View source for Etynodiol

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = 
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| verifiedrevid = 
| IUPAC_name = (3''S'',8''R'',9''S'',10''R'',13''S'',14''S'',17''R'')-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1''H''-cyclopenta[''a'']phenanthrene-3,17-diol
| image = Etynodiol.svg
| width = 225px

<!--Clinical data-->
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| routes_of_administration = 
| class = [[Progestin]]; [[Progestogen]]

<!--Pharmacokinetic data-->
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<!-- Identifiers -->
| CAS_number_Ref = 
| CAS_number = 1231-93-2
| CAS_supplemental = 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9E01C36A9S
| ATC_prefix = G03
| ATC_suffix = DC06
| ATC_supplemental = 
| PubChem = 
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| ChemSpiderID_Ref = 
| ChemSpiderID = 14017
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| synonyms = Ethynodiol; 3β-Hydroxynorethisterone; 17α-Ethynylestr-4-ene-3β,17β-diol

<!--Chemical data-->
| C=20 | H=28 | O=2
| SMILES = O[C@@H]4/C=C3\[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)C)CC4
| StdInChI_Ref = 
| 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/h1,12,14-18,21-22H,4-11H2,2H3/t14-,15-,16+,17+,18-,19-,20-/m0/s1
| StdInChIKey_Ref = 
| StdInChIKey = JYILPERKVHXLNF-QMNUTNMBSA-N
}}

'''Etynodiol''', or '''ethynodiol''', is a [[steroid]]al [[progestin]] of the [[19-nortestosterone]] group which was never marketed.<ref name="Macdonald1997">{{cite book | vauthors = Macdonald F | title = Dictionary of Pharmacological Agents | url = https://books.google.com/books?id=A0THacd46ZsC&pg=PA1454 | access-date = 12 May 2012 | year = 1997 | publisher = CRC Press | isbn = 978-0-412-46630-4 | page = 1454}}</ref><ref name="IndexNominum2000">{{cite book | title = Index Nominum 2000: International Drug Directory | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA422 | access-date = 30 May 2012 | year = 2000 | publisher = Taylor & Francis US | isbn = 978-3-88763-075-1 | page = 422}}</ref><ref name="SchindlerCampagnoli2003">{{cite journal | vauthors = Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH | title = Classification and pharmacology of progestins | journal = Maturitas | volume = 46 | pages = S7–S16 | date = December 2003 | issue = Suppl 1 | pmid = 14670641 | doi = 10.1016/j.maturitas.2003.09.014 }}</ref> A [[acetyl|diacylated]] derivative, [[etynodiol diacetate]], is used as a [[hormonal contraceptive]].<ref name="Macdonald1997" /><ref name="IndexNominum2000" /> ''Etynodiol'' is sometimes used as a synonym for ''etynodiol diacetate''.

<!-- Society and culture -->
It was patented in 1955.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=478 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA478 |language=en}}</ref>

==Pharmacology==
Etynodiol is a [[prodrug]] of [[norethisterone]], and is converted immediately and completely into norethisterone.<ref name="ShoupeHaseltine2012">{{cite book| vauthors = Shoupe D, Haseltine FP |title=Contraception|url=https://books.google.com/books?id=cpDhBwAAQBAJ&pg=PA21|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4612-2730-4|pages=21–}}</ref><ref name="Bhattacharya2003">{{cite book|author=Bhattacharya|title=Pharmacology, 2/e|url=https://books.google.com/books?id=X3cCZQCrrjcC&pg=PA378|date=1 January 2003|publisher=Elsevier India|isbn=978-81-8147-009-6|pages=378–}}</ref><ref name="HumansOrganization2007">{{cite book|author1=IARC Working Group on the Evaluation of Carcinogenic Risks to Humans|author2=World Health Organization|author3=International Agency for Research on Cancer|title=Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy|url=https://books.google.com/books?id=aGDU5xibtNgC&pg=PA146|year=2007|publisher=World Health Organization|isbn=978-92-832-1291-1|pages=146–}}</ref> Etynodiol is an [[metabolic intermediate|intermediate]] in the conversion of the prodrug [[lynestrenol]] into norethisterone.<ref name="pmid2256526">{{cite journal | vauthors = Hammerstein J | title = Prodrugs: advantage or disadvantage? | journal = American Journal of Obstetrics and Gynecology | volume = 163 | issue = 6 Pt 2 | pages = 2198–203 | date = December 1990 | pmid = 2256526 | doi = 10.1016/0002-9378(90)90561-K }}</ref>

{{Relative affinities of norethisterone, metabolites, and prodrugs}}

==Chemistry==
{{See also|List of progestogens}}

Etynodiol is a 19-nortestosterone derivative. Structurally, it is almost identical to norethisterone and [[lynestrenol]], differing only in its C3 substituent. Whereas norethisterone has a [[ketone]] at C3 and lynestrenol has no substituent at C3, etynodiol has a [[hydroxyl group]] at the position.

===Synthesis===
[[File:Ethynodiol diacetate synthesis.svg|thumb|left|700px|Ethynodiol diacetate synthesis:<ref>{{cite journal | vauthors = Klimstra PD, Colton FB | title = The synthesis of 3beta-hydroxyestr-4-en-17-one and 3beta-hydroxyandrost-4-en-17-one | journal = Steroids | volume = 10 | issue = 4 | pages = 411–24 | date = October 1967 | pmid = 6064262 | doi = 10.1016/0039-128X(67)90119-5 }}</ref> F. B. Colton, {{US patent|2843609}} (1958 to [[G.D. Searle, LLC|Searle]]). Prepn of the 3-acetate, 17-acetate, and diacetate: P. D. Klimstra, {{US patent|3176013}} (1965 to Searle); see also:<ref>{{Cite journal | doi = 10.1016/0040-4020(59)80066-1| title = Synthesis of 3β-hydroxy analogues of steroidal hormones, a biologically active class of compounds| journal = Tetrahedron| volume = 5| pages = 15–26| year = 1959| vauthors = Sondheimer F, Klibansky Y }}</ref>]]{{Clear}}

==Society and culture==

===Generic names===
''Etynodiol'' is the [[generic term|generic name]] of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, while ''ethynodiol'' is its {{abbrlink|BAN|British Approved Name}}.<ref name="Macdonald1997" /><ref name="IndexNominum2000" />

== References ==
{{Reflist}}

{{Progesterone receptor modulators}}
{{Estrogen receptor modulators}}
{{Androgen receptor modulators}}

[[Category:Ethynyl compounds]]
[[Category:Anabolic–androgenic steroids]]
[[Category:Diols]]
[[Category:Estranes]]
[[Category:Prodrugs]]
[[Category:Progestogens]]
[[Category:Synthetic estrogens]]