Bolandione

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 Edit this at Wikidata
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)

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]

  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.