Dequalinium

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Dequalinium
Clinical data
Trade namesDequadin, Fluomizin, Vablys, Naxyl, others
Routes of
administration		By mouth, intravaginal
ATC code
Legal status
Legal status
Identifiers
  • 1,1'-decane-1,10-diylbis(4-amino-2-methylquinolinium) decyl]-2-methyl-4-quinolin-1-iumamine dichloride
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC30H40N4
Molar mass456.678 g·mol−1
3D model (JSmol)
  • c12ccccc1c(cc([n+]2CCCCCCCCCC[n+]4c3ccccc3c(N)cc4C)C)N
  • 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
  • Key:PCSWXVJAIHCTMO-UHFFFAOYSA-P

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

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

Medical uses

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Throat lozenge

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Dequalinium chloride 0.25 mg is available as an over-the-counter throat lozenge under brand names such as Dequadin and SP Troche. Mouthwash and buccal sprays at 0.5 % concentration are also available.[3][unreliable medical source?] In this form is it used to treat minor infections of the mouth and throat. It can help with tonsillitis but is not effective in cases of streptococci infections.[4]

Vaginal antiseptic

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Dequalinium chloride is available as a 10 mg prescription vaginal tablet for treating vaginal bacterial conditions (i.e. bacterial vaginosis and aerobic vaginitis). Brand names include Fluomizin, Vablys, and Naxyl.[3][5] It has been available in much of Europe for several decades[6] and was launched in Canada in 2022.[5] It is non-inferior to the antibiotic metronidazole in the treatment of bacterial vaginosis.[6][7][8]

Topical cream

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In Austria, dequalinium chloride is combined with bacitracin and diphenylpyraline in Eucillin "B", an antibiotic cream. This cream is the first dequalinium-containing product to enter Austria in 1967.[3]

Spectrum of activity

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Dequalinium salts have broad bactericidal and fungicidal activity.[9] In OTC oral products containing a low concentration, the product is instead described as a bacteriostat.[citation needed]

Dequalinium salts may have antimalarial activities.[10]

Adverse effects

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Dequalinium may cause skin necrosis "if administered on intertriginous skin areas under occlusive conditions".[10]

History

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Dequalinium was first described by M Babbs and colleagues in 1956, as the first agent of the bisquaternary ammonium chemical class.[11]

References

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Further reading

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