Mefloquine hydrochloride (CHEM019632)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:21:03 UTC
Update Date2016-11-09 01:16:02 UTC
Accession NumberCHEM019632
Identification
Common NameMefloquine hydrochloride
ClassSmall Molecule
DescriptionMefloquine, sold under the brand names Lariam among others, is a medication used to prevent or treat malaria. When used for prevention it is typically started before potential exposure and continued for several weeks after potential exposure. It can be used to treat mild or moderate malaria but is not recommended for severe malaria. It is taken by mouth.Common side effects include vomiting, diarrhea, headaches, and a rash. Serious side effects include potentially long-term mental health problems such as depression, hallucinations, and anxiety and neurological side effects such as poor balance, seizures, and ringing in the ears. It is therefore not recommended in people with a history of mental health problems or epilepsy. It appears to be safe during pregnancy and breastfeeding.Mefloquine was developed by the United States Army in the 1970s and came into use in the mid 1980s. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale price in the developing world is about US$0.6–1.3 per dose. In the United Kingdom it costs the NHS £1.82 per dose. In the United States it costs about $10 a dose.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
MephloquineMeSH
LariamMeSH
MefloquineMeSH
Roche brand OF mefloquine hydrochlorideMeSH
Hoffmann la roche brand OF mefloquine hydrochlorideMeSH
Hoffmann-la roche brand OF mefloquine hydrochlorideMeSH
Chemical FormulaC17H17ClF6N2O
Average Molecular Mass414.773 g/mol
Monoisotopic Mass414.093 g/mol
CAS Registry Number51773-92-3
IUPAC Name(S)-[2,8-bis(trifluoromethyl)quinolin-4-yl](2R)-piperidin-2-ylmethanol hydrochloride
Traditional Name(-)-mefloquine hydrochloride
SMILESCl.[H][C@](O)(C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F)[C@@]1([H])CCCCN1
InChI IdentifierInChI=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
InChI KeyWESWYMRNZNDGBX-YLCXCWDSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 4-quinolinemethanols. These are organoheterocyclic compounds containing a quinoline moiety substituted at the 4-position with a methanol.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub Class4-quinolinemethanols
Direct Parent4-quinolinemethanols
Alternative Parents
Substituents
  • 4-quinolinemethanol
  • Aralkylamine
  • Piperidine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Secondary amine
  • Azacycle
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic nitrogen compound
  • Amine
  • Alkyl halide
  • Aromatic alcohol
  • Alkyl fluoride
  • Hydrochloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.58 m³·mol⁻¹ChemAxon
Polarizability32.12 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-2379000000-c78ceebdc429fe31700eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-825d3620fdf0522f1406Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000900000-825d3620fdf0522f1406Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0000900000-825d3620fdf0522f1406Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-b9a319ec6eb9dd4b2d58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-b9a319ec6eb9dd4b2d58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0000900000-b9a319ec6eb9dd4b2d58Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT000311
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMefloquine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID65329
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available