Dequalinium

Dequalinium
Clinical data
Trade names	Dequadin, Fluomizin, Vablys, others
Routes of; administration	By mouth intravaginal
ATC code	D08AH01 (WHO) G01AC05 (WHO), R02AA02 (WHO);
Legal status
Legal status	CA: ℞-only; UK: POM (Prescription only);
Identifiers
	IUPAC name 1,1'-decane-1,10-diylbis(4-amino-2-methylquinolinium) decyl]-2-methyl-4-quinolin-1-iumamine dichloride;
CAS Number	6707-58-0;
PubChem CID	2993;
IUPHAR/BPS	2313;
DrugBank	DB04209;
ChemSpider	2886;
UNII	E7QC7V26B8;
ChEBI	CHEBI:31466;
ChEMBL	ChEMBL333826; ChEMBL121663;
CompTox Dashboard (EPA)	DTXSID3045144 ;
ECHA InfoCard	100.007.575
Chemical and physical data
Formula	C30H40N4
Molar mass	456.678 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c12ccccc1c(cc([n+]2CCCCCCCCCC[n+]4c3ccccc3c(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.^[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]

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.^{[citation needed]}

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]

References

^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
^ "Fluomizin Summary of Product Characteristics (SmPC)". (emc). 12 October 2022. Retrieved 14 April 2024.
^ ^a ^b ^c "Dequalinium". DrugBank Online.
^ Krämer W (April 1977). "[Treatment of tonsillitis with dequalinium chloride]". Fortschritte der Medizin (in German). 95 (16): 1108–1110. PMID 856702.
^ 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.
^ ^a ^b 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.
^ 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.

External links

Comparative Study of Efficacy of 10 mg Dequalinium Chloride (Fluomizin) in the Local Treatment of Bacterial Vaginosis

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[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.

[DB04209-3] "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] 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.

[p22113995-6] 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.

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