DEQUALINIUM ACETATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C30H40N4.2C2H3O2
Molecular Weight	574.7534
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC([O-])=O.CC([O-])=O.CC1=CC(N)=C2C=CC=CC2=[N+]1CCCCCCCCCC[N+]3=C4C=CC=CC4=C(N)C=C3C

InChI

InChIKey=IWYNVAJACBPVLT-UHFFFAOYSA-N

InChI=1S/C30H38N4.2C2H4O2/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;2*1-2(3)4/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3;2*1H3,(H,3,4)

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
Pharmacological characterization of small-conductance Ca(2+)-activated K(+) channels stably expressed in HEK 293 cells.	2000 Mar	10696100
Activity of potassium channel-blockers in breast cancer.	2003 Jul-Aug	12926074
DQAsome-mediated delivery of plasmid DNA toward mitochondria in living cells.	2003 Sep 19	14499196
Crystal structures of QacR-diamidine complexes reveal additional multidrug-binding modes and a novel mechanism of drug charge neutralization.	2004 Apr 2	14726520
State-dependent block of CNG channels by dequalinium.	2004 Mar	14981138
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
Flow injection spectrofluorimetric study of the supramolecular interaction between beta-cyclodextrin and dequalinium chloride and its analytical application.	2005 Jul	15911412
Induction of petite mutants in yeast Saccharomyces cerevisiae by the anticancer drug dequalinium.	2005 May 2	15790492
[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
[Diagnosis and treatment of infectious pharyngeal inflammation].	2008	19008844
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
Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening.	2009 Jul	19525487
Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents.	2010 Jul	20116850
Identification of a κ-opioid agonist as a potent and selective lead for drug development against human African trypanosomiasis.	2010 Nov 15	20696141
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

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 ACETATE

Official Name

English

QUINOLINIUM, 1,1'-(1,10-DECANEDIYL)BIS(4-AMINO-2-METHYL-, DIACETATE

Systematic Name

English

1,1'-(DECANE-1,10-DIYL)BIS(4-AMINO-2-METHYLQUINOLINIUM) DIACETATE

Systematic Name

English

Dequalinium acetate [WHO-DD]

Common Name

English

DEQUALINIUM ACETATE [INCI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C795