Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C30H40N4.2C11H19O2 |
| Molecular Weight | 823.2001 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[O-]C(=O)CCCCCCCCC=C.[O-]C(=O)CCCCCCCCC=C.CC1=[N+](CCCCCCCCCC[N+]2=C(C)C=C(N)C3=CC=CC=C23)C4=CC=CC=C4C(N)=C1
InChI
InChIKey=ADVZBZHXUINOFY-UHFFFAOYSA-N
InChI=1S/C30H38N4.2C11H20O2/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*1-2-3-4-5-6-7-8-9-10-11(12)13/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3;2*2H,1,3-10H2,(H,12,13)
| Molecular Formula | C11H20O2 |
| Molecular Weight | 184.2753 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C30H38N4 |
| Molecular Weight | 454.6495 |
| 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) |
|||
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 |
|---|---|---|
| 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. | 2011-08-01 |
|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011-07-14 |
|
| Identification of a κ-opioid agonist as a potent and selective lead for drug development against human African trypanosomiasis. | 2010-11-15 |
|
| Selective targeting of neuroblastoma tumour-initiating cells by compounds identified in stem cell-based small molecule screens. | 2010-09 |
|
| [The treatment of MRSA colonized middle ear; case report and literature review]. | 2010-07 |
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| Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. | 2010-07 |
|
| Re-engineering the mitochondrial genomes in mammalian cells. | 2010-06 |
|
| Alpha-tocopherol transfer protein disruption confers resistance to malarial infection in mice. | 2010-04-19 |
|
| Involvement of ATP-sensitive K(+) channels in the peripheral antinociceptive effect induced by the alpha(2)-adrenoceptor agonist xylazine. | 2009-12 |
|
| Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay. | 2009-09-14 |
|
| Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening. | 2009-07 |
|
| New method for the quantification of dequalinium cations in pharmaceutical samples by absorption and fluorescence diode array thin-layer chromatography. | 2009-06-19 |
|
| Effect of dequalinium on the oxidative stress in Plasmodium berghei-infected erythrocytes. | 2009-06 |
|
| Real-time analysis of amyloid fibril formation of alpha-synuclein using a fibrillation-state-specific fluorescent probe of JC-1. | 2009-03-01 |
|
| Determination of antibacterial quaternary ammonium compound in lozenges and human serum by resonance light scattering technique. | 2008-11-04 |
|
| Disintegration of amyloid fibrils of alpha-synuclein by dequalinium. | 2008-10 |
|
| Molecular and cellular basis of small--and intermediate-conductance, calcium-activated potassium channel function in the brain. | 2008-10 |
|
| Functional analyses reveal an important role for tyrosine residues in the staphylococcal multidrug efflux protein QacA. | 2008-09-16 |
|
| QacR-cation recognition is mediated by a redundancy of residues capable of charge neutralization. | 2008-08-05 |
|
| Nanocarrier-assisted sub-cellular targeting to the site of mitochondria improves the pro-apoptotic activity of paclitaxel. | 2008-08 |
|
| Dequalinium-induced cell death of yeast expressing alpha-synuclein-GFP fusion protein. | 2008-07 |
|
| Bis-tetrahydroisoquinoline derivatives: AG525E1, a new step in the search for non-quaternary non-peptidic small conductance Ca(2+)-activated K(+) channel blockers. | 2008-06-01 |
|
| Electron crystallography reveals plasticity within the drug binding site of the small multidrug transporter EmrE. | 2008-04-04 |
|
| Apical SK potassium channels and Ca2+-dependent anion secretion in endometrial epithelial cells. | 2008-02-01 |
|
| 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 |
|
| Potassium channel openers accelerate epidermal barrier recovery. | 2007-11 |
|
| Synthesis and radioligand binding studies of bis-isoquinolinium derivatives as small conductance Ca(2+)-activated K(+) channel blockers. | 2007-10-18 |
|
| Mechanisms of relaxing response induced by rat/mouse hemokinin-1 in porcine coronary arteries: roles of potassium ion and nitric oxide. | 2007-08-13 |
|
| Dequalinium induces cell death in human leukemia cells by early mitochondrial alterations which enhance ROS production. | 2007-07 |
|
| Synthesis, antifungal and haemolytic activity of a series of bis(pyridinium)alkanes. | 2007-05-15 |
|
| Involvement of chloride channel coupled GABA(C) receptors in the peripheral antinociceptive effect induced by GABA(C) receptor agonist cis-4-aminocrotonic acid. | 2007-03-13 |
|
| Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC). | 2007-02 |
|
| Plasmodium berghei: in vitro and in vivo activity of dequalinium. | 2007-01 |
|
| Inhibition of protein kinase C by dequalinium analogues: structure-activity studies on head group variations. | 2006-12-01 |
|
| [Treatment of urogenital infections in lower part of the genital organs in pregnant women which are at risk of miscarriage]. | 2006-11-15 |
|
| Baclofen, an agonist at peripheral GABAB receptors, induces antinociception via activation of TEA-sensitive potassium channels. | 2006-11 |
|
| Dequalinium-induced protofibril formation of alpha-synuclein. | 2006-02-10 |
|
| Mitochondrial leader sequence--plasmid DNA conjugates delivered into mammalian cells by DQAsomes co-localize with mitochondria. | 2005-10 |
|
| Effects of the antitumoural dequalinium on NB4 and K562 human leukemia cell lines. Mitochondrial implication in cell death. | 2005-10 |
|
| Mutation of the pore glutamate affects both cytoplasmic and external dequalinium block in the rat olfactory CNGA2 channel. | 2005-07 |
|
| Flow injection spectrofluorimetric study of the supramolecular interaction between beta-cyclodextrin and dequalinium chloride and its analytical application. | 2005-07 |
|
| Essential roles of Homer-1a in homeostatic regulation of pyramidal cell excitability: a possible link to clinical benefits of electroconvulsive shock. | 2005-06 |
|
| Induction of petite mutants in yeast Saccharomyces cerevisiae by the anticancer drug dequalinium. | 2005-05-02 |
|
| Pharmacology of acetylcholine-mediated cell signaling in the lateral line organ following efferent stimulation. | 2005-05 |
|
| Tetraethylammonium exacerbates ischemic neuronal injury in rat cerebrocortical slice cultures. | 2005-01-31 |
|
| 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 |
|
| The influence of hypotonicity on large-conductance calcium-activated potassium channels in human retinal pigment epithelial cells. | 2004-12 |
|
| Determination for micro amounts of nucleic acids by a resonance light scattering technique with dequalinium chloride. | 2001-10-31 |
Patents
Sample Use Guides
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
89J4L3V7VP
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| Record Status |
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| Record Version |
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100000087752
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243-639-2
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