Mefloquine

Mefloquine
Clinical data
Trade namesLariam, Mephaquin, Mefliam, others
AHFS/Drugs.comMonograph
MedlinePlusa603030
License data
Pregnancy
category
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismExtensive liver; main metabolite is inactive
Elimination half-life2 to 4 weeks
ExcretionPrimarily bile and feces; urine (9% as unchanged drug, 4% as primary metabolite)
Identifiers
  • [(R*,S*)-2,8-Bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H16F6N2O
Molar mass378.318 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • FC(F)(F)c2cccc1c(cc(nc12)C(F)(F)F)[C@H](O)[C@@H]3NCCCC3
  • 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 checkY
  • Key:XEEQGYMUWCZPDN-DOMZBBRYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Mefloquine, sold under the brand name Lariam among others, is a medication used to prevent or treat malaria.[4] When used for prevention it is typically started before potential exposure and continued for several weeks after potential exposure.[4] It can be used to treat mild or moderate malaria but is not recommended for severe malaria.[4] It is taken by mouth.[4]

Common side effects include vomiting, diarrhea, headaches, sleep disorders, and a rash.[4] 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.[4] It is therefore not recommended in people with a history of mental health problems or epilepsy.[4] It appears to be safe during pregnancy and breastfeeding.[1]

Mefloquine was developed by the United States Army in the 1970s and came into use in the mid-1980s.[5][6][7] It is on the World Health Organization's List of Essential Medicines.[8][9] It is available as a generic medication.[4]

  1. ^ a b "Mefloquine (Lariam) Use During Pregnancy". Drugs.com. Retrieved 31 March 2019.
  2. ^ "Lariam 250 mg tablets - Summary of Product Characteristics (SmPC)". (emc). 3 April 2019. Retrieved 8 September 2020.
  3. ^ "Lariam brand of mefloquine hydrochloride tablets". DailyMed. Retrieved 9 October 2022.
  4. ^ a b c d e f g h "Mefloquine Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 2015-12-08. Retrieved 27 Nov 2015.
  5. ^ Croft AM (April 2007). "A lesson learnt: the rise and fall of Lariam and Halfan". Journal of the Royal Society of Medicine. 100 (4): 170–174. doi:10.1177/014107680710011411. PMC 1847738. PMID 17404338.
  6. ^ Ravina E (2011). The evolution of drug discovery : from traditional medicines to modern drugs (1. Aufl. ed.). Weinheim: Wiley-VCH. p. 136. ISBN 9783527326693.
  7. ^ Farrar J, Hotez PJ, Junghanss T (2013). Manson's tropical diseases (23rd ed.). Oxford: Elsevier/Saunders. p. 569. ISBN 9780702053061.
  8. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  9. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.