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Merck
CN

M2319

Mefloquine hydrochloride

≥98% (HPLC), Cx36 and Cx50 blocker, powder

Synonym(s):

(AS)-rel-a-(2R)-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol monohydrochloride

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About This Item

Empirical Formula (Hill Notation):
C17H17ClF6N2O
CAS Number:
51773-92-3
Molecular Weight:
414.77
NACRES:
NA.77
PubChem Substance ID:
24724536
UNSPSC Code:
12352202
EC Number:
257-412-0
MDL number:
MFCD00797519

Key Documents

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Product Name

Mefloquine hydrochloride, ≥98% (HPLC), powder

InChI

1S/C17H16F6N2O.ClH/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;1H/t12-,15+;/m1./s1

InChI key

WESWYMRNZNDGBX-YLCXCWDSSA-N

SMILES string

Cl[H].[H][C@@]1(CCCCN1)[C@@H](O)c2cc(nc3c(cccc23)C(F)(F)F)C(F)(F)F

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white

solubility

DMSO: soluble 38 mg/mL, H2O: insoluble

Quality Level

100

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Application

Mefloquine hydrochloride has been used:
  • to treat cochlear organotypic cultures with various doses to evaluate its role in cellular pathway involved in apoptosis
  • in screening for in vitro antischistosomal activity
  • in cytotoxicity assay of glioblastoma cells

Biochem/physiol Actions

Blocker of gap junction channels Cx36 and Cx50.
Mefloquine is broadly used as an antimalarial drug. It inhibits 80S ribosomes of Plasmodium. It has numerous side effects like anxiety, dizziness, tremor, headache, and hearing loss. Mefloquine damages cochlear and vestibular hair cells through apoptosis. It also damages spiral ganglion neurons, degenerates cortical neuron and disrupts neuronal calcium homeostasis.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000294579
0000294579
0000196117
0000196117
0000134876

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Mahadeo A Sukhai et al.
The Journal of clinical investigation, 123(1), 315-328 (2012-12-04)
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Identification of plumbagin and sanguinarine as effective chemotherapeutic agents for treatment of schistosomiasis
Zhang SM and Coultas KA
International Journal for Parasitology, Drugs and Drug Resistance, 3(11), 28-34 (2013)
Rithea Leang et al.
Antimicrobial agents and chemotherapy, 57(2), 818-826 (2012-12-05)
We describe here the results of antimalarial therapeutic efficacy studies conducted in Cambodia from 2008 to 2010. A total of 15 studies in four sentinel sites were conducted using dihydroartemisinin-piperaquine (DP) for the treatment of Plasmodium falciparum infection and chloroquine
Matshawandile Tukulula et al.
European journal of medicinal chemistry, 57, 259-267 (2012-10-16)
A series of new arylamino quinoline derivatives was designed based on the quinine and mefloquine scaffolds and evaluated in vitro for antiplasmodial and antimycobacterial activities. A number of these compounds exhibited significant activity against the drug-sensitive 3D7 and drug-resistant K1
Regulation of hypoxia-induced autophagy in glioblastoma involves ATG9A
Rahim SAA, et al.
British Journal of Cancer, 117(6), 813-813 (2017)
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