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Abandoned drugs
Estradiol benzoate cyclooctenyl ether
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    Estradiol benzoate cyclooctenyl ether

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    EBCO
    Estradiol benzoate cyclooctenyl ether.svg
    Clinical data
    Other names EBCO; Estradiol 3-benzoate 17β-cyclooctenyl ether
    Routes of
    administration    		 By mouth
    Drug class Estrogen; Estrogen ester; Estrogen ether
    Identifiers
    • [(8R,9S,13S,14S,17S)-17-[(1E)-cycloocten-1-yl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate
    CAS Number
    PubChem CID
    ChemSpider
    Chemical and physical data
    Formula C33H40O3
    Molar mass 484.680 g·mol−1
    3D model (JSmol)
    • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O/C/4=C/CCCCCC4)CCC5=C3C=CC(=C5)OC(=O)C6=CC=CC=C6
    • InChI=1S/C33H40O3/c1-33-21-20-28-27-17-15-26(36-32(34)23-10-6-5-7-11-23)22-24(27)14-16-29(28)30(33)18-19-31(33)35-25-12-8-3-2-4-9-13-25/h5-7,10-12,15,17,22,28-31H,2-4,8-9,13-14,16,18-21H2,1H3/b25-12+/t28-,29-,30+,31+,33+/m1/s1
    • Key:DOFNLZKUGHVIMH-UQWKGHMASA-N

    Estradiol benzoate cyclooctenyl ether (EBCO), or estradiol 3-benzoate 17β-cyclooctenyl ether, is a synthetic estrogen as well as estrogen ester and ether – specifically, the C3 benzoate ester and C17β cyclooctenyl ether of estradiol – which was described in the early 1970s and was never marketed. It has been found to have a dramatically prolonged duration of action with oral administration in animals, similarly to the related compound quinestrol (the 3-cyclopentyl ether of ethinylestradiol). A single oral dose of EBCO sustained high uterus weights for 3 weeks in rats. This long-lasting activity may be due to storage of EBCO in fat. It appears that EBCO is absorbed satisfactorily from the gastrointestinal tract, at least partially survives first-pass metabolism in the liver and intestines, and is then sequestered into fat, from which it is slowly released and activated into estradiol. In contrast to quinestrol, the oral activity of EBCO is greatly improved when it is delivered in an oil solution as opposed to an aqueous vehicle.

    See also



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