View source for Chemistry:Dequalinium

{{Short description|Chemical compound}}
{{Infobox drug
| drug_name = Dequalinium chloride
| INN               =
| type              = <!-- empty -->
| image             = Dequalinium chloride.png
| alt               =
| caption           =
<!-- Clinical data -->
| pronounce         =
| tradename         = Dequadin, SP Troche, Fluomizin, Vablys
| Drugs.com         =
| MedlinePlus       =
| pregnancy_AU      = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment =
| pregnancy_category=
| routes_of_administration = Topical oral; topical intravaginal
| ATCvet            =
| ATC_prefix = D08
| ATC_suffix = AH01
| ATC_supplemental = {{ATC|G01|AC05}}, {{ATC|R02|AA02}}
<!-- Legal status -->
| legal_AU          = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_AU_comment  =
| legal_BR          = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment  =
| legal_CA          = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment  =
| legal_DE          = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment  =
| legal_NZ          = <!-- Class A, B, C -->
| legal_NZ_comment  =
| legal_UK          = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment  =
| legal_US          = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_US_comment  =
| legal_EU          =
| legal_EU_comment  =
| legal_UN          = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment  =
| legal_status      = OTC (oral), Rx (vaginal)
<!-- Pharmacokinetic data -->
| bioavailability   =
| protein_bound     =
| metabolism        =
| metabolites       =
| onset             =
| elimination_half-life =
| duration_of_action=
| excretion         =
<!-- Identifiers -->
| CAS_number        = 6707-58-0
| PubChem           = 2993
| ChemSpiderID = 2886
| DrugBank = DB04209
| ChEBI = 31466
| ChEMBL = 333826
| ChEMBL2 = 121663
| UNII = E7QC7V26B8
| IUPHAR_ligand = 2313
<!-- Chemical and physical data -->
| 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 [[Chemistry:Quaternary ammonium cation|quaternary ammonium cation]] and [[Chemistry:Bolaamphiphile|bolaamphiphile]] commonly available as the dichloride salt. It is useful as an [[Chemistry:Antiseptic|antiseptic]] and [[Chemistry:Disinfectant|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&nbsp;mg is available as an over-the-counter [[Medicine:Throat lozenge|throat lozenge]] under brand names such as ''Dequadin'' and ''SP Troche''. Mouthwash and buccal sprays at 0.5 % concentration are also available.<ref name=DB04209>{{cite web |title=Dequalinium |url=https://go.drugbank.com/drugs/DB04209 | work = DrugBank Online }}</ref> 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 [[Biology:Streptococcus|streptococci]] infections.<ref>{{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 }}</ref>

The product is also available as a 10&nbsp;mg prescription vaginal tablet for treating vaginal bacterial conditions (i.e. bacterial Vaginosis and aerobic vaginitis). Brand names include ''Fluomizin'' and ''Vablys''.<ref name=DB04209/>

In Austria, dequalinium chloride is combined with [[Chemistry:Bacitracin|bacitracin]] and [[Chemistry:Diphenylpyraline|diphenylpyraline]] in ''Eucillin "B"'', an antibiotic cream. This cream is the first dequalinium-containing product to enter Austria in 1967.<ref name=DB04209/>

=== Spectrum of activity ===
Dequalinium salts have broad bactericidal and fungicidal activity.<ref>{{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 }}</ref> 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.<ref name=p22113995>{{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 }}</ref>

== Adverse effects ==
Dequalinium may cause skin necrosis "if administered on intertriginous skin areas under occlusive conditions".<ref name=p22113995/>

== History ==
Dequalinium was first described by M Babbs and colleagues in 1956, as the first agent of the bisquaternary ammonium chemical class.<ref>{{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 }}</ref>

== References ==
{{reflist}}

== 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 }}
{{refend}}

== External links ==
* [http://www.wipo.int/ipdl/en/madrid/key.jsp?KEY=804560 International Mark - Fluomizin(804560)]{{Dead link|date=July 2019 |bot=InternetArchiveBot |fix-attempted=yes }}
* [http://www.medinova.ch/en/products/gynaekologie/fluomizin.html Medinova Fluomizin]
* [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}}

[[Category:Quinolines]]
[[Category:Quaternary ammonium compounds]]
[[Category:Antiseptics]]


{{Sourceattribution|Dequalinium}}