Norvinisterone

Last updated
Norvinisterone
Norvinisterone.svg
Clinical data
Trade names Neoprogestin, Nor-Progestelea
Other namesVinylnortestosterone; 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
  • None
Identifiers
  • (8R,9S,10R,13S,14S,17R)-17-ethenyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
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]
  • O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@](O)(\C=C)CC[C@H]3[C@@H]1CC2)C)CC4
  • InChI=1S/C20H28O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h3,12,15-18,22H,1,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
  • Key:VOJYZDFYEHKHAP-XGXHKTLJSA-N

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.

Contents

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

Norvinisterone was used in hormonal contraception to prevent pregnancy. [1] [3]

Pharmacology

Pharmacodynamics

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

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

Norvinisterone was synthesized in 1953 [2] and was studied in humans by 1960. [8]

Society and culture

Generic names

Norvinisterone is the generic name of the drug and its INN Tooltip International Nonproprietary Name. [2] It is also known as vinylnortestosterone and is known by its developmental code name SC-4641. [2] [1]

Brand names

Norvinisterone was marketed under the brand names Neoprogestin and Nor-Progestelea by Syntex. [2] [1]

Availability

Norgesterone is no longer marketed and hence is no longer available in any country. [7]

References

  1. 1 2 3 4 5 Budavari S, ed. (1989). "6637: Norvinisterone". Merck Index (11th ed.). Rahway, N.J.: Merck & Co. ISBN   978-0-911910-28-5.
  2. 1 2 3 4 5 6 7 8 9 10 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.
  3. 1 2 Juo PS (21 December 2001). Concise Dictionary of Biomedicine and Molecular Biology. CRC Press. pp. 774–. ISBN   978-1-4200-4130-9.
  4. ↑ 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.
  5. 1 2 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.
  6. 1 2 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.
  7. 1 2 http://www.micromedexsolutions.com/micromedex2/%5B%5D
  8. 1 2 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.
  9. ↑ 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.
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