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 names	Mesterolone cypionate; Mesterolone cyclopentylpropionate; Mesterolone cyclopentanepropionate
Routes of administration	Intramuscular injection
Drug class	Androgen; 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
Formula	C29H44O3
Molar mass	440.668 g·mol^−1
3D model (JSmol)	Interactive image
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

• List of androgen esters

References

1. US Patent 3908007, Herrmann, W. M.; Horowski, R. & Itil, T. M. et al., "Treatment of mental depression", published 1975 
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.