Norgesterone

Last updated
Norgesterone
Norgesterone.svg
Clinical data
Trade names Vestalin (with EE Tooltip 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 class Progestogen; 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
Formula C20H28O2
Molar mass 300.442 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. [1] [2] [3] [4] It was used in combination with the estrogen ethinylestradiol. [2] [3] [4] It is taken by mouth. [5] [6]

Contents

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]

Synthesis

The chemical synthesis has been described: [11] [12] [13]

Norgesterone synthesis.svg

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. [8] [9]

Society and culture

Generic names

Norgesterone is the generic name of the drug and its INN Tooltip International Nonproprietary Name. [1] It has also been referred to as norvinodrel, vinylestrenolone, and vinylnoretynodrel. [1] [14]

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. 1 2 3 4 5 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. 1 2 3 4 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. 1 2 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. 1 2 3 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. 1 2 3 4 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. 1 2 "Steroid hormone compositions and method of using same".
  9. 1 2 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. 1 2 3 http://www.micromedexsolutions.com/micromedex2/%5B%5D
  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.
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