DEQUALINIUM CHLORIDE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C30H40N4.2Cl
Molecular Weight	527.571
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LTNZEXKYNRNOGT-UHFFFAOYSA-N

InChI=1S/C30H38N4.2ClH/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;2*1H

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

Molecular Formula	ClH
Molecular Weight	36.461
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
Towards mitochondrial gene therapy: DQAsomes as a strategy.	2001	11378519
DQAsome/DNA complexes release DNA upon contact with isolated mouse liver mitochondria.	2001 Aug 10	11489326
Suramin prevents cerebellar granule cell-death induced by dequalinium.	2001 Feb	11137882
Mitochondrial DNA metabolism targeting drugs.	2001 Jul 2	11377810
Cationic bolasomes with delocalized charge centers as mitochondria-specific DNA delivery systems.	2001 Jul 2	11377808
Delocalized lipophilic cations selectively target the mitochondria of carcinoma cells.	2001 Jul 2	11377803
Structure and design of polymeric surfactant-based drug delivery systems.	2001 Jun 15	11516494
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
The noradrenergic inhibition of an apamin-sensitive, small-conductance Ca2+-activated K+ channel in hypothalamic gamma-aminobutyric acid neurons: pharmacology, estrogen sensitivity, and relevance to the control of the reproductive axis.	2001 Oct	11561059
Determination for micro amounts of nucleic acids by a resonance light scattering technique with dequalinium chloride.	2001 Oct 31	18968413
Characterisation of [(125)I]-apamin binding sites in rat brain membranes with HE293 cells transfected with SK channel subtypes.	2001 Sep	11522325
Expression and activity of potassium ion channels in human prostate cancer.	2002 Dec 1	12183081
Involvement of ATP-sensitive K(+) channels in the peripheral antinociceptive effect induced by dipyrone.	2002 May 24	12191581
Modulation of small conductance calcium-activated potassium (SK) channels: a new challenge in medicinal chemistry.	2003 Apr	12678783
Gelsolin suppresses tumorigenicity through inhibiting PKC activation in a human lung cancer cell line, PC10.	2003 Feb 24	12592377
Dequalinium: a novel, high-affinity blocker of CNGA1 channels.	2003 Jan	12508052
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
Crystal structures of QacR-diamidine complexes reveal additional multidrug-binding modes and a novel mechanism of drug charge neutralization.	2004 Apr 2	14726520
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 receptor for activated C-kinase-I (RACK-I) anchors activated PKC-beta on melanosomes.	2004 Jul 15	15252133
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
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).	2007 Feb	17200835
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
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
Dequalinium-induced cell death of yeast expressing alpha-synuclein-GFP fusion protein.	2008 Jul	18322792
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 17:35:16 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:16 GMT 2025`
Record UNII	XYS8INN1I6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLUOMIZIN

Preferred Name

English

DEQUALINIUM CHLORIDE

Official Name

English

DEQUALINIUM CHLORIDE [MI]

Common Name

English

DEQUALINIUM CHLORIDE [MART.]

Common Name

English

DEKAMIN

Common Name

English

GNF-PF-5483

Code

English

1,1'-(1,10-DECANEDIYL)BIS-(4-AMINO-2-METHYLQUINOLINIUM CHLORIDE)

Common Name

English

DEQUALINIUM CHLORIDE [EP MONOGRAPH]

Common Name

English

NSC-166454

Code

English

Dequalinium chloride [WHO-DD]

Common Name

English

BAQD-10

Code

English

BAQD 10

Code

English

DECAMINE

Common Name

English

DEQUALINIUM DICHLORIDE

Common Name

English

1,10-DECAMETHYLENE-BIS(4-AMINOQUINALDINIUM CHLORIDE)

Common Name

English

dequalinium chloride [INN]

Common Name

English

1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM CHLORIDE)

Common Name

English

DEQUALINIUM CHLORIDE [JAN]

Common Name

English

NORDMAN

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C795