Norgesterone

Norgesterone
Clinical data
Trade names	Vestalin (with EE)
Other names	Norvinodrel; 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
	IUPAC name (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	13563-60-5;
PubChem CID	65606;
ChemSpider	59047;
UNII	YFS274763Y;
CompTox Dashboard (EPA)	DTXSID60159482 ;
Chemical and physical data
Formula	C20H28O2
Molar mass	300.435 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC12CCC3C(C1CCC2(C=C)O)CCC4=C3CCC(=O)C4;
	InChI 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]

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]

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.[1] It has also been referred to as norvinodrel, vinylestrenolone, and vinylnoretynodrel.[1][11]

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

J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 887–. ISBN 978-1-4757-2085-3.
Wassef SA, Sami G, Hamid EA (1970). "Effect of switching with oral contraceptives". Egypt Popul Fam Plann Rev. 3 (1): 77–93. PMID 12254511.
Lars Philip Bengtsson; M. Tausk (September 1972). Pharmacology of the endocrine system and related drugs: progesterone, progestational drugs and antifertility agents. Pergamon Press.
Cynthia A. Challener (1 December 2001). Chiral Drugs. Wiley. ISBN 978-0-566-08411-9.
Boris Rubio L (November 1966). "[Vinylestrenolone: a new progestational hormone. Results of its cyclic administration]". Minerva Ginecol (in Italian). 18 (21): 1215–7. PMID 5997085.
Samaja, B. A., & Prandini, B. (1974). The influence of estrogenic and/or progestogenic treatment on some parameters of lipid metabolism: a controlled clinical study. Endokrinologie, 63(1), 76-84. https://www.popline.org/node/492815
Ruggieri, Pietro de; Matscher, Rodolfo; Lupo, Corrado; Spazzoli, Giacomo (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.
https://patents.google.com/patent/US3062713A/en
D'Incerti Bonini L, Pagani C (April 1962). "[Clinical investigations of the progestational activity of vinylestrenolone]". Ann Ostet Ginecol (in Italian). 84: 279–85. PMID 13883015.
http://www.micromedexsolutions.com/micromedex2/
J.P. Lavery; J.S. Sanfilippo (6 December 2012). Pediatric and Adolescent Obstetrics and Gynecology. Springer Science & Business Media. pp. 236–. ISBN 978-1-4612-5064-7.

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[Elks2014-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 887–. ISBN 978-1-4757-2085-3.

[pmid12254511-2] Wassef SA, Sami G, Hamid EA (1970). "Effect of switching with oral contraceptives". Egypt Popul Fam Plann Rev. 3 (1): 77–93. PMID 12254511.

[BengtssonTausk1972-3] Lars Philip Bengtsson; M. Tausk (September 1972). Pharmacology of the endocrine system and related drugs: progesterone, progestational drugs and antifertility agents. Pergamon Press.

[Challener2001-4] Cynthia A. Challener (1 December 2001). Chiral Drugs. Wiley. ISBN 978-0-566-08411-9.

[pmid5997085-5] Boris Rubio L (November 1966). "[Vinylestrenolone: a new progestational hormone. Results of its cyclic administration]". Minerva Ginecol (in Italian). 18 (21): 1215–7. PMID 5997085.

[SamajaPrandini1974-6] Samaja, B. A., & Prandini, B. (1974). The influence of estrogenic and/or progestogenic treatment on some parameters of lipid metabolism: a controlled clinical study. Endokrinologie, 63(1), 76-84. https://www.popline.org/node/492815

[RuggieriMatscher1965-7] Ruggieri, Pietro de; Matscher, Rodolfo; Lupo, Corrado; Spazzoli, Giacomo (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.

[US3062713A-8] ttps://patents.google.com/patent/US3062713A/en

[pmid13883015-9] D'Incerti Bonini L, Pagani C (April 1962). "[Clinical investigations of the progestational activity of vinylestrenolone]". Ann Ostet Ginecol (in Italian). 84: 279–85. PMID 13883015.

[Micromedex-10] ttp://www.micromedexsolutions.com/micromedex2/

[LaverySanfilippo2012-11] J.P. Lavery; J.S. Sanfilippo (6 December 2012). Pediatric and Adolescent Obstetrics and Gynecology. Springer Science & Business Media. pp. 236–. ISBN 978-1-4612-5064-7.