Bolandione

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]

Bolandione
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 InfoCard100.010.906
Chemical and physical data
FormulaC18H24O2
Molar mass272.388 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 checkY
  • Key:JRIZOGLBRPZBLQ-QXUSFIETSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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

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. 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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