Mefloquine hydrochlorideProduct ingredient for Mefloquine

Name
Mefloquine hydrochloride
Drug Entry
Mefloquine

Malaria is a protozoan disease that places an enormous burden on human health in endemic areas around the world. The 2020 World Health Organization malaria report indicates a 60% decrease in the global malaria fatality rate between 2000 to 2019.14 Despite this, malaria remains a significant cause of morbidity and mortality; 90% of deaths from malaria occur in Africa. Individuals at the highest risk for malaria are those in disease naïve populations, children under age 5, refugees in Central and Eastern Africa, nonimmune civilian and military travelers, pregnant women, and immigrants traveling to their place of origin.15

Mefloquine, commonly known as Lariam, is an antimalarial drug used for the prevention and treatment of malaria caused by infection with Plasmodium vivax and Plasmodium falciparum. The drug was initially discovered by the Walter Reed Army Institute of Research (WRAIR) during a malaria drug discovery program between 1963 until 1976. It was approved by the FDA in 1989, and was first marketed by Hoffman Laroche.5 This drug has been the subject of widespread controversy due to concerns regarding neurotoxic effects; product information warns of potential serious neuropsychiatric effects.5,13

Accession Number
DBSALT000311
Structure
Synonyms
Mefloquine HCl
UNII
326VC85GV6
CAS Number
51742-86-0
Weight
Average: 414.773
Monoisotopic: 414.093360113
Chemical Formula
C17H17ClF6N2O
InChI Key
WESWYMRNZNDGBX-YLCXCWDSSA-N
InChI
InChI=1S/C17H16F6N2O.ClH/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11;/h3-5,8,12,15,24,26H,1-2,6-7H2;1H/t12-,15+;/m1./s1
IUPAC Name
(S)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2R)-piperidin-2-yl]methanol hydrochloride
SMILES
Cl.[H][C@](O)(C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F)[C@@]1([H])CCCCN1
PubChem Compound
65329
ChemSpider
58813
ChEBI
6719
ChEMBL
CHEMBL1606
Wikipedia
Mefloquine
Predicted Properties
PropertyValueSource
Water Solubility0.038 mg/mLALOGPS
logP3.1ALOGPS
logP4.11Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)13.79Chemaxon
pKa (Strongest Basic)9.46Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area45.15 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity82.58 m3·mol-1Chemaxon
Polarizability32.12 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon