| Identification | More | [Name]
Dequalinium chloride | [CAS]
522-51-0 | [Synonyms]
1,1'-(1,10-DECANEDIYL)BIS(4-AMINO-2-METHYLQUINOLINIUM) DICHLORIDE
1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM CHLORIDE)
1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM) DICHLORIDE
DECA
DEQUALINIUM CHLORIDE
DEQUALINIUM DICHLORIDE
1,1’-decamethylenebis(4-amino-quinaldiniudichloride
1,10-decamethylene-bis(4-aminoquinaldiniumchloride)
baqd10
decamethylenebis(4-aminoquinaldiniumchloride)
decamine(pharmaceutical)
dekadin
dekamin
dequadin
dequadinchloride
dequafungan
dequavagyn
dequavet
efisol
eriosept | [EINECS(EC#)]
208-330-9 | [Molecular Formula]
C30H40Cl2N4 | [MDL Number]
MFCD00063502 | [Molecular Weight]
527.57 | [MOL File]
522-51-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White or yellowish-white powder, hygroscopic. | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
VA0700000
| [F ]
8 |
| Hazard Information | Back Directory | [Description]
MitoBloCK-12 (522-51-0) attenuates mitochondrial protein import (4-10 μM). Discovered in a screen of FDA-approved drugs. Blocks translocation of a mutant form of alanine: glyoxylate aminotransferase (AGT) to the mitochondria and restores AGT trafficking to peroxisomes.1?Also reduces oxalate accumulation and thus has potential to treat patients with primary hyperoxaluria 1 who possess mutations in AGT.1?Also displays antimicrobial activity2, inhibits apamin-sensitive K+?channels3?and induces apoptosis by inhibiting XIAP4. | [Chemical Properties]
White or yellowish-white powder, hygroscopic. | [Originator]
Dequsan,Sante | [Uses]
antiinfectant, antineoplastic | [Uses]
Bacteriostat, antiseptic. | [Uses]
Dequalinium Chloride is a quaternary ammonium cation and the active ingredient in various medications including antiseptic and anti-malarial agents. | [Definition]
ChEBI: An organic chloride salt that is the dichloride salt of 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. | [storage]
Store at -20°C | [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 |
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