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Molecular properties generated using the CDK
|Compound class||Synthetic organic|
|Ligand families/groups||Antimalarial ligands|
|Approved drug?||Yes (FDA (1989), UK (1989))|
|WHO Essential Medicine||WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.|
|International Nonproprietary Names|
|GNF-Pf-5544 | Lariam® | Ro-21-5998-001 | WR-142490|
|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 . 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) . 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.
|CAS Registry No.||53230-10-7 (source: Scifinder)|
|GtoPdb PubChem SID||178101069|
|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|
|Search UniChem for chemical match using the InChIKey||XEEQGYMUWCZPDN-UHFFFAOYSA-N|
|Search UniChem for chemicals with the same backbone||XEEQGYMUWCZPDN|