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
Precursor or Precursors may refer to:
*Precursor (religion), a forerunner, predecessor
** The Precursor, John the Baptist
Science and technology
* Precursor (bird), a hypothesized genus of fossil birds that was composed of fossilized parts of unr ...
of the
anabolic-androgenic steroid
Anabolic steroids, also known more properly as anabolic–androgenic steroids (AAS), are steroidal androgens that include natural androgens like testosterone (medication), testosterone as well as synthetic androgens that are structurally related ...
(AAS)
nandrolone
Nandrolone, also known as 19-nortestosterone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate (brand name Durabolin). Nandrolon ...
(19-nortestosterone). Until 2005, bolandione was available without prescription in United States, where it was marketed as a
prohormone
A prohormone is a committed Precursor (chemistry), 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 fol ...
, but it is now classified as a
Schedule III drug. It is also banned from use in many sports, including the
Olympic Games
The modern Olympic Games or Olympics (french: link=no, Jeux olympiques) are the leading international sporting events featuring summer and winter sports competitions in which thousands of athletes from around the world participate in a var ...
, under the
World Anti-Doping Code
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 ...
. Bolandione is readily metabolized to nandrolone after oral administration, but its potency to
transactivate In the context of gene regulation: transactivation is the increased rate of gene expression triggered either by biological processes or by artificial means, through the expression of an intermediate transactivator protein.
In the context of rece ...
the
androgen receptor
The androgen receptor (AR), also known as NR3C4 (nuclear receptor subfamily 3, group C, member 4), is a type of nuclear receptor that is activated by binding any of the androgenic hormones, including testosterone and dihydrotestosterone in th ...
dependent reporter gene expression is 10 times lower as compared to
dihydrotestosterone
Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone. The enzyme 5α-reductase catalyzes the formation of DHT from testosterone in certain tissues includi ...
(DHT).
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".
''In vivo'' experiments in
castrated
Castration is any action, surgical, chemical, or otherwise, by which an individual loses use of the testicles: the male gonad. Surgical castration is bilateral orchiectomy (excision of both testicles), while chemical castration uses pharmaceut ...
rats demonstrated that
subcutaneous treatment with bolandione resulted only in a stimulation of the weight of the
levator ani
The levator ani is a broad, thin muscle group, situated on either side of the pelvis. It is formed from three muscle components: the pubococcygeus, the iliococcygeus, and the puborectalis.
It is attached to the inner surface of each side of the ...
muscle, while the
prostate
The prostate is both an Male accessory gland, accessory gland of the male reproductive system and a muscle-driven mechanical switch between urination and ejaculation. It is found only in some mammals. It differs between species anatomically, ...
and seminal vesicle weights remained completely unaffected. In contrast to its metabolite nandrolone, bolandione highly selectively stimulates the growth of the
skeletal muscle
Skeletal muscles (commonly referred to as muscles) are organs of the vertebrate muscular system and typically are attached by tendons to bones of a skeleton. The muscle cells of skeletal muscles are much longer than in the other types of muscl ...
s but has only weak
androgenic
An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This incl ...
properties.
[
In the early 2000s, contamination of ]androstenedione
Androstenedione, or 4-androstenedione (abbreviated as A4 or Δ4-dione), 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 dehydroepia ...
products with traces of bolandione caused false positives for doping tests for nandrolone
Nandrolone, also known as 19-nortestosterone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate (brand name Durabolin). Nandrolon ...
because 19-norandrosterone is a metabolite of both nandrolone
Nandrolone, also known as 19-nortestosterone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate (brand name Durabolin). Nandrolon ...
and bolandione. In a randomized controlled trial
A randomized controlled trial (or randomized control trial; RCT) is a form of scientific experiment used to control factors not under direct experimental control. Examples of RCTs are clinical trials that compare the effects of drugs, surgical te ...
trace contamination of androstenedione with bolandione was sufficient for users of androstenedione to test positive for nandrolone. This detail became less relevant after bolandione and 4-androstenedione were banned by major sporting bodies.
See also
* List of androgens/anabolic steroids
This is a list of androgens/ anabolic steroids (AAS) or testosterone derivatives. Esters are mostly not included in this list; for esters, see here instead. The major classes of testosterone derivatives include the following (as well as combinat ...
References
Androgens and anabolic steroids
Diketones
Estranes
Estrogens
Prodrugs
Progestogens
World Anti-Doping Agency prohibited substances
{{Genito-urinary-drug-stub