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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
134361
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
534
Target ID: heteromeric CNGA1+CNGB1 channels
Blocker
534
Inhibitor
8228
 11.5 µM [Ki]
Inhibitor
8228
 14.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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.
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.
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.
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

PubMed

TitleDatePubMed
Towards mitochondrial gene therapy: DQAsomes as a strategy.
2001
Structural mechanisms of QacR induction and multidrug recognition.
2001 Dec 7
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
Voltage-gated potassium ion channels in colon cancer.
2002 Sep-Oct
Cloning and expression of a small-conductance Ca(2+)-activated K+ channel from the mouse cochlea: coexpression with alpha9/alpha10 acetylcholine receptors.
2004 Apr
Additive antinociceptive effect of the combination of diazoxide, an activator of ATP-sensitive K+ channels, and sodium nitroprusside and dibutyryl-cGMP.
2004 Apr 5
The influence of hypotonicity on large-conductance calcium-activated potassium channels in human retinal pigment epithelial cells.
2004 Dec
The receptor for activated C-kinase-I (RACK-I) anchors activated PKC-beta on melanosomes.
2004 Jul 15
Study of the involvement of K+ channels in the peripheral antinociception of the kappa-opioid receptor agonist bremazocine.
2004 Jun 28
Tetraethylammonium exacerbates ischemic neuronal injury in rat cerebrocortical slice cultures.
2005 Jan 31
Flow injection spectrofluorimetric study of the supramolecular interaction between beta-cyclodextrin and dequalinium chloride and its analytical application.
2005 Jul
Pharmacology of acetylcholine-mediated cell signaling in the lateral line organ following efferent stimulation.
2005 May
[Treatment of urogenital infections in lower part of the genital organs in pregnant women which are at risk of miscarriage].
2006 Apr-May
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
Potassium channel openers accelerate epidermal barrier recovery.
2007 Nov
Synthesis and radioligand binding studies of bis-isoquinolinium derivatives as small conductance Ca(2+)-activated K(+) channel blockers.
2007 Oct 18
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
Electron crystallography reveals plasticity within the drug binding site of the small multidrug transporter EmrE.
2008 Apr 4
Dequalinium-induced cell death of yeast expressing alpha-synuclein-GFP fusion protein.
2008 Jul
Molecular and cellular basis of small--and intermediate-conductance, calcium-activated potassium channel function in the brain.
2008 Oct
Involvement of ATP-sensitive K(+) channels in the peripheral antinociceptive effect induced by the alpha(2)-adrenoceptor agonist xylazine.
2009 Dec
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.
2009 Sep 14
Alpha-tocopherol transfer protein disruption confers resistance to malarial infection in mice.
2010 Apr 19
[The treatment of MRSA colonized middle ear; case report and literature review].
2010 Jul
Identification of a κ-opioid agonist as a potent and selective lead for drug development against human African trypanosomiasis.
2010 Nov 15
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 Thu Jul 06 13:36:09 UTC 2023
Edited
by admin
on Thu Jul 06 13:36:09 UTC 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 Thu Jul 06 13:36:09 UTC 2023 , Edited by admin on Thu Jul 06 13:36:09 UTC 2023
PRIMARY
SMS_ID
100000087752
Created by admin on Thu Jul 06 13:36:09 UTC 2023 , Edited by admin on Thu Jul 06 13:36:09 UTC 2023
PRIMARY
CAS
20246-15-5
Created by admin on Thu Jul 06 13:36:09 UTC 2023 , Edited by admin on Thu Jul 06 13:36:09 UTC 2023
PRIMARY
FDA UNII
89J4L3V7VP
Created by admin on Thu Jul 06 13:36:09 UTC 2023 , Edited by admin on Thu Jul 06 13:36:09 UTC 2023
PRIMARY
PUBCHEM
57371009
Created by admin on Thu Jul 06 13:36:09 UTC 2023 , Edited by admin on Thu Jul 06 13:36:09 UTC 2023
PRIMARY
ECHA (EC/EINECS)
243-639-2
Created by admin on Thu Jul 06 13:36:09 UTC 2023 , Edited by admin on Thu Jul 06 13:36:09 UTC 2023
PRIMARY
Related Record Type Details
Structure of DEQUALINIUM
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DEQUALINIUM
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