Dequalinium Explained

Tradename:Dequadin, Fluomizin, Vablys, others
Routes Of Administration:By mouth intravaginal
Atc Prefix:D08
Atc Suffix:AH01
Atc Supplemental:,
Legal Ca:Rx-only
Legal Ca Comment:[1]
Legal Uk:POM
Legal Uk Comment:[2]
Cas Number:6707-58-0
Pubchem:2993
Chemspiderid:2886
Drugbank:DB04209
Chebi:31466
Chembl:333826
Chembl2:121663
Unii:E7QC7V26B8
Iuphar Ligand:2313
Iupac Name:1,1'-decane-1,10-diylbis(4-amino-2-methylquinolinium)decyl]-2-methyl-4-quinolin-1-iumamine dichloride
Stdinchi: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
Stdinchikey:PCSWXVJAIHCTMO-UHFFFAOYSA-P
C:30
H:40
N:4
Smiles:c12ccccc1c(cc([n+]2CCCCCCCCCC[n+]4c3ccccc3c(N)cc4C)C)N

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.[3] 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]

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.[3]

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

Dequalinium salts have broad bactericidal and fungicidal activity.[5] In OTC oral products containing a low concentration, the product is instead described as a bacteriostat.

Dequalinium salts may have antimalarial activities.[6]

Adverse effects

Dequalinium may cause skin necrosis "if administered on intertriginous skin areas under occlusive conditions".[6]

History

Dequalinium was first described by M Babbs and colleagues in 1956, as the first agent of the bisquaternary ammonium chemical class.[7]

Further reading

External links

Notes and References

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