Misplaced Pages

Norgesterone

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Chemical compound Pharmaceutical compound
Norgesterone
Clinical data
Trade namesVestalin (with EETooltip ethinylestradiol)
Other namesNorvinodrel; Vinylestrenolone; Vinilestrenolone; Vinylnoretynodrel; 17α-Vinylestr-5(10)-en-17-ol-3-one; 17α-Vinyl-δ-19-nortestosterone
Routes of
administration		By mouth
Drug classProgestogen; 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-dodecahydrocyclopentaphenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H28O2
Molar mass300.442 g·mol
3D model (JSmol)
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. It was used in combination with the estrogen ethinylestradiol. It is taken by mouth.

Norgesterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has no androgenic activity.

Norgesterone was first described in 1962. It is no longer available.

Medical uses

Norgesterone was used in combination with ethinylestradiol in birth control pills to prevent pregnancy. It is no longer available.

Pharmacology

Pharmacodynamics

Norgesterone is a progestogen, and hence is an agonist of the progesterone receptor. Unlike related progestins, it is virtually devoid of androgenic activity in animal assays.

Chemistry

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

Norgesterone, also known as 17α-vinyl-δ-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. Analogues of norgesterone include norvinisterone (17α-vinyl-19-nortestosterone) and vinyltestosterone (17α-vinyltestosterone).

History

Norgesterone was first described in 1962.

Society and culture

Generic names

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

Brand names

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

Availability

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

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). "". 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). "". Annali di Ostetricia e Ginecologia (in Italian). 84: 279–285. PMID 13883015.
  10. ^ http://www.micromedexsolutions.com/micromedex2/
  11. 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.
Progestogens and antiprogestogens
Progestogens
(and progestins)
PRTooltip Progesterone receptor agonists
Antiprogestogens
SPRMsTooltip Selective progesterone receptor modulators
PRTooltip Progesterone receptor antagonists
See also
Progesterone receptor modulators
Androgens and antiandrogens
Estrogens and antiestrogens
List of progestogens
Progesterone receptor modulators
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
Categories: