Identification

Summary

Dequalinium is a quaternary ammonium cation antimicrobial agent used to treat common infections of the mouth and throat, as well as vaginal candidiasis.

Generic Name
Dequalinium
DrugBank Accession Number
DB04209
Background

Dequalinium is an antibacterial agent with multi-targeted actions. It also possesses antifungal, antiparasitic, antiviral, anticancer, and neuroprotective properties.9 It is a quaternary ammonium compound,10 as it consists of an amphipathic cation with two aminoquinaldinium rings at both ends of a long hydrophobic hydrocarbon chain. Due to its flexible structure, dequalinium was investigated to build drug and gene delivery systems.9

First used as an antiseptic and disinfectant in the 1950s, dequalinium is still found in various OTC products to treat conditions of oral infections and inflammation.9 It is also used in vaginal tablets to treat bacterial vaginosis.10

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 456.6654
Monoisotopic: 456.3252973
Chemical Formula
C30H40N4
Synonyms
  • 1,1'-(1,10-Decanediyl)bis(4-amino-2-methylquinolinium) dichloride
  • 1,1'-Decamethylenebis(4-aminoquinaldinium chloride)
  • Decamethylenebis(4-aminoquinaldinium chloride)
External IDs
  • LSM-5846

Pharmacology

Indication

Dequalinium is used in several OTC products to treat mouth infections and inflammation, such as tonsillitis, pharyngitis, and gingivitis.9 As vaginal tablets, dequalinium is indicated for the treatment of bacterial vaginosis in adult women under 55 years of age.10

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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

In vitro, dequalinium possesses antimicrobial activity against gram-positive and gram-negative bacteria, yeasts, and protozoa.6 Dequalinium has a rapid bactericidal and fungicidal action.1 The antiparasitic and antiviral properties of dequalinium have also been noted. For example, dequalinium can bind to the membrane-proximal external region (MPER) of the spike envelope of the human immunodeficiency virus HIV-1.9

As with other quaternary ammonium compounds similar to dequalinium, gram-positive bacteria are more sensitive to dequalinium than gram-negative bacteria.6,10 The bactericidal and fungicidal effects of dequalinium can occur within 30 to 60 minutes.7 According to in vitro studies, the minimal inhibitory concentration (MIC) for dequalinium against relevant vaginal pathogens ranges from 0.2 to ≥ 1024 µg/mL.10

There is evidence that dequalinium exhibits anticancer activity in human leukemia cells: dequalinium induces a cytotoxic effect by altering redox balance, downregulating Raf/MEK/ERK1/2 and PI3K/Akt signalling pathways, and promoting apoptosis of leukemic cells.3,4,5 Dequalinium was also shown to block small conductance Ca2+-activated K+ channels, called SK channels, which are often expressed in some cancer cells to play a role in cell proliferation and migration.9 One study showed that dequalinium reduced macrophage motility in mice, inhibiting macrophage infiltration of irradiated tumours and attenuating local metastasis.2

Interestingly, dequalinium was shown to modulate and induce self-oligomerization of alpha-synuclein, a synaptic protein known to cause aggregates in several neurodegenerative disorders. This finding highlights the neuroprotective actions of dequalinium; however, further investigations are warranted as dequalinium is a neurotoxic agent.9

Mechanism of action

Dequalinium has multiple modes of action. Dequalinium absorbs into the bacterial cell surface and diffuses through the cell wall, disrupting bacterial cell permeability.6,9 It is taken up by the bacteria rapidly.9 Once in the bacteria, dequalinium denatures proteins involved in the respiratory chain and glycolysis of bacteria, interfering with bacterial cell metabolism and ribosomal protein synthesis.1,6,9 By inhibiting bacterial F1-ATPase, dequalinium inhibits mitochondrial ATP synthesis and blocks glucose metabolism. These molecular actions ultimately deplete bacterial energy sources.1 As dequalinium accumulates in the mitochondria, it is considered a mitochondrial poison.8,9

Dequalinium can also precipitate nucleic acids, as it can intercalate one of its quinoline chromophores between DNA base pairs.1,9 Depending on the drug concentration, dequalinium can lyse the bacterial cell by promoting osmotic imbalance.1,6

