Details
Stereochemistry | ACHIRAL |
Molecular Formula | C30H40N4 |
Molecular Weight | 456.6654 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 2 |
SHOW SMILES / InChI
SMILES
CC1=CC(N)=C2C=CC=CC2=[N+]1CCCCCCCCCC[N+]3=C4C=CC=CC4=C(N)C=C3C
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
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 |
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 |
---|---|---|---|
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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The pharmacology of hSK1 Ca2+-activated K+ channels expressed in mammalian cell lines. | 2000 Feb |
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Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds. | 2000 Jul 28 |
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Pharmacological characterization of small-conductance Ca(2+)-activated K(+) channels stably expressed in HEK 293 cells. | 2000 Mar |
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Structural mechanisms of QacR induction and multidrug recognition. | 2001 Dec 7 |
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Suramin prevents cerebellar granule cell-death induced by dequalinium. | 2001 Feb |
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Mitochondrial DNA metabolism targeting drugs. | 2001 Jul 2 |
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Pharmacological characterisation of the human small conductance calcium-activated potassium channel hSK3 reveals sensitivity to tricyclic antidepressants and antipsychotic phenothiazines. | 2001 May |
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Occupational allergic contact dermatitis from alkylammonium amidobenzoate. | 2001 May-Jun |
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Antimicrobial activity of dequalinium chloride against leading germs of vaginal infections. | 2002 |
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DQAsome-mediated delivery of plasmid DNA toward mitochondria in living cells. | 2003 Sep 19 |
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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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Additive antinociceptive effect of the combination of diazoxide, an activator of ATP-sensitive K+ channels, and sodium nitroprusside and dibutyryl-cGMP. | 2004 Apr 5 |
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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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Small conductance Ca2+-activated K+ channels as targets of CNS drug development. | 2004 Jun |
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Study of the involvement of K+ channels in the peripheral antinociception of the kappa-opioid receptor agonist bremazocine. | 2004 Jun 28 |
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State-dependent block of CNG channels by dequalinium. | 2004 Mar |
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Cilostazol, an inhibitor of type 3 phosphodiesterase, stimulates large-conductance, calcium-activated potassium channels in pituitary GH3 cells and pheochromocytoma PC12 cells. | 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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Mechanisms of relaxing response induced by rat/mouse hemokinin-1 in porcine coronary arteries: roles of potassium ion and nitric oxide. | 2007 Aug 13 |
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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 |
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Synthesis, antifungal and haemolytic activity of a series of bis(pyridinium)alkanes. | 2007 May 15 |
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Potassium channel openers accelerate epidermal barrier recovery. | 2007 Nov |
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Synthesis and radioligand binding studies of bis-isoquinolinium derivatives as small conductance Ca(2+)-activated K(+) channel blockers. | 2007 Oct 18 |
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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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Electron crystallography reveals plasticity within the drug binding site of the small multidrug transporter EmrE. | 2008 Apr 4 |
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Apical SK potassium channels and Ca2+-dependent anion secretion in endometrial epithelial cells. | 2008 Feb 1 |
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Dequalinium-induced cell death of yeast expressing alpha-synuclein-GFP fusion protein. | 2008 Jul |
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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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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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Effect of dequalinium on the oxidative stress in Plasmodium berghei-infected erythrocytes. | 2009 Jun |
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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).
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:58:55 GMT 2025
by
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on
Mon Mar 31 17:58:55 GMT 2025
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Record UNII |
E7QC7V26B8
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Record Status |
Validated (UNII)
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WHO-ATC |
D08AH01
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NCI_THESAURUS |
C795
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R02AA02
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QR02AA02
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G01AC05
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QG01AC05
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WHO-VATC |
QD08AH01
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SUB01590MIG
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DEQUALINIUM
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DTXSID4046941
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E7QC7V26B8
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2993
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4376
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C83661
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3226
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6707-58-0
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DB04209
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D003868
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100000087753
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