U.S. law. [6]

"Designer steroids" and adulterated supplements

In view of a total ban from 2004, manufacturers cannot launch next AAS, presently they are interested in substances that are related to hormones, but do not affect testosterone. These include derivatives e.g. methoxydienone (methoxygonadiene; Ethyl Methoxy Gona), methasterone (so called Superdrol or S-Drol) and many others, sometimes called "designer steroids". Such compounds although harmful, do not infringe the Anabolic Steroid Control Act because they do not have any impact on the testosterone level. Owing to the same reason, they did not assist in building muscle and are not applicable in supporting – it is typical that the descriptions of these compounds try to manipulate the chemical concepts, but do not even mention the possibility of raising testosterone – because they do not even have such a potential. [7]

After the publicity of the fraud in the media [8] many manufacturers lost the trust, and the U.S. health authorities began to eliminate suspicious products. The research carried out by state laboratories confirmed that "designer steroids" are, in fact, pharmaceuticals like metandienone, stanazolol, methylstenbolone, boldenone, chlorodehydromethyltestosterone, DHT, and oxandrolone, added to supplements in a random manner. [9] Supplements with different names and described ingredients could have the same steroid (e.g., chlorodehydromethylandrostenediol (Halodrol), desoxymethyltestosterone (Madol, Pheraplex), others) and sometimes supplements with similar names could have different ingredients (e.g. Finabolic). [7]

Regulation in the United States and Europe

Following the introduction of the Anabolic Steroid Control Act, labeling products derived from plant extracts with the help of chemical symbols of organic substances found in these plants or creating names for these substances which referred to prohibited AAS became a popular marketing practice employed by American manufacturers. No analogical act targeting athlete supplementation is in force in the European Union; however each country has its own regulations concerning substances with medicinal properties. Due to the above, one can come in contact with the sale of supplements with names identical to or resembling those questioned by the RDA in the United States (S-DROL, HALODROL, etc.). Laboratory controls indicate that products which declare to include prohormones, prohibited in the USA, in fact contain "classic" AAS of the previous generation. [10] Many consumers in Europe did not know that it was illegal produce prohormones in the USA after the year 2004 and thought that were consuming various versions of the previously acclaimed supplement, while in fact consuming steroids of unknown origin. In situations like ones described above the purchaser of this fake substance knows neither the type nor the dosage of the ingested hormone, and thus cannot plan a safe gastro-protective regime or supplementary treatment. The consumer also cannot gain access to information concerning the possible long-term consequences of treatment with the unspecified hormone. This has led to the popularity of special forums on which consumers could share their experiences with the substances, yet the fake products could have radically different components, despite similar descriptions and names. Supplement manufacturers who have made a name for themselves and want to remain on the market are currently elaborating AAS based on natural substances (usually plant-derived). In Europe these products are called prohormones.

Producers who still want to offer supplements supporting the hormonal balance can still employ the natural compounds. Known in the field of prohormones Patrick Arnold (the one who introduced 1-AD and the first prohormones) is currently working on ursolic acid, on the other hand in Eastern Europe manufacturers launch supplements based on buteins, [11] - natural compounds considered as the strongest aromatase inhibitors. [12]

List of androgen/AAS prohormones

Related Research Articles

<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).

Androstenediol may refer to:

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

1-Androstenediol, or 5α-androst-1-ene-3β,17β-diol, also known as 4,5α-dihydro-δ1-4-androstenediol, is a prohormone of 1-testosterone (Δ1-DHT). It has been used as a dietary supplement, and is identified by the World Anti-Doping Agency as a prohibited substance related to anabolic steroids.

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

1-Testosterone, also known as δ1-dihydrotestosterone (δ1-DHT), as well as dihydroboldenone, is a synthetic anabolic–androgenic steroid (AAS) and a 5α-reduced derivative of boldenone (Δ1-testosterone). It differs from testosterone by having a 1(2)-double bond instead of a 4(5)-double bond in its A ring. It was legally sold online in the United States until 2005, when it was reclassified as a Schedule III drug.

