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Details

Stereochemistry ACHIRAL
Molecular Formula C30H40N4.2C11H19O2
Molecular Weight 823.2001
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEQUALINIUM UNDECENATE

SMILES

[O-]C(=O)CCCCCCCCC=C.[O-]C(=O)CCCCCCCCC=C.CC1=[N+](CCCCCCCCCC[N+]2=C(C)C=C(N)C3=C2C=CC=C3)C4=C(C=CC=C4)C(N)=C1

InChI

InChIKey=ADVZBZHXUINOFY-UHFFFAOYSA-N
InChI=1S/C30H38N4.2C11H20O2/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*1-2-3-4-5-6-7-8-9-10-11(12)13/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3;2*2H,1,3-10H2,(H,12,13)

HIDE SMILES / InChI
Molecular Formula C11H20O2
Molecular Weight 184.2753
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
cGMP-gated cation channel alpha-1
4
Target ID: P29973
Gene ID: 1259.0
Gene Symbol: CNGA1
Target Organism: Homo sapiens (Human)
Blocker
537
heteromeric CNGA1+CNGB1 channels
4
Target ID: heteromeric CNGA1+CNGB1 channels
Blocker
537
Inhibitor
8297
 11.5 µM [Ki]
Inhibitor
8297
 14.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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.
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.
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.
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

PubMed

TitleDatePubMed
Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds.
2000 Jul 28
Pharmacological characterization of small-conductance Ca(2+)-activated K(+) channels stably expressed in HEK 293 cells.
2000 Mar
Structure and design of polymeric surfactant-based drug delivery systems.
2001 Jun 15
Local treatment of vaginal infections of varying etiology with dequalinium chloride or povidone iodine. A randomised, double-blind, active-controlled, multicentric clinical study.
2002
Antimicrobial activity of dequalinium chloride against leading germs of vaginal infections.
2002
Expression and activity of potassium ion channels in human prostate cancer.
2002 Dec 1
Involvement of ATP-sensitive K(+) channels in the peripheral antinociceptive effect induced by dipyrone.
2002 May 24
Modulation of small conductance calcium-activated potassium (SK) channels: a new challenge in medicinal chemistry.
2003 Apr
Gelsolin suppresses tumorigenicity through inhibiting PKC activation in a human lung cancer cell line, PC10.
2003 Feb 24
Dequalinium: a novel, high-affinity blocker of CNGA1 channels.
2003 Jan
The receptor for activated C-kinase-I (RACK-I) anchors activated PKC-beta on melanosomes.
2004 Jul 15
State-dependent block of CNG channels by dequalinium.
2004 Mar
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
Flow injection spectrofluorimetric study of the supramolecular interaction between beta-cyclodextrin and dequalinium chloride and its analytical application.
2005 Jul
Essential roles of Homer-1a in homeostatic regulation of pyramidal cell excitability: a possible link to clinical benefits of electroconvulsive shock.
2005 Jun
Pharmacology of acetylcholine-mediated cell signaling in the lateral line organ following efferent stimulation.
2005 May
Mitochondrial leader sequence--plasmid DNA conjugates delivered into mammalian cells by DQAsomes co-localize with mitochondria.
2005 Oct
Dequalinium-induced protofibril formation of alpha-synuclein.
2006 Feb 10
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).
2007 Feb
Plasmodium berghei: in vitro and in vivo activity of dequalinium.
2007 Jan
Dequalinium induces cell death in human leukemia cells by early mitochondrial alterations which enhance ROS production.
2007 Jul
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
Synthesis, antifungal and haemolytic activity of a series of bis(pyridinium)alkanes.
2007 May 15
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
Disintegration of amyloid fibrils of alpha-synuclein by dequalinium.
2008 Oct
Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening.
2009 Jul
Real-time analysis of amyloid fibril formation of alpha-synuclein using a fibrillation-state-specific fluorescent probe of JC-1.
2009 Mar 1
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.
2009 Sep 14
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
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

GB 745956
4
US4946849 A
4

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 Dec 16 08:10:30 GMT 2023
Edited
by admin
on Sat Dec 16 08:10:30 GMT 2023
Record UNII
89J4L3V7VP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEQUALINIUM UNDECENATE
WHO-DD  
Common Name English
Dequalinium undecenate [WHO-DD]
Common Name English
QUINALDINIUM, 1,1'-DECAMETHYLENEBIS(4-AMINO-, DI-10-UNDECENOATE
Systematic Name English
DEQUALINIUM DI-10-UNDECENATE
Common Name English
10-UNDECENOIC ACID, ION(1-), 1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM) (2:1)
Systematic Name English
10-UNDECENOIC ACID, ION(1-), 1,1'-(1,10-DECANEDIYL)BIS(4-AMINO-2-METHYLQUINOLINIUM) (2:1)
Systematic Name English
Code System Code Type Description
EVMPD
SUB01593MIG
Created by admin on Sat Dec 16 08:10:30 GMT 2023 , Edited by admin on Sat Dec 16 08:10:30 GMT 2023
PRIMARY
SMS_ID
100000087752
Created by admin on Sat Dec 16 08:10:30 GMT 2023 , Edited by admin on Sat Dec 16 08:10:30 GMT 2023
PRIMARY
CAS
20246-15-5
Created by admin on Sat Dec 16 08:10:30 GMT 2023 , Edited by admin on Sat Dec 16 08:10:30 GMT 2023
PRIMARY
FDA UNII
89J4L3V7VP
Created by admin on Sat Dec 16 08:10:30 GMT 2023 , Edited by admin on Sat Dec 16 08:10:30 GMT 2023
PRIMARY
PUBCHEM
57371009
Created by admin on Sat Dec 16 08:10:30 GMT 2023 , Edited by admin on Sat Dec 16 08:10:30 GMT 2023
PRIMARY
ECHA (EC/EINECS)
243-639-2
Created by admin on Sat Dec 16 08:10:30 GMT 2023 , Edited by admin on Sat Dec 16 08:10:30 GMT 2023
PRIMARY
Related Record Type Details
Structure of DEQUALINIUM
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DEQUALINIUM
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