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Abandoned drugs
Pipendoxifene
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    Pipendoxifene

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    Pipendoxifene
    Pipendoxifene skeletal.svg
    Clinical data
    Other names ERA-923
    Identifiers
    • 2-(4-hydroxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ChEMBL
    Chemical and physical data
    Formula C29H32N2O3
    Molar mass 456.586 g·mol−1
    3D model (JSmol)
    • CC1=C(N(C2=C1C=C(C=C2)O)CC3=CC=C(C=C3)OCCN4CCCCC4)C5=CC=C(C=C5)O
    • InChI=1S/C29H32N2O3/c1-21-27-19-25(33)11-14-28(27)31(29(21)23-7-9-24(32)10-8-23)20-22-5-12-26(13-6-22)34-18-17-30-15-3-2-4-16-30/h5-14,19,32-33H,2-4,15-18,20H2,1H3
    • Key:JICOGKJOQXTAIP-UHFFFAOYSA-N

    Pipendoxifene (INN) (developmental code name ERA-923) is a nonsteroidal selective estrogen receptor modulator (SERM) that was under development by Ligand Pharmaceuticals and Wyeth-Ayerst Laboratories (now Wyeth) for the treatment of breast cancer but was not marketed. It is a member of the 2-phenylindole group of SERMs and is structurally related to zindoxifene and the marketed bazedoxifene. The drug reached phase II clinical trials before its development was discontinued. It was synthesized at the same time as bazedoxifene and was intended as a backup drug for bazedoxifene, only to be developed further if bazedoxifene had failed in clinical trials. No further development was reported after 2002 and it was formally announced that development had been terminated in November 2005.

    Unlike the SERM raloxifene, pipendoxifene is devoid of uterotrophic activity in immature/ovariectomized rodents.

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