522-51-0 Usage
Description
Dequalinium chloride, also known by its brand names Decabis, Dequacaine, Dequafungan, Dequin, Faringina, Gargilon, Grocreme, Labosept, Maltyl, Phylletten, Soor-gel, Sorot, and Tetesept, is an organic chloride salt that is the dichloride salt of dequalinium. It is a quaternary ammonium cation and has been discovered in a screen of FDA-approved drugs. Dequalinium chloride attenuates mitochondrial protein import and has potential applications in various fields due to its antimicrobial, anti-infectant, and antineoplastic properties.
Uses
1. Used in Pharmaceutical Industry:
Dequalinium chloride is used as an active ingredient in various medications for its antimicrobial and antiseptic properties. It is particularly effective in treating bacterial infections and acts as a bacteriostat.
2. Used in Anticancer Applications:
Dequalinium chloride is used as an antineoplastic agent, demonstrating potential in the treatment of cancer. It modulates several oncological signaling pathways and has shown to induce apoptosis by inhibiting XIAP.
3. Used in Antimicrobial Applications:
Dequalinium chloride is used as an anti-infectant due to its antimicrobial activity. It is effective in reducing the growth and spread of various microorganisms, making it a valuable component in the development of new medications and treatments.
4. Used in Mitochondrial Protein Import Inhibition:
Dequalinium chloride is used to attenuate mitochondrial protein import, which has potential applications in the treatment of patients with primary hyperoxaluria who possess mutations in AGT. By blocking the translocation of a mutant form of alanine: glyoxylate aminotransferase (AGT) to the mitochondria, it restores AGT trafficking to peroxisomes and reduces oxalate accumulation.
5. Used in Inhibition of Apamin-sensitive K+ Channels:
Dequalinium chloride is used to inhibit apamin-sensitive K+ channels, which can have potential applications in the treatment of various conditions related to ion channel dysfunction.
Originator
Dequsan,Sante
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.
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 522-51-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 2 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 522-51:
(5*5)+(4*2)+(3*2)+(2*5)+(1*1)=50
50 % 10 = 0
So 522-51-0 is a valid CAS Registry Number.
InChI:InChI=1/C30H38N4.2ClH/c1-23-21-27(31)25-15-9-11-17-29(25)33(23)19-13-7-5-3-4-6-8-14-20-34-24(2)22-28(32)26-16-10-12-18-30(26)34;;/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3;2*1H
522-51-0Relevant articles and documents
Preparation method of dequalinium chloride
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, (2020/05/01)
The invention relates to a preparation method of dequalinium chloride. The method comprises the following steps: reacting 2-methyl-4-chloroquinoline, used as a starting material, with p-methoxybenzylamine to obtain an amination intermediate II, carrying out a debenzylation reaction on the intermediate to obtain 2-methyl-4-aminoquinaldine, then reacting the 2-methyl-4-aminoquinaldine with 1,10-diiododecane to obtain dequalinium iodide, continuously reacting the dequalinium iodide with hydrochloric acid to obtain dequalinium chloride, and finally recrystallizing with a mixed solvent to obtain refined dequalinium chloride. The preparation method of the dequalinium chloride does not adopt a highly toxic solvent nitrobenzene, and adopts a nontoxic or low-toxicity solvent, and the reaction temperature is reduced in the reaction process, so the method is environmentally friendly, and the reaction conditions are simple; and the refined dequalinium chloride product is prepared through recrystallization using the mixed solvent, so impurities in the dequalinium chloride process are controllable, the yield and purity of the prepared dequalinium chloride are high, the product quality is stable,and the method is suitable for industrial production.
Preparation method of dequalinium chloride and its analogues
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Paragraph 0063; 0092-0097, (2017/07/20)
The invention provides a preparation method of dequalinium chloride and its analogues and concretely relates to a preparation method of a compound shown in the formula I. The preparation method comprises (1) adding a compound shown in the formula II into a solution containing Cl and water so that the materials undergo a reaction, and (2) adding an oxidizing agent into the product of the step (1) so that the mixture undergoes a reaction, wherein R and R1 are independently selected from H atoms and C1-C6 alkyl and n is 4-20. The preparation method has a high yield.