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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 of DEQUALINIUM

SMILES

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

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P29973
Gene ID: 1259.0
Gene Symbol: CNGA1
Target Organism: Homo sapiens (Human)
Target ID: heteromeric CNGA1+CNGB1 channels
11.5 µM [Ki]
14.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
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
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
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
The pharmacology of hSK1 Ca2+-activated K+ channels expressed in mammalian cell lines.
2000 Feb
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
Structural mechanisms of QacR induction and multidrug recognition.
2001 Dec 7
Suramin prevents cerebellar granule cell-death induced by dequalinium.
2001 Feb
Mitochondrial DNA metabolism targeting drugs.
2001 Jul 2
Pharmacological characterisation of the human small conductance calcium-activated potassium channel hSK3 reveals sensitivity to tricyclic antidepressants and antipsychotic phenothiazines.
2001 May
Occupational allergic contact dermatitis from alkylammonium amidobenzoate.
2001 May-Jun
Antimicrobial activity of dequalinium chloride against leading germs of vaginal infections.
2002
DQAsome-mediated delivery of plasmid DNA toward mitochondria in living cells.
2003 Sep 19
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
Small conductance Ca2+-activated K+ channels as targets of CNS drug development.
2004 Jun
Study of the involvement of K+ channels in the peripheral antinociception of the kappa-opioid receptor agonist bremazocine.
2004 Jun 28
State-dependent block of CNG channels by dequalinium.
2004 Mar
Cilostazol, an inhibitor of type 3 phosphodiesterase, stimulates large-conductance, calcium-activated potassium channels in pituitary GH3 cells and pheochromocytoma PC12 cells.
2004 Mar
Approaches to mitochondrial gene therapy.
2004 Sep
Tetraethylammonium exacerbates ischemic neuronal injury in rat cerebrocortical slice cultures.
2005 Jan 31
Mechanisms of relaxing response induced by rat/mouse hemokinin-1 in porcine coronary arteries: roles of potassium ion and nitric oxide.
2007 Aug 13
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
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
[Diagnosis and treatment of infectious pharyngeal inflammation].
2008
Electron crystallography reveals plasticity within the drug binding site of the small multidrug transporter EmrE.
2008 Apr 4
Apical SK potassium channels and Ca2+-dependent anion secretion in endometrial epithelial cells.
2008 Feb 1
Dequalinium-induced cell death of yeast expressing alpha-synuclein-GFP fusion protein.
2008 Jul
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
Determination of antibacterial quaternary ammonium compound in lozenges and human serum by resonance light scattering technique.
2008 Nov 4
Involvement of ATP-sensitive K(+) channels in the peripheral antinociceptive effect induced by the alpha(2)-adrenoceptor agonist xylazine.
2009 Dec
Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening.
2009 Jul
Effect of dequalinium on the oxidative stress in Plasmodium berghei-infected erythrocytes.
2009 Jun
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
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
Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents.
2010 Jul
Re-engineering the mitochondrial genomes in mammalian cells.
2010 Jun
Identification of a κ-opioid agonist as a potent and selective lead for drug development against human African trypanosomiasis.
2010 Nov 15
Selective targeting of neuroblastoma tumour-initiating cells by compounds identified in stem cell-based small molecule screens.
2010 Sep
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

Sample Use Guides

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 Mon Mar 31 17:58:55 GMT 2025
Edited
by admin
on Mon Mar 31 17:58:55 GMT 2025
Record UNII
E7QC7V26B8
Record Status Validated (UNII)
Record Version
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Name Type Language
DEQUALINIUM
WHO-DD  
Common Name English
DEQUALINIUM CATION
Preferred Name English
1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM)
Systematic Name English
Dequalinium [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC D08AH01
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
NCI_THESAURUS C795
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
WHO-ATC R02AA02
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
WHO-VATC QR02AA02
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
WHO-ATC G01AC05
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
WHO-VATC QG01AC05
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
WHO-VATC QD08AH01
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
Code System Code Type Description
EVMPD
SUB01590MIG
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
PRIMARY
WIKIPEDIA
DEQUALINIUM
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID4046941
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
PRIMARY
FDA UNII
E7QC7V26B8
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
PRIMARY
PUBCHEM
2993
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
PRIMARY
DRUG CENTRAL
4376
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
PRIMARY
NCI_THESAURUS
C83661
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
PRIMARY
RXCUI
3226
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
PRIMARY RxNorm
CAS
6707-58-0
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
PRIMARY
DRUG BANK
DB04209
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
PRIMARY
MESH
D003868
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
PRIMARY
SMS_ID
100000087753
Created by admin on Mon Mar 31 17:58:55 GMT 2025 , Edited by admin on Mon Mar 31 17:58:55 GMT 2025
PRIMARY
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ACTIVE MOIETY