TargetActionsOrganism
AE3 ubiquitin-protein ligase XIAP
antagonist
inhibitor
Humans
UcGMP-gated cation channel alpha-1
blocker
Humans
UCalcium-activated potassium channel subunit alpha-1
inhibitor
Humans
UHTH-type transcriptional regulator QacR
regulator
Staphylococcus aureus
UResponse regulator RamR
regulator
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
UCalmodulin
antagonist
Humans
USmall conductance calcium-activated potassium channel protein 3
blocker
Humans
UProtein kinase C
inhibitor
Humans
UAlpha-synuclein
modulator
Humans
UL-cysteine:1D-myo-inositol 2-amino-2-deoxy-alpha-D-glucopyranoside ligase
inhibitor
Mycobacterium tuberculosis (strain ATCC 25177 / H37Ra)
Absorption

Following vaginal administration, dequalinium is not readily absorbed into the systemic circulation. The concentration of dequalinium chloride in vaginal fluid was 2000 to 4000 mg/L in vitro after dissolution of one vaginal tablet (equivalent of 10 mg dequalinium chloride) in an estimated 2.5 to 5 mg/L of vaginal fluid.10

Volume of distribution

There is no information available.

Protein binding

There is no information available.

Metabolism

There is no information available.

Route of elimination

There is no information available.

Half-life

There is no information available.

Clearance

There is no information available.

Adverse Effects
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Toxicity

The LD50 was 18300 ug/kg following intraperitoneal administration and 70 mg/kg following subcutaneous administration in mice.11 There is limited clinical experience of drug overdose with dequalinium. While dequalinium is generally well tolerated and considered as safe at recommended therapeutic doses, dequalinium is a neurotoxic agent and mitochondrial poison. At a high dose in mice, the drug caused damages to the liver and kidneys, and caused renal and hepatic failure.9

