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Abandoned drugs
Estradiol 17β-acetate
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    Estradiol 17β-acetate

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    Not to be confused with Estradiol acetate.
    Estradiol 17β-acetate
    Estradiol acetate.svg
    Clinical data
    Drug class Estrogen; Estrogen ester
    Identifiers
    • [(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] acetate
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard 100.110.039
    Chemical and physical data
    Formula C20H26O3
    Molar mass 314.425 g·mol−1
    3D model (JSmol)
    • CC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)O)C
    • InChI=1S/C20H26O3/c1-12(21)23-19-8-7-18-17-5-3-13-11-14(22)4-6-15(13)16(17)9-10-20(18,19)2/h4,6,11,16-19,22H,3,5,7-10H2,1-2H3/t16-,17-,18+,19+,20+/m1/s1
    • Key:QAHOQNJVHDHYRN-SLHNCBLASA-N

    Estradiol 17β-acetate is an estrogen and an estrogen ester—specifically, the C17β acetate ester of estradiol—which was never marketed. It is the C17β positional isomer of the better-known and clinically used estradiol ester estradiol acetate (estradiol 3-acetate; Femtrace).

    Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors
    Estrogen Other names RBA (%)a REP (%)b
    ER ERα ERβ
    Estradiol E2 100 100 100
    Estradiol 3-sulfate E2S; E2-3S ? 0.02 0.04
    Estradiol 3-glucuronide E2-3G ? 0.02 0.09
    Estradiol 17β-glucuronide E2-17G ? 0.002 0.0002
    Estradiol benzoate EB; Estradiol 3-benzoate 10 1.1 0.52
    Estradiol 17β-acetate E2-17A 31–45 24 ?
    Estradiol diacetate EDA; Estradiol 3,17β-diacetate ? 0.79 ?
    Estradiol propionate EP; Estradiol 17β-propionate 19–26 2.6 ?
    Estradiol valerate EV; Estradiol 17β-valerate 2–11 0.04–21 ?
    Estradiol cypionate EC; Estradiol 17β-cypionate ?c 4.0 ?
    Estradiol palmitate Estradiol 17β-palmitate 0 ? ?
    Estradiol stearate Estradiol 17β-stearate 0 ? ?
    Estrone E1; 17-Ketoestradiol 11 5.3–38 14
    Estrone sulfate E1S; Estrone 3-sulfate 2 0.004 0.002
    Estrone glucuronide E1G; Estrone 3-glucuronide ? <0.001 0.0006
    Ethinylestradiol EE; 17α-Ethynylestradiol 100 17–150 129
    Mestranol EE 3-methyl ether 1 1.3–8.2 0.16
    Quinestrol EE 3-cyclopentyl ether ? 0.37 ?
    Footnotes: a = Relative binding affinities (RBAs) were determined via in-vitro displacement of labeled estradiol from estrogen receptors (ERs) generally of rodent uterine cytosol. Estrogen esters are variably hydrolyzed into estrogens in these systems (shorter ester chain length -> greater rate of hydrolysis) and the ER RBAs of the esters decrease strongly when hydrolysis is prevented. b = Relative estrogenic potencies (REPs) were calculated from half-maximal effective concentrations (EC50) that were determined via in-vitro β‐galactosidase (β-gal) and green fluorescent protein (GFP) production assays in yeast expressing human ERα and human ERβ. Both mammalian cells and yeast have the capacity to hydrolyze estrogen esters. c = The affinities of estradiol cypionate for the ERs are similar to those of estradiol valerate and estradiol benzoate (figure). Sources: See template page.

    See also




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