4-Fluoroestradiolのソースを表示

{{Short description|Chemical compound}}
{{Distinguish|16α-Fluoroestradiol}}
{{Drugbox
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| IUPAC_name = (8''R'',9''S'',13''S'',14''S'',17''S'')-4-fluoro-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[''a'']phenanthrene-3,17-diol
| image = 4-Fluoroestradiol.svg
| width = 

<!--Clinical data-->
| tradename = 
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = 
| legal_UK = 
| legal_US = 
| legal_status = 
| routes_of_administration = 
| class = [[Estrogen (medication)|Estrogen]]

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = 

<!-- Identifiers -->
| CAS_number_Ref = 
| CAS_number = 1881-37-4
| CAS_supplemental = 
| ATC_prefix = 
| ATC_suffix = 
| ATC_supplemental = 
| PubChem = 10085622
| IUPHAR_ligand = 
| DrugBank_Ref = 
| DrugBank = 
| ChemSpiderID_Ref = 
| ChemSpiderID = 8261159
| UNII = 
| KEGG = 
| ChEBI = 
| ChEMBL = 1627337
| synonyms = 4-FE2; 4-F-17β-E2; 4-Fluoro-17β-estradiol; 4-Fluoroestra-1,3,5-(10)-triene-3,17β-diol; NSC-94528

<!--Chemical data-->
| C=18 | H=23 | F=1 | O=2
| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4F)O
| StdInChI_Ref = 
| StdInChI = 1S/C18H23FO2/c1-18-9-8-11-10-4-6-15(20)17(19)13(10)3-2-12(11)14(18)5-7-16(18)21/h4,6,11-12,14,16,20-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1
| StdInChIKey_Ref = 
| StdInChIKey = QZFXMXJXAUMHQR-ZHIYBZGJSA-N
}}

'''4-Fluoroestradiol''' ('''4-FE2''') is a [[synthetic compound|synthetic]] [[estrogen (medication)|estrogen]] and a [[chemical derivative|derivative]] of [[estradiol (medication)|estradiol]] which was never marketed.<ref name="pmid6310247">{{cite journal | vauthors = Martucci CP | title = The role of 2-methoxyestrone in estrogen action | journal = Journal of Steroid Biochemistry | volume = 19 | issue = 1B | pages = 635–638 | date = July 1983 | pmid = 6310247 | doi = 10.1016/0022-4731(83)90229-7 }}</ref> It is specifically the 4-[[fluoro]] [[structural analog|analogue]] of estradiol.<ref name="pmid6310247" /> 4-Fluoroestradiol has 180 ± 43% of the [[affinity (pharmacology)|affinity]] of estradiol for the [[estrogen receptor]] of rat [[uterine]] [[cytosol]] and shows [[potency (pharmacology)|potent]] [[uterotrophic]] activity similar to that of estradiol in mice and rats.<ref name="pmid6310247" /><ref name="pmid6621038">{{cite journal | vauthors = Longcope C, Rafkind I, Arunachalam T, Caspi E | title = Biological activities of 4-fluoro estrogen analogues | journal = Journal of Steroid Biochemistry | volume = 19 | issue = 3 | pages = 1325–1328 | date = September 1983 | pmid = 6621038 | doi = 10.1016/0022-4731(83)90158-9 }}</ref> It has been [[radiolabel|label]]ed with [[fluorine-18]] (<sup>18</sup>F) for potential use in [[medical imaging]].<ref name="pmid544526">{{cite journal | vauthors = Eakins MN, Palmer AJ, Waters SL | title = Studies in the rat with 18F-4-fluoro-oestradiol and 18F-4-fluoro-oestrone as potential prostate scanning agents: comparison with 125I-2-iodo-oestradiol and 125I-2,4-di-iodo-oestradiol | journal = The International Journal of Applied Radiation and Isotopes | volume = 30 | issue = 11 | pages = 695–700 | date = November 1979 | pmid = 544526 | doi = 10.1016/0020-708x(79)90111-x }}</ref><ref name="pmid8212070">{{cite journal | vauthors = Cummins CH | title = Radiolabeled steroidal estrogens in cancer research | journal = Steroids | volume = 58 | issue = 6 | pages = 245–259 | date = June 1993 | pmid = 8212070 | doi = 10.1016/0039-128x(93)90069-y | s2cid = 29080385 }}</ref><ref name="JasemThiemann2016">{{cite journal| vauthors = Al Jasem Y, Thiemann T, Gano L, Oliveira MC |title=Fluorinated steroids and their derivatives|journal=Journal of Fluorine Chemistry|volume=185|year=2016|pages=48–85|issn=0022-1139|doi=10.1016/j.jfluchem.2016.03.009|bibcode=2016JFluC.185...48J }}</ref>

{{Selected biological properties of endogenous estrogens in rats}}

== See also ==
* [[16α-Fluoroestradiol]]

== References ==
{{Reflist}}

{{Estrogen receptor modulators}}

{{DEFAULTSORT:Fluoroestradiol, 4-}}
[[Category:Abandoned drugs]]
[[Category:Secondary alcohols]]
[[Category:Estranes]]
[[Category:Fluoroarenes]]
[[Category:Hydroxyarenes]]
[[Category:Synthetic estrogens]]

{{Steroid-stub}}
{{Genito-urinary-drug-stub}}