U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C30H40N4.2Cl
Molecular Weight 527.571
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEQUALINIUM CHLORIDE

SMILES

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

InChI

InChIKey=LTNZEXKYNRNOGT-UHFFFAOYSA-N
InChI=1S/C30H38N4.2ClH/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;2*1H

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

Molecular Formula ClH
Molecular Weight 36.461
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
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
Towards mitochondrial gene therapy: DQAsomes as a strategy.
2001
Suramin prevents cerebellar granule cell-death induced by dequalinium.
2001 Feb
Occupational allergic contact dermatitis from alkylammonium amidobenzoate.
2001 May-Jun
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
Determination for micro amounts of nucleic acids by a resonance light scattering technique with dequalinium chloride.
2001 Oct 31
Isothermic titration calorimetry to study CMCs of neutral surfactants and of the liposome-forming bolaamphiphile dequalinium.
2002 Feb-May
Small-conductance calcium-activated K+ channels are expressed in pancreatic islets and regulate glucose responses.
2003 Aug
In vivo biodistribution of erythrocytes and polyethyleneglycol-phosphatidylethanolamine micelles carrying the antitumour agent dequalinium.
2003 Sep
DQAsome-mediated delivery of plasmid DNA toward mitochondria in living cells.
2003 Sep 19
Crystal structures of QacR-diamidine complexes reveal additional multidrug-binding modes and a novel mechanism of drug charge neutralization.
2004 Apr 2
Study of the involvement of K+ channels in the peripheral antinociception of the kappa-opioid receptor agonist bremazocine.
2004 Jun 28
Cilostazol, an inhibitor of type 3 phosphodiesterase, stimulates large-conductance, calcium-activated potassium channels in pituitary GH3 cells and pheochromocytoma PC12 cells.
2004 Mar
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
Baclofen, an agonist at peripheral GABAB receptors, induces antinociception via activation of TEA-sensitive potassium channels.
2006 Nov
Mechanisms of relaxing response induced by rat/mouse hemokinin-1 in porcine coronary arteries: roles of potassium ion and nitric oxide.
2007 Aug 13
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).
2007 Feb
Potassium channel openers accelerate epidermal barrier recovery.
2007 Nov
Apical SK potassium channels and Ca2+-dependent anion secretion in endometrial epithelial cells.
2008 Feb 1
Functional analyses reveal an important role for tyrosine residues in the staphylococcal multidrug efflux protein QacA.
2008 Sep 16
Involvement of ATP-sensitive K(+) channels in the peripheral antinociceptive effect induced by the alpha(2)-adrenoceptor agonist xylazine.
2009 Dec
Effect of dequalinium on the oxidative stress in Plasmodium berghei-infected erythrocytes.
2009 Jun
Alpha-tocopherol transfer protein disruption confers resistance to malarial infection in mice.
2010 Apr 19
Re-engineering the mitochondrial genomes in mammalian cells.
2010 Jun
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 Fri Dec 15 15:00:55 GMT 2023
Edited
by admin
on Fri Dec 15 15:00:55 GMT 2023
Record UNII
XYS8INN1I6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEQUALINIUM CHLORIDE
EP   INCI   INN   JAN   MART.   MI   WHO-DD  
INCI   INN  
Official Name English
FLUOMIZIN
Brand Name English
DEQUALINIUM CHLORIDE [MI]
Common Name English
DEQUALINIUM CHLORIDE [MART.]
Common Name English
DEKAMIN
Common Name English
DEQUALINIUM CHLORIDE [INCI]
Common Name English
GNF-PF-5483
Code English
1,1'-(1,10-DECANEDIYL)BIS-(4-AMINO-2-METHYLQUINOLINIUM CHLORIDE)
Common Name English
DEQUALINIUM CHLORIDE [EP MONOGRAPH]
Common Name English
NSC-166454
Code English
Dequalinium chloride [WHO-DD]
Common Name English
BAQD-10
Code English
BAQD 10
Code English
DECAMINE
Common Name English
DEQUALINIUM DICHLORIDE
Common Name English
1,10-DECAMETHYLENE-BIS(4-AMINOQUINALDINIUM CHLORIDE)
Common Name English
dequalinium chloride [INN]
Common Name English
1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM CHLORIDE)
Common Name English
DEQUALINIUM CHLORIDE [JAN]
Common Name English
NORDMAN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C795
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
Code System Code Type Description
NSC
166454
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
INN
746
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
PUBCHEM
10649
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
ChEMBL
CHEMBL333826
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
CHEBI
31466
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
CAS
522-51-0
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
SMS_ID
100000091069
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
EVMPD
SUB06985MIG
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
DRUG BANK
DBSALT001926
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
MERCK INDEX
m4184
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID3045144
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
FDA UNII
XYS8INN1I6
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
RXCUI
3120
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C77046
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-330-9
Created by admin on Fri Dec 15 15:00:56 GMT 2023 , Edited by admin on Fri Dec 15 15:00:56 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY