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 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
Structural mechanisms of QacR induction and multidrug recognition.	2001 Dec 7	11739955
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
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
Characterisation of [(125)I]-apamin binding sites in rat brain membranes with HE293 cells transfected with SK channel subtypes.	2001 Sep	11522325
Antimicrobial activity of dequalinium chloride against leading germs of vaginal infections.	2002	12404886
Expression and activity of potassium ion channels in human prostate cancer.	2002 Dec 1	12183081
Voltage-gated potassium ion channels in colon cancer.	2002 Sep-Oct	12168055
Modulation of small conductance calcium-activated potassium (SK) channels: a new challenge in medicinal chemistry.	2003 Apr	12678783
The selective in vitro cytotoxicity of carcinoma cells by AZT is enhanced by concurrent treatment with delocalized lipophilic cations.	2003 Jul 30	12893431
Cloning and expression of a small-conductance Ca(2+)-activated K+ channel from the mouse cochlea: coexpression with alpha9/alpha10 acetylcholine receptors.	2004 Apr	14657188
Crystal structures of QacR-diamidine complexes reveal additional multidrug-binding modes and a novel mechanism of drug charge neutralization.	2004 Apr 2	14726520
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
The influence of hypotonicity on large-conductance calcium-activated potassium channels in human retinal pigment epithelial cells.	2004 Dec	15684815
The receptor for activated C-kinase-I (RACK-I) anchors activated PKC-beta on melanosomes.	2004 Jul 15	15252133
Small conductance Ca2+-activated K+ channels as targets of CNS drug development.	2004 Jun	15180477
Study of the involvement of K+ channels in the peripheral antinociception of the kappa-opioid receptor agonist bremazocine.	2004 Jun 28	15212969
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
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
Baclofen, an agonist at peripheral GABAB receptors, induces antinociception via activation of TEA-sensitive potassium channels.	2006 Nov	17016510
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).	2007 Feb	17200835
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
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
Nanocarrier-assisted sub-cellular targeting to the site of mitochondria improves the pro-apoptotic activity of paclitaxel.	2008 Aug	18686127
QacR-cation recognition is mediated by a redundancy of residues capable of charge neutralization.	2008 Aug 5	18616285
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
Molecular and cellular basis of small--and intermediate-conductance, calcium-activated potassium channel function in the brain.	2008 Oct	18597044
Functional analyses reveal an important role for tyrosine residues in the staphylococcal multidrug efflux protein QacA.	2008 Sep 16	18793443
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).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:29:28 GMT 2023` Edited by `admin` on `Fri Dec 15 15:29:28 GMT 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