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Abandoned drugs
Nitromifene
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    Nitromifene

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    Nitromifene
    Nitromifene.svg
    Clinical data
    Other names CI-628; CN-5518; CN-55945
    Identifiers
    • 1-[2-[4-[1-(4-Methoxyphenyl)-2-nitro-2-phenylethenyl]phenoxy]ethyl]pyrrolidine
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C27H28N2O4
    Molar mass 444.531 g·mol−1
    3D model (JSmol)
    • COC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)[N+](=O)[O-])C3=CC=C(C=C3)OCCN4CCCC4
    • InChI=1S/C27H28N2O4/c1-32-24-13-9-21(10-14-24)26(27(29(30)31)23-7-3-2-4-8-23)22-11-15-25(16-12-22)33-20-19-28-17-5-6-18-28/h2-4,7-16H,5-6,17-20H2,1H3
    • Key:MFKMXUFMHOCZHP-UHFFFAOYSA-N

    Nitromifene (INN; also as the citrate salt nitromifene citrate (USAN), developmental code names CI-628, CN-5518, CN-55945) is a nonsteroidal selective estrogen receptor modulator (SERM) related to triphenylethylenes like tamoxifen that was never marketed. It is a mixture of (E)- and (Z)-isomers that possess similar antiestrogenic activity. The drug was described in 1966. Along with tamoxifen, nafoxidine, and clomifene, it was one of the earliest SERMs.

    Nitromifene has been found to dissociate from the estrogen receptor 250-fold faster than estradiol. This may be involved in its antagonistic activity at the estrogen receptor.




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