Dechaliniumchlorid

Bezeichnung:Dechaliniumchlorid

CAS-Nr522-51-0

Englisch Name:Dequalinium chloride

CBNumberCB3193093

SummenformelC30H40Cl2N4

Molgewicht527.57

MOL-Datei522-51-0.mol

Synonyma

Dechaliniumchlorid

Dechaliniumchlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	≥300 °C(lit.)
storage temp.	2-8°C
Löslichkeit	Slightly soluble in water and in ethanol (96 per cent).
Aggregatzustand	Solid
Farbe	Beige
Merck	13,2930
Stabilität	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 Datenbank	522-51-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36-37/39
WGK Germany	3
RTECS-Nr.	VA0700000
F	8

Gefahreninformationscode (GHS)

Dequalinium chloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
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).
Chemische Eigenschaften
White or yellowish-white powder, hygroscopic.
Originator
Dequsan,Sante
Verwenden
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.
Trademarks
Decabis;Dequacaine;Dequafungan;Dequin;Faringina;Gargilon;Grocreme;Labosept;Maltyl;Phylletten;Soor-gel;Sorot;Tetesept.
Therapeutic Function
Antiseptic, Antifungal
Weltgesundheitsorganisation (WHO)
Skin reactions to dequalinium chloride, including necrotic lesions, have been reported. It remains available as a mouth and throat disinfectant in many countries.
Allgemeine Beschreibung
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.
Biologische Aktivität
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.
Einzelnachweise
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 Upstream-Materialien And Downstream Produkte

Dechaliniumchlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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