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcenocoumarolThe risk or severity of bleeding can be increased when Dequalinium is combined with Acenocoumarol.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Dequalinium.
DicoumarolThe risk or severity of bleeding can be increased when Dequalinium is combined with Dicoumarol.
EstetrolThe therapeutic efficacy of Estetrol can be decreased when used in combination with Dequalinium.
FluindioneThe risk or severity of bleeding can be increased when Dequalinium is combined with Fluindione.
LactuloseThe therapeutic efficacy of Lactulose can be decreased when used in combination with Dequalinium.
PhenindioneThe risk or severity of bleeding can be increased when Dequalinium is combined with Phenindione.
PhenprocoumonThe risk or severity of bleeding can be increased when Dequalinium is combined with Phenprocoumon.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Dequalinium.
Typhoid vaccineThe therapeutic efficacy of Typhoid vaccine can be decreased when used in combination with Dequalinium.
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dequalinium acetateP8W4UX112S4028-98-2IWYNVAJACBPVLT-UHFFFAOYSA-N
Dequalinium bromideNot AvailableNot AvailableNot applicable
Dequalinium chlorideXYS8INN1I6522-51-0LTNZEXKYNRNOGT-UHFFFAOYSA-N
Dequalinium iodideNot AvailableNot AvailableNot applicable
Dequalinium undecenoateNot AvailableNot AvailableNot applicable
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
VablysTablet10 mgVaginalDuchesnay Inc.2022-05-17Not applicableCanada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AXCEL DEXXON LOZENGESLozengeOralKOTRA PHARMA (M) SDN. BHD.2020-09-08Not applicableMalaysia flag
Citrex DQM Lozenges Lemon Ginger 0.25mgLozenge0.25 mgOralIDAMAN PHARMA MANUFACTURING SDN BHD2020-09-082021-12-12Malaysia flag
Citrex DQM Lozenges Lemon Honey 0.25mgLozengeOralIDAMAN PHARMA MANUFACTURING SDN BHD2020-09-08Not applicableMalaysia flag
Citrex DQM Lozenges Orange 0.25mgLozengeOralIDAMAN PHARMA MANUFACTURING SDN BHD2020-09-08Not applicableMalaysia flag
DELINLozenge0.25 mgOralบริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด2020-06-22Not applicableThailand flag
Dequa 250 mcg LozengesLozengeOralDYNAPHARM (M) SDN BHD2020-09-08Not applicableMalaysia flag
DequadinLozenge0.25 mgOralBoyd Pharmaceuticals Inc.1997-04-01Not applicableCanada flag
DEQUADIN LEMONLozengeOralSTERLING DRUG (MALAYA) SDN. BHD.2020-09-08Not applicableMalaysia flag
DEQUADIN LOZENGE (ORIGINAL)LozengeOralSTERLING DRUG (MALAYA) SDN. BHD.2020-09-08Not applicableMalaysia flag
DEQUADIN LOZENGE LEMONLozengeOralSTERLING DRUG (MALAYA) SDN. BHD.2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DECATYLEN LOZENGEDequalinium chloride (0.25 mg) + Cinchocaine hydrochloride (0.03 mg)LozengeOralAPEX PHARMA MARKETING PTE. LTD.1990-06-25Not applicable
DEQ LOZENGEDequalinium chloride (0.25 mg) + Tyrothricin (1 mg)TabletOralATLANTIC PHARMACEUTICAL (S) PTE LTD1990-01-13Not applicable
Dequonal - LösungDequalinium chloride (0.015 g) + Benzalkonium chloride (0.035 g)SolutionOralChemische Fabrik Kreussler & Co Gmb H1981-06-25Not applicableAustria flag
Eucillin "B" - SalbeDequalinium chloride (4 mg) + Bacitracin (500 IU) + Diphenylpyraline hydrochloride (1 mg)OintmentTopicalSigmapharm Arzneimittel Gmb H1967-07-27Not applicableAustria flag
JASIMENTH C PASTILLESDequalinium chloride (0.45 mg) + Anise oil (0.7 mg) + Ascorbic acid (20 mg) + Levomenthol (1 mg)PastilleOralPRIME PHARMACEUTICAL SDN. BHD.2020-09-08Not applicableMalaysia flag
ดีโตรDequalinium (0.25 MG) + Benzocaine (5 MG)LozengeOralบริษัท เอเชี่ยนยูเนี่ยนแล็บบอราตอรี่ จำกัด จำกัด1987-07-13Not applicableThailand flag
ยาอมดีโทซDequalinium (0.25 MG) + Ascorbic acid (50 MG)LozengeOralบริษัท ไทย พี ดี เคมีคอล จำกัด จำกัด1985-06-29Not applicableThailand flag

Categories

ATC Codes
D08AH01 — DequaliniumR02AA02 — DequaliniumG01AC05 — Dequalinium
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Aminoquinolines and derivatives
Direct Parent
4-aminoquinolines
Alternative Parents
Methylpyridines / Aminopyridines and derivatives / Pyridinium derivatives / Benzenoids / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Hydrocarbon derivatives / Organic cations
Substituents
4-aminoquinoline / Amine / Aminopyridine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Methylpyridine / Organic cation
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinolinium ion (CHEBI:41872)
Affected organisms
  • Candida albicans and other yeasts
  • Trichomonas vaginalis, Giardia duodenalis, and Entamoeba histolytica
  • Bacteria and protozoa
  • Bacteroides
  • Peptostreptococcus

Chemical Identifiers

UNII
E7QC7V26B8
CAS number
6707-58-0
InChI Key
PCSWXVJAIHCTMO-UHFFFAOYSA-P
InChI
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
IUPAC Name
4-amino-1-[10-(4-amino-2-methylquinolin-1-ium-1-yl)decyl]-2-methylquinolin-1-ium
SMILES
CC1=CC(N)=C2C=CC=CC2=[N+]1CCCCCCCCCC[N+]1=C(C)C=C(N)C2=C1C=CC=C2

