:Etynodiol
{{Short description|Chemical compound}}
{{Drugbox
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| IUPAC_name = (3S,8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
| image = Etynodiol.svg
| width = 225px
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| class = Progestin; Progestogen
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| CAS_number_Ref =
| CAS_number = 1231-93-2
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| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9E01C36A9S
| ATC_prefix = G03
| ATC_suffix = DC06
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| ChemSpiderID_Ref =
| ChemSpiderID = 14017
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| synonyms = Ethynodiol; 3β-Hydroxynorethisterone; 17α-Ethynylestr-4-ene-3β,17β-diol
| 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
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Etynodiol, or ethynodiol, is a steroidal progestin of the 19-nortestosterone group which was never marketed.{{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}}{{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}}{{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 }} A diacylated derivative, etynodiol diacetate, is used as a hormonal contraceptive. Etynodiol is sometimes used as a synonym for etynodiol diacetate.
Pharmacology
Etynodiol is a prodrug of norethisterone, and is converted immediately and completely into norethisterone.{{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–}}{{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–}}{{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–}} Etynodiol is an intermediate in the conversion of the prodrug lynestrenol into norethisterone.{{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 }}
{{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). Prepn of the 3-acetate, 17-acetate, and diacetate: P. D. Klimstra, {{US patent|3176013}} (1965 to Searle); see also:{{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 }}]]{{Clear}}
Society and culture
=Generic names=
Etynodiol is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, while ethynodiol is its {{abbrlink|BAN|British Approved Name}}.
References
{{Reflist}}
{{Progesterone receptor modulators}}
{{Estrogen receptor modulators}}
{{Androgen receptor modulators}}