Mesterolone cipionate

Mesterolone cipionate is a synthetic anabolic–androgenic steroid and an androgen ester – specifically, the C17β cypionate ester of mesterolone – which was never marketed.[1][2][3] It is administered via intramuscular injection once every two weeks and acts as a long-acting prodrug of mesterolone.[3] The drug was studied in the treatment of depression in men along with mesterolone in the mid-1970s but was never introduced for medical use.[1][3]

Mesterolone cipionate
Clinical data
Other namesMesterolone cypionate; Mesterolone cyclopentylpropionate; Mesterolone cyclopentanepropionate
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester
Identifiers
IUPAC name
  • [(1S,5S,8R,9S,10S,13S,14S,17S)-1,10,13-trimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate
Chemical and physical data
FormulaC29H44O3
Molar mass440.668 g·mol−1
3D model (JSmol)
SMILES
  • [H][C@@]12CC[C@H](OC(=O)CCC3CCCC3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2(C)CC(=O)C[C@H](C)[C@]12C
InChI
  • InChI=1S/C29H44O3/c1-19-17-21(30)18-27(2)15-13-22-23-10-11-25(28(23,3)16-14-24(22)29(19,27)4)32-26(31)12-9-20-7-5-6-8-20/h20,22-24H,5-18H2,1-4H3/t22-,23-,24-,27-,28-,29+/m0/s1
  • Key:TWDIZPBGCLXSNS-PAXVTGJLSA-N

See also

References
  1. Herrmann, W. M., Horowski, R., Itil, T. M., Kehr, W., Palenschat, D., Paschelke, G., & Wachtel, H. (1975). U.S. Patent No. 3,908,007. Treatment of mental depression. Washington, DC: U.S. Patent and Trademark Office. https://www.google.com/patents/US3908007
  2. Spona J (1976). "Action of steroids on LH-RH provoked gonadotropin release". Endocrinol. Exp. 10 (2): 91–100. PMID 776594.
  3. Kövary PM, Lenau H, Niermann H, Zierden E, Wagner H (1977). "Testosterone levels and gonadotrophins in Klinefelter's patients treated with injections of mesterolone cipionate". Arch Dermatol Res. 258 (3): 289–94. doi:10.1007/bf00561132. PMID 883846. S2CID 1222130.



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