References

General References
  1. Mendling W, Weissenbacher ER, Gerber S, Prasauskas V, Grob P: Use of locally delivered dequalinium chloride in the treatment of vaginal infections: a review. Arch Gynecol Obstet. 2016 Mar;293(3):469-84. doi: 10.1007/s00404-015-3914-8. Epub 2015 Oct 27. [Article]
  2. Timaner M, Bril R, Kaidar-Person O, Rachman-Tzemah C, Alishekevitz D, Kotsofruk R, Miller V, Nevelsky A, Daniel S, Raviv Z, Rotenberg SA, Shaked Y: Dequalinium blocks macrophage-induced metastasis following local radiation. Oncotarget. 2015 Sep 29;6(29):27537-54. doi: 10.18632/oncotarget.4826. [Article]
  3. Sancho P, Galeano E, Estan MC, Ganan-Gomez I, Boyano-Adanez Mdel C, Garcia-Perez AI: Raf/MEK/ERK signaling inhibition enhances the ability of dequalinium to induce apoptosis in the human leukemic cell line K562. Exp Biol Med (Maywood). 2012 Aug;237(8):933-42. doi: 10.1258/ebm.2012.011423. Epub 2012 Aug 8. [Article]
  4. Garcia-Perez AI, Galeano E, Nieto E, Sancho P: Dequalinium induces human leukemia cell death by affecting the redox balance. Leuk Res. 2011 Oct;35(10):1395-401. doi: 10.1016/j.leukres.2011.03.012. Epub 2011 Apr 8. [Article]
  5. Garcia-Perez AI, Galeano E, Nieto E, Estan MC, Sancho P: Dequalinium induces cytotoxicity in human leukemia NB4 cells by downregulation of Raf/MEK/ERK and PI3K/Akt signaling pathways and potentiation of specific inhibitors of these pathways. Leuk Res. 2014 Jul;38(7):795-803. doi: 10.1016/j.leukres.2014.01.009. Epub 2014 Jan 28. [Article]
  6. Della Casa V, Noll H, Gonser S, Grob P, Graf F, Pohlig G: Antimicrobial activity of dequalinium chloride against leading germs of vaginal infections. Arzneimittelforschung. 2002;52(9):699-705. [Article]
  7. D'Auria FD, Simonetti G, Strippoli V: [Antimicrobial characteristics of a tincture of dequalinium chloride]. Ann Ig. 1989 Sep-Oct;1(5):1227-41. [Article]
  8. Weiss MJ, Wong JR, Ha CS, Bleday R, Salem RR, Steele GD Jr, Chen LB: Dequalinium, a topical antimicrobial agent, displays anticarcinoma activity based on selective mitochondrial accumulation. Proc Natl Acad Sci U S A. 1987 Aug;84(15):5444-8. [Article]
  9. Bailly C: Medicinal applications and molecular targets of dequalinium chloride. Biochem Pharmacol. 2021 Apr;186:114467. doi: 10.1016/j.bcp.2021.114467. Epub 2021 Feb 10. [Article]
  10. Health Canada Approved Drug Products: VABLYS (Dequalinium) Vaginal Tablets [Link]
  11. Cayman Chemical: Dequalinium MSDS [Link]
PubChem Compound
2993
PubChem Substance
46507206
ChemSpider
2886
BindingDB
50048403
RxNav
3226
ChEBI
41872
ChEMBL
CHEMBL333826
ZINC
ZINC000001655706
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
DEQ
Drugs.com
Drugs.com Drug Page
Wikipedia
Dequalinium
PDB Entries
1jt6 / 1oyd / 3arp / 3art / 3br1 / 3br2 / 3bt9 / 3btj / 3vw0

