Testosterone benzoate

Testosterone benzoate, or testosterone 17β-benzoate, also known as androst-4-en-17β-ol-3-one 17β-benzoate, is a synthetic, injected anabolic–androgenic steroid (AAS) and an androgen ester – specifically, the benzoate C17β ester of testosterone – which was never marketed.[1][2] It is a prodrug of testosterone and, when administered via intramuscular injection, is associated with a long-lasting depot effect and extended duration of action.[3][4][5] The drug was first described in 1936 and was the first androgen ester and ester of testosterone to be synthesized.[6]

Testosterone benzoate
Clinical data
Other namesTestosterone 17β-benzoate; Androst-4-en-17β-ol-3-one 17β-benzoate
Routes of
administration		Intramuscular injection
Identifiers
IUPAC name
  • [(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] benzoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.016.575
Chemical and physical data
FormulaC26H32O3
Molar mass392.539 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)C4=CC=CC=C4)CCC5=CC(=O)CC[C@]35C
InChI
  • InChI=1S/C26H32O3/c1-25-14-12-19(27)16-18(25)8-9-20-21-10-11-23(26(21,2)15-13-22(20)25)29-24(28)17-6-4-3-5-7-17/h3-7,16,20-23H,8-15H2,1-2H3/t20-,21-,22-,23-,25-,26-/m0/s1
  • Key:RZJSCADWIWNGKI-IXKNJLPQSA-N

See also

References
  1. Yalkowsky SH, He Y, Jain P (19 April 2016). Handbook of Aqueous Solubility Data, Second Edition. CRC Press. pp. 1313–. ISBN 978-1-4398-0246-5.
  2. Archer T, Hansen S (5 September 2013). Behavioral Biology: Neuroendocrine Axis. Psychology Press. pp. 76–. ISBN 978-1-134-76125-8.
  3. CIBA Foundation Symposium (17 September 2009). Hormones, Psychology and Behaviour, Volume 3: Book I of Colloquia on Endocrinology. John Wiley & Sons. pp. 260–. ISBN 978-0-470-71486-7.
  4. Schaefer B (26 May 2015). Natural Products in the Chemical Industry. Springer. pp. 540–. ISBN 978-3-642-54461-3.
  5. Lamparczyk H (21 August 1992). CRC Handbook of Chromatography: Analysis and Characterization of Steroids. CRC Press. pp. 34–. ISBN 978-0-8493-3008-7.
  6. Parkes AS (1936). "Increasing the Effectiveness of Testosterone". The Lancet. 228 (5899): 674–676. doi:10.1016/S0140-6736(00)80929-0. ISSN 0140-6736.
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