Norgesterone
Chemical compound
From Wikipedia, the free encyclopedia
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.[1][2][3][4] It was used in combination with the estrogen ethinylestradiol.[2][3][4] It is taken by mouth.[5][6]
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| Trade names | Vestalin (with EE) |
| Other names | Norvinodrel; Vinylestrenolone; Vinilestrenolone; Vinylnoretynodrel; 17α-Vinylestr-5(10)-en-17-ol-3-one; 17α-Vinyl-δ5(10)-19-nortestosterone |
| Routes of administration | By mouth |
| Drug class | Progestogen; Progestin |
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| Chemical and physical data | |
| Formula | C20H28O2 |
| Molar mass | 300.442 g·mol−1 |
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Norgesterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[7] It has no androgenic activity.[7]
Norgesterone was first described in 1962.[8][9] It is no longer available.[10]
Medical uses
Norgesterone was used in combination with ethinylestradiol in birth control pills to prevent pregnancy.[2] It is no longer available.[10]
Pharmacology
Pharmacodynamics
Norgesterone is a progestogen, and hence is an agonist of the progesterone receptor.[7] Unlike related progestins, it is virtually devoid of androgenic activity in animal assays.[7]
Chemistry
Norgesterone, also known as 17α-vinyl-δ5(10)-19-nortestosterone or as 17α-vinylestr-5(10)-en-17β-ol-3-one, is a synthetic estrane steroid and a derivative of testosterone and 19-nortestosterone.[1] Analogues of norgesterone include norvinisterone (17α-vinyl-19-nortestosterone) and vinyltestosterone (17α-vinyltestosterone).[1]
Synthesis
The chemical synthesis has been described:[11][12][13]
The birch reduction of mestranol (1) gives 17a-vinyl-1,4-Dihydroestradiol 3-methyl ether (2). Quenching in oxalic acid (a weak acid) hydrolyzes the enol-ether, completing the synthesis of norgesterone (3). {Hydrolyzing under more vigorous conditions would result in conjugation of the olefinic bond to the enone position as occurred under the synthesis of nandrolone.}
History
Society and culture
Generic names
Norgesterone is the generic name of the drug and its INN.[1] It has also been referred to as norvinodrel, vinylestrenolone, and vinylnoretynodrel.[1][14]
Brand names
Norgesterone was marketed in combination with ethinylestradiol, an estrogen, as a birth control pill under the brand name Vestalin.[2][3][4]
Availability
Norgesterone is no longer marketed and hence is no longer available in any country.[10]