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Details

Stereochemistry ACHIRAL
Molecular Formula C30H40N4.2C2H3O2
Molecular Weight 574.7547
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEQUALINIUM ACETATE

SMILES

Cc1cc(=N)c2ccccc2n1CCCCCCCCCCn3c(C)cc(=N)c4ccccc43.CC(=O)O.CC(=O)O

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 454.6506
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Additive antinociceptive effect of the combination of diazoxide, an activator of ATP-sensitive K+ channels, and sodium nitroprusside and dibutyryl-cGMP.
2004 Apr 5
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
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
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
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
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
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
Potassium channel openers accelerate epidermal barrier recovery.
2007 Nov
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
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
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).
Substance Class Chemical
Created
by admin
on Sat Jun 26 10:46:55 UTC 2021
Edited
by admin
on Sat Jun 26 10:46:55 UTC 2021
Record UNII
P8W4UX112S
Record Status Validated (UNII)
Record Version
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Name Type Language
DEQUALINIUM ACETATE
INCI   WHO-DD  
INCI  
Official Name English
DEQUALINIUM ACETATE [WHO-DD]
Common Name English
QUINOLINIUM, 1,1'-(1,10-DECANEDIYL)BIS(4-AMINO-2-METHYL-, DIACETATE
Systematic Name English
1,1'-(DECANE-1,10-DIYL)BIS(4-AMINO-2-METHYLQUINOLINIUM) DIACETATE
Systematic Name English
DEQUALINIUM ACETATE [INCI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C795
Created by admin on Sat Jun 26 10:46:55 UTC 2021 , Edited by admin on Sat Jun 26 10:46:55 UTC 2021
Code System Code Type Description
EVMPD
SUB01591MIG
Created by admin on Sat Jun 26 10:46:55 UTC 2021 , Edited by admin on Sat Jun 26 10:46:55 UTC 2021
PRIMARY
FDA UNII
P8W4UX112S
Created by admin on Sat Jun 26 10:46:55 UTC 2021 , Edited by admin on Sat Jun 26 10:46:55 UTC 2021
PRIMARY
ECHA (EC/EINECS)
223-712-5
Created by admin on Sat Jun 26 10:46:55 UTC 2021 , Edited by admin on Sat Jun 26 10:46:55 UTC 2021
PRIMARY
DRUG BANK
DBSALT002402
Created by admin on Sat Jun 26 10:46:55 UTC 2021 , Edited by admin on Sat Jun 26 10:46:55 UTC 2021
PRIMARY
NCI_THESAURUS
C83662
Created by admin on Sat Jun 26 10:46:55 UTC 2021 , Edited by admin on Sat Jun 26 10:46:55 UTC 2021
PRIMARY
EPA CompTox
4028-98-2
Created by admin on Sat Jun 26 10:46:55 UTC 2021 , Edited by admin on Sat Jun 26 10:46:55 UTC 2021
PRIMARY
CAS
4028-98-2
Created by admin on Sat Jun 26 10:46:55 UTC 2021 , Edited by admin on Sat Jun 26 10:46:55 UTC 2021
PRIMARY
PUBCHEM
19939
Created by admin on Sat Jun 26 10:46:55 UTC 2021 , Edited by admin on Sat Jun 26 10:46:55 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY