Human Metabolome Database Version 3.5

Showing metabocard for Mefloquine (HMDB14502)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:49 -0600
Update Date 2013-02-08 17:31:43 -0700
HMDB ID HMDB14502
Secondary Accession Numbers None
Metabolite Identification
Common Name Mefloquine
Description Mefloquine is only found in individuals that have used or taken this drug. It is a phospholipid-interacting antimalarial drug (antimalarials). It is very effective against plasmodium falciparum with very few side effects. [PubChem]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.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Mefloquinone
Chemical Formula C17H16F6N2O
Average Molecular Weight 378.3122
Monoisotopic Molecular Weight 378.116682374
IUPAC Name [2,8-bis(trifluoromethyl)quinolin-4-yl](piperidin-2-yl)methanol
Traditional IUPAC Name mefloquine
CAS Registry Number 53230-10-7
SMILES OC(C1CCCCN1)C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F
InChI Identifier InChI=1S/C17H16F6N2O/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
InChI Key XEEQGYMUWCZPDN-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Quinolines and Derivatives
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • organofluorine compound(ChEBI)
  • piperidines(ChEBI)
  • quinolines(ChEBI)
  • secondary alcohol(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • Organic Halide
  • Organofluoride
  • Piperidine
  • Pyridine
  • Secondary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct Parent Quinolines and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Antimalarials
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility 3.80e-02 g/L Not Available
LogP 3.9 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.038 g/L ALOGPS
LogP 3.10 ALOGPS
LogP 4.11 ChemAxon
LogS -4.00 ALOGPS
pKa (strongest acidic) 13.79 ChemAxon
pKa (strongest basic) 9.46 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 45.15 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 82.58 ChemAxon
Polarizability 31.73 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00358
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00358
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00358 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 3906 Link_out
KEGG Compound ID C07633 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Mefloquine Link_out
NuGOwiki Link HMDB14502 Link_out
Metagene Link HMDB14502 Link_out
METLIN ID Not Available
PubChem Compound 4046 Link_out
PDB ID Not Available
ChEBI ID 63681 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Acetylcholinesterase
Reactions: Not Available
Gene Name: ACHE
Uniprot ID: P22303 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cholinesterase
Reactions: Not Available
Gene Name: BCHE
Uniprot ID: P06276 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 19A1
Reactions: Not Available
Gene Name: CYP19A1
Uniprot ID: P11511 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hemoglobin subunit alpha
Reactions: Not Available
Gene Name: HBA1
Uniprot ID: P69905 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenosine receptor A2a
Reactions: Not Available
Gene Name: ADORA2A
Uniprot ID: P29274 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Multidrug resistance protein 1
Reactions: Not Available
Gene Name: ABCB1
Uniprot ID: P08183 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA