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M2319

Sigma-Aldrich

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
EC Number:
257-412-0
MDL number:
MFCD00797519
UNSPSC Code:
12352202
PubChem Substance ID:
24724536
NACRES:
NA.77

Key Documents

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Product Name

Mefloquine hydrochloride, ≥98% (HPLC), powder

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white

solubility

DMSO: soluble 38 mg/mL
H2O: insoluble

SMILES string

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

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

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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_germany

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
105M4760V
124M4705V
023M4704V
111M4707V
011M4714V

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Chanaki Amaratunga et al.
The Lancet. Infectious diseases, 12(11), 851-858 (2012-09-04)
Artemisinin-resistant Plasmodium falciparum has been reported in Pailin, western Cambodia, detected as a slow parasite clearance rate in vivo. Emergence of this phenotype in western Thailand and possibly elsewhere threatens to compromise the effectiveness of all artemisinin-based combination therapies. Parasite
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)
Sophie Zaloumis et al.
Malaria journal, 11, 303-303 (2012-08-31)
Mechanistic within-host models relating blood anti-malarial drug concentrations with the parasite-time profile help in assessing dosing schedules and partner drugs for new anti-malarial treatments. A comprehensive simulation study to assess the utility of a stage-specific pharmacokinetic-pharmacodynamic (PK-PD) model for predicting
The Plasmodium falciparum cytoplasmic translation apparatus: a promising therapeutic target not yet exploited by clinically approved anti-malarials
Sheridan CM, et al.
Malaria Journal, 17(1), 465-465 (2018)
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