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Dequalinium

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(Redirected from Dequalinium chloride) Chemical compound
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Pharmaceutical compound
Dequalinium
Clinical data
Trade namesDequadin, Fluomizin, Vablys, others
Routes of
administration		By mouth intravaginal
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • 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
CompTox Dashboard (EPA)
ECHA InfoCard100.007.575 Edit this at Wikidata
Chemical and physical data
FormulaC30H40N4
Molar mass456.678 g·mol
3D model (JSmol)
SMILES
  • c12ccccc1c(cc(2CCCCCCCCCC4c3ccccc3c(N)cc4C)C)N
InChI
  • 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

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. 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.

The product is also available as a 10 mg prescription vaginal tablet for treating vaginal bacterial conditions (i.e. bacterial Vaginosis and aerobic vaginitis). Brand names include Fluomizin and Vablys.

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.

Spectrum of activity

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

Dequalinium salts may have antimalarial activities.

Adverse effects

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

History

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

References

  1. "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
  2. "Fluomizin Summary of Product Characteristics (SmPC)". (emc). 12 October 2022. Retrieved 14 April 2024.
  3. ^ "Dequalinium". DrugBank Online.
  4. Krämer W (April 1977). "". Fortschritte der Medizin (in German). 95 (16): 1108–1110. PMID 856702.
  5. Mendling W, Weissenbacher ER, Gerber S, Prasauskas V, Grob P (March 2016). "Use of locally delivered dequalinium chloride in the treatment of vaginal infections: a review". Archives of Gynecology and Obstetrics. 293 (3): 469–484. doi:10.1007/s00404-015-3914-8. PMC 4757629. PMID 26506926.
  6. ^ Tischer M, Pradel G, Ohlsen K, Holzgrabe U (January 2012). "Quaternary ammonium salts and their antimicrobial potential: targets or nonspecific interactions?". ChemMedChem. 7 (1): 22–31. doi:10.1002/cmdc.201100404. PMID 22113995. S2CID 26326417.
  7. Babbs M, Collier HO, Austin WC, Potter MD, Taylor EP (February 1956). "Salts of decamethylene-bis-4-aminoquinaldinium (dequadin); a new antimicrobial agent". The Journal of Pharmacy and Pharmacology. 8 (2): 110–119. doi:10.1111/j.2042-7158.1956.tb12138.x. PMID 13307403. S2CID 30103639.

Further reading

  • Gamboa-Vujicic G, Emma DA, Liao SY, Fuchtner C, Manetta A (March 1993). "Toxicity of the mitochondrial poison dequalinium chloride in a murine model system". Journal of Pharmaceutical Sciences. 82 (3): 231–235. doi:10.1002/jps.2600820302. PMID 8450414.

External links

Antiseptics and disinfectants (D08)
Acridine derivatives
Biguanides and amidines
Phenol and derivatives
Nitrofuran derivatives
Iodine products
Quinoline derivatives
Quaternary ammonium compounds
Mercurial products
Silver compounds
Alcohols
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Gynecological anti-infectives and antiseptics (G01)
Antibiotics
Arsenic compounds
Quinoline derivatives
Organic acids
Sulfonamides
Antifungals
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