Dequalinium chloride

Dequalinium chloride Basic information
Product Name:Dequalinium chloride
Synonyms:1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM CHLORIDE);1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM) DICHLORIDE;1,1'-(1,10-DECANEDIYL)BIS(4-AMINO-2-METHYLQUINOLINIUM) DICHLORIDE;DEQUALINIUM CHLORIDE;DEQUALINIUM DICHLORIDE;DECA;dequadinchloride;dequafungan
CAS:522-51-0
MF:C30H40Cl2N4
MW:527.57
EINECS:208-330-9
Product Categories:FLUOMIZIN;Potassium channel;522-51-0
Mol File:522-51-0.mol
Dequalinium chloride Structure
Dequalinium chloride Chemical Properties
Melting point ≥300 °C(lit.)
storage temp. 2-8°C
solubility Slightly soluble in water and in ethanol (96 per cent).
form neat
color Beige
Merck 13,2930
Stability:Stable for 2 years as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 3 months.
InChIKeyLTNZEXKYNRNOGT-UHFFFAOYSA-N
CAS DataBase Reference522-51-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37/39
WGK Germany 3
RTECS VA0700000
8
MSDS Information
ProviderLanguage
Dequalinium chloride English
SigmaAldrich English
Dequalinium chloride Usage And Synthesis
DescriptionDequalinium Chloride is a a potent and selective non-peptide blocker of the apamin-sensitive small conductance Ca2+-activated K+ channel (IC50 = 1.1 mM).
Chemical PropertiesWhite or yellowish-white powder, hygroscopic.
OriginatorDequsan,Sante
UsesDequalinium Chloride is a quaternary ammonium cation and the active ingredient in various medications including antiseptic and anti-malarial agents.
DefinitionChEBI: Dequalinium chloride is an organic chloride salt that is the dichloride salt of dequalinium. It has a role as an antiseptic drug, a mitochondrial NADH:ubiquinone reductase inhibitor, an antifungal agent and an antineoplastic agent. It contains a dequalinium.
Manufacturing Processa) 15 g of 4-aminoquinaldine, 15 g of decamethylene diiodide and 200 ml of methyl ethyl ketone were refluxed together for 400 hours. The mixture was allowed to cool, the precipitate filtered off, washed with methyl ethyl ketone, and 1,1'-decamethylenebis(4-aminoquinaldinium chloride) recrystallized from ethyl alcohol containing a little methyl alcohol.
b) 160 g of 4-aminoquinaldine, 174 g of decamethylene diiodide and 1,500 ml of methyl isobutyl carbinol were heated together at 120°C for 90 hours. The mixture was allowed to cool, the precipitate filtered off, washed with methyl ethyl ketone and 1,1'-decamethylenebis(4-aminoquinaldinium chloride) recrystallized from ethyl alcohol containing a little methyl alcohol.
b) 160 g of 4-aminoquinaldine, 174 g of decamethylene diiodide and 1,500 ml of methyl isobutyl carbinol were heated together at 120°C for 90 hours. The mixture was allowed to cool, the precipitate filtered off, washed with methyl ethyl ketone and 1,1'-decamethylenebis(4-aminoquinaldinium chloride) recrystallized from ethyl alcohol containing a little methyl alcohol.

Brand nameDecabis;Dequacaine;Dequafungan;Dequin;Faringina;Gargilon;Grocreme;Labosept;Maltyl;Phylletten;Soor-gel;Sorot;Tetesept.
Therapeutic FunctionAntiseptic, Antifungal
World Health Organization (WHO)Skin reactions to dequalinium chloride, including necrotic lesions, have been reported. It remains available as a mouth and throat disinfectant in many countries.
General DescriptionDequalinium Chloride is a topical bacteriostat that is available as various salts. It is used in wound dressings and mouth infections and may also have antifungal action, but may cause skin ulceration.
Biological ActivityDequalinium is a quaternary ammonium cation with diverse biological activities. It has antifungal activity against C. albicans, C. glabrata, and C. krusei (MICs = 0.5-2, 64-256, and 128 μg/ml, respectively), antitrichomonal activity against T. vaginalis (MICs = 28.8-230.4 μg/ml), and antibacterial activity against a panel of aerobic and facultative anaerobic bacteria (MICs = 0.25-256 μg/ml). Dequalinium inhibits apamin binding to, and net potassium loss mediated by, SKCa channels in guinea pig hepatocytes stimulated by angiotensin II (Item No. 17150). In vivo, dequalinium (1-10 mg/kg) inhibits primary and recurrent tumor growth in a W163 rat colon carcinoma isograft model.
References1) Miyata?et al.?(2014),?Pharmacologic rescue of an enzyme-trafficking defect in primary hyperoxaluria 1; Proc. Natl. Acad. Sci. USA?111?14406
2) Frey Tirri?et al.?(2011),?Antimicrobial topical agents used in the vagina; Curr. Probl. Dermatol.?40?36
3) Castle?et al.?(1993),?Dequalinium: a potent inhibitor of apamin-sensitive K+ channels in hepatocytes and of nicotinic responses in skeletal muscle; Eur. J. Pharmacol.?236?201
4) Orzaez?et al.?(2011),?Characterization of dequalinium as a XIAP antagonist that targets the BIR2 domain; Apoptosis?16?460
Dequalinium chloride Preparation Products And Raw materials
Raw materials1,10-DIIODODECANE-->4-AMINO-2-METHYLQUINOLINE
Methylene Chloride Cetylpyridinium chloride Methyl Bensulfuron methyl Calcium chloride Sodium chloride Ferric chloride Choline chloride Kresoxim-methyl Trospium chloride Sulfuryl chloride Ammonium chloride Cobalt chloride Polyvinyl chloride Methyl acrylate Potassium chloride Methyl bromide 2-​[[(2-​ethylphenyl)​(2-​hydroxyethyl)​amino]​methyl]​-​3,​3-​difluoro-Propanenitrile

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