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Details

Stereochemistry RACEMIC
Molecular Formula C17H16F6N2O.CH4O3S
Molecular Weight 474.418
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEFLOQUINE MESYLATE

SMILES

CS(O)(=O)=O.O[C@H]([C@H]1CCCCN1)C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F

InChI

InChIKey=GFKKBAFIZVIFAZ-YLCXCWDSSA-N
InChI=1S/C17H16F6N2O.CH4O3S/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;1-5(2,3)4/h3-5,8,12,15,24,26H,1-2,6-7H2;1H3,(H,2,3,4)/t12-,15+;/m1./s1

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H16F6N2O
Molecular Weight 378.3122
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
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.
Substance Class Chemical
Created
by admin
on Tue Oct 22 13:54:58 UTC 2019
Edited
by admin
on Tue Oct 22 13:54:58 UTC 2019
Record UNII
642Y4F6L0K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEFLOQUINE MESYLATE
Common Name English
4-QUINOLINEMETHANOL, .ALPHA.-(2R)-2-PIPERIDINYL-2,8-BIS(TRIFLUOROMETHYL)-, (.ALPHA.S)-REL-, METHANESULFONATE (1:1)
Common Name English
MEFLOQUINE METHANESULFONATE
Common Name English
4-QUINOLINEMETHANOL, .ALPHA.-2-PIPERIDINYL-2,8-BIS(TRIFLUOROMETHYL)-, (R*,S*)-(+/-)-, MONOMETHANESULFONATE (SALT)
Common Name English
Code System Code Type Description
EPA CompTox
64003-26-5
Created by admin on Tue Oct 22 13:54:58 UTC 2019 , Edited by admin on Tue Oct 22 13:54:58 UTC 2019
PRIMARY
PUBCHEM
71587223
Created by admin on Tue Oct 22 13:54:58 UTC 2019 , Edited by admin on Tue Oct 22 13:54:58 UTC 2019
PRIMARY
CAS
64003-26-5
Created by admin on Tue Oct 22 13:54:58 UTC 2019 , Edited by admin on Tue Oct 22 13:54:58 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY