16α-Iodo-E2のソースを表示

{{Short description|Chemical compound}}
{{Drugbox
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| IUPAC_name = (8R,9S,13S,14S,16R,17R)-16-iodo-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
| image = 16-Iodoestradiol structure.svg
| width = 220

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<!-- Identifiers -->
| CAS_number_Ref = 
| CAS_number = 7450-34-2
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| PubChem = 67087
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| ChemSpiderID_Ref = 
| ChemSpiderID = 60437
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| ChEMBL = 342892

<!--Chemical data-->
| C=18 | H=23 | I=1 | O=2
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| smiles = C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)I)CCC4=C3C=CC(=C4)O
| StdInChI_Ref = 
| StdInChI = 1S/C18H23IO2/c1-18-7-6-13-12-5-3-11(20)8-10(12)2-4-14(13)15(18)9-16(19)17(18)21/h3,5,8,13-17,20-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1
| StdInChIKey_Ref = 
| StdInChIKey = SSYGGPAGDDGXAF-ZXXIGWHRSA-N
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'''16α-Iodo-E2''', or '''16α-iodoestradiol''', is a [[synthetic compound|synthetic]], [[steroid]]al, potent [[estrogen]] with slight preference for the [[ERα]] over the [[ERβ]] that is used in [[scientific research]].<ref name="pmid15548008">{{cite journal | vauthors = Manas ES, Unwalla RJ, Xu ZB, Malamas MS, Miller CP, Harris HA, Hsiao C, Akopian T, Hum WT, Malakian K, Wolfrom S, Bapat A, Bhat RA, Stahl ML, Somers WS, Alvarez JC | title = Structure-based design of estrogen receptor-beta selective ligands | journal = J. Am. Chem. Soc. | volume = 126 | issue = 46 | pages = 15106–19 | year = 2004 | pmid = 15548008 | doi = 10.1021/ja047633o }}</ref><ref name="pmid18690843">{{cite journal | vauthors = Chen GG, Vlantis AC, Zeng Q, van Hasselt CA | title = Regulation of cell growth by estrogen signaling and potential targets in thyroid cancer | journal = Curr Cancer Drug Targets | volume = 8 | issue = 5 | pages = 367–77 | year = 2008 | pmid = 18690843 | doi = 10.2174/156800908785133150}}</ref> The K<sub>D</sub> of 16α-iodo-E2 for the ERα is 0.6 nM and for the ERβ is 0.24 nM, a 4-fold difference in [[affinity (pharmacology)|affinity]], whereas [[estradiol]] is considered to have similar affinity for the two receptor subtypes.<ref name="pmid18690843" /> Unlike the case of the much weaker [[estriol]] (16α-hydroxyestradiol), 16α-iodo-E2 is considered to be equipotent with estradiol in terms of estrogenic activity.<ref name="pmid3795941">{{cite journal | vauthors = Hochberg RB, Zielinski JE, Duax WL, Strong P | title = The molecular structure of 16 alpha-iodo-17 beta-estradiol, a high affinity ligand for the estrogen receptor | journal = J. Steroid Biochem. | volume = 25 | issue = 5A | pages = 615–8 | year = 1986 | pmid = 3795941 | doi = 10.1016/0022-4731(86)90002-6}}</ref> [[Radiolabel]]ed [16α-<sup>125</sup>I]iodo-E2 has been employed in [[medical imaging|imaging]] to study the [[estrogen receptor]].<ref name="pmid8212070">{{cite journal | vauthors = Cummins CH | title = Radiolabeled steroidal estrogens in cancer research | journal = Steroids | volume = 58 | issue = 6 | pages = 245–59 | year = 1993 | pmid = 8212070 | doi = 10.1016/0039-128x(93)90069-y| s2cid = 29080385 }}</ref>

==See also==
* [[16α-LE2]]
* [[Clomestrone]]
* [[Mytatrienediol]]
* [[GTx-758]]

==References==
{{reflist|30em}}

{{Estrogen receptor modulators}}

[[Category:Estranes]]
[[Category:Organoiodides]]
[[Category:Synthetic estrogens]]


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