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Abandoned drugs
4-Fluoroestradiol
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    4-Fluoroestradiol

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    Not to be confused with 16α-Fluoroestradiol.
    4-Fluoroestradiol
    4-Fluoroestradiol.svg
    Clinical data
    Other names 4-FE2; 4-F-17β-E2; 4-Fluoro-17β-estradiol; 4-Fluoroestra-1,3,5-(10)-triene-3,17β-diol; NSC-94528
    Drug class Estrogen
    Identifiers
    • (8R,9S,13S,14S,17S)-4-fluoro-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
    CAS Number
    PubChem CID
    ChemSpider
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C18H23FO2
    Molar mass 290.378 g·mol−1
    3D model (JSmol)
    • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4F)O
    • InChI=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
    • Key:QZFXMXJXAUMHQR-ZHIYBZGJSA-N

    4-Fluoroestradiol (4-FE2) is a synthetic estrogen and a derivative of estradiol which was never marketed. It is specifically the 4-fluoro analogue of estradiol. 4-Fluoroestradiol has 180 ± 43% of the affinity of estradiol for the estrogen receptor of rat uterine cytosol and shows potent uterotrophic activity similar to that of estradiol in mice and rats. It has been labeled with fluorine-18 (18F) for potential use in medical imaging.

    Selected biological properties of endogenous estrogens in rats
    Estrogen ER RBA (%) Uterine weight (%) Uterotrophy LH levels (%) SHBG RBA (%)
    Control – 100 – 100 –
    Estradiol (E2) 100 506 ± 20 +++ 12–19 100
    Estrone (E1) 11 ± 8 490 ± 22 +++ ? 20
    Estriol (E3) 10 ± 4 468 ± 30 +++ 8–18 3
    Estetrol (E4) 0.5 ± 0.2 ? Inactive ? 1
    17α-Estradiol 4.2 ± 0.8 ? ? ? ?
    2-Hydroxyestradiol 24 ± 7 285 ± 8 +b 31–61 28
    2-Methoxyestradiol 0.05 ± 0.04 101 Inactive ? 130
    4-Hydroxyestradiol 45 ± 12 ? ? ? ?
    4-Methoxyestradiol 1.3 ± 0.2 260 ++ ? 9
    4-Fluoroestradiola 180 ± 43 ? +++ ? ?
    2-Hydroxyestrone 1.9 ± 0.8 130 ± 9 Inactive 110–142 8
    2-Methoxyestrone 0.01 ± 0.00 103 ± 7 Inactive 95–100 120
    4-Hydroxyestrone 11 ± 4 351 ++ 21–50 35
    4-Methoxyestrone 0.13 ± 0.04 338 ++ 65–92 12
    16α-Hydroxyestrone 2.8 ± 1.0 552 ± 42 +++ 7–24 <0.5
    2-Hydroxyestriol 0.9 ± 0.3 302 +b ? ?
    2-Methoxyestriol 0.01 ± 0.00 ? Inactive ? 4
    Notes: Values are mean ± SD or range. ER RBA = Relative binding affinity to estrogen receptors of rat uterine cytosol. Uterine weight = Percentage change in uterine wet weight of ovariectomized rats after 72 hours with continuous administration of 1 μg/hour via subcutaneously implanted osmotic pumps. LH levels = Luteinizing hormone levels relative to baseline of ovariectomized rats after 24 to 72 hours of continuous administration via subcutaneous implant. Footnotes: a = Synthetic (i.e., not endogenous). b = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: See template.

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