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Abandoned drugs
Estradiol palmitate
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    Estradiol palmitate

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    Estradiol palmitate
    Estradiol palmitate structure.svg
    Clinical data
    Trade names Esmopal
    Other names Estradiol monopalmitate; Estradiol hexadecanoate; Estradiol 17β-hexadecanoate
    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] hexadecanoate
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    CompTox Dashboard (EPA)
    ECHA InfoCard 100.024.819
    Chemical and physical data
    Formula C34H54O3
    Molar mass 510.803 g·mol−1
    3D model (JSmol)
    • CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C
    • InChI=1S/C34H54O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-33(36)37-32-22-21-31-30-19-17-26-25-27(35)18-20-28(26)29(30)23-24-34(31,32)2/h18,20,25,29-32,35H,3-17,19,21-24H2,1-2H3/t29-,30-,31+,32+,34+/m1/s1
    • Key:XQKLZLWOOGGXMV-KWXXMMNJSA-N

    Estradiol palmitate (brand name Esmopal), or estradiol monopalmitate, also known as estradiol 17β-hexadecanoate, is a naturally occurringsteroidal estrogen and an estrogen ester – specifically, the C17β palmitate ester of estradiol. It occurs in the body as a very long-lasting metabolite and prohormone of estradiol. The compound has no affinity for the estrogen receptor, requiring transformation into estradiol for its estrogenic activity. In addition to its endogenous role, estradiol palmitate was formerly used as a fattening agent in chickens under the brand name Esmopal.

    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.

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