Uses
Gestonorone Caproate, is a pro-drug of Gestonorone, which is a steroidal progestin. It has been shown to have accelerated body weight gain and caused the atrophy of the prostate, uterus, and seminal vesicles in rats. It is also an inhibitor of the reductive pathway of Testosterone (T155000) metabolism.
Manufacturing Process
2 Methods of producing of 17-α-hydroxyl-19-norprogesteron-17-capronate:
1. To a solution of 1.0 g 17-α-hydroxy-19-norprogesteron in 32 ml capronic
acid anhydride 1.32 g p-toluesulfonate (1 mole hydrate) were added, and
allowed to stand for 3 h at 37°C. To the solution 1.43 ml conc. hydrochloric
acid in 143 ml methanol were added and all this also for 1 h was left under
N2. Then mixture was washed with water and treated with ether. Ether extract
was washed with water, and dried with Na2SO4. After that ether was distilled
and residue was recrystallised with isopropyl ether. 1.1 g of 17-α-hydroxyl-19-
norprogesteron-17-capronate was obtained, melting point 123°-124°C.
2. 2.0 g 3-methoxy-17α-hydroxy-17β-acetyl-δ2,5(10)-oestradien, 60 ml
capronic acid anhydride, 2.6 g p-toluensulfonate and 18.0 g water were mixed
and left for 6 h at room temperature. Then solution obtained was treated
ether and sodium bicarbonate and washed with water. Etheral solution was
dried over sodium sulfate. After distillation of ether 3.1 g 3,17α-dihydroxy-
δ3,5-19-norpregnadien-3,17-dicapronate was produced.
To solution of 3.1 g 3,17α-dihydroxy-δ3,5-19-norpregnadien-3,17-dicapronate
in 250 ml methanol 2.5 g conc. hydrochloric acid were added and mixture was
left for 1 h. Then mixture was filtered and residue was washed. After
recrystallisation with isopropyl ether 17-α-hydroxyl-19-norprogesteron-17-
capronate was obtained, melting point 121°-123°C.
