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Norgesterone

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. It was used in combination with the estrogen ethinylestradiol. It is taken by mouth.

Last revised
May 31, 2026
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Wikipedia ↗
Norgesterone
Clinical data
Trade namesVestalin (with EETooltip ethinylestradiol)
Other namesNorvinodrel; Vinylestrenolone; Vinilestrenolone; Vinylnoretynodrel; 17α-Vinylestr-5(10)-en-17-ol-3-one; 17α-Vinyl-δ5(10)-19-nortestosterone
Routes of
administration		By mouth
Drug classProgestogen; Progestin
ATC code
  • None
Identifiers
  • (8R,9S,13S,14S,17R)-17-ethenyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-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)
  • CC12CCC3C(C1CCC2(C=C)O)CCC4=C3CCC(=O)C4
  • 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/h3,16-18,22H,1,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1
  • Key:YPVUHOBTCWJYNQ-SLHNCBLASA-N

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.1234 It was used in combination with the estrogen ethinylestradiol.234 It is taken by mouth.56

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 1962.89 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:111213

source ↗

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

Norgesterone was first described in 1962.89

Society and culture

Generic names

Norgesterone is the generic name of the drug and its INNTooltip International Nonproprietary Name.1 It has also been referred to as norvinodrel, vinylestrenolone, and vinylnoretynodrel.114

Brand names

Norgesterone was marketed in combination with ethinylestradiol, an estrogen, as a birth control pill under the brand name Vestalin.234

Availability

Norgesterone is no longer marketed and hence is no longer available in any country.10

References

References

  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 887–. ISBN 978-1-4757-2085-3.
  2. Wassef SA, Sami G, Hamid EA (June 1970). "Effect of switching with oral contraceptives". The Egyptian Population and Family Planning Review. 3 (1): 77–93. PMID 12254511.
  3. Bengtsson LP, Tausk M (September 1972). Pharmacology of the endocrine system and related drugs: progesterone, progestational drugs and antifertility agents. Pergamon Press. ISBN 9780080157450.
  4. Challener CA (1 December 2001). Chiral Drugs. Wiley. ISBN 978-0-566-08411-9.
  5. Boris Rubio L (November 1966). "[Vinylestrenolone: a new progestational hormone. Results of its cyclic administration]". Minerva Ginecologica (in Italian). 18 (21): 1215–1217. PMID 5997085.
  6. Samaja BA, Prandini B (March 1974). "The influence of estrogenic and-or progestogenic treatment on some parameters of lipid metabolism (a controlled clinical study)". Endokrinologie. 63 (1): 76–84. PMID 4140086. Archived from the original on 2018-02-28.
  7. de Ruggieri P, Matscher R, Lupo C, Spazzoli G (1965). "Biological properties of 17α-vinyl-5(10)-estrene-17β-ol-3-one (norvinodrel) as a progestational and claudogenic compound". Steroids. 5 (1): 73–91. doi:10.1016/0039-128X(65)90133-9. ISSN 0039-128X.
  8. "Steroid hormone compositions and method of using same".
  9. D'Incerti Bonini L, Pagani C (April 1962). "[Clinical investigations of the progestational activity of vinylestrenolone]". Annali di Ostetricia e Ginecologia (in Italian). 84: 279–285. PMID 13883015.
  10. http://www.micromedexsolutions.com/micromedex2/
  11. (page 5772) Kettle, S. F. A.; de la Mare, P. B. D.; Lomas, J. S.; Pacini, H. A.; Pavlath, A. E.; Cotter, J. L.; Gore, P. H.; Hoskins, J. A.; Wladislaw, B.; Giora, A.; Miller, J. D.; Prince, R. H.; Keen, I. M.; Tuck, D. G.; Faithful, B. D.; Haslam, E.; Marriott, J. E.; Gill, G. B.; Williams, Gareth H.; Barker, C. C.; Hallas, G.; Thornber, M. N.; Crombie, D. A.; Shaw, S.; Bird, C. W.; Colvin, E. W.; Parker, W.; Fields, Ellis K.; Leslie, J.; Hamer, D.; Hallas, G.; Downie, I. M.; Morris, G.; Hiscock, A. K.; Whitehurst, J. S.; Green, M.; Tipping, A. E.; van Es, T.; Staskun, B.; Trahanovsky, Walter S.; Young, L. Brewster; Bristow, P. A.; Khowaja, M.; Tillett, J. G.; Fischer, A.; Hutchinson, R. E. J.; Topsom, R. D.; Carruthers, W.; Watkins, D. A. M.; Knight, J. A.; Roberts, John C.; Underwood, J. G. (1965). "Notes". Journal of the Chemical Society (Resumed): 5737. doi:10.1039/jr9650005737.
  12. Ruggieri Pietro De & Ferrari Carlo, U.S. patent 2,983,735 (1961 to Ormonoterapia Richter SpA).
  13. Ruggieri Pietro De & Ferrari Carlo, U.S. patent 3,062,713 (1962 Ormonoterapia Richter).
  14. Greydanus DE (6 December 2012). "Contraception". In Lavery JP, Sanfilippo JS (eds.). Pediatric and Adolescent Obstetrics and Gynecology. Springer Science & Business Media. pp. 236–. ISBN 978-1-4612-5064-7.