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M2319

Sigma-Aldrich

Mefloquine hydrochloride

≥98% (HPLC), 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:
Molecular Weight:
414.77
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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.
Blocker of gap junction channels Cx36 and Cx50.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ryutaro Tanizaki et al.
Malaria journal, 12, 128-128 (2013-04-17)
This is the first case of Plasmodium knowlesi infection in a Japanese traveller returning from Malaysia. In September 2012, a previously healthy 35-year-old Japanese man presented to National Center for Global Health and Medicine in Tokyo with a two-day history
Addition of exogenous NAD+ prevents mefloquine-induced neuroaxonal and hair cell degeneration through reduction of caspase-3-mediated apoptosis in cochlear organotypic cultures
Ding D, et al.
Testing, 8(11), e79817-e79817 (2013)
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)
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
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

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