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Dequalinium

Chemical compound


Chemical compound

FieldValue
imageDequalinium chloride.png
image_classskin-invert-image
tradenameDequadin, Fluomizin, Vablys, Naxyl, others
pregnancy_AU
routes_of_administrationBy mouth, intravaginal
ATC_prefixD08
ATC_suffixAH01
ATC_supplemental,
legal_AU
legal_BR
legal_CARx-only
legal_CA_comment
legal_DE
legal_NZ
legal_UKPOM
legal_UK_comment
legal_US
legal_UN
CAS_number6707-58-0
PubChem2993
ChemSpiderID2886
DrugBankDB04209
ChEBI31466
ChEMBL333826
ChEMBL2121663
UNIIE7QC7V26B8
IUPHAR_ligand2313
IUPAC_name1,1'-decane-1,10-diylbis(4-amino-2-methylquinolinium)
StdInChI1S/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
StdInChIKeyPCSWXVJAIHCTMO-UHFFFAOYSA-P
C30H=40N=4
SMILESc12ccccc1c(cc([n+]2CCCCCCCCCC[n+]4c3ccccc3c(N)cc4C)C)N

| Drugs.com =

| elimination_half-life =

decyl]-2-methyl-4-quinolin-1-iumamine dichloride

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

Throat lozenge

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.

Vaginal antiseptic

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. It has been available in much of Europe for several decades and was launched in Canada in 2022. It is non-inferior to the antibiotic metronidazole in the treatment of bacterial vaginosis.

Topical cream

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

References

  1. (3 August 2022). "Health product highlights 2021: Annexes of products approved in 2021".
  2. (12 October 2022). "Fluomizin Summary of Product Characteristics (SmPC)".
  3. "Dequalinium". DrugBank Online.
  4. (April 1977). "[Treatment of tonsillitis with dequalinium chloride]". Fortschritte der Medizin.
  5. (23 June 2022). "Dequalinium chloride vaginal tablet".
  6. (May 2024). "Dequalinium Chloride-An Emerging Option in the Sparse Landscape of Bacterial Vaginosis Therapies". JAMA Netw Open.
  7. (May 2024). "Efficacy of Dequalinium Chloride vs Metronidazole for the Treatment of Bacterial Vaginosis: A Randomized Clinical Trial". JAMA Netw Open.
  8. (November 2024). "Dequalinium Is Noninferior to Metronidazole for Bacterial Vaginosis". Am Fam Physician.
  9. (March 2016). "Use of locally delivered dequalinium chloride in the treatment of vaginal infections: a review". Archives of Gynecology and Obstetrics.
  10. (January 2012). "Quaternary ammonium salts and their antimicrobial potential: targets or nonspecific interactions?". ChemMedChem.
  11. (February 1956). "Salts of decamethylene-bis-4-aminoquinaldinium (dequadin); a new antimicrobial agent". The Journal of Pharmacy and Pharmacology.
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