General
Preferred name
MEFLOQUINE
Synonyms
MEFLOQUINE HYDROCHLORIDE ()
Mefloquine?HCl ()
WR-142490 ()
NSC-157387 ()
Mefloquine HCl ()
Fansimef ()
RO-215998001 ()
RO-21-5998 ()
Lariam ()
Mefloquini hydrochloridum ()
RO 21-5998/001 ()
Loriam ()
GNF-Pf-5544 ()
NSC-758233 ()
Mefaquin ()
Ro-215998 ()
WR 142,490 ()
RO 21-5998 ()
P&D ID
PD010082
CAS
53230-10-7
49752-90-1
51773-92-3
Tags
natural product
drug
available
Drug Status
investigational
approved
Drug indication
Antimalarial
Malaria
Max Phase
Phase 4
First approval
1989
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION
Mefloquine belongs to the aryl amino alcohols, a chemical class of antimalarial drugs that includes , and .
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. (GtoPdb)
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. (GtoPdb)
PHARMACODYNAMICS
Mefloquine is an antimalarial agent which acts as a blood schizonticide. Mefloquine is active against the erythrocytic stages of Plasmodium species. However, the drug has no effect against the exoerythrocytic (hepatic) stages of the parasite. Mefloquine is effective against malaria parasites resistant to chloroquine. Mefloquine is a chiral molecule. It is reported that while the (+) enantiomer primarily mediates an antimalarial activity, the (-) enantiomer contribute to the psychotrophic effects by specifically binding to adenosine receptors in the central nervous system.
DESCRIPTION
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.
Mefloquine is one of the key antimalarials listed in the WHO 20th Essential Medicines List (2017).
The administerd form contains the mefloquine hydrochloride salt.
Mefloquine is one of the key antimalarials listed in the WHO 20th Essential Medicines List (2017).
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
6
Organisms
9
Compound Sets
16
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
DrugBank
DrugBank Approved Drugs
DrugMAP
DrugMAP Approved Drugs
DrugMatrix
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
Prestwick Chemical Library
ReFrame library
The Spectrum Collection
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
48
Molecular Weight
378.12
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
2
Rotatable Bonds
2
Ring Count
3
Aromatic Ring Count
2
cLogP
4.45
TPSA
45.15
Fraction CSP3
0.47
Chiral centers
2.0
Largest ring
6.0
QED
0.76
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
MOA
Unknown molecular target
Target
Ferriprotoporphyrin IX
Therapeutic Class
Antimalarials
Source data
