mefloquine

Also known as WR-142490, GNF-Pf-5544, alpha-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol, [(R*,S*)-2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol, Ro-215998, Lariam, Mefloquin, Mefloquina

Mefloquine, sold under the brand name Lariam among others, is a medication used to prevent or treat malaria. When used for prevention it is typically started before potential exposure and continued for several weeks after potential exposure. It can be used to treat mild or moderate malaria but is not recommended for severe malaria. It is taken by mouth.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 458774403
Drug.image: Mefloquine chemical structure.svg
Drug.image_class: skin-invert-image
Drug.width: 185px
Drug.tradename: Lariam, Mephaquin, Mefliam, others
Drug.MedlinePlus: a603030
Drug.DailyMedID: Mefloquine
Drug.pregnancy_AU: B3
Drug.routes_of_administration: Oral
Drug.class: Antimalarial
Drug.ATC_prefix: P01
Drug.ATC_suffix: BC02
Drug.legal_AU: S4
Drug.legal_CA: Rx-only
Drug.legal_UK: POM
Drug.legal_US: Rx-only

via Wikipedia infobox

Chemical data

Formula: C17H16F6N2O
Molecular weight: 378.31 g/mol
IUPAC name: [2,8-bis(trifluoromethyl)quinolin-4-yl]-piperidin-2-ylmethanol
SMILES: C1CCNC(C1)C(C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O
InChIKey: XEEQGYMUWCZPDN-UHFFFAOYSA-N
XLogP: 3.6
Polar surface area: 45.2 Å²
H-bond donors: 2
H-bond acceptors: 9
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1989
Admin. routes: oral
Indications: malaria, Plasmodium falciparum malaria, progressive multifocal leukoencephalopathy, urinary schistosomiasis

via ChEMBL · EBI

Research

3,628 papers

Mefloquine as a prophylaxis for malaria needs to be revisited.International journal for parasitology. Drugs and drug resistance · 2021
Cellular targets of mefloquine.Toxicology · 2021
Review of the mechanism underlying mefloquine-induced neurotoxicity.Critical reviews in toxicology · 2021
Mefloquine.BMJ (Clinical research ed.) · 1994
Mefloquine for malaria prophylaxis in military personnel.BMJ military health · 2020

via PubMed

Wikidata facts

Subclass of: heterocyclic compound
Mass: 378.116682
Has use: medication

Show 8 more facts

Commons category: Mefloquine
chemical formula: C₁₇H₁₆F₆N₂O
significant drug interaction: droperidol
World Health Organisation international non-proprietary name: mefloquine
medical condition treated: malaria
canonical SMILES: C1CCNC(C1)C(C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O
defined daily dose: 1
subject has role: malaria prophylaxis

Sources (6)

via Wikidata · CC0

~15 min read

Encyclopedic overview

20 sections

Contents

Medical uses
Malaria prevention
Malaria treatment
Resistance to mefloquine
Contraindications
Pregnancy and breastfeeding
Adverse effects
Neurologic and psychiatric
Cardiac
Pharmacology
Pharmacodynamics
Off-target activities
Pharmacokinetics
Chemistry
History
Military
Research
References
Further reading
External links

Common side effects include vomiting, diarrhea, headaches, sleep disorders, and a rash. Serious side effects include potentially long-term mental health problems such as depression, hallucinations, and anxiety and neurological side effects such as poor balance, seizures, and ringing in the ears. It is therefore not recommended in people with a history of mental health problems or epilepsy. It appears to be safe during pregnancy and breastfeeding.

Excerpted from Wikipedia’s “mefloquine” article, available under the CC BY-SA 4.0 licence.