DEQUALINIUM

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 Search

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

Description
Sources: https://www.drugs.com/uk/fluomizin-10-mg-vaginal-tablets-leaflet.html
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
cGMP-gated cation channel alpha-1 4 Target ID: P29973 Gene ID: 1259.0 Gene Symbol: CNGA1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12508052	Blocker 537
heteromeric CNGA1+CNGB1 channels 4 Target ID: heteromeric CNGA1+CNGB1 channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/12508052	Blocker 537
Protein kinase C alpha 20 Target ID: CHEMBL299 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9442087	Inhibitor 8297	11.5 µM [Ki]
Protein kinase C beta 21 Target ID: CHEMBL3045 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9442087	Inhibitor 8297	14.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Bacterial vaginosis 10 Sources: https://www.drugs.com/uk/fluomizin-10-mg-vaginal-tablets-leaflet.html http://adisinsight.springer.com/trials/700249655	Curative	Approved 8429	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.
Oral thrush 5 Sources: http://www.netdoctor.co.uk/medicines/mouth-and-teeth/a6534/dequadin-lozenges-dequalinium/	Curative	Approved 8429	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.
Aphthous ulcers 10 Sources: http://www.netdoctor.co.uk/medicines/mouth-and-teeth/a6534/dequadin-lozenges-dequalinium/	Curative	Approved 8429	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.
Sore throat 18 Sources: http://www.netdoctor.co.uk/medicines/mouth-and-teeth/a6534/dequadin-lozenges-dequalinium/	Curative	Approved 8429	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

Title	Date	PubMed
The pharmacology of hSK1 Ca2+-activated K+ channels expressed in mammalian cell lines.	2000 Feb	10683185
Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds.	2000 Jul 28	10915830
Pharmacological characterization of small-conductance Ca(2+)-activated K(+) channels stably expressed in HEK 293 cells.	2000 Mar	10696100
Towards mitochondrial gene therapy: DQAsomes as a strategy.	2001	11378519
DQAsome/DNA complexes release DNA upon contact with isolated mouse liver mitochondria.	2001 Aug 10	11489326
Mitochondrial DNA metabolism targeting drugs.	2001 Jul 2	11377810
Cationic bolasomes with delocalized charge centers as mitochondria-specific DNA delivery systems.	2001 Jul 2	11377808
Delocalized lipophilic cations selectively target the mitochondria of carcinoma cells.	2001 Jul 2	11377803
Occupational allergic contact dermatitis from alkylammonium amidobenzoate.	2001 May-Jun	11358732
Expression and activity of potassium ion channels in human prostate cancer.	2002 Dec 1	12183081
Involvement of ATP-sensitive K(+) channels in the peripheral antinociceptive effect induced by dipyrone.	2002 May 24	12191581
Small-conductance calcium-activated K+ channels are expressed in pancreatic islets and regulate glucose responses.	2003 Aug	12882916
Gelsolin suppresses tumorigenicity through inhibiting PKC activation in a human lung cancer cell line, PC10.	2003 Feb 24	12592377
The selective in vitro cytotoxicity of carcinoma cells by AZT is enhanced by concurrent treatment with delocalized lipophilic cations.	2003 Jul 30	12893431
Activity of potassium channel-blockers in breast cancer.	2003 Jul-Aug	12926074
Structural basis of multiple drug-binding capacity of the AcrB multidrug efflux pump.	2003 May 9	12738864
In vivo biodistribution of erythrocytes and polyethyleneglycol-phosphatidylethanolamine micelles carrying the antitumour agent dequalinium.	2003 Sep	12957627
DQAsome-mediated delivery of plasmid DNA toward mitochondria in living cells.	2003 Sep 19	14499196
Small conductance Ca2+-activated K+ channels as targets of CNS drug development.	2004 Jun	15180477
Cilostazol, an inhibitor of type 3 phosphodiesterase, stimulates large-conductance, calcium-activated potassium channels in pituitary GH3 cells and pheochromocytoma PC12 cells.	2004 Mar	14645120
Approaches to mitochondrial gene therapy.	2004 Sep	15384945
Flow injection spectrofluorimetric study of the supramolecular interaction between beta-cyclodextrin and dequalinium chloride and its analytical application.	2005 Jul	15911412
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	21655370
[Diagnosis and treatment of infectious pharyngeal inflammation].	2008	19008844
Dequalinium-induced cell death of yeast expressing alpha-synuclein-GFP fusion protein.	2008 Jul	18322792
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	18436444
Molecular and cellular basis of small--and intermediate-conductance, calcium-activated potassium channel function in the brain.	2008 Oct	18597044
Involvement of ATP-sensitive K(+) channels in the peripheral antinociceptive effect induced by the alpha(2)-adrenoceptor agonist xylazine.	2009 Dec	20019444
Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening.	2009 Jul	19525487
Effect of dequalinium on the oxidative stress in Plasmodium berghei-infected erythrocytes.	2009 Jun	19205739
New method for the quantification of dequalinium cations in pharmaceutical samples by absorption and fluorescence diode array thin-layer chromatography.	2009 Jun 19	19446824
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.	2009 Sep 14	19750012
Alpha-tocopherol transfer protein disruption confers resistance to malarial infection in mice.	2010 Apr 19	20403155
[The treatment of MRSA colonized middle ear; case report and literature review].	2010 Jul	20617476
Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents.	2010 Jul	20116850
Re-engineering the mitochondrial genomes in mammalian cells.	2010 Jun	21189990
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	21548882
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

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).

Name

Type

Language

DEQUALINIUM

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