Bolandione

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Bolandione
Bolandione.svg
Clinical data
Other names19-Norandrostenedione; Estr-4-ene-3,17-dione; 19-Norandrost-4-en-3,17-dione
Routes of
administration 		By mouth
Legal status
Legal status
Identifiers
  • (8R,9S,10R,13S,14S)-13-Methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.010.906 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C18H24O2
Molar mass 272.388 g·mol−1
3D model (JSmol)
  • O=C4/C=C3/CC[C@@H]2[C@H](CC[C@@]1(C(=O)CC[C@H]12)C)[C@H]3CC4
  • InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-16H,2-9H2,1H3/t13-,14+,15+,16-,18-/m0/s1 Yes check.svgY
  • Key:JRIZOGLBRPZBLQ-QXUSFIETSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Bolandione, also known as 19-norandrostenedione, as well as 19-norandrost-4-en-3,17-dione or estr-4-ene-3,17-dione, is a precursor of the anabolic-androgenic steroid (AAS) nandrolone (19-nortestosterone). Until 2005, bolandione was available without prescription in United States, where it was marketed as a prohormone, but it is now classified as a Schedule III drug. It is also banned from use in many sports, including the Olympic Games, under the World Anti-Doping Code. [1] Bolandione is readily metabolized to nandrolone after oral administration, but its potency to transactivate the androgen receptor dependent reporter gene expression is 10 times lower as compared to dihydrotestosterone (DHT). [2]

Contents

Animal studies

Scientific studies have shown that oral administration of bolandione is "a very ineffective strategy for stimulating skeletal muscle mass increases but may be associated with side effects". [3]

In vivo experiments in castrated rats demonstrated that subcutaneous treatment with bolandione resulted only in a stimulation of the weight of the levator ani muscle, while the prostate and seminal vesicle weights remained completely unaffected. In contrast to its metabolite nandrolone, bolandione highly selectively stimulates the growth of the skeletal muscles but has only weak androgenic properties. [2]

Society and culture

In the early 2000s, contamination of androstenedione products with traces of bolandione caused false positives for doping tests for nandrolone because 19-norandrosterone is a metabolite of both nandrolone and bolandione. In a randomized controlled trial trace contamination of androstenedione with bolandione was sufficient for users of androstenedione to test positive for nandrolone. [4] This detail became less relevant after bolandione and 4-androstenedione were banned by major sporting bodies.

See also

Related Research Articles

<span class="mw-page-title-main">Tetrahydrogestrinone</span> Synthetic and orally active anabolic–androgenic steroid (AAS)

Tetrahydrogestrinone (THG), known by the nickname The Clear, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was developed by Patrick Arnold and was used by a number of high-profile athletes such as Marion Jones, Barry Bonds, and Dwain Chambers.

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">Nandrolone</span> Anabolic steroid

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat.

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

19-Norandrosterone, also known as 5α-estran-3α-ol-17-one, is a metabolite of nandrolone (19-nortestosterone) and bolandione (19-norandrostenedione) that is formed by 5α-reductase. It is on the list of substances prohibited by the World Anti-Doping Agency since it is a detectable metabolite of nandrolone, an anabolic-androgenic steroid (AAS). Consumption of androstendione products contaminated with traces of bolandione may also result in testing positive for nandrolone.

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

Trenbolone acetate, sold under brand names such as Finajet and Finaplix among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, specifically to increase the profitability of livestock by promoting muscle growth in cattle. It is given by injection into muscle.

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

Desoxymethyltestosterone (DMT), known by the nicknames Madol and Pheraplex, is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-methylated derivative of dihydrotestosterone (DHT) which was never marketed for medical use. It was one of the first designer steroids to be marketed as a performance-enhancing drug to athletes and bodybuilders.

<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">Dienedione</span> Chemical compound

Dienedione, also known as estra-4,9-diene-3,17-dione, is a synthetic, orally active anabolic-androgenic steroid (AAS) of the 19-nortestosterone group that was never introduced for medical use. It is thought to be a prohormone of dienolone. The drug became a controlled substance in the US on January 4, 2010, and is classified as a Schedule III anabolic steroid under the United States Controlled Substances Act. Previous to this, it was sold as a bodybuilding supplement within the United States, and often mistakenly marketed as a prohormone for trenbolone, a veterinary steroid. Prior to its scheduling, it was part of a number of supplements that were seized during FDA enforcement of Bodybuilding.com for selling unapproved new drugs. The actual active metabolite, dienolone, is almost identical to trenbolone structurally, but lacks the C11 double bond.

<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:

<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">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">19-Noretiocholanolone</span> Chemical compound

19-Noretiocholanolone, also known as 5β-estran-3α-ol-17-one, is a metabolite of nandrolone (19-nortestosterone) and bolandione (19-norandrostenedione) that is formed by 5α-reductase. It is on the list of substances prohibited by the World Anti-Doping Agency since it is a detectable metabolite of nandrolone, an anabolic-androgenic steroid (AAS).

<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">Trendione</span> Chemical compound

Trendione, also known as estra-4,9,11-triene-3,17-dione, is an androgen prohormone as well as metabolite of the anabolic steroid trenbolone. Trendione is to trenbolone as androstenedione is to testosterone. The compound is inactive itself, showing more than 100-fold lower affinity for the androgen and progesterone receptors than trenbolone. It is a designer steroid and has been sold on the internet as a "nutritional supplement". Trendione is listed in the United States Designer Anabolic Steroid Control Act of 2014.

<span class="mw-page-title-main">Structure–activity relationships of anabolic steroids</span>

The structure–activity relationships (SAR) of anabolic steroids (AAS) have been extensively studied.

References

  1. ↑ "The World Anti-Doping Code: The 2012 Prohibited List" (PDF). World Anti-Doping Agency. Archived from the original (PDF) on 2012-05-13. Retrieved 2012-07-16.
  2. 1 2 Diel P, Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schänzer W, et al. (April 2008). "The prohormone 19-norandrostenedione displays selective androgen receptor modulator (SARM) like properties after subcutaneous administration". Toxicology Letters. 177 (3): 198–204. doi:10.1016/j.toxlet.2008.01.014. PMID   18325697.
  3. ↑ Parr MK, Laudenbach-Leschowsky U, Höfer N, Schänzer W, Diel P (July 2009). "Anabolic and androgenic activity of 19-norandrostenedione after oral and subcutaneous administration--analysis of side effects and metabolism". Toxicology Letters. 188 (2): 137–141. doi:10.1016/j.toxlet.2009.03.024. PMID   19446246.
  4. ↑ Catlin DH, Leder BZ, Ahrens B, Starcevic B, Hatton CK, Green GA, Finkelstein JS (2000). "Trace contamination of over-the-counter androstenedione and positive urine test results for a nandrolone metabolite". JAMA. 284 (20): 2618–2621. doi: 10.1001/jama.284.20.2618 . PMID   11086369.
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