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Details

Stereochemistry RACEMIC
Molecular Formula C17H16F6N2O
Molecular Weight 378.3122
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEFLOQUINE

SMILES

O[C@H]([C@H]1CCCCN1)C2=C3C=CC=C(C3=NC(=C2)C(F)(F)F)C(F)(F)F

InChI

InChIKey=XEEQGYMUWCZPDN-DOMZBBRYSA-N
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/t12-,15+/m1/s1

HIDE SMILES / InChI

Description

Mefloquine, sold under the brand names Lariam among others, is a medication used to for the treatment of mild to moderate acute malaria caused by Mefloquineuine-susceptible strains of Plasmodium falciparum (both chloroquine-susceptible and resistant strains) or by Plasmodium vivax. Also for the prophylaxis of Plasmodium falciparum and Plasmodium vivax malaria infections, including prophylaxis of chloroquine-resistant strains of Plasmodium falciparum. Mefloquine 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. According to some research, the (+) enantiomer is more effective in treating malaria, and the (-) enantiomer specifically binds to adenosine receptors in the central nervous system, which may explain some of its psychotropic effects.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
46.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MEFLOQUINE HYDROCHLORIDE
PubMed

PubMed

TitleDatePubMed
The effect of artemisinine, its derivatives and mefloquine against chloroquine-resistant strains of Plasmodium falciparum in vitro.
1992 Jul-Aug
Design, synthesis, and pharmacological evaluation of mefloquine-based ligands as novel antituberculosis agents.
2007 Nov
Mefloquine neurotoxicity: a literature review.
2009 Jan
Idiosyncratic quinoline central nervous system toxicity: Historical insights into the chronic neurological sequelae of mefloquine.
2014 Aug
Patents

Sample Use Guides

In Vivo Use Guide
Treatment of mild to moderate malaria in adults caused by mefloquine-susceptible strains of P. falciparum or by P. vivax: Dosage: Five tablets (1250 mg) mefloquine hydrochloride to be given as a single oral dose. The drug should not be taken on an empty stomach and should be administered with at least 8 oz (240 mL) of water. The recommended prophylactic dose of mefloquine is approximately 5 mg/kg body weight once weekly. One 250 mg mefloquine hydrochloride tablet should be taken once weekly in pediatric patients weighing over 45 kg.
Route of Administration: Oral
In Vitro Use Guide
Mefloquine inhibited chloroquine-resistant strains of Plasmodium falciparum in vitro. The EC50 values for mefloquine were 46-185 nM. At higher concentrations, strains K1 and LS21 were fully inhibited, while with strain T996 mefloquine did not fully inhibit even at the highest concentration, 1.28 x 10(-6) M.
Name Type Language
MEFLOQUINE
HSDB   INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
MEFLOQUINE [INN]
Common Name English
(DL-ERYTHRO-.ALPHA.-2-PIPERIDYL-2,8-BIS(TRIFLUOROMETHYL)-4-QUINOLINEMETHANOL
Common Name English
MEFLOQUINE [MI]
Common Name English
RO-215998
Code English
WR 142,490
Code English
MEFLOQUINE [WHO-DD]
Common Name English
MEFLOQUINE [USAN]
Common Name English
4-QUINOLINEMETHANOL, .ALPHA.-2-PIPERIDINYL-2,8-BIS(TRIFLUOROMETHYL)-, (R*,S*)-(+/-)-
Common Name English
MEFLOQUINE [VANDF]
Common Name English
RO 21-5998
Code English
MEFLOQUINE [HSDB]
Common Name English
Classification Tree Code System Code
WHO-ATC P01BC02
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
WHO-ATC P01BF02
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
NDF-RT N0000175482
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 6.5.3.2
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
LIVERTOX 592
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
Code System Code Type Description
WIKIPEDIA
MEFLOQUINE
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY
MESH
D015767
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY
DRUG BANK
DB00358
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY
EPA CompTox
53230-10-7
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY
ChEMBL
CHEMBL416956
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY
RXCUI
6694
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY RxNorm
CAS
53230-10-7
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY
IUPHAR
4252
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY
NCI_THESAURUS
C61827
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY
EVMPD
SUB08709MIG
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY
PUBCHEM
40692
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY SWITZERF
HSDB
53230-10-7
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY
MERCK INDEX
M7142
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY Merck Index
INN
3777
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY
LactMed
53230-10-7
Created by admin on Tue Mar 06 11:20:13 UTC 2018 , Edited by admin on Tue Mar 06 11:20:13 UTC 2018
PRIMARY