cingestol

{{Short description|Chemical compound}}

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| IUPAC_name = (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,4,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

| image = Cingestol.svg

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| tradename = Lutisan

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| routes_of_administration = Oral

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| CAS_number_Ref =

| CAS_number = 16915-71-2

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| PubChem = 11954351

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| ChemSpiderID = 10128646

| UNII = VLJ9702J11

| C=20 | H=28 | O=1

| smiles = C[C@]12CC[C@H]3[C@@H](CC=C4CCCC[C@H]34)[C@@H]1CC[C@@]2(O)C#C

| StdInChI_Ref =

| StdInChI = 1S/C20H28O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h1,8,15-18,21H,4-7,9-13H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1

| StdInChIKey_Ref =

| StdInChIKey = HSYWFJBHXIUUCZ-XGXHKTLJSA-N

| synonyms = 19-Nor-17α-pregn-5-en-20-yn-17β-ol; O.V. 28{{cite book| vauthors = Tausk M |title= Pharmacology of Hormones |url= https://books.google.com/books?id=9WhNAQAAIAAJ |year=1975|publisher=Thieme|isbn=978-3-13-518901-7|page=126,129}}{{cite book|title=Concours médical|url=https://books.google.com/books?id=_UQgAQAAMAAJ|year=1976|page=1083}}

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Cingestol (INN, USAN) (former tentative brand name Lutisan),{{cite book|title=Registry of Toxic Effects of Chemical Substances|url=https://books.google.com/books?id=dRFV2ZV6DT0C|year=1987|publisher=National Institute for Occupational Safety and Health|page=2995}} also known as 17α-ethynylestr-5-en-17β-ol,{{cite book| vauthors= Brotherton J |title=Sex hormone pharmacology|url=https://books.google.com/books?id=zt5sAAAAMAAJ|year=1976|publisher=Academic Press|isbn=978-0-12-137250-7|page=12}} is a steroidal progestin of the 19-nortestosterone group{{cite book | vauthors = Korolkovas A |title=Essentials of Medicinal Chemistry|url=https://books.google.com/books?id=6hxtAAAAMAAJ|date=16 August 1988|publisher=Wiley|isbn=978-0-471-88356-2}}{{cite book|title=WHO Technical Report Series|url=https://books.google.com/books?id=WlQYAAAAMAAJ|year=1981|publisher=World Health Organization|page=75|isbn = 9789241206570}} that was never 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=PA279|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=279–}} It was synthesized in 1969 and was developed in the 1970s by Organon as a low-dose, progestogen-only contraceptive,{{cite book| vauthors = Tapingkae A |title=Directory of selected scholars and researchers in Southeast Asia|url=https://books.google.com/books?id=mB4gAQAAMAAJ|year=1974|publisher=Regional Institute of Higher Education and Development|page=687}}{{cite book| vauthors = Briggs MH, Briggs M |title=Biochemical contraception: prospects for human development|url=https://books.google.com/books?id=7pRsAAAAMAAJ|year=1976|publisher=Academic Press|isbn=978-0-12-134640-9|page=283}}{{cite journal | vauthors = Aref I, Hefnawi F, Kandil O, Aziz MT | title = Effect of minipills on physiologic responses of human cervical mucus, endometrium, and ovary | journal = Fertility and Sterility | volume = 24 | issue = 8 | pages = 578–583 | date = August 1973 | pmid = 4124151 | doi = 10.1016/s0015-0282(16)39850-8 | doi-access = }}{{cite journal | vauthors = Kićović PM, Kovacević S, Djokic LJ, Milojević S, Janoskov J, Behlilović B, Jeremić N | title = Clinical evaluation of a new low dose progestagen-only contraceptive containing cingestol | journal = International Journal of Fertility | volume = 19 | issue = 3 | pages = 171–175 | year = 1974 | pmid = 4375129 | url = http://www.popline.org/node/494146 }} but in 1984, was still described as "under investigation".{{cite book| vauthors = Cutting WC, Csáky TZ, Barnes BA |author1-link=Windsor C. Cutting|title=Cutting's Handbook of Pharmacology: The Actions and Uses of Drugs|url=https://books.google.com/books?id=B-1sAAAAMAAJ|year=1984|publisher=Appleton-Century-Crofts|isbn=978-0-8385-1418-4|page=439}} The drug is an isomer of lynestrenol with the double bond between C5 and C6.