QuickView for mefloquine (compound)

Summary
General Info

PubChem

PubChem Compound 3000506

Name:	Mefloquine
PubChem Compound ID:	3000506
Description:	A phospholipid-interacting antimalarial drug (ANTIMALARIALS). It is very effective against PLASMODIUM FALCIPARUM with very few side effects.
Molecular formula:	C₁₇H₁₆F₆N₂O
Molecular weight:	378.312 g/mol
Synonyms:	RTI1172-1-1; (+/-)-threo-4-Quinolinemethanol, .alpha.-2-piperidinyl-2,8-bis(trifluoromethyl)-; AIDS055324; AIDS007692; (+)-threo-4-Quinolinemethanol, .alpha.-2-piperidinyl-2,8-bis(trifluoromethyl)-; RTI1173-1-1; AIDS-055324; (+)-Threo-Mefloquine; AIDS-007692

DrugBank

Identification

Name:	Mefloquine
Name (isomeric):	DB00358
Drug Type:	small molecule
Description:	A phospholipid-interacting antimalarial drug (ANTIMALARIALS). It is very effective against PLASMODIUM FALCIPARUM with very few side effects.
Synonyms:	Mefloquinone; Mefloquine HCL
Brand:	Lariam
Category:	Antimalarials
CAS number:	53230-10-7

Pharmacology

Indication:	For the treatment of mild to moderate acute malaria caused by Mefloquineuine-susceptible strains of <i>Plasmodium falciparum</i> (both chloroquine-susceptible and resistant strains) or by <i>Plasmodium vivax</i>. Also for the prophylaxis of <i>Plasmodium falciparum</i> and <i>Plasmodium vivax</i> malaria infections, including prophylaxis of chloroquine-resistant strains of <i>Plasmodium falciparum</i>.
Pharmacology:	Mefloquine is an antimalarial agent which acts as a blood schizonticide. Mefloquine is active against the erythrocytic stages of Plasmodium species. However, the drug has no effect against the exoerythrocytic (hepatic) stages of the parasite. Mefloquine is effective against malaria parasites resistant to chloroquine. Mefloquine is a chiral molecule... show more » Mefloquine is an antimalarial agent which acts as a blood schizonticide. Mefloquine is active against the erythrocytic stages of Plasmodium species. However, the drug has no effect against the exoerythrocytic (hepatic) stages of the parasite. Mefloquine is effective against malaria parasites resistant to chloroquine. Mefloquine is a chiral molecule. According to some research, the (+) enantiomer is more effective in treating malaria, and the (-) enantiomer specifically binds to adenosine receptors in the central nervous system, which may explain some of its psychotropic effects. show less «
Mechanism of Action:	Mefloquine has been found to produce swelling of the Plasmodium falciparum food vacuoles. It may act by forming toxic complexes with free heme that damage membranes and interact with other plasmodial components.
Absorption:	Well absorbed from the gastrointestinal tract. The presence of food significantly enhances the rate and extent of absorption.
Protein binding:	98%
Biotransformation:	Hepatic. Two metabolites have been identified in humans. The main metabolite, 2,8-bis-trifluoromethyl-4-quinoline carboxylic acid, is inactive against Plasmodium falciparum. The second metabolite, an alcohol, is present in minute quantities.
Route of elimination:	There is evidence that mefloquine is excreted mainly in the bile and feces. Urinary excretion of unchanged mefloquine and its main metabolite under steady-state condition accounted for about 9% and 4% of the dose, respectively.
Half Life:	2 to 4 weeks
Clearance:	30 mL/min
Toxicity:	Oral, rat: LD₅₀ = 880 mg/kg. Symptoms of overdose include nausea, vomiting, and weight loss.
Affected organisms:	Plasmodium

Interactions

Food interaction:

Avoid alcohol.

Take with a full glass of water.

Take with food.

Drug interaction:

Anisindione	Mefloquine may increase the anticoagulant effect of anisindione.
Warfarin	Mefloquine may increase the anticoagulant effect of warfarin.
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.
Vorinostat	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Halofantrine	Increased risk of cardiac toxicity

Anisindione	Mefloquine may increase the anticoagulant effect of anisindione.
Warfarin	Mefloquine may increase the anticoagulant effect of warfarin.
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.
Vorinostat	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Halofantrine	Increased risk of cardiac toxicity
Rifampin	Rifampin lowers mefloquine levels
Zonisamide	Mefloquine may decrease the serum concentration and therapeutic effect of zonisamide. Concomitant therapy is contraindicated in patients with history of convulsions.
Vigabatrin	Mefloquine may decrease the serum concentration of Vigabatrin. This may increase the risk of seizure in patients receiving Vigabatrin to prevent seizures. Consider alternate therapy or monitor for changes in Vigabatrin serum concentration, therapeutic or adverse effects if Mefloquin is initiated, discontinued or dose changed.
Acenocoumarol	Mefloquine may increase the anticoagulant effect of acenocoumarol.
Lumefantrine	Mefloquine may increase the adverse effects of lumefantrine. Combination therapy is contraindicated unless there are no other treatment options.
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of mefloquine by decreasing its metabolism. Additive QTc prolongation may also occur. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of mefloquine if voriconazole is initiated, discontinued or dose changed.
Tacrolimus	Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Topotecan	The p-glycoprotein inhibitor, Mefloquine, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
Ritonavir	Mefloquine decreases the effect of ritonavir
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.
Tiagabine	Mefloquine increases the risk of seizure and is contraindicated in persons with a history of convulsions. Possible reduction in the therapeutic effect of Tiagabine when used for other indications may also occur.
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).
Artemether	Mefloquine may increase the adverse effects of artemether. Combination therapy is contraindicated unless there are no other treatment options.
Trimipramine	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Telithromycin	Telithromycin may reduce clearance of Mefloquine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Mefloquine if Telithromycin is initiated, discontinued or dose changed.
Dicumarol	Mefloquine may increase the anticoagulant effect of dicumarol.
Ziprasidone	Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy should be avoided.

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Targets

Ferriprotoporphyrin IX

Hemoglobin subunit alpha

Adenosine A2a receptor

Enzymes

Transporters

Multidrug resistance protein 1