DEQUALINIUM

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C30H40N4
Molecular Weight	456.6654
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	2

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(N)=C2C=CC=CC2=[N+]1CCCCCCCCCC[N+]3=C4C=CC=CC4=C(N)C=C3C

InChI

InChIKey=PCSWXVJAIHCTMO-UHFFFAOYSA-P

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

HIDE SMILES / InChI

Molecular Formula	C30H38N4
Molecular Weight	454.6495
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/uk/fluomizin-10-mg-vaginal-tablets-leaflet.html
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800041300 | http://www.netdoctor.co.uk/medicines/mouth-and-teeth/a6534/dequadin-lozenges-dequalinium/ | https://en.wikipedia.org/wiki/Dequalinium

Dequalinium is a quaternary ammonium cation commonly available as the dichloride salt. Dequalinium chloride has an antiseptic effect against a wide range of bacteria, yeasts, and some fungi and viruses. It kills the micro-organisms associated with various mild infections of the mouth and throat. Also, Dequalinium chloride is active against the bacteria which cause bacterial vaginosis. Dequalinium Chloride (DECA) is a PKC inhibitor and high-affinity blocker CNGA1 channel, and nearly as effective on heteromeric CNGA1+CNGB1 channels. Common side effects are: vaginal discharge; vaginal itching or vaginal burning; vaginal yeast infection (thrush); tender tongue.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
cGMP-gated cation channel alpha-1 4 Target ID: P29973 Gene ID: 1259.0 Gene Symbol: CNGA1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12508052	Blocker 555
heteromeric CNGA1+CNGB1 channels 4 Target ID: heteromeric CNGA1+CNGB1 channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/12508052	Blocker 555
Protein kinase C alpha 21 Target ID: CHEMBL299 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9442087	Inhibitor 8504	11.5 µM [Ki]
Protein kinase C beta 22 Target ID: CHEMBL3045 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9442087	Inhibitor 8504	14.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Bacterial vaginosis 10 Sources: https://www.drugs.com/uk/fluomizin-10-mg-vaginal-tablets-leaflet.html http://adisinsight.springer.com/trials/700249655	Curative	Approved 8583	Fluomizin Approved Use Dequalinium chloride has an antiseptic effect against a wide range of bacteria, yeasts, and some fungi and viruses. Dequalinium chloride is active against the bacteria which cause bacterial vaginosis.
Oral thrush 5 Sources: http://www.netdoctor.co.uk/medicines/mouth-and-teeth/a6534/dequadin-lozenges-dequalinium/	Curative	Approved 8583	Dequadin lozenges Approved Use Dequalinium chloride has an antiseptic effect against a wide range of bacteria, yeasts, and some fungi and viruses. It kills the micro-organisms associated with various mild infections of the mouth and throat.
Aphthous ulcers 10 Sources: http://www.netdoctor.co.uk/medicines/mouth-and-teeth/a6534/dequadin-lozenges-dequalinium/	Curative	Approved 8583	Dequadin lozenges Approved Use Anginova is used for the local treatment of acute inflammatory diseases in the mouth and throat area such as sore throat, difficulty swallowing, thrush, aphthous ulcers, etc. and as an adjuvant medication for angina.
Sore throat 18 Sources: http://www.netdoctor.co.uk/medicines/mouth-and-teeth/a6534/dequadin-lozenges-dequalinium/	Curative	Approved 8583	Dequadin lozenges Approved Use Anginova is used for the local treatment of acute inflammatory diseases in the mouth and throat area such as sore throat, difficulty swallowing, thrush, aphthous ulcers, etc. and as an adjuvant medication for angina

