mefloquine   

GtoPdb Ligand ID: 4252

Synonyms: GNF-Pf-5544 | Lariam® | Ro-21-5998-001 | WR-142490
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.
2D Structure
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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
SMILES / InChI / InChIKey
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
Download 2D Structure
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Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel