DEQUALINIUM ACETATE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C30H40N4.2C2H3O2
Molecular Weight	574.7534
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=IWYNVAJACBPVLT-UHFFFAOYSA-N

InChI=1S/C30H38N4.2C2H4O2/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;2*1-2(3)4/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3;2*1H3,(H,3,4)

HIDE SMILES / InChI

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count

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

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
Determination for micro amounts of nucleic acids by a resonance light scattering technique with dequalinium chloride.	2001 Oct 31	18968413
The influence of hypotonicity on large-conductance calcium-activated potassium channels in human retinal pigment epithelial cells.	2004 Dec	15684815
Type IVB piliated Salmonella typhi enhance IL-6 and NF-kappaB production in human monocytic THP-1 cells through activation of protein kinase C.	2005	16164036
Tetraethylammonium exacerbates ischemic neuronal injury in rat cerebrocortical slice cultures.	2005 Jan 31	15680257
Mutation of the pore glutamate affects both cytoplasmic and external dequalinium block in the rat olfactory CNGA2 channel.	2005 Jul	15928936
Flow injection spectrofluorimetric study of the supramolecular interaction between beta-cyclodextrin and dequalinium chloride and its analytical application.	2005 Jul	15911412
Essential roles of Homer-1a in homeostatic regulation of pyramidal cell excitability: a possible link to clinical benefits of electroconvulsive shock.	2005 Jun	16026461
Pharmacology of acetylcholine-mediated cell signaling in the lateral line organ following efferent stimulation.	2005 May	15615825
Induction of petite mutants in yeast Saccharomyces cerevisiae by the anticancer drug dequalinium.	2005 May 2	15790492
Mitochondrial leader sequence--plasmid DNA conjugates delivered into mammalian cells by DQAsomes co-localize with mitochondria.	2005 Oct	16154389
Effects of the antitumoural dequalinium on NB4 and K562 human leukemia cell lines. Mitochondrial implication in cell death.	2005 Oct	15893819
[Treatment of urogenital infections in lower part of the genital organs in pregnant women which are at risk of miscarriage].	2006 Apr-May	17100185
Inhibition of protein kinase C by dequalinium analogues: structure-activity studies on head group variations.	2006 Dec 1	16962331
Dequalinium-induced protofibril formation of alpha-synuclein.	2006 Feb 10	16330551
Baclofen, an agonist at peripheral GABAB receptors, induces antinociception via activation of TEA-sensitive potassium channels.	2006 Nov	17016510
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
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).	2007 Feb	17200835
Plasmodium berghei: in vitro and in vivo activity of dequalinium.	2007 Jan	16814285
Dequalinium induces cell death in human leukemia cells by early mitochondrial alterations which enhance ROS production.	2007 Jul	17250890
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
ETS-1 and ETS-2 are upregulated in a transgenic mouse model of pigmented ocular neoplasm.	2008	18958307
Electron crystallography reveals plasticity within the drug binding site of the small multidrug transporter EmrE.	2008 Apr 4	18295794
Nanocarrier-assisted sub-cellular targeting to the site of mitochondria improves the pro-apoptotic activity of paclitaxel.	2008 Aug	18686127
QacR-cation recognition is mediated by a redundancy of residues capable of charge neutralization.	2008 Aug 5	18616285
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
Disintegration of amyloid fibrils of alpha-synuclein by dequalinium.	2008 Oct	18691634
Molecular and cellular basis of small--and intermediate-conductance, calcium-activated potassium channel function in the brain.	2008 Oct	18597044
Functional analyses reveal an important role for tyrosine residues in the staphylococcal multidrug efflux protein QacA.	2008 Sep 16	18793443
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
New method for the quantification of dequalinium cations in pharmaceutical samples by absorption and fluorescence diode array thin-layer chromatography.	2009 Jun 19	19446824
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 17:51:29 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:29 GMT 2025`
Record UNII	P8W4UX112S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1,1'-(DECANE-1,10-DIYL)BIS(4-AMINO-2-METHYLQUINOLINIUM) DIACETATE

Preferred Name

English

DEQUALINIUM ACETATE

Official Name

English

QUINOLINIUM, 1,1'-(1,10-DECANEDIYL)BIS(4-AMINO-2-METHYL-, DIACETATE

Systematic Name

English

Dequalinium acetate [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C795