Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C30H40N4.2C2H3O2 |
| Molecular Weight | 574.7534 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC([O-])=O.CC([O-])=O.CC1=CC(N)=C2C=CC=CC2=[N+]1CCCCCCCCCC[N+]3=C4C=CC=CC4=C(N)C=C3C
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)
| 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 |
| 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 |
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) |
|||
Target ID: heteromeric CNGA1+CNGB1 channels |
|||
Target ID: CHEMBL299 |
11.5 µM [Ki] | ||
Target ID: CHEMBL3045 |
14.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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. |
|||
| 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. |
|||
| 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. |
|||
| 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 |
|---|---|---|
| Determination for micro amounts of nucleic acids by a resonance light scattering technique with dequalinium chloride. | 2001 Oct 31 |
|
| The influence of hypotonicity on large-conductance calcium-activated potassium channels in human retinal pigment epithelial cells. | 2004 Dec |
|
| 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 |
|
| Tetraethylammonium exacerbates ischemic neuronal injury in rat cerebrocortical slice cultures. | 2005 Jan 31 |
|
| 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 |
|
| Baclofen, an agonist at peripheral GABAB receptors, induces antinociception via activation of TEA-sensitive potassium channels. | 2006 Nov |
|
| Mechanisms of relaxing response induced by rat/mouse hemokinin-1 in porcine coronary arteries: roles of potassium ion and nitric oxide. | 2007 Aug 13 |
|
| 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 |
|
| Potassium channel openers accelerate epidermal barrier recovery. | 2007 Nov |
|
| Synthesis and radioligand binding studies of bis-isoquinolinium derivatives as small conductance Ca(2+)-activated K(+) channel blockers. | 2007 Oct 18 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:46:07 UTC 2023
by
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on
Wed Jul 05 22:46:07 UTC 2023
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| Record UNII |
P8W4UX112S
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C795
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SUB01591MIG
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P8W4UX112S
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223-712-5
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DBSALT002402
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C83662
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DTXSID80193267
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4028-98-2
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19939
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100000087751
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