Norvinisterone

Norvinisterone
Clinical data
Trade namesNeoprogestin, Nor-Progestelea
Other namesVinylnortestosterone; SC-4641; 17α-Vinyl-19-nortestosterone; 17α-Vinylestr-4-en-17β-ol-3-one
Routes of
administration		By mouth
Drug classProgestogen; 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
FormulaC20H28O2
Molar mass300.442 g·mol−1
3D model (JSmol)
Melting point169 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.

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

See also: List of progestogens and List of androgens/anabolic steroids

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 INNTooltip 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. ^ 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.
  2. ^ 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.
  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.
  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. ^ 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.
  6. ^ 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.
  7. ^ a b http://www.micromedexsolutions.com/micromedex2/[permanent dead link‍]
  8. ^ 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.
  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.