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Abandoned drugs
Nafoxidine
Другие языки:

    Nafoxidine

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    Nafoxidine
    Nafoxidine.svg
    Clinical data
    Other names U-11,000A; NSC-70735
    Routes of
    administration    		 By mouth
    ATC code
    • None
    Identifiers
    • 1-[2-[4-(6-Methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl]pyrrolidine
    CAS Number
    PubChem CID
    IUPHAR/BPS
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard 100.222.756
    Chemical and physical data
    Formula C29H31NO2
    Molar mass 425.572 g·mol−1
    3D model (JSmol)
    • COC1=CC2=C(C=C1)C(=C(CC2)C3=CC=CC=C3)C4=CC=C(C=C4)OCCN5CCCC5
    • InChI=1S/C29H31NO2/c1-31-26-14-16-28-24(21-26)11-15-27(22-7-3-2-4-8-22)29(28)23-9-12-25(13-10-23)32-20-19-30-17-5-6-18-30/h2-4,7-10,12-14,16,21H,5-6,11,15,17-20H2,1H3
    • Key:JEYWNNAZDLFBFF-UHFFFAOYSA-N

    Nafoxidine (INN; developmental code names U-11,000A) or nafoxidine hydrochloride (USAN) is a nonsteroidal selective estrogen receptor modulator (SERM) or partial antiestrogen of the triphenylethylene group that was developed for the treatment of advanced breast cancer by Upjohn in the 1970s but was never marketed. It was developed at around the same time as tamoxifen and clomifene, which are also triphenylethylene derivatives. The drug was originally synthesized by the fertility control program at Upjohn as a postcoital contraceptive, but was subsequently repurposed for the treatment of breast cancer. Nafoxidine was assessed in clinical trials in the treatment of breast cancer and was found to be effective. However, it produced side effects including ichthyosis, partial hair loss, and phototoxicity of the skin in almost all patients, and this resulted in the discontinuation of its development.

    Nafoxidine is a long-acting estrogen receptor ligand, with a nuclear retention in the range of 24 to 48 hours or more.

    Comparison of early clinical experience with antiestrogens for advanced breast cancer
    Antiestrogen Dosage Year(s) Response rate Toxicity
    Ethamoxytriphetol 500–4,500 mg/day 1960 25% Acute psychotic episodes
    Clomifene 100–300 mg/day 1964–1974 34% Fears of cataracts
    Nafoxidine 180–240 mg/day 1976 31% Cataracts, ichthyosis, photophobia
    Tamoxifen 20–40 mg/day 1971–1973 31% Transient thrombocytopeniaa
    Footnotes: a = "The particular advantage of this drug is the low incidence of troublesome side effects (25)." "Side effects were usually trivial (26)." Sources:



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