mefloquine   Click here for help

GtoPdb Ligand ID: 4252

Synonyms: GNF-Pf-5544 | Lariam® | Ro-21-5998-001 | WR-142490
Approved drug PDB Ligand Antimalarial Ligand
mefloquine is an approved drug (FDA (1989), UK (1989))
Compound class: Synthetic organic
Comment: Mefloquine belongs to the aryl amino alcohols, a chemical class of antimalarial drugs that includes quinine, lumefantrine and halofantrine.
The approved drug is a racemic mixture of (R,S)- and (S,R)-enantiomers. We show the chemical structure without stereochemistry to represent the mixture and the non-isomeric structure is also represented in the PubChem and ChEMBL entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 40692 and PubChem CID 456309. PubChem lists 9 stereoisotopes.
The administerd form contains the mefloquine hydrochloride salt.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.

Activity at non-malarial protein targets:
Racemic mefloquine has been identified as an antagonist of the human adenosine A2A and A1 receptors, with nanomolar binding affinities [8]. The (11R,2'S) isomer of mefloquine (PubChem CID 456309) has been determined as the most potent A2A binder, with a Ki of 61 nM (Ki vs. A1 receptor is 255 nM) [4]. It has been suggested that off-target activity at human adenosine receptors may contribute towards the adverse neuropsychiatric side-effects that are associated with mefloquine use.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 45.15
Molecular weight 378.12
XLogP 3.87
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC(c1cc(nc2c1cccc2C(F)(F)F)C(F)(F)F)C1CCCCN1
Isomeric SMILES OC(c1cc(nc2c1cccc2C(F)(F)F)C(F)(F)F)C1CCCCN1
InChI 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
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1989), UK (1989))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
[2,8-bis(trifluoromethyl)quinolin-4-yl]-piperidin-2-ylmethanol
International Nonproprietary Names Click here for help
INN number INN
3777 mefloquine
Synonyms Click here for help
GNF-Pf-5544 | Lariam® | Ro-21-5998-001 | WR-142490
Database Links Click here for help
Specialist databases
GPCRdb Ligand mefloquine
Reactome Drug Reactome logo R-ALL-9695406
Reactome Reaction Reactome logo R-HSA-9695415
Other databases
CAS Registry No. 53230-10-7 (source: Scifinder)
ChEMBL Ligand CHEMBL416956
DrugBank Ligand DB00358
GtoPdb PubChem SID 178101069
PubChem CID 4046
RCSB PDB Ligand YMZ
Search Google for chemical match using the InChIKey XEEQGYMUWCZPDN-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XEEQGYMUWCZPDN
Search PubMed clinical trials mefloquine
Search PubMed titles mefloquine
Search PubMed titles/abstracts mefloquine
UniChem Compound Search for chemical match using the InChIKey XEEQGYMUWCZPDN-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XEEQGYMUWCZPDN-UHFFFAOYSA-N
Wikipedia Mefloquine