Halofantrine
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| Clinical data | |
|---|---|
| Trade names | Halfan |
| AHFS/Drugs.com | Consumer Drug Information |
| MedlinePlus | a603030 |
| Routes of administration |
Oral |
| ATC code | |
| Pharmacokinetic data | |
| Protein binding | 60–70% |
| Metabolism | Hepatic (CYP3A4-mediated) |
| Biological half-life | 6–10 days |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| ECHA InfoCard | 100.067.346 |
| Chemical and physical data | |
| Formula | C26H30Cl2F3NO |
| Molar mass | 500.423 g/mol |
| 3D model (Jmol) | |
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Halofantrine is a drug used to treat malaria. Halofantrine's structure contains a substituted phenanthrene, and is related to the antimalarial drugs quinine and lumefantrine. Marketed as Halfan, halofantrine is never used to prevent malaria and its mode of action is unknown, although a crystallographic study showed that it binds to hematin in vitro, suggesting a possible mechanism of action. Halofantrine has also been shown to bind to plasmpesin, a haemoglobin degrading enzyme unique to the malarial parasites.
Halofantrine was developed at SRI International for the Walter Reed Army Institute of Research from 1965 to 1975 by a team led by medicinal chemist William Colwell.
Halofantrine can cause abdominal pain, diarrhoea, vomiting, rash, headache, itching and elevated liver enzymes.
It can be associated with cardiotoxicity. The most dangerous side effect is cardiac arrhythmias: halofantrine causes significant QT prolongation, and this effect is seen even at standard doses. The drug should therefore not be given to patients with cardiac conduction defects and should not be combined with mefloquine. A survey from 2009 suggests that the drug is safe when correctly administered.
Consumption of grapefruit combined with certain medications can cause serious side effects, even death. Halofantrine combined with this fruit or grapefruit juice is dangerous. The mechanism of action is inhibition of CYP3A4, which is necessary to metabolize the drug and eliminate it from the body. Without CYP3A4, levels of the drug will become toxic in the body.
The mechanism of action of halofantrine is unknown. The absorption of halofantrine is erratic, but is increased when taken with fatty food. Because of fears of toxicity due to increased halofantrine blood levels, halofantrine should be taken on an empty stomach.
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Wikipedia