Bolazine

Bolazine (INN), also known as 2α-methyl-5α-androstan-17β-ol-3-one azine, is a synthetic androgen/anabolic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed.[1] It is not orally active and is used as the ester prodrug bolazine capronate (brand name Roxilon Inject) via depot intramuscular injection.[1] Bolazine has a unique and unusual chemical structure, being a dimer of drostanolone linked at the C3 position of the A-ring by an azine group, and reportedly acts as a prodrug of drostanolone.[2]

Bolazine
Clinical data
Other names2α-methyl-5α-androstan-17β-ol-3-one azine
Identifiers
IUPAC name
  • (2R,3E,5S,8R,9S,10S,13S,14S,17S)-3-[(E)-[(10S,13R)-15-hydroxy-2,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-ylidene]hydrazinylidene]-2,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC40H64N2O2
Molar mass604.964 g·mol−1
3D model (JSmol)
SMILES
  • C[C@@]23[C@](CC[C@]4([H])[C@@]([H])3CC[C@@]5(C)[C@]([H])4CC[C@@H]5O)([H])C/C([C@H](C)C2)=N/N=C1[C@H](C)C[C@@]6(C)[C@](CC[C@]7([H])[C@@]([H])6CC[C@@]8(C)[C@]([H])7CC[C@@H]8O)([H])C/1
InChI
  • InChI=1S/C40H64N2O2/c1-23-21-39(5)25(7-9-27-29-11-13-35(43)37(29,3)17-15-31(27)39)19-33(23)41-42-34-20-26-8-10-28-30-12-14-36(44)38(30,4)18-16-32(28)40(26,6)22-24(34)2/h23-32,35-36,43-44H,7-22H2,1-6H3/b41-33+,42-34+/t23-,24-,25+,26+,27+,28+,29+,30+,31+,32+,35+,36+,37+,38+,39+,40+/m1/s1 N
  • Key:BQDZMZRUXNFTQT-KSJDNICASA-N N
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See also

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 653–. ISBN 978-1-4757-2085-3.
  2. Clemens R, Pressman P (2015). "Nutritional and Dietary Supplements: Code or Concern". Preventive Nutrition. pp. 47–62. doi:10.1007/978-3-319-22431-2_3. ISBN 978-3-319-22430-5.
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