DEQUALINIUM

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 Search

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
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 511
Target ID: heteromeric CNGA1+CNGB1 channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/12508052	Blocker 511
Protein kinase C alpha 18 Target ID: CHEMBL299 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9442087	Inhibitor 7728	11.5 µM [Ki]
Protein kinase C beta 20 Target ID: CHEMBL3045 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9442087	Inhibitor 7728	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 8043	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 8043	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 8043	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 8043	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
Structural mechanisms of QacR induction and multidrug recognition.	2001 Dec 7	11739955
Delocalized lipophilic cations selectively target the mitochondria of carcinoma cells.	2001 Jul 2	11377803
Structure and design of polymeric surfactant-based drug delivery systems.	2001 Jun 15	11516494
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	11561059
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
Gelsolin suppresses tumorigenicity through inhibiting PKC activation in a human lung cancer cell line, PC10.	2003 Feb 24	12592377
Activity of potassium channel-blockers in breast cancer.	2003 Jul-Aug	12926074
Additive antinociceptive effect of the combination of diazoxide, an activator of ATP-sensitive K+ channels, and sodium nitroprusside and dibutyryl-cGMP.	2004 Apr 5	15063156
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
Induction of petite mutants in yeast Saccharomyces cerevisiae by the anticancer drug dequalinium.	2005 May 2	15790492
Effects of the antitumoural dequalinium on NB4 and K562 human leukemia cell lines. Mitochondrial implication in cell death.	2005 Oct	15893819
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
Plasmodium berghei: in vitro and in vivo activity of dequalinium.	2007 Jan	16814285
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
[Diagnosis and treatment of infectious pharyngeal inflammation].	2008	19008844
ETS-1 and ETS-2 are upregulated in a transgenic mouse model of pigmented ocular neoplasm.	2008	18958307
Determination of antibacterial quaternary ammonium compound in lozenges and human serum by resonance light scattering technique.	2008 Nov 4	18585882
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
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.	2009 Sep 14	19750012
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 `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

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