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 

Solid

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

VA0700000

F 

8

MSDS

• Language:English Provider:Dequalinium chloride
• Language:English Provider:SigmaAldrich

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

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