Chemistry:Norgesterone
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| Clinical data | |
|---|---|
| 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 |
| 3D model (JSmol) | |
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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]
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]
History
Norgesterone was first described in 1962.[8][9]
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][11]
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]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 887–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA887.
- ↑ 2.0 2.1 2.2 2.3 "Effect of switching with oral contraceptives". The Egyptian Population and Family Planning Review 3 (1): 77–93. June 1970. PMID 12254511.
- ↑ 3.0 3.1 3.2 Pharmacology of the endocrine system and related drugs: progesterone, progestational drugs and antifertility agents. Pergamon Press. September 1972. ISBN 9780080157450. https://books.google.com/books?id=Nv5sAAAAMAAJ.
- ↑ 4.0 4.1 4.2 Chiral Drugs. Wiley. 1 December 2001. ISBN 978-0-566-08411-9. https://books.google.com/books?id=hyhtAAAAMAAJ.
- ↑ "[Vinylestrenolone: a new progestational hormone. Results of its cyclic administration]" (in it). Minerva Ginecologica 18 (21): 1215–1217. November 1966. PMID 5997085.
- ↑ "The influence of estrogenic and-or progestogenic treatment on some parameters of lipid metabolism (a controlled clinical study)". Endokrinologie 63 (1): 76–84. March 1974. PMID 4140086. https://www.popline.org/node/492815.
- ↑ 7.0 7.1 7.2 7.3 "Biological properties of 17α-vinyl-5(10)-estrene-17β-ol-3-one (norvinodrel) as a progestational and claudogenic compound". Steroids 5 (1): 73–91. 1965. doi:10.1016/0039-128X(65)90133-9. ISSN 0039-128X.
- ↑ 8.0 8.1 "Steroid hormone compositions and method of using same". https://patents.google.com/patent/US3062713A/en.
- ↑ 9.0 9.1 "[Clinical investigations of the progestational activity of vinylestrenolone]" (in it). Annali di Ostetricia e Ginecologia 84: 279–285. April 1962. PMID 13883015.
- ↑ 10.0 10.1 10.2 http://www.micromedexsolutions.com/micromedex2/[yes|permanent dead link|dead link}}]
- ↑ "Contraception". Pediatric and Adolescent Obstetrics and Gynecology. Springer Science & Business Media. 6 December 2012. pp. 236–. ISBN 978-1-4612-5064-7. https://books.google.com/books?id=l9XTBwAAQBAJ&pg=PA236.
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