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 u ...

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 as well as synthetic androgens that are structurally related and have similar effects t ...

(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 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 ...

, 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 multi ...

, 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 k ...

. Bolandione is readily metabolized to nandrolone after oral administration, but its potency to transactivate 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 ...

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 pharmac ...

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 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, chemically, and phys ...

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 m ...

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 dehy ...

products with traces of bolandione caused false positives for doping tests for

because 19-norandrosterone is a metabolite of both

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 t ...

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.

References

Androgens and anabolic steroids Diketones Estranes Estrogens Prodrugs Progestogens World Anti-Doping Agency prohibited substances {{Genito-urinary-drug-stub

See also

References