Halofantrine

Ric N. Price, Julie A. Simpson, James S. McCarthy

    Research output: Chapter in Book/Report/Conference proceedingChapter

    Abstract

    Halofantrine is an arylaminoalcohol anti-malarial drug that was first identified as a potential anti-malarial agent by the World War II Chemotherapy program and subsequently developed by the Walter Reed Army Institute of Research (Schuster and Canfield, 1989). It was first marketed in 1984 as Halfan by Smith Kline and French. The chemical structure of halofantrine is [R, S]-1,3-dichloro-α-[2-{dibutylamino} ethyl]-6-fluoromethyl 1-9-phenanthrenemethanol hydrochloride, its molecular formula is C26H30O2F3NO, and its molecular weight is 500.4 g/mol. Halofantrine is a racemate with two enantiomers, forming a molecular structure similar to that of the other class II schizonticidal drugs (quinine, mefloquine, and lumefantrine). The chemical structure is shown in Figure 179.1. The drug was marketed for use as a treatment for acute malaria until it was recognized that its variable pharmacokinetic profile, particularly its pronounced food effect, resulted in some individuals developing a lifethreatening prolongation of the QT interval, leading to torsades de pointes and sudden cardiac death. As a consequence, the drug was withdrawn from the market. Halofantrine was available for oral administration in tablet form (250 mg), capsules, and flavored suspension, and in an intravenous preparation.

    Original languageEnglish
    Title of host publicationKucers the Use of Antibiotics
    Subtitle of host publicationA Clinical Review of Antibacterial, Antifungal, Antiparasitic, and Antiviral Drugs, Seventh Edition
    PublisherCRC Press
    Chapter179
    Pages3091-3096
    Number of pages6
    Volume3
    Edition7th
    ISBN (Electronic)9781498747967
    ISBN (Print)9781498747950
    DOIs
    Publication statusPublished - 1 Jan 2017

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  • Cite this

    Price, R. N., Simpson, J. A., & McCarthy, J. S. (2017). Halofantrine. In Kucers the Use of Antibiotics: A Clinical Review of Antibacterial, Antifungal, Antiparasitic, and Antiviral Drugs, Seventh Edition (7th ed., Vol. 3, pp. 3091-3096). CRC Press. https://doi.org/10.1201/9781498747967