Norgesterone

{{Short description|Chemical compound}}

{{Drugbox

| 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

| image = Norgesterone.svg

| width = 225px

| tradename = Vestalin (with {{abbrlink|EE|ethinylestradiol}})

| pregnancy_category =

| legal_status =

| routes_of_administration = By mouth

| class = Progestogen; Progestin

| bioavailability =

| protein_bound =

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| CAS_number = 13563-60-5

| ATC_prefix = None

| ATC_suffix =

| PubChem = 65606

| ChemSpiderID = 59047

| UNII = YFS274763Y

| synonyms = Norvinodrel; Vinylestrenolone; Vinilestrenolone; Vinylnoretynodrel; 17α-Vinylestr-5(10)-en-17-ol-3-one; 17α-Vinyl-δ⁵⁽¹⁰⁾-19-nortestosterone

| C=20 | H=28 | O=2

| SMILES = CC12CCC3C(C1CCC2(C=C)O)CCC4=C3CCC(=O)C4

| StdInChI = 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

| StdInChIKey = 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.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA887|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=887–}}{{cite journal | vauthors = Wassef SA, Sami G, Hamid EA | title = Effect of switching with oral contraceptives | journal = The Egyptian Population and Family Planning Review | volume = 3 | issue = 1 | pages = 77–93 | date = June 1970 | pmid = 12254511 }}{{cite book| vauthors = Bengtsson LP, Tausk M |title=Pharmacology of the endocrine system and related drugs: progesterone, progestational drugs and antifertility agents|url=https://books.google.com/books?id=Nv5sAAAAMAAJ|date=September 1972|publisher=Pergamon Press|isbn=9780080157450}}{{cite book| vauthors = Challener CA |title=Chiral Drugs|url=https://books.google.com/books?id=hyhtAAAAMAAJ|date=1 December 2001|publisher=Wiley|isbn=978-0-566-08411-9}} It was used in combination with the estrogen ethinylestradiol. It is taken by mouth.{{cite journal | vauthors = Boris Rubio L | title = [Vinylestrenolone: a new progestational hormone. Results of its cyclic administration] | language = it | journal = Minerva Ginecologica | volume = 18 | issue = 21 | pages = 1215–1217 | date = November 1966 | pmid = 5997085 }}{{cite journal | vauthors = Samaja BA, Prandini B | title = The influence of estrogenic and-or progestogenic treatment on some parameters of lipid metabolism (a controlled clinical study) | journal = Endokrinologie | volume = 63 | issue = 1 | pages = 76–84 | date = March 1974 | pmid = 4140086 | doi = | url = https://www.popline.org/node/492815 | archive-url = https://web.archive.org/web/20180228161735/https://www.popline.org/node/492815 | archive-date=2018-02-28 }}

Norgesterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.{{cite journal| vauthors = de Ruggieri P, Matscher R, Lupo C, Spazzoli G |title=Biological properties of 17α-vinyl-5(10)-estrene-17β-ol-3-one (norvinodrel) as a progestational and claudogenic compound|journal=Steroids|volume=5|issue=1|year=1965|pages=73–91|issn=0039-128X|doi=10.1016/0039-128X(65)90133-9}} It has no androgenic activity.

Norgesterone was first described in 1962.{{Cite web|url=https://patents.google.com/patent/US3062713A/en|title = Steroid hormone compositions and method of using same}}{{cite journal | vauthors = D'Incerti Bonini L, Pagani C | title = [Clinical investigations of the progestational activity of vinylestrenolone] | language = it | journal = Annali di Ostetricia e Ginecologia | volume = 84 | pages = 279–285 | date = April 1962 | pmid = 13883015 }} It is no longer available.