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Details

Stereochemistry ACHIRAL
Molecular Formula C30H40N4.2Cl
Molecular Weight 527.5724
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEQUALINIUM CHLORIDE

SMILES

Cc1cc(=N)c2ccccc2n1CCCCCCCCCCn3c(C)cc(=N)c4ccccc43.Cl.Cl

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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C30H38N4
Molecular Weight 454.6506
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
Towards mitochondrial gene therapy: DQAsomes as a strategy.
2001
DQAsome/DNA complexes release DNA upon contact with isolated mouse liver mitochondria.
2001 Aug 10
Occupational allergic contact dermatitis from alkylammonium amidobenzoate.
2001 May-Jun
Characterisation of [(125)I]-apamin binding sites in rat brain membranes with HE293 cells transfected with SK channel subtypes.
2001 Sep
Local treatment of vaginal infections of varying etiology with dequalinium chloride or povidone iodine. A randomised, double-blind, active-controlled, multicentric clinical study.
2002
Antimicrobial activity of dequalinium chloride against leading germs of vaginal infections.
2002
Voltage-gated potassium ion channels in colon cancer.
2002 Sep-Oct
Modulation of small conductance calcium-activated potassium (SK) channels: a new challenge in medicinal chemistry.
2003 Apr
Small-conductance calcium-activated K+ channels are expressed in pancreatic islets and regulate glucose responses.
2003 Aug
The selective in vitro cytotoxicity of carcinoma cells by AZT is enhanced by concurrent treatment with delocalized lipophilic cations.
2003 Jul 30
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
The influence of hypotonicity on large-conductance calcium-activated potassium channels in human retinal pigment epithelial cells.
2004 Dec
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
Induction of petite mutants in yeast Saccharomyces cerevisiae by the anticancer drug dequalinium.
2005 May 2
[Treatment of urogenital infections in lower part of the genital organs in pregnant women which are at risk of miscarriage].
2006 Apr-May
Dequalinium-induced protofibril formation of alpha-synuclein.
2006 Feb 10
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
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
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
Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening.
2009 Jul
[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
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

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 Fri Jun 25 21:09:42 UTC 2021
Edited
by admin
on Fri Jun 25 21:09:42 UTC 2021
Record UNII
XYS8INN1I6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEQUALINIUM CHLORIDE
EP   INCI   INN   JAN   MART.   MI   WHO-DD  
INCI   INN  
Official Name English
FLUOMIZIN
Brand Name English
DEQUALINIUM CHLORIDE [MI]
Common Name English
DEQUALINIUM CHLORIDE [MART.]
Common Name English
DEKAMIN
Common Name English
DEQUALINIUM CHLORIDE [INCI]
Common Name English
GNF-PF-5483
Code English
1,1'-(1,10-DECANEDIYL)BIS-(4-AMINO-2-METHYLQUINOLINIUM CHLORIDE)
Common Name English
DEQUALINIUM CHLORIDE [EP MONOGRAPH]
Common Name English
NSC-166454
Code English
BAQD-10
Code English
BAQD 10
Code English
DECAMINE
Common Name English
DEQUALINIUM DICHLORIDE
Common Name English
DEQUALINIUM CHLORIDE [WHO-DD]
Common Name English
1,10-DECAMETHYLENE-BIS(4-AMINOQUINALDINIUM CHLORIDE)
Common Name English
DEQUALINIUM CHLORIDE [INN]
Common Name English
1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM CHLORIDE)
Common Name English
DEQUALINIUM CHLORIDE [JAN]
Common Name English
NORDMAN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C795
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
Code System Code Type Description
INN
746
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
PRIMARY
PUBCHEM
10649
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
PRIMARY
ChEMBL
CHEMBL333826
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
PRIMARY
CAS
522-51-0
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
PRIMARY
EVMPD
SUB06985MIG
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
PRIMARY
DRUG BANK
DBSALT001926
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
PRIMARY
MERCK INDEX
M4184
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
PRIMARY Merck Index
EPA CompTox
522-51-0
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
PRIMARY
FDA UNII
XYS8INN1I6
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
PRIMARY
RXCUI
3120
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C77046
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-330-9
Created by admin on Fri Jun 25 21:09:42 UTC 2021 , Edited by admin on Fri Jun 25 21:09:42 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY