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Details

Stereochemistry ACHIRAL
Molecular Formula C30H40N4
Molecular Weight 456.6665
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of DEQUALINIUM

SMILES

Cc1cc(=[NH2+])c2ccccc2n1CCCCCCCCCCn3c(C)cc(=[NH2+])c4ccccc43

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

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

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
Structural mechanisms of QacR induction and multidrug recognition.
2001 Dec 7
Delocalized lipophilic cations selectively target the mitochondria of carcinoma cells.
2001 Jul 2
Structure and design of polymeric surfactant-based drug delivery systems.
2001 Jun 15
The noradrenergic inhibition of an apamin-sensitive, small-conductance Ca2+-activated K+ channel in hypothalamic gamma-aminobutyric acid neurons: pharmacology, estrogen sensitivity, and relevance to the control of the reproductive axis.
2001 Oct
Determination for micro amounts of nucleic acids by a resonance light scattering technique with dequalinium chloride.
2001 Oct 31
Isothermic titration calorimetry to study CMCs of neutral surfactants and of the liposome-forming bolaamphiphile dequalinium.
2002 Feb-May
Gelsolin suppresses tumorigenicity through inhibiting PKC activation in a human lung cancer cell line, PC10.
2003 Feb 24
Activity of potassium channel-blockers in breast cancer.
2003 Jul-Aug
Additive antinociceptive effect of the combination of diazoxide, an activator of ATP-sensitive K+ channels, and sodium nitroprusside and dibutyryl-cGMP.
2004 Apr 5
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
Induction of petite mutants in yeast Saccharomyces cerevisiae by the anticancer drug dequalinium.
2005 May 2
Effects of the antitumoural dequalinium on NB4 and K562 human leukemia cell lines. Mitochondrial implication in cell death.
2005 Oct
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
Plasmodium berghei: in vitro and in vivo activity of dequalinium.
2007 Jan
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
[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
Determination of antibacterial quaternary ammonium compound in lozenges and human serum by resonance light scattering technique.
2008 Nov 4
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
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.
2009 Sep 14
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 06:03:26 UTC 2021
Edited
by admin
on Sat Jun 26 06:03:26 UTC 2021
Record UNII
E7QC7V26B8
Record Status Validated (UNII)
Record Version
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Name Type Language
DEQUALINIUM
WHO-DD  
Common Name English
1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM)
Systematic Name English
DEQUALINIUM [WHO-DD]
Common Name English
DEQUALINIUM CATION
Common Name English
Classification Tree Code System Code
WHO-ATC D08AH01
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
NCI_THESAURUS C795
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
WHO-ATC R02AA02
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
WHO-VATC QR02AA02
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
WHO-ATC G01AC05
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
WHO-VATC QG01AC05
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
WHO-VATC QD08AH01
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
Code System Code Type Description
EVMPD
SUB01590MIG
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
WIKIPEDIA
DEQUALINIUM
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
EPA CompTox
6707-58-0
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
FDA UNII
E7QC7V26B8
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
PUBCHEM
2993
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
DRUG CENTRAL
4376
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
NCI_THESAURUS
C83661
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
RXCUI
3226
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY RxNorm
CAS
6707-58-0
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
DRUG BANK
DB04209
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
MESH
D003868
Created by admin on Sat Jun 26 06:03:26 UTC 2021 , Edited by admin on Sat Jun 26 06:03:26 UTC 2021
PRIMARY
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY