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Details

Stereochemistry ACHIRAL
Molecular Formula C30H40N4.2C11H19O2
Molecular Weight 823.2021
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEQUALINIUM UNDECENATE

SMILES

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

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)

HIDE SMILES / InChI

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

Molecular Formula C11H20O2
Molecular Weight 184.2757
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
Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds.
2000 Jul 28
Towards mitochondrial gene therapy: DQAsomes as a strategy.
2001
DQAsome/DNA complexes release DNA upon contact with isolated mouse liver mitochondria.
2001 Aug 10
Delocalized lipophilic cations selectively target the mitochondria of carcinoma cells.
2001 Jul 2
Pharmacological characterisation of the human small conductance calcium-activated potassium channel hSK3 reveals sensitivity to tricyclic antidepressants and antipsychotic phenothiazines.
2001 May
Characterisation of [(125)I]-apamin binding sites in rat brain membranes with HE293 cells transfected with SK channel subtypes.
2001 Sep
Antimicrobial activity of dequalinium chloride against leading germs of vaginal infections.
2002
Modulation of small conductance calcium-activated potassium (SK) channels: a new challenge in medicinal chemistry.
2003 Apr
Dequalinium: a novel, high-affinity blocker of CNGA1 channels.
2003 Jan
The selective in vitro cytotoxicity of carcinoma cells by AZT is enhanced by concurrent treatment with delocalized lipophilic cations.
2003 Jul 30
Structural basis of multiple drug-binding capacity of the AcrB multidrug efflux pump.
2003 May 9
In vivo biodistribution of erythrocytes and polyethyleneglycol-phosphatidylethanolamine micelles carrying the antitumour agent dequalinium.
2003 Sep
DQAsome-mediated delivery of plasmid DNA toward mitochondria in living cells.
2003 Sep 19
Crystal structures of QacR-diamidine complexes reveal additional multidrug-binding modes and a novel mechanism of drug charge neutralization.
2004 Apr 2
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
Cilostazol, an inhibitor of type 3 phosphodiesterase, stimulates large-conductance, calcium-activated potassium channels in pituitary GH3 cells and pheochromocytoma PC12 cells.
2004 Mar
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
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
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
Mitochondrial leader sequence--plasmid DNA conjugates delivered into mammalian cells by DQAsomes co-localize with mitochondria.
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
Dequalinium induces cell death in human leukemia cells by early mitochondrial alterations which enhance ROS production.
2007 Jul
Potassium channel openers accelerate epidermal barrier recovery.
2007 Nov
[Diagnosis and treatment of infectious pharyngeal inflammation].
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
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
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
New method for the quantification of dequalinium cations in pharmaceutical samples by absorption and fluorescence diode array thin-layer chromatography.
2009 Jun 19
Alpha-tocopherol transfer protein disruption confers resistance to malarial infection in mice.
2010 Apr 19
Selective targeting of neuroblastoma tumour-initiating cells by compounds identified in stem cell-based small molecule screens.
2010 Sep
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 16:35:51 UTC 2021
Edited
by admin
on Sat Jun 26 16:35:51 UTC 2021
Record UNII
89J4L3V7VP
Record Status Validated (UNII)
Record Version
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Name Type Language
DEQUALINIUM UNDECENATE
WHO-DD  
Common Name English
DEQUALINIUM UNDECENATE [WHO-DD]
Common Name English
QUINALDINIUM, 1,1'-DECAMETHYLENEBIS(4-AMINO-, DI-10-UNDECENOATE
Systematic Name English
DEQUALINIUM DI-10-UNDECENATE
Common Name English
10-UNDECENOIC ACID, ION(1-), 1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM) (2:1)
Systematic Name English
10-UNDECENOIC ACID, ION(1-), 1,1'-(1,10-DECANEDIYL)BIS(4-AMINO-2-METHYLQUINOLINIUM) (2:1)
Systematic Name English
Code System Code Type Description
EVMPD
SUB01593MIG
Created by admin on Sat Jun 26 16:35:51 UTC 2021 , Edited by admin on Sat Jun 26 16:35:51 UTC 2021
PRIMARY
CAS
20246-15-5
Created by admin on Sat Jun 26 16:35:51 UTC 2021 , Edited by admin on Sat Jun 26 16:35:51 UTC 2021
PRIMARY
FDA UNII
89J4L3V7VP
Created by admin on Sat Jun 26 16:35:51 UTC 2021 , Edited by admin on Sat Jun 26 16:35:51 UTC 2021
PRIMARY
PUBCHEM
57371009
Created by admin on Sat Jun 26 16:35:51 UTC 2021 , Edited by admin on Sat Jun 26 16:35:51 UTC 2021
PRIMARY
ECHA (EC/EINECS)
243-639-2
Created by admin on Sat Jun 26 16:35:51 UTC 2021 , Edited by admin on Sat Jun 26 16:35:51 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY