:Dequalinium
{{Short description|Chemical compound}}
{{Expand German|date=September 2023}}
{{Infobox drug
| image = Dequalinium chloride.png
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| pronounce =
| tradename = Dequadin, Fluomizin, Vablys, Naxyl, others
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| routes_of_administration = By mouth, intravaginal
| ATC_prefix = D08
| ATC_suffix = AH01
| ATC_supplemental = {{ATC|G01|AC05}}, {{ATC|R02|AA02}}
| legal_AU =
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| legal_CA = Rx-only
| legal_CA_comment = {{cite web | title=Health product highlights 2021: Annexes of products approved in 2021 | website=Health Canada | date=3 August 2022 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-product-highlights-2021/appendices.html | access-date=25 March 2024}}
| legal_DE =
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| legal_UK = POM
| legal_US =
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| bioavailability =
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| 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
=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.{{cite web |title=Dequalinium |url=https://go.drugbank.com/drugs/DB04209 | work = DrugBank Online }}{{Unreliable medical source|date=April 2024}} 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.{{cite journal | vauthors = Krämer W | title = [Treatment of tonsillitis with dequalinium chloride] | language = de | journal = Fortschritte der Medizin | volume = 95 | issue = 16 | pages = 1108–1110 | date = April 1977 | pmid = 856702 }}
=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.{{cite web | title=Dequalinium chloride vaginal tablet | website=AdisInsight | date=23 June 2022 | url=https://adisinsight.springer.com/drugs/800041300 | access-date=26 February 2025}} It has been available in much of Europe for several decades{{cite journal | vauthors = Carter KA, Tuddenham S, Brotman RM | title = Dequalinium Chloride-An Emerging Option in the Sparse Landscape of Bacterial Vaginosis Therapies | journal = JAMA Netw Open | volume = 7 | issue = 5 | pages = e248606 | date = May 2024 | pmid = 38696175 | pmc = 11423866 | doi = 10.1001/jamanetworkopen.2024.8606 | url = }} and was launched in Canada in 2022. It is non-inferior to the antibiotic metronidazole in the treatment of bacterial vaginosis.{{cite journal | vauthors = Carter KA, Tuddenham S, Brotman RM | title = Dequalinium Chloride-An Emerging Option in the Sparse Landscape of Bacterial Vaginosis Therapies | journal = JAMA Netw Open | volume = 7 | issue = 5 | pages = e248606 | date = May 2024 | pmid = 38696175 | pmc = 11423866 | doi = 10.1001/jamanetworkopen.2024.8606 | url = }}{{cite journal | vauthors = Raba G, Durkech A, Malík T, Bassfeld D, Grob P, Hurtado-Chong A | title = Efficacy of Dequalinium Chloride vs Metronidazole for the Treatment of Bacterial Vaginosis: A Randomized Clinical Trial | journal = JAMA Netw Open | volume = 7 | issue = 5 | pages = e248661 | date = May 2024 | pmid = 38696172 | pmc = 11066704 | doi = 10.1001/jamanetworkopen.2024.8661 | url = }}{{cite journal | vauthors = Slawson DC | title = Dequalinium Is Noninferior to Metronidazole for Bacterial Vaginosis | journal = Am Fam Physician | volume = 110 | issue = 5 | pages = 543 | date = November 2024 | pmid = 39556645 | doi = | url = }}
=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.{{cite journal | vauthors = Mendling W, Weissenbacher ER, Gerber S, Prasauskas V, Grob P | title = Use of locally delivered dequalinium chloride in the treatment of vaginal infections: a review | journal = Archives of Gynecology and Obstetrics | volume = 293 | issue = 3 | pages = 469–484 | date = March 2016 | pmid = 26506926 | doi = 10.1007/s00404-015-3914-8 | pmc = 4757629 }} In OTC oral products containing a low concentration, the product is instead described as a bacteriostat.{{cn|date=September 2023}}
Dequalinium salts may have antimalarial activities.{{cite journal | vauthors = Tischer M, Pradel G, Ohlsen K, Holzgrabe U | title = Quaternary ammonium salts and their antimicrobial potential: targets or nonspecific interactions? | journal = ChemMedChem | volume = 7 | issue = 1 | pages = 22–31 | date = January 2012 | pmid = 22113995 | doi = 10.1002/cmdc.201100404 | s2cid = 26326417 }}
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.{{cite journal | vauthors = Babbs M, Collier HO, Austin WC, Potter MD, Taylor EP | title = Salts of decamethylene-bis-4-aminoquinaldinium (dequadin); a new antimicrobial agent | journal = The Journal of Pharmacy and Pharmacology | volume = 8 | issue = 2 | pages = 110–119 | date = February 1956 | pmid = 13307403 | doi = 10.1111/j.2042-7158.1956.tb12138.x | s2cid = 30103639 }}
References
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Further reading
{{refbegin}}
- {{cite journal | vauthors = Gamboa-Vujicic G, Emma DA, Liao SY, Fuchtner C, Manetta A | title = Toxicity of the mitochondrial poison dequalinium chloride in a murine model system | journal = Journal of Pharmaceutical Sciences | volume = 82 | issue = 3 | pages = 231–235 | date = March 1993 | pmid = 8450414 | doi = 10.1002/jps.2600820302 }}
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External links
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- [http://clinicaltrials.gov/ct2/show/NCT01125410 Comparative Study of Efficacy of 10 mg Dequalinium Chloride (Fluomizin) in the Local Treatment of Bacterial Vaginosis]
{{Antiseptics and disinfectants}}
{{Gynecological anti-infectives and antiseptics}}