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentVulvovaginal Candidiasis1
3CompletedTreatmentBacterial Vaginosis (BV)1
Not AvailableCompletedNot AvailableBacterial Vaginoses1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
LozengeOral
TabletOral
LozengeOral0.25 mg
LozengeOral
TabletOral0.25 mg
SolutionOral
SprayOral
LozengeOral.25 mg / loz
SolutionBuccal0.5 % w/v
LiquidOral0.5 %
SolutionOral
InsertVaginal
SolutionTopical
OintmentTopical
TabletVaginal10 mg
TabletVaginal
PastilleOral
PastilleOral
SolutionOral1 mg/10ml
LozengeOral0.25 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US4946849No1990-08-072002-10-01US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
boiling point (°C)300https://datasheets.scbt.com/sds/aghs/en/sc-214869.pdf
Predicted Properties
PropertyValueSource
Water Solubility4.77e-07 mg/mLALOGPS
logP0.16ALOGPS
logP-3.6ChemAxon
logS-9ALOGPS
pKa (Strongest Basic)-0.34ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area59.8 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity147 m3·mol-1ChemAxon
Polarizability56.76 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5208
Blood Brain Barrier+0.924
Caco-2 permeable+0.5756
P-glycoprotein substrateSubstrate0.6725
P-glycoprotein inhibitor INon-inhibitor0.7203
P-glycoprotein inhibitor IIInhibitor0.7281
Renal organic cation transporterInhibitor0.6769
CYP450 2C9 substrateNon-substrate0.8745
CYP450 2D6 substrateNon-substrate0.5072
CYP450 3A4 substrateNon-substrate0.5434
CYP450 1A2 substrateNon-inhibitor0.6703
CYP450 2C9 inhibitorNon-inhibitor0.9119
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.6677
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5512
Ames testAMES toxic0.5875
CarcinogenicityNon-carcinogens0.9063
BiodegradationNot ready biodegradable0.9969
Rat acute toxicity2.6736 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.823
hERG inhibition (predictor II)Inhibitor0.9123
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
Inhibitor
General Function
Zinc ion binding
Specific Function
Multi-functional protein which regulates not only caspases and apoptosis, but also modulates inflammatory signaling and immunity, copper homeostasis, mitogenic kinase signaling, cell proliferation,...
Gene Name
XIAP
Uniprot ID
P98170
Uniprot Name
E3 ubiquitin-protein ligase XIAP
Molecular Weight
56684.41 Da
References
  1. Orzaez M, Gortat A, Sancho M, Carbajo RJ, Pineda-Lucena A, Palacios-Rodriguez Y, Perez-Paya E: Characterization of dequalinium as a XIAP antagonist that targets the BIR2 domain. Apoptosis. 2011 May;16(5):460-7. doi: 10.1007/s10495-011-0582-4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Blocker
General Function
Voltage-gated potassium channel activity
Specific Function
Visual signal transduction is mediated by a G-protein coupled cascade using cGMP as second messenger. This protein can be activated by cyclic GMP which leads to an opening of the cation channel and...
Gene Name
CNGA1
Uniprot ID
P29973
Uniprot Name
cGMP-gated cation channel alpha-1
Molecular Weight
79584.825 Da
References
  1. Rosenbaum T, Islas LD, Carlson AE, Gordon SE: Dequalinium: a novel, high-affinity blocker of CNGA1 channels. J Gen Physiol. 2003 Jan;121(1):37-47. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity
Specific Function
Potassium channel activated by both membrane depolarization or increase in cytosolic Ca(2+) that mediates export of K(+). It is also activated by the concentration of cytosolic Mg(2+). Its activati...
Gene Name
KCNMA1
Uniprot ID
Q12791
Uniprot Name
Calcium-activated potassium channel subunit alpha-1
Molecular Weight
137558.115 Da
References
  1. Castle NA, Haylett DG, Morgan JM, Jenkinson DH: Dequalinium: a potent inhibitor of apamin-sensitive K+ channels in hepatocytes and of nicotinic responses in skeletal muscle. Eur J Pharmacol. 1993 May 19;236(2):201-7. [Article]
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Unknown
Actions
Regulator
General Function
Transcriptional repressor of qacA. Binds to IR1, an unusually long 28 bp operator, which is located downstream from the qacA promoter and overlaps its transcription start site. QacR is induced from its IR1 site by binding to one of many structurally dissimilar cationic lipophilic compounds, which are also substrates of QacA.
Specific Function
Dna binding
Gene Name
qacR
Uniprot ID
P0A0N4
Uniprot Name
HTH-type transcriptional regulator QacR
