Norgesterone
Norgesterone, also known as norvinodrel or vinylestrenolone and sold under the brand name Vestalin, is a progestin medication which was formerly used in birth control pills for women but is now no longer marketed. It was used in combination with the estrogen ethinylestradiol. It is taken by mouth.
Norgesterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has no androgenic activity.
Norgesterone was first described in 1962. It is no longer available.
Medical uses
Norgesterone was used in combination with ethinylestradiol in birth control pills to prevent pregnancy. It is no longer available.Pharmacology
Pharmacodynamics
Norgesterone is a progestogen, and hence is an agonist of the progesterone receptor. Unlike related progestins, it is virtually devoid of androgenic activity in animal assays.Chemistry
Norgesterone, also known as 17α-vinyl-δ5-19-nortestosterone or as 17α-vinylestr-5-en-17β-ol-3-one, is a synthetic estrane steroid and a derivative of testosterone and 19-nortestosterone. Analogues of norgesterone include norvinisterone and vinyltestosterone.Synthesis
The chemical synthesis has been described:The birch reduction of mestranol gives 17a-vinyl-1,4-Dihydroestradiol 3-methyl ether. Quenching in oxalic acid hydrolyzes the enol-ether, completing the synthesis of norgesterone.