PubMed

Title	Date	PubMed
The pharmacology of hSK1 Ca2+-activated K+ channels expressed in mammalian cell lines.	2000 Feb	10683185
Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds.	2000 Jul 28	10915830
Pharmacological characterization of small-conductance Ca(2+)-activated K(+) channels stably expressed in HEK 293 cells.	2000 Mar	10696100
Structural mechanisms of QacR induction and multidrug recognition.	2001 Dec 7	11739955
Suramin prevents cerebellar granule cell-death induced by dequalinium.	2001 Feb	11137882
Mitochondrial DNA metabolism targeting drugs.	2001 Jul 2	11377810
Pharmacological characterisation of the human small conductance calcium-activated potassium channel hSK3 reveals sensitivity to tricyclic antidepressants and antipsychotic phenothiazines.	2001 May	11369031
Occupational allergic contact dermatitis from alkylammonium amidobenzoate.	2001 May-Jun	11358732
Antimicrobial activity of dequalinium chloride against leading germs of vaginal infections.	2002	12404886
DQAsome-mediated delivery of plasmid DNA toward mitochondria in living cells.	2003 Sep 19	14499196
Cloning and expression of a small-conductance Ca(2+)-activated K+ channel from the mouse cochlea: coexpression with alpha9/alpha10 acetylcholine receptors.	2004 Apr	14657188
Additive antinociceptive effect of the combination of diazoxide, an activator of ATP-sensitive K+ channels, and sodium nitroprusside and dibutyryl-cGMP.	2004 Apr 5	15063156
The influence of hypotonicity on large-conductance calcium-activated potassium channels in human retinal pigment epithelial cells.	2004 Dec	15684815
The receptor for activated C-kinase-I (RACK-I) anchors activated PKC-beta on melanosomes.	2004 Jul 15	15252133
Small conductance Ca2+-activated K+ channels as targets of CNS drug development.	2004 Jun	15180477
Study of the involvement of K+ channels in the peripheral antinociception of the kappa-opioid receptor agonist bremazocine.	2004 Jun 28	15212969
State-dependent block of CNG channels by dequalinium.	2004 Mar	14981138
Cilostazol, an inhibitor of type 3 phosphodiesterase, stimulates large-conductance, calcium-activated potassium channels in pituitary GH3 cells and pheochromocytoma PC12 cells.	2004 Mar	14645120
Approaches to mitochondrial gene therapy.	2004 Sep	15384945
Tetraethylammonium exacerbates ischemic neuronal injury in rat cerebrocortical slice cultures.	2005 Jan 31	15680257
Mechanisms of relaxing response induced by rat/mouse hemokinin-1 in porcine coronary arteries: roles of potassium ion and nitric oxide.	2007 Aug 13	17560993
Involvement of chloride channel coupled GABA(C) receptors in the peripheral antinociceptive effect induced by GABA(C) receptor agonist cis-4-aminocrotonic acid.	2007 Mar 13	17316706
Synthesis, antifungal and haemolytic activity of a series of bis(pyridinium)alkanes.	2007 May 15	17383187
Potassium channel openers accelerate epidermal barrier recovery.	2007 Nov	17916210
Synthesis and radioligand binding studies of bis-isoquinolinium derivatives as small conductance Ca(2+)-activated K(+) channel blockers.	2007 Oct 18	17867663
G-Protein Inwardly Rectifying Potassium Channel 1 (GIRK1) Knockdown Decreases Beta-Adrenergic, MAP Kinase and Akt Signaling in the MDA-MB-453 Breast Cancer Cell Line.	2008	21655370
[Diagnosis and treatment of infectious pharyngeal inflammation].	2008	19008844
Electron crystallography reveals plasticity within the drug binding site of the small multidrug transporter EmrE.	2008 Apr 4	18295794
Apical SK potassium channels and Ca2+-dependent anion secretion in endometrial epithelial cells.	2008 Feb 1	18048454
Dequalinium-induced cell death of yeast expressing alpha-synuclein-GFP fusion protein.	2008 Jul	18322792
Bis-tetrahydroisoquinoline derivatives: AG525E1, a new step in the search for non-quaternary non-peptidic small conductance Ca(2+)-activated K(+) channel blockers.	2008 Jun 1	18436444
Determination of antibacterial quaternary ammonium compound in lozenges and human serum by resonance light scattering technique.	2008 Nov 4	18585882
Involvement of ATP-sensitive K(+) channels in the peripheral antinociceptive effect induced by the alpha(2)-adrenoceptor agonist xylazine.	2009 Dec	20019444
Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening.	2009 Jul	19525487
Effect of dequalinium on the oxidative stress in Plasmodium berghei-infected erythrocytes.	2009 Jun	19205739
Real-time analysis of amyloid fibril formation of alpha-synuclein using a fibrillation-state-specific fluorescent probe of JC-1.	2009 Mar 1	19007333
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.	2009 Sep 14	19750012
Alpha-tocopherol transfer protein disruption confers resistance to malarial infection in mice.	2010 Apr 19	20403155
[The treatment of MRSA colonized middle ear; case report and literature review].	2010 Jul	20617476
Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents.	2010 Jul	20116850
Re-engineering the mitochondrial genomes in mammalian cells.	2010 Jun	21189990
Identification of a κ-opioid agonist as a potent and selective lead for drug development against human African trypanosomiasis.	2010 Nov 15	20696141
Selective targeting of neuroblastoma tumour-initiating cells by compounds identified in stem cell-based small molecule screens.	2010 Sep	20721990
Metabolic oxidative stress elicited by the copper(II) complex [Cu(isaepy)2] triggers apoptosis in SH-SY5Y cells through the induction of the AMP-activated protein kinase/p38MAPK/p53 signalling axis: evidence for a combined use with 3-bromopyruvate in neuroblastoma treatment.	2011 Aug 1	21548882
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

1 vaginal tablet (10 mg) daily for 6 days

Route of Administration: Other

In Vitro Use Guide

multidrug-resistant lines were less sensitive than parental cell lines to the intrinsic growth inhibitory effects of dequalinium (IC50, 4.4 versus 0.3 microM in multidrug-resistant and sensitive P388 cells, respectively).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:55 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:55 GMT 2025`
Record UNII	E7QC7V26B8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEQUALINIUM

Common Name

English

DEQUALINIUM CATION

Preferred Name

English

1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM)

Systematic Name

English

Dequalinium [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

D08AH01