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]
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.
^
abDiel 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.
PMID18325697.
^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.
PMID19446246.