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| | 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 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. | | InChIKey | LTNZEXKYNRNOGT-UHFFFAOYSA-N | | CAS DataBase Reference | 522-51-0(CAS DataBase Reference) |
| | Dequalinium chloride Usage And Synthesis |
| Description | Dequalinium 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 Properties | White or yellowish-white powder, hygroscopic. | | Originator | Dequsan,Sante | | Uses | Dequalinium Chloride is a quaternary ammonium cation and the active ingredient in various medications including antiseptic and anti-malarial agents. | | Definition | ChEBI: 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 Process | a) 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 name | Decabis;Dequacaine;Dequafungan;Dequin;Faringina;Gargilon;Grocreme;Labosept;Maltyl;Phylletten;Soor-gel;Sorot;Tetesept. | | Therapeutic Function | Antiseptic, 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 Description | Dequalinium 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 Activity | Dequalinium 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. | | References | 1) 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 |
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