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Abandoned drugs
Droloxifene
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    Droloxifene

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    Droloxifene
    Droloxifene.svg
    Clinical data
    Other names FK-435; ICI-79280; K-060; K-21060E; RP-60850; 3-Hydroxytamoxifen; 3-OH-TAM
    Routes of
    administration    		 Oral
    Pharmacokinetic data
    Elimination half-life 19–37 hours
    Identifiers
    • 3-[(E)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard 100.102.640
    Chemical and physical data
    Formula C26H29NO2
    Molar mass 387.523 g·mol−1
    3D model (JSmol)
    • CC/C(=C(/C1=CC=C(C=C1)OCCN(C)C)\C2=CC(=CC=C2)O)/C3=CC=CC=C3
    • InChI=1S/C26H29NO2/c1-4-25(20-9-6-5-7-10-20)26(22-11-8-12-23(28)19-22)21-13-15-24(16-14-21)29-18-17-27(2)3/h5-16,19,28H,4,17-18H2,1-3H3/b26-25+
    • Key:ZQZFYGIXNQKOAV-OCEACIFDSA-N

    Droloxifene (INN, USAN) (former developmental code names FK-435, ICI-79280, K-060, K-21060E, RP-60850), also known as 3-hydroxytamoxifen, is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was developed originally in Germany and later in Japan for the treatment of breast cancer, osteoporosis in men and postmenopausal women, and cardiovascular disorders but was abandoned and never marketed. It reached phase II and phase III clinical trials for these indications before development was discontinued in 2000. The drug was found to be significantly less effective than tamoxifen in the treatment of breast cancer in two phase III clinical trials.

    Droloxifene is an analogue of tamoxifen, specifically 3-hydroxytamoxifen, but has been said to have 10- to 60-fold increased affinity for the estrogen receptor and reduced partial estrogen agonistic activity. The affinity of droloxifene for the estrogen receptor ranges from 0.2 to 15.2% relative to estradiol in different studies. For comparison, the ranges are 0.06 to 16% for tamoxifen and 0.1 to 12% for clomifene. Droloxifene causes a dose-dependent decrease in luteinizing hormone and follicle-stimulating hormone levels, indicating that it has antigonadotropic activity, and dose-dependently increases sex hormone-binding globulin levels, indicating that it has estrogenic activity in the liver. Similarly to tamoxifen, droloxifene has partial estrogenic effects in the uterus. Unlike tamoxifen, droloxifene does not produce DNA adduct or liver tumors in animals.

    See also

    External links


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