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Details

Stereochemistry ACHIRAL
Molecular Formula C30H40N4
Molecular Weight 456.6654
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of DEQUALINIUM

SMILES

CC1=[N+](CCCCCCCCCC[N+]2=C(C)C=C(N)C3=C2C=CC=C3)C4=C(C=CC=C4)C(N)=C1

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 454.6495
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
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
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
Gelsolin suppresses tumorigenicity through inhibiting PKC activation in a human lung cancer cell line, PC10.
2003 Feb 24
The selective in vitro cytotoxicity of carcinoma cells by AZT is enhanced by concurrent treatment with delocalized lipophilic cations.
2003 Jul 30
Activity of potassium channel-blockers in breast cancer.
2003 Jul-Aug
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
The influence of hypotonicity on large-conductance calcium-activated potassium channels in human retinal pigment epithelial cells.
2004 Dec
Small conductance Ca2+-activated K+ channels as targets of CNS drug development.
2004 Jun
State-dependent block of CNG channels by dequalinium.
2004 Mar
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
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
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
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
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
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
Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening.
2009 Jul
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

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 Wed Jul 05 22:59:15 UTC 2023
Edited
by admin
on Wed Jul 05 22:59:15 UTC 2023
Record UNII
E7QC7V26B8
Record Status Validated (UNII)
Record Version
  • Download
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 Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
NCI_THESAURUS C795
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
WHO-ATC R02AA02
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
WHO-VATC QR02AA02
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
WHO-ATC G01AC05
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
WHO-VATC QG01AC05
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
WHO-VATC QD08AH01
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
Code System Code Type Description
EVMPD
SUB01590MIG
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
PRIMARY
WIKIPEDIA
DEQUALINIUM
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
PRIMARY
EPA CompTox
DTXSID4046941
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
PRIMARY
FDA UNII
E7QC7V26B8
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
PRIMARY
PUBCHEM
2993
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
PRIMARY
DRUG CENTRAL
4376
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
PRIMARY
NCI_THESAURUS
C83661
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
PRIMARY
RXCUI
3226
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
PRIMARY RxNorm
CAS
6707-58-0
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
PRIMARY
DRUG BANK
DB04209
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
PRIMARY
MESH
D003868
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
PRIMARY
SMS_ID
100000087753
Created by admin on Wed Jul 05 22:59:15 UTC 2023 , Edited by admin on Wed Jul 05 22:59:15 UTC 2023
PRIMARY
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ACTIVE MOIETY