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
- External Links
- PubChem Compound
- 65329
- ChemSpider
- 58813
- ChEBI
- 6719
- ChEMBL
- CHEMBL1606
- Wikipedia
- Mefloquine
- Predicted Properties
Property Value Source Water Solubility 0.038 mg/mL ALOGPS logP 3.1 ALOGPS logP 4.11 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 13.79 Chemaxon pKa (Strongest Basic) 9.46 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 45.15 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 82.58 m3·mol-1 Chemaxon Polarizability 32.12 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon