Testosterone palmitate

Testosterone palmitate, also known as testosterone hexadecanoate, testosterone 17β-palmitate, and androst-4-en-17β-ol-3-one 17β-palmitate, is an anabolic-androgenic steroid (AAS) and an androgen ester – specifically, the C17β palmitate (hexadecanoate) ester of testosterone – which was never marketed.[1][2][3] 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.[1]

Testosterone palmitate
Clinical data
Other namesTestosterone hexadecanoate; Testosterone 17β-palmitate; Androst-4-en-17β-ol-3-one 17β-palmitate
Routes of
administration		Oral, 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] hexadecanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC35H58O3
Molar mass526.846 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
InChI
  • InChI=1S/C35H58O3/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-33(37)38-32-21-20-30-29-19-18-27-26-28(36)22-24-34(27,2)31(29)23-25-35(30,32)3/h26,29-32H,4-25H2,1-3H3/t29-,30-,31-,32-,34-,35-/m0/s1
  • Key:OKFBXYQPCPWWRP-SHDAAXGTSA-N

Testosterone palmitate is a longer-chain ester of testosterone compared to testosterone undecanoate.[1] Relative to testosterone undecanoate, testosterone palmitate shows higher oral bioavailability.[1] However, no free testosterone was observed after administration of testosterone palmitate, suggesting that it is not hydrolyzed as efficiently as testosterone undecanoate.[1] On the other hand, another study found that testosterone palmitate was hydrolyzed in humans.[4]

See also

References
  1. Touitou E, Barry BW (27 November 2006). Enhancement in Drug Delivery. CRC Press. pp. 122–. ISBN 978-1-4200-0481-6.
  2. Josephy E, Radt F (1 December 2013). Elsevier's Encyclopaedia of Organic Chemistry: Series III: Carboisocyclic Condensed Compounds. Springer. pp. 3048–. ISBN 978-3-662-25863-7.
  3. United States. Environmental Protection Agency. Office of Toxic Substances (1977). Toxic Substances Control Act (TSCA): PL 94-469 : Candidate List of Chemical Substances. Environmental Protection Agency, Office of Toxic Substances. pp. 315–.
  4. Dissertation Abstracts International: The sciences and engineering. University Microfilms. 1990. p. 4857.


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