QuickView for Halofantrine (compound)

Summary
General Info

PubChem

PubChem Compound 37392

Name:	halofantrine
PubChem Compound ID:	37392
Molecular formula:	C₂₆H₃₁Cl₃F₃NO
Molecular weight:	536.884 g/mol
Synonyms:	1,3-Dichloro-alpha-(2-(dibutylamino)ethyl)-6-(trifluoromethyl)phenanthren-1-methanol hydrochloride; Halfan (TN); 9-Phenanthrenemethanol, 1,3-dichloro-alpha-(2-(dibutylamino)ethyl)-6-(trifluoromethyl)-, hydrochloride; 1-(1,3-Dichloro-6-trifluoromethyl-9-phenanthryl)-3-(di-n-butylamino)propanol hydrochloride; Halfan; 1,3-Dichloro-6-trifluoromethyl-9-(3-(dibutylamino)-1-hydroxypropyl)phenanthrene HCl; Halofantrino [Spanish]; 36167-63-2; 1,3-Dichloro-alpha-(2-(dibutylamino)ethyl)-6-(trifluoromethyl)-9-phenanthrenemethanol hydrochloride; 106927-11-1. show more » 1,3-Dichloro-alpha-(2-(dibutylamino)ethyl)-6-(trifluoromethyl)phenanthren-1-methanol hydrochloride; Halfan (TN); 9-Phenanthrenemethanol, 1,3-dichloro-alpha-(2-(dibutylamino)ethyl)-6-(trifluoromethyl)-, hydrochloride; 1-(1,3-Dichloro-6-trifluoromethyl-9-phenanthryl)-3-(di-n-butylamino)propanol hydrochloride; Halfan; 1,3-Dichloro-6-trifluoromethyl-9-(3-(dibutylamino)-1-hydroxypropyl)phenanthrene HCl; Halofantrino [Spanish]; 36167-63-2; 1,3-Dichloro-alpha-(2-(dibutylamino)ethyl)-6-(trifluoromethyl)-9-phenanthrenemethanol hydrochloride; 106927-11-1; SK&F-102866; D02485; EINECS 252-895-4; Halofantrine Hydrochloride [USAN]; WR-171,669; Halofantrine hydrochloride; WR-171669; WR 171669; 9-(3-(dibutylamino)-1-hydroxypropyl)-1,3-dichloro-6-(trifluoromethyl)phenanthrene hydrochloride; (+-)-Halofantrine hydrochloride; Halofantrine hydrochloride (USAN) show less «

DrugBank

Identification

Name:	halofantrine
Name (isomeric):	DB01218
Drug Type:	small molecule
Synonyms:	Halofantrinum [INN-Latin]; Halofantrine [Usan]; Halofantrina [INN-Spanish]
Brand:	Halfan
Category:	Antimalarials, Antiprotozoals
CAS number:	69756-53-2

Pharmacology

Indication:	For treatment of Severe malaria
Pharmacology:	Halofantrine is a synthetic antimalarial which acts as a blood schizonticide. It is effective against multi drug resistant (including mefloquine resistant) P. falciparum malaria.
Mechanism of Action:	The mechanism of action of Halofantrine may be similar to that of chloroquine, quinine, and mefloquine; by forming toxic complexes with ferritoporphyrin IX that damage the membrane of the parasite.
Protein binding:	60-70%;
Biotransformation:	Hepatic
Half Life:	6-10 days
Toxicity:	Side effects incldue coughing noisy, rattling, troubled breathing, loss of appetite, aches and pain in joints, indigestion,and skin itching or rash.
Affected organisms:	Plasmodium

Interactions

Food interaction:

Take on an empty stomach, bioavailability is 6 times higher when drug is taken with high fat meals. Risks of cardiac toxicity are then increased.

Drug interaction:

Thiothixene	May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
Thioridazine	Increased risk of cardiotoxicity and arrhythmias
Vorinostat	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Bicalutamide	CYP3A4 Inhibitors like bicalutamide may increase the serum concentration of halofantrine. Extreme caution, with possibly increased monitoring of cardiac status (e.g., ECG), should be used with concurrent use of halofantrine with any moderate CYP3A4 inhibitor(s).
Clotrimazole	CYP3A4 Inhibitors (Moderate) such as clotrmazole may increase the serum concentration of halofantrine. Extreme caution, with possibly increased monitoring of cardiac status (e.g., ECG), should be used with concurrent use of halofantrine with any moderate CYP3A4 inhibitor(s).

Thiothixene	May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
Thioridazine	Increased risk of cardiotoxicity and arrhythmias
Vorinostat	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Bicalutamide	CYP3A4 Inhibitors like bicalutamide may increase the serum concentration of halofantrine. Extreme caution, with possibly increased monitoring of cardiac status (e.g., ECG), should be used with concurrent use of halofantrine with any moderate CYP3A4 inhibitor(s).
Clotrimazole	CYP3A4 Inhibitors (Moderate) such as clotrmazole may increase the serum concentration of halofantrine. Extreme caution, with possibly increased monitoring of cardiac status (e.g., ECG), should be used with concurrent use of halofantrine with any moderate CYP3A4 inhibitor(s).
Verapamil	Verapamil, a moderate CYP3A4 inhibitor, may increase the serum concentration of Halofantrine by decreasing its metabolism. Extreme caution with increased cardiac status monitoring should be used during concomitant therapy.
Quinupristin	This combination presents an increased risk of toxicity
Tacrolimus	Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Posaconazole	Contraindicated co-administration
Artemether	Halofantrine may increase the adverse effects of artemether. Combination therapy is contraindicated unless there are no other treatment options.
Conivaptan	CYP3A4 Inhibitors (Strong) may increase the serum concentration of Fluticasone (Oral Inhalation). Concurrent use of orally inhaled fluticasone with strong CYP3A4 inhibitors is not recommended.
Voriconazole	Voriconazole may increase the serum concentration of halofantrine by decreasing its metabolism by CYP3A4. Concomitant therapy should be avoided due to the concentration-dependent risk of QTc prolongation related to halofantrine.
Toremifene	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
Zuclopenthixol	Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Telithromycin	Telithromycin may reduce clearance of Halofantrine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Halofantrine if Telithromycin is initiated, discontinued or dose changed.
Trimipramine	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Mefloquine	Increased risk of cardiac toxicity
Ziprasidone	Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy should be avoided.
Lumefantrine	Halofantrine may increase the adverse effects of lumefantrine. Additive QTc-prolongation may occur. Combination therapy is contraindicated and therapies should not be administered within one month of each other due to the long half-life of lumefantrine.
Mesoridazine	Increased risk of cardiotoxicity and arrhythmias

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Targets

Ferriprotoporphyrin IX

Potassium voltage-gated channel subfamily H member 2

Enzymes