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Norgesterone
Clinical data
Trade names	Vestalin (with EETooltip ethinylestradiol)
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	300.442 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 INNTooltip International Nonproprietary Name.^[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

^ ^a ^b ^c ^d ^e 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.
^ ^a ^b ^c ^d 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.
^ ^a ^b ^c Bengtsson LP, Tausk M (September 1972). Pharmacology of the endocrine system and related drugs: progesterone, progestational drugs and antifertility agents. Pergamon Press. ISBN 9780080157450.
^ ^a ^b ^c Challener CA (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 Ginecologica (in Italian). 18 (21): 1215–1217. PMID 5997085.
^ 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.
^ ^a ^b ^c ^d 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.
^ ^a ^b "Steroid hormone compositions and method of using same".
^ ^a ^b 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.
^ ^a ^b ^c http://www.micromedexsolutions.com/micromedex2/^{[permanent dead link‍]}
^ 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.