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Abandoned drugs
Cyclodiol
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    Cyclodiol

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    Cyclodiol
    Cyclodiol.svg
    Clinical data
    Other names ZK-115194; Cycloestradiol; 14α,17α-Ethano-17β-estradiol; 14α,17α-Ethanoestra-1,3,5(10)-triene-3,17β-diol; 14,21-Cyclo-19-norpregna-1,3,5(10)-triene-3,17α-diol
    Routes of
    administration    		 By mouth
    Drug class Estrogen
    Pharmacokinetic data
    Bioavailability 33 ± 19%
    Elimination half-life 28.7 hours
    Identifiers
    • (8R,9S,13S)-13-Methyl-7,8,9,11,12,13,15,16-octahydro-14,17-ethanocyclopenta[a]phenanthrene-3,17(6H)-diol
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C20H26O2
    Molar mass 298.426 g·mol−1
    3D model (JSmol)
    • C[C@]12CC[C@H]3[C@H](C14CCC2(CC4)O)CCC5=C3C=CC(=C5)O
    • InChI=1S/C20H26O2/c1-18-7-6-16-15-4-3-14(21)12-13(15)2-5-17(16)19(18)8-10-20(18,22)11-9-19/h3-4,12,16-17,21-22H,2,5-11H2,1H3/t16-,17-,18+,19?,20?/m1/s1
    • Key:YGXXZMDWSWSCSI-UYUJGIFYSA-N

    Cyclodiol (developmental code name ZK-115194; also known as 14α,17α-ethano-17β-estradiol) is a synthetic estrogen which was studied in the 1990s and was never marketed. It is a derivative of estradiol with a bridge between the C14α and C17α positions. Cyclodiol has 100% of the relative binding affinity of estradiol for the human ERα and similar transactivational capacity as estradiol at the receptor. It has comparable potency to estradiol when administered by subcutaneous injection. The drug shows genotoxicity similarly to estradiol. Cyclodiol showed an absolute bioavailability of 33 ± 19% and an elimination half-life of 28.7 hours in pharmacokinetic studies in women.

    See also




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