Dequalinium

Last updated
Dequalinium
Dequalinium chloride.png
Clinical data
Trade names Dequadin, 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
CompTox Dashboard (EPA)
ECHA InfoCard 100.007.575 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C30H40N4
Molar mass 456.678 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.

Contents

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. [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

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

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. [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

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

History

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

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. 1 2 3 "Dequalinium". DrugBank Online.
  4. ↑ Krämer W (April 1977). "[Treatment of tonsillitis with dequalinium chloride]". Fortschritte der Medizin (in German). 95 (16): 1108–1110. PMID   856702.
  5. 1 2 "Dequalinium chloride vaginal tablet". AdisInsight. 23 June 2022. Retrieved 26 February 2025.
  6. 1 2 Carter KA, Tuddenham S, Brotman RM (May 2024). "Dequalinium Chloride-An Emerging Option in the Sparse Landscape of Bacterial Vaginosis Therapies". JAMA Netw Open. 7 (5): e248606. doi:10.1001/jamanetworkopen.2024.8606. PMC   11423866 . PMID   38696175.
  7. ↑ Raba G, Durkech A, Malík T, Bassfeld D, Grob P, Hurtado-Chong A (May 2024). "Efficacy of Dequalinium Chloride vs Metronidazole for the Treatment of Bacterial Vaginosis: A Randomized Clinical Trial". JAMA Netw Open. 7 (5): e248661. doi:10.1001/jamanetworkopen.2024.8661. PMC   11066704 . PMID   38696172.
  8. ↑ Slawson DC (November 2024). "Dequalinium Is Noninferior to Metronidazole for Bacterial Vaginosis". Am Fam Physician. 110 (5): 543. PMID   39556645.
  9. ↑ 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.
  10. 1 2 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.
  11. ↑ 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

This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.