Δ4-Tiboloneのソースを表示

{{short description|Chemical compound}}
{{Drugbox
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| IUPAC_name = (7''R'',8''R'',9''S'',10''R'',13''S'',14''S'',17''R'')-17-Ethynyl-17-hydroxy-7,13-dimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[''a'']phenanthren-3-one
| image = Δ4-Tibolone.svg
| width = 225px
| image2 = Δ4-Tibolone molecule ball.png
| width2 = 235px

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<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 1162-60-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = LHZ8R2OW0M
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| PubChem = 22814761
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| ChemSpiderID = 18532860
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| synonyms = ORG-OM-38; Delta-4-Tibolone; 7α-Methylnorethisterone; 7α-Methyl-17α-ethynyl-19-nortestosterone; 17α-Ethynyl-17β-hydroxy-7α-methyl-4-estren-3-one

<!--Chemical data-->
| C=21 | H=28 | O=2
| SMILES = C[C@@H]1CC2=CC(=O)CC[C@@H]2[C@@H]3[C@@H]1[C@@H]4CC[C@]([C@]4(CC3)C)(C#C)O
| StdInChI_Ref = 
| StdInChI = 1S/C21H28O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,12-13,16-19,23H,5-11H2,2-3H3/t13-,16+,17-,18+,19-,20+,21+/m1/s1
| StdInChIKey_Ref = 
| StdInChIKey = WAOKMNBZWBGYIK-KIURNNQRSA-N
}}

'''δ<sup>4</sup>-Tibolone''' (developmental code name '''ORG-OM-38'''), also known as '''7α-methylnorethisterone''' or as '''7α-methyl-17α-ethynyl-19-nortestosterone''', is a [[synthetic compound|synthetic]] [[androgen]] and [[progestin]] which was never marketed.<ref name="pmid16112947">{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | pages = 3–63 | year = 2005 | issue = Suppl 1 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 | url = http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf}}</ref><ref name="pmid19464167">{{cite journal | vauthors = Escande A, Servant N, Rabenoelina F, Auzou G, Kloosterboer H, Cavaillès V, Balaguer P, Maudelonde T | title = Regulation of activities of steroid hormone receptors by tibolone and its primary metabolites | journal = J. Steroid Biochem. Mol. Biol. | volume = 116 | issue = 1–2 | pages = 8–14 | year = 2009 | pmid = 19464167 | doi = 10.1016/j.jsbmb.2009.03.008 | s2cid = 18346113 | url = http://www.hal.inserm.fr/inserm-00396319/document}}</ref> The compound is a major [[active metabolite]] of [[tibolone]], which itself is a [[prodrug]] of δ<sup>4</sup>-tibolone along with [[3α-hydroxytibolone]] and [[3β-hydroxytibolone]] (which, in contrast to δ<sup>4</sup>-tibolone, are [[estrogen (medication)|estrogen]]s).<ref name="pmid16112947" /> Tibolone and δ<sup>4</sup>-tibolone are thought to be responsible for the androgenic and progestogenic activity of tibolone, while 3α-hydroxytibolone and 3β-hydroxytibolone are thought to be responsible for its [[estrogen (medication)|estrogenic]] activity.<ref name="pmid16112947" />

==See also==
* [[List of androgens/anabolic steroids]]
* [[List of progestogens]]

==References==
{{Reflist}}


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

{{DISPLAYTITLE:δ<sup>4</sup>-Tibolone}}

{{DEFAULTSORT:Tibolone, delta4-}}

[[Category:Abandoned drugs]]
[[Category:Tertiary alcohols]]
[[Category:Alkene derivatives]]
[[Category:Ethynyl compounds]]
[[Category:Anabolic–androgenic steroids]]
[[Category:Estranes]]
[[Category:Human drug metabolites]]
[[Category:Ketones]]
[[Category:Progestogens]]


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{{Steroid-stub}}