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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 of DEQUALINIUM CHLORIDE

SMILES

[Cl-].[Cl-].CC1=[N+](CCCCCCCCCC[N+]2=C(C)C=C(N)C3=C2C=CC=C3)C4=C(C=CC=C4)C(N)=C1

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P29973
Gene ID: 1259.0
Gene Symbol: CNGA1
Target Organism: Homo sapiens (Human)
Target ID: heteromeric CNGA1+CNGB1 channels
11.5 µM [Ki]
14.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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.
Curative
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.
Curative
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.
Curative
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

PubMed

TitleDatePubMed
Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds.
2000 Jul 28
Local treatment of vaginal infections of varying etiology with dequalinium chloride or povidone iodine. A randomised, double-blind, active-controlled, multicentric clinical study.
2002
Antimicrobial activity of dequalinium chloride against leading germs of vaginal infections.
2002
Expression and activity of potassium ion channels in human prostate cancer.
2002 Dec 1
Isothermic titration calorimetry to study CMCs of neutral surfactants and of the liposome-forming bolaamphiphile dequalinium.
2002 Feb-May
Modulation of small conductance calcium-activated potassium (SK) channels: a new challenge in medicinal chemistry.
2003 Apr
Cloning and expression of a small-conductance Ca(2+)-activated K+ channel from the mouse cochlea: coexpression with alpha9/alpha10 acetylcholine receptors.
2004 Apr
The influence of hypotonicity on large-conductance calcium-activated potassium channels in human retinal pigment epithelial cells.
2004 Dec
The receptor for activated C-kinase-I (RACK-I) anchors activated PKC-beta on melanosomes.
2004 Jul 15
State-dependent block of CNG channels by dequalinium.
2004 Mar
Approaches to mitochondrial gene therapy.
2004 Sep
Tetraethylammonium exacerbates ischemic neuronal injury in rat cerebrocortical slice cultures.
2005 Jan 31
Flow injection spectrofluorimetric study of the supramolecular interaction between beta-cyclodextrin and dequalinium chloride and its analytical application.
2005 Jul
Pharmacology of acetylcholine-mediated cell signaling in the lateral line organ following efferent stimulation.
2005 May
Induction of petite mutants in yeast Saccharomyces cerevisiae by the anticancer drug dequalinium.
2005 May 2
Effects of the antitumoural dequalinium on NB4 and K562 human leukemia cell lines. Mitochondrial implication in cell death.
2005 Oct
[Treatment of urogenital infections in lower part of the genital organs in pregnant women which are at risk of miscarriage].
2006 Apr-May
Inhibition of protein kinase C by dequalinium analogues: structure-activity studies on head group variations.
2006 Dec 1
Dequalinium-induced protofibril formation of alpha-synuclein.
2006 Feb 10
Baclofen, an agonist at peripheral GABAB receptors, induces antinociception via activation of TEA-sensitive potassium channels.
2006 Nov
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).
2007 Feb
Plasmodium berghei: in vitro and in vivo activity of dequalinium.
2007 Jan
Dequalinium induces cell death in human leukemia cells by early mitochondrial alterations which enhance ROS production.
2007 Jul
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
[Diagnosis and treatment of infectious pharyngeal inflammation].
2008
ETS-1 and ETS-2 are upregulated in a transgenic mouse model of pigmented ocular neoplasm.
2008
QacR-cation recognition is mediated by a redundancy of residues capable of charge neutralization.
2008 Aug 5
Apical SK potassium channels and Ca2+-dependent anion secretion in endometrial epithelial cells.
2008 Feb 1
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
Determination of antibacterial quaternary ammonium compound in lozenges and human serum by resonance light scattering technique.
2008 Nov 4
Disintegration of amyloid fibrils of alpha-synuclein by dequalinium.
2008 Oct
Molecular and cellular basis of small--and intermediate-conductance, calcium-activated potassium channel function in the brain.
2008 Oct
Involvement of ATP-sensitive K(+) channels in the peripheral antinociceptive effect induced by the alpha(2)-adrenoceptor agonist xylazine.
2009 Dec
Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening.
2009 Jul
New method for the quantification of dequalinium cations in pharmaceutical samples by absorption and fluorescence diode array thin-layer chromatography.
2009 Jun 19
Real-time analysis of amyloid fibril formation of alpha-synuclein using a fibrillation-state-specific fluorescent probe of JC-1.
2009 Mar 1
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.
2009 Sep 14
Alpha-tocopherol transfer protein disruption confers resistance to malarial infection in mice.
2010 Apr 19
[The treatment of MRSA colonized middle ear; case report and literature review].
2010 Jul
Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents.
2010 Jul
Re-engineering the mitochondrial genomes in mammalian cells.
2010 Jun
Identification of a κ-opioid agonist as a potent and selective lead for drug development against human African trypanosomiasis.
2010 Nov 15
Selective targeting of neuroblastoma tumour-initiating cells by compounds identified in stem cell-based small molecule screens.
2010 Sep
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
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Sample Use Guides

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).
Name Type Language
DEQUALINIUM CHLORIDE
EP   INCI   INN   JAN   MART.   MI   WHO-DD  
INCI   INN  
Official Name English
FLUOMIZIN
Brand Name English
DEQUALINIUM CHLORIDE [MI]
Common Name English
DEQUALINIUM CHLORIDE [MART.]
Common Name English
DEKAMIN
Common Name English
DEQUALINIUM CHLORIDE [INCI]
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
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
Code System Code Type Description
NSC
166454
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
INN
746
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PRIMARY
PUBCHEM
10649
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
ChEMBL
CHEMBL333826
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
CHEBI
31466
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
CAS
522-51-0
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PRIMARY
SMS_ID
100000091069
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
EVMPD
SUB06985MIG
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
DRUG BANK
DBSALT001926
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
MERCK INDEX
m4184
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID3045144
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PRIMARY
FDA UNII
XYS8INN1I6
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
RXCUI
3120
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C77046
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-330-9
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY