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Details

Stereochemistry ACHIRAL
Molecular Formula C30H40N4
Molecular Weight 456.6665
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of DEQUALINIUM

SMILES

Cc1cc(=[NH2+])c2ccccc2n1CCCCCCCCCCn3c(C)cc(=[NH2+])c4ccccc43

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

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
Determination for micro amounts of nucleic acids by a resonance light scattering technique with dequalinium chloride.
2001 Oct 31
Modulation of small conductance calcium-activated potassium (SK) channels: a new challenge in medicinal chemistry.
2003 Apr
Activity of potassium channel-blockers in breast cancer.
2003 Jul-Aug
In vivo biodistribution of erythrocytes and polyethyleneglycol-phosphatidylethanolamine micelles carrying the antitumour agent dequalinium.
2003 Sep
Cloning and expression of a small-conductance Ca(2+)-activated K+ channel from the mouse cochlea: coexpression with alpha9/alpha10 acetylcholine receptors.
2004 Apr
Crystal structures of QacR-diamidine complexes reveal additional multidrug-binding modes and a novel mechanism of drug charge neutralization.
2004 Apr 2
The receptor for activated C-kinase-I (RACK-I) anchors activated PKC-beta on melanosomes.
2004 Jul 15
Small conductance Ca2+-activated K+ channels as targets of CNS drug development.
2004 Jun
Study of the involvement of K+ channels in the peripheral antinociception of the kappa-opioid receptor agonist bremazocine.
2004 Jun 28
State-dependent block of CNG channels by dequalinium.
2004 Mar
Approaches to mitochondrial gene therapy.
2004 Sep
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
Mutation of the pore glutamate affects both cytoplasmic and external dequalinium block in the rat olfactory CNGA2 channel.
2005 Jul
Flow injection spectrofluorimetric study of the supramolecular interaction between beta-cyclodextrin and dequalinium chloride and its analytical application.
2005 Jul
Essential roles of Homer-1a in homeostatic regulation of pyramidal cell excitability: a possible link to clinical benefits of electroconvulsive shock.
2005 Jun
Mitochondrial leader sequence--plasmid DNA conjugates delivered into mammalian cells by DQAsomes co-localize with mitochondria.
2005 Oct
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
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
Synthesis, antifungal and haemolytic activity of a series of bis(pyridinium)alkanes.
2007 May 15
[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
Electron crystallography reveals plasticity within the drug binding site of the small multidrug transporter EmrE.
2008 Apr 4
Nanocarrier-assisted sub-cellular targeting to the site of mitochondria improves the pro-apoptotic activity of paclitaxel.
2008 Aug
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
Dequalinium-induced cell death of yeast expressing alpha-synuclein-GFP fusion protein.
2008 Jul
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
Functional analyses reveal an important role for tyrosine residues in the staphylococcal multidrug efflux protein QacA.
2008 Sep 16
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
Effect of dequalinium on the oxidative stress in Plasmodium berghei-infected erythrocytes.
2009 Jun
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
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
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
WHO-DD  
Common Name English
1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM)
Systematic Name English
DEQUALINIUM [WHO-DD]
Common Name English
DEQUALINIUM CATION
Common Name English
Classification Tree Code System Code
WHO-ATC D08AH01
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
NCI_THESAURUS C795
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
WHO-ATC R02AA02
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
WHO-VATC QR02AA02
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
WHO-ATC G01AC05
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
WHO-VATC QG01AC05
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
WHO-VATC QD08AH01
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
Code System Code Type Description
EVMPD
SUB01590MIG
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
WIKIPEDIA
DEQUALINIUM
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
EPA CompTox
6707-58-0
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
FDA UNII
E7QC7V26B8
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
PUBCHEM
2993
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
DRUG CENTRAL
4376
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
NCI_THESAURUS
C83661
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
RXCUI
3226
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY RxNorm
CAS
6707-58-0
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
DRUG BANK
DB04209
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
MESH
D003868
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY