Norvinisterone
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| Clinical data | |
|---|---|
| Trade names | Neoprogestin, Nor-Progestelea |
| Other names | Vinylnortestosterone; SC-4641; 17α-Vinyl-19-nortestosterone; 17α-Vinylestr-4-en-17β-ol-3-one |
| Routes of administration | By mouth |
| Drug class | Progestogen; Progestin; Androgen; Anabolic steroid |
| ATC code |
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| Identifiers | |
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| CAS Number | |
| PubChem CID | |
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| Chemical and physical data | |
| Formula | C20H28O2 |
| Molar mass | 300.442 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 169 to 171 °C (336 to 340 °F) [1] |
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Norvinisterone, sold under the brand names Neoprogestin and Nor-Progestelea, is a progestin and androgen/anabolic steroid (AAS) medication which was used in Europe but is now no longer marketed.[1][2][3][4][5] It is taken by mouth.
Norvinisterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[2] It has androgenic activity.[6]
Norvinisterone was synthesized in 1953.[2] It is no longer available.[7]
Medical uses
[edit]Norvinisterone was used in hormonal contraception to prevent pregnancy.[1][3]
Pharmacology
[edit]Pharmacodynamics
[edit]Norvinisterone is a progestogen.[2][8][5] It appears to be quite androgenic, with about one-third and one-fifth of the androgenic and anabolic activity, respectively, of nandrolone in animal bioassays.[6] However, it has also been reported to have little anabolic activity.[9]
Chemistry
[edit]Norvinisterone, also known as 17α-vinyl-19-nortestosterone or as 17α-vinylestr-4-en-17β-ol-3-one, is a synthetic estrane steroid and a derivative of testosterone and 19-nortestosterone.[2] Analogues of norvinisterone include the progestin norgesterone and the AAS vinyltestosterone.[2]
History
[edit]Norvinisterone was synthesized in 1953[2] and was studied in humans by 1960.[8]
Society and culture
[edit]Generic names
[edit]Norvinisterone is the generic name of the drug and its INN.[2] It is also known as vinylnortestosterone and is known by its developmental code name SC-4641.[2][1]
Brand names
[edit]Norvinisterone was marketed under the brand names Neoprogestin and Nor-Progestelea by Syntex.[2][1]
Availability
[edit]Norgesterone is no longer marketed and hence is no longer available in any country.[7]
References
[edit]- ^ a b c d e Budavari S, ed. (1989). "6637: Norvinisterone". Merck Index (11th ed.). Rahway, N.J.: Merck & Co. ISBN 978-0-911910-28-5.
- ^ a b c d e f g h i j Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 889–. ISBN 978-1-4757-2085-3.
- ^ a b Juo PS (21 December 2001). Concise Dictionary of Biomedicine and Molecular Biology. CRC Press. pp. 774–. ISBN 978-1-4200-4130-9.
- ^ List PH, Hörhammer L (12 March 2013). Chemikalien und Drogen Teil A: N-Q. Springer Berlin Heidelberg. pp. 274–. ISBN 978-3-642-65035-2.
- ^ a b Meyerson BJ (August 1967). "Relationship between the anesthetic and gestagenic action and estrous behavior-inducing activity of different progestins". Endocrinology. 81 (2): 369–374. doi:10.1210/endo-81-2-369. PMID 4952012.
- ^ a b Saunders FJ, Drill VA (May 1956). "The myotrophic and androgenic effects of 17-ethyl-19-nortestosterone and related compounds". Endocrinology. 58 (5): 567–572. doi:10.1210/endo-58-5-567. PMID 13317831.
- ^ a b http://www.micromedexsolutions.com/micromedex2/[permanent dead link]
- ^ a b Martinez Montes EA, Bagnati EP, Zapata AC, Bur GE (March 1960). "[Clinical trial of a new luteoid: norvinisterone]". El Dia Medico (in Spanish). 32: 194–197. PMID 14421807.
- ^ Schedl HP, Delea C, Bartter FC (August 1959). "Structure-activity relationships of anabolic steroids: role of the 19-methyl group". The Journal of Clinical Endocrinology and Metabolism. 19 (8): 921–935. doi:10.1210/jcem-19-8-921. PMID 14442516.