mefloquine

Ligand id: 4252

Name: mefloquine

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1989), UK (1989))
IUPAC Name
[2,8-bis(trifluoromethyl)quinolin-4-yl]-piperidin-2-ylmethanol
International Nonproprietary Names
INN number INN
3777 mefloquine
Synonyms
GNF-Pf-5544 | Lariam® | Ro-21-5998-001 | WR-142490
Comments
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 [7]. 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.
Database Links
CAS Registry No. 53230-10-7 (source: Scifinder)
ChEMBL Ligand CHEMBL416956
DrugBank Ligand DB00358
GtoPdb PubChem SID 178101069
PubChem CID 4046
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
Search UniChem for chemical match using the InChIKey XEEQGYMUWCZPDN-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone XEEQGYMUWCZPDN
Wikipedia Mefloquine