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
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
DescriptionCurator'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
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P29973 Gene ID: 1259.0 Gene Symbol: CNGA1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12508052 |
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Target ID: heteromeric CNGA1+CNGB1 channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/12508052 |
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Target ID: CHEMBL299 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9442087 |
11.5 µM [Ki] | ||
Target ID: CHEMBL3045 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9442087 |
14.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Fluomizin Approved UseDequalinium 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. |
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Curative | Dequadin lozenges Approved UseDequalinium 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. |
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Curative | Dequadin lozenges Approved UseAnginova 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. |
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Curative | Dequadin lozenges Approved UseAnginova 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 |
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Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds. | 2000 Jul 28 |
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Local treatment of vaginal infections of varying etiology with dequalinium chloride or povidone iodine. A randomised, double-blind, active-controlled, multicentric clinical study. | 2002 |
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Antimicrobial activity of dequalinium chloride against leading germs of vaginal infections. | 2002 |
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Expression and activity of potassium ion channels in human prostate cancer. | 2002 Dec 1 |
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Isothermic titration calorimetry to study CMCs of neutral surfactants and of the liposome-forming bolaamphiphile dequalinium. | 2002 Feb-May |
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Modulation of small conductance calcium-activated potassium (SK) channels: a new challenge in medicinal chemistry. | 2003 Apr |
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Cloning and expression of a small-conductance Ca(2+)-activated K+ channel from the mouse cochlea: coexpression with alpha9/alpha10 acetylcholine receptors. | 2004 Apr |
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The influence of hypotonicity on large-conductance calcium-activated potassium channels in human retinal pigment epithelial cells. | 2004 Dec |
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The receptor for activated C-kinase-I (RACK-I) anchors activated PKC-beta on melanosomes. | 2004 Jul 15 |
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State-dependent block of CNG channels by dequalinium. | 2004 Mar |
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Approaches to mitochondrial gene therapy. | 2004 Sep |
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Tetraethylammonium exacerbates ischemic neuronal injury in rat cerebrocortical slice cultures. | 2005 Jan 31 |
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Flow injection spectrofluorimetric study of the supramolecular interaction between beta-cyclodextrin and dequalinium chloride and its analytical application. | 2005 Jul |
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Pharmacology of acetylcholine-mediated cell signaling in the lateral line organ following efferent stimulation. | 2005 May |
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Induction of petite mutants in yeast Saccharomyces cerevisiae by the anticancer drug dequalinium. | 2005 May 2 |
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Effects of the antitumoural dequalinium on NB4 and K562 human leukemia cell lines. Mitochondrial implication in cell death. | 2005 Oct |
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[Treatment of urogenital infections in lower part of the genital organs in pregnant women which are at risk of miscarriage]. | 2006 Apr-May |
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Inhibition of protein kinase C by dequalinium analogues: structure-activity studies on head group variations. | 2006 Dec 1 |
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Dequalinium-induced protofibril formation of alpha-synuclein. | 2006 Feb 10 |
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Baclofen, an agonist at peripheral GABAB receptors, induces antinociception via activation of TEA-sensitive potassium channels. | 2006 Nov |
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Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC). | 2007 Feb |
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Plasmodium berghei: in vitro and in vivo activity of dequalinium. | 2007 Jan |
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Dequalinium induces cell death in human leukemia cells by early mitochondrial alterations which enhance ROS production. | 2007 Jul |
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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 |
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[Diagnosis and treatment of infectious pharyngeal inflammation]. | 2008 |
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ETS-1 and ETS-2 are upregulated in a transgenic mouse model of pigmented ocular neoplasm. | 2008 |
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QacR-cation recognition is mediated by a redundancy of residues capable of charge neutralization. | 2008 Aug 5 |
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Apical SK potassium channels and Ca2+-dependent anion secretion in endometrial epithelial cells. | 2008 Feb 1 |
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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 |
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Determination of antibacterial quaternary ammonium compound in lozenges and human serum by resonance light scattering technique. | 2008 Nov 4 |
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Disintegration of amyloid fibrils of alpha-synuclein by dequalinium. | 2008 Oct |
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Molecular and cellular basis of small--and intermediate-conductance, calcium-activated potassium channel function in the brain. | 2008 Oct |
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Involvement of ATP-sensitive K(+) channels in the peripheral antinociceptive effect induced by the alpha(2)-adrenoceptor agonist xylazine. | 2009 Dec |
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Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening. | 2009 Jul |
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New method for the quantification of dequalinium cations in pharmaceutical samples by absorption and fluorescence diode array thin-layer chromatography. | 2009 Jun 19 |
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Real-time analysis of amyloid fibril formation of alpha-synuclein using a fibrillation-state-specific fluorescent probe of JC-1. | 2009 Mar 1 |
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Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay. | 2009 Sep 14 |
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Alpha-tocopherol transfer protein disruption confers resistance to malarial infection in mice. | 2010 Apr 19 |
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[The treatment of MRSA colonized middle ear; case report and literature review]. | 2010 Jul |
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Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. | 2010 Jul |
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Re-engineering the mitochondrial genomes in mammalian cells. | 2010 Jun |
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Identification of a κ-opioid agonist as a potent and selective lead for drug development against human African trypanosomiasis. | 2010 Nov 15 |
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Selective targeting of neuroblastoma tumour-initiating cells by compounds identified in stem cell-based small molecule screens. | 2010 Sep |
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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 |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2297765
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).
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NCI_THESAURUS |
C795
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208-330-9
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ACTIVE MOIETY
SUBSTANCE RECORD