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

Methandriol, also known as methylandrostenediol, is an androgen and anabolic steroid (AAS) medication which was developed by Organon and is used in both oral and injectable formulations. It is an orally active 17α-alkylated AAS and a derivative of the endogenous androgen prohormone androstenediol.

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

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

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

Bolandiol is an anabolic-androgenic steroid (AAS) that was never marketed. However, a dipropionate ester derivative, bolandiol dipropionate, has been marketed. Bolandiol and its dipropionate ester are unique among AASs in that they reportedly also possesses estrogenic and progestogenic activity.

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

1-Androstenedione, or 5α-androst-1-ene-3,17-dione, also known as 4,5α-dihydro-δ1-4-androstenedione, is a synthetic androgen and anabolic steroid. It is a 5α-reduced isomer of the endogenous steroid 4-androstenedione and acts as an androgen prohormone of 1-testosterone (4,5α-dihydro-δ1-testosterone), a derivative of dihydrotestosterone (DHT).

Androstenedione may refer to:

Androstenolone may refer to:

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 additional peptide chains to certain ends, that makes hormone receptor binding sites located on its peptide hormone chain segments inaccessible. Prohormones can travel the blood stream as a hormone in an inactivated form, ready to be activated later in the cell by post-translational modification.

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

Chloromethylandrostenediol (CMA), also known as 4-chloro-17α-methyl-androst-4-ene-3β,17β-diol, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a 17α-alkylated derivative of 4-androstenediol that was never marketed. It was first encountered in 2005 when it was introduced as a "dietary supplement" and putative prohormone under the name Promagnon by an online vendor called Peak Performance Laboratories. CMA was voluntarily discontinued by Gaspari Nutrition in late 2006, likely fearing government sanctions if it continued to sell the product.

<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">19-Nor-5-androstenedione</span> Synthetic, orally active anabolic steroid

19-Nor-5-androstenedione, also known as estr-5-ene-3,17-dione, 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">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.

References

  1. ↑ Risto Erkkola (2006). The Menopause. Elsevier. pp. 5–. ISBN   978-0-444-51830-9.
  2. ↑ “What are Prohormones? Archived 2022-01-14 at the Wayback Machine ?”, Dench City, 13 Jan. 2022.
  3. ↑ Lommer D, Dorfman RI, Forchelli E. Reversal of the 3 -hydroxysteroid dehydrogenase-isomerase reactions in rat adrenals. Steroidologia. 1970;1(3):175-82.
  4. ↑ WARD MG, ENGEL LL. REVERSAL OF THE 3-BETA-HYDROXYSTEROID DEHYDROGENASE-ISOMERASE REACTIONS. CONVERSION OF ANDROST-4-ENE-3,17-DIONE-4-14C TO 3-BETA-HYDROXYANDROST-4-EN-17-ONE-14C AND 3-BETA-HYDROXYANDROST-5EN-17-ONE-14C. J Biol Chem. 1964 Oct;239:PC3604-6.
  5. 1 2 "Public Law 108-358-Oct. 22, 2004" (PDF). 108th US Congress. October 22, 2004. Retrieved July 8, 2007.
  6. 1 2 3 Steroid Law– Anabolic Steroid Control Act steroid-abuse.org
  7. 1 2 hugesupplements.com, Details section
  8. ↑ Amy Shipley "Steroids Detected In Dietary Tablets" "Washington Post" Staff Writer, November 30, 2005
  9. ↑ Polish Anti-Doping Agency (WADA Partner Archived 2013-05-12 at the Wayback Machine ) Report 01-2009 Archived 2013-11-10 at the Wayback Machine
  10. ↑ U.S. Food and Drug Administration fda.gov
  11. ↑ S.Amboziak "Aromatase in the dock" 09.2012
  12. ↑ Wang Y. "The plant polyphenol butein inhibits testosterone-induced proliferation in breast cancer cells expressing aromatase" Life Sci. 2005 May 20;77(1):39-51.
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