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

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
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 534
Target ID: heteromeric CNGA1+CNGB1 channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/12508052	Blocker 534
Protein kinase C alpha 20 Target ID: CHEMBL299 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9442087	Inhibitor 8228	11.5 µM [Ki]
Protein kinase C beta 21 Target ID: CHEMBL3045 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9442087	Inhibitor 8228	14.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Bacterial vaginosis 11 Sources: https://www.drugs.com/uk/fluomizin-10-mg-vaginal-tablets-leaflet.html http://adisinsight.springer.com/trials/700249655	Curative	Approved 8360	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 8360	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 8360	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 8360	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
Determination for micro amounts of nucleic acids by a resonance light scattering technique with dequalinium chloride.	2001 Oct 31	18968413
Isothermic titration calorimetry to study CMCs of neutral surfactants and of the liposome-forming bolaamphiphile dequalinium.	2002 Feb-May	12604038
Modulation of small conductance calcium-activated potassium (SK) channels: a new challenge in medicinal chemistry.	2003 Apr	12678783
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
The influence of hypotonicity on large-conductance calcium-activated potassium channels in human retinal pigment epithelial cells.	2004 Dec	15684815
Small conductance Ca2+-activated K+ channels as targets of CNS drug development.	2004 Jun	15180477
State-dependent block of CNG channels by dequalinium.	2004 Mar	14981138
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
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	16164036
Tetraethylammonium exacerbates ischemic neuronal injury in rat cerebrocortical slice cultures.	2005 Jan 31	15680257
Essential roles of Homer-1a in homeostatic regulation of pyramidal cell excitability: a possible link to clinical benefits of electroconvulsive shock.	2005 Jun	16026461
Pharmacology of acetylcholine-mediated cell signaling in the lateral line organ following efferent stimulation.	2005 May	15615825
Mitochondrial leader sequence--plasmid DNA conjugates delivered into mammalian cells by DQAsomes co-localize with mitochondria.	2005 Oct	16154389
[Treatment of urogenital infections in lower part of the genital organs in pregnant women which are at risk of miscarriage].	2006 Apr-May	17100185
Inhibition of protein kinase C by dequalinium analogues: structure-activity studies on head group variations.	2006 Dec 1	16962331
Dequalinium-induced protofibril formation of alpha-synuclein.	2006 Feb 10	16330551
Baclofen, an agonist at peripheral GABAB receptors, induces antinociception via activation of TEA-sensitive potassium channels.	2006 Nov	17016510
Mechanisms of relaxing response induced by rat/mouse hemokinin-1 in porcine coronary arteries: roles of potassium ion and nitric oxide.	2007 Aug 13	17560993
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).	2007 Feb	17200835
Plasmodium berghei: in vitro and in vivo activity of dequalinium.	2007 Jan	16814285
Dequalinium induces cell death in human leukemia cells by early mitochondrial alterations which enhance ROS production.	2007 Jul	17250890
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	17316706
Synthesis, antifungal and haemolytic activity of a series of bis(pyridinium)alkanes.	2007 May 15	17383187
Potassium channel openers accelerate epidermal barrier recovery.	2007 Nov	17916210
Synthesis and radioligand binding studies of bis-isoquinolinium derivatives as small conductance Ca(2+)-activated K(+) channel blockers.	2007 Oct 18	17867663
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
ETS-1 and ETS-2 are upregulated in a transgenic mouse model of pigmented ocular neoplasm.	2008	18958307
Electron crystallography reveals plasticity within the drug binding site of the small multidrug transporter EmrE.	2008 Apr 4	18295794
Apical SK potassium channels and Ca2+-dependent anion secretion in endometrial epithelial cells.	2008 Feb 1	18048454
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
Disintegration of amyloid fibrils of alpha-synuclein by dequalinium.	2008 Oct	18691634
Functional analyses reveal an important role for tyrosine residues in the staphylococcal multidrug efflux protein QacA.	2008 Sep 16	18793443
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
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
Identification of a κ-opioid agonist as a potent and selective lead for drug development against human African trypanosomiasis.	2010 Nov 15	20696141
Selective targeting of neuroblastoma tumour-initiating cells by compounds identified in stem cell-based small molecule screens.	2010 Sep	20721990
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).

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

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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