1253-28-7

Depostat,Schering AG

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.

ChEBI: Gestonorone caproate is an organic molecular entity.

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.

Progestin