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Dequalinium

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Dequalinium chloride
Names
IUPAC name
1,1'-decane-1,10-diylbis(4-amino-2-methylquinolinium) decyl]-2-methyl-4-quinolin-1-iumamine dichloride
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.575 Edit this at Wikidata
MeSH Dequalinium
UNII
  • InChI=1S/C30H38N4/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/p+2 checkY
    Key: PCSWXVJAIHCTMO-UHFFFAOYSA-P checkY
  • InChI=1/C30H38N4/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/p+2
    Key: PCSWXVJAIHCTMO-SKRXCDHZAO
  • c12ccccc1c(cc([n+]2CCCCCCCCCC[n+]4c3ccccc3c(N)cc4C)C)N
Properties
C30H40Cl2N4
Molar mass 527.58 g·mol−1
Pharmacology
D08AH01 (WHO) G01AC05 (WHO), R02AA02 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Dequalinium is a quaternary ammonium cation commonly available as the dichloride salt. The bromide, iodide, acetate, and undecenoate salts are known as well. Dequalinium chloride is the active ingredient of several medications:

Dequadin an antiseptic and disinfectant. It is a topical bacteriostat. It is used in wound dressings and mouth infections and may also have antifungal action. It may cause skin ulceration.

Fluomizin, vaginal tablets containing 10 mg dequalinium chloride, are used for treating vaginal bacterial conditions (i.e. Bacterial Vaginosis and aerobic vaginitis).

The dequalinium dication is symmetrical, containing two quaternary quinolinium units linked by an N-decylene chain.

Applications

Dequalinium salts may be used to treat malaria.[1] As dequalinium chloride, it can be used in lozenges to cure sore throats however while this is effective in vitro, it is not effective in cases of streptococci infections [2]

References

  1. ^ "US Patent 4946849". United States Patents and Trademarks Office (USPTO). 10 October 1989. Retrieved 2008-03-15.
  2. ^ Krämer W. (1977). "[Treatment of tonsilitis with dequalinium chloride]". Fortschr. Med. (in German). 95 (16): 1108–10. PMID 856702.

Further reading

  • Gamboa-Vujicic, Gisela; Emma, Dennis A.; Liao, Shu Y.; Fuchtner, Carlos; Manetta, Alberto (1993). "Toxicity of the mitochondrial poison dequalinium chloride in a murine model system". Journal of Pharmaceutical Sciences. 82 (3): 231–5. doi:10.1002/jps.2600820302. PMID 8450414.


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