Molecular Weight
22174.175 Da
References
  1. Peters KM, Schuman JT, Skurray RA, Brown MH, Brennan RG, Schumacher MA: QacR-cation recognition is mediated by a redundancy of residues capable of charge neutralization. Biochemistry. 2008 Aug 5;47(31):8122-9. doi: 10.1021/bi8008246. Epub 2008 Jul 11. [Article]
  2. Murray DS, Schumacher MA, Brennan RG: Crystal structures of QacR-diamidine complexes reveal additional multidrug-binding modes and a novel mechanism of drug charge neutralization. J Biol Chem. 2004 Apr 2;279(14):14365-71. doi: 10.1074/jbc.M313870200. Epub 2004 Jan 15. [Article]
Kind
Protein
Organism
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Pharmacological action
Unknown
Actions
Regulator
General Function
A transcription factor required for aerial hyphae formation on rich medium (PubMed:12100547, PubMed:12453210). Activates transcription of ramC. Might be part of a two-component regulatory system (PubMed:12453210). Binds the promoter of ramC (PubMed:12100547, PubMed:12453210). Non-phosphorylated protein cooperatively binds multiple sites in the ramC promoter. Has not been seen to autophosphorylate using the small molecule phosphodonors phosphoramidate, acetyl phosphate or carbamoyl phosphate (PubMed:16051268). Upon low expression suppresses the bald (bld, no aerial hyphae) phenotype of citA but not bldJ mutants; higher expression also suppresses the bldJ mutant as well as several other bld mutations, inducing SapB production even on media where SapB is normally not produced (PubMed:12453210). Expression of the ram locus (ramA, ramB and ramR) induces rapid aerial mycelium formation in S.lividans (PubMed:8206859). Overexpression suppresses the no aerial hyphae phenotype of a chaplin-negative strain, probably by inducing expression of SapB (PubMed:17462011). Overexpression of RamR show there are about 280 genes having at least a threefold increase or fourfold decrease in RNA abundance versus wild-type including gene cluster SCO4072-SCO4075 (PubMed:16925552).
Specific Function
Dna binding
Gene Name
ramR
Uniprot ID
Q7AKE4
Uniprot Name
Response regulator RamR
Molecular Weight
21489.545 Da
References
  1. Bailly C: Medicinal applications and molecular targets of dequalinium chloride. Biochem Pharmacol. 2021 Apr;186:114467. doi: 10.1016/j.bcp.2021.114467. Epub 2021 Feb 10. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Titin binding
Specific Function
Calmodulin mediates the control of a large number of enzymes, ion channels, aquaporins and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number...
Gene Name
CALM1
Uniprot ID
P0DP23
Uniprot Name
Calmodulin
Molecular Weight
16837.47 Da
References
  1. Bailly C: Medicinal applications and molecular targets of dequalinium chloride. Biochem Pharmacol. 2021 Apr;186:114467. doi: 10.1016/j.bcp.2021.114467. Epub 2021 Feb 10. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Blocker
General Function
Small conductance calcium-activated potassium channel activity
Specific Function
Forms a voltage-independent potassium channel activated by intracellular calcium. Activation is followed by membrane hyperpolarization. Thought to regulate neuronal excitability by contributing to ...
Gene Name
KCNN3
Uniprot ID
Q9UGI6
Uniprot Name
Small conductance calcium-activated potassium channel protein 3
Molecular Weight
82025.305 Da
References
  1. Bailly C: Medicinal applications and molecular targets of dequalinium chloride. Biochem Pharmacol. 2021 Apr;186:114467. doi: 10.1016/j.bcp.2021.114467. Epub 2021 Feb 10. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Calcium-activated, phospholipid- and diacylglycerol (DAG)-dependent serine/threonine-protein kinase that is involved in positive and negative regulation of cell proliferation, apoptosis, differenti...

Components:
References
  1. Bailly C: Medicinal applications and molecular targets of dequalinium chloride. Biochem Pharmacol. 2021 Apr;186:114467. doi: 10.1016/j.bcp.2021.114467. Epub 2021 Feb 10. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Modulator
General Function
Not Available
Specific Function
Not Available
Gene Name
SNCA
Uniprot ID
P37840
Uniprot Name
Alpha-synuclein
Molecular Weight
14460.155 Da
References
  1. Bailly C: Medicinal applications and molecular targets of dequalinium chloride. Biochem Pharmacol. 2021 Apr;186:114467. doi: 10.1016/j.bcp.2021.114467. Epub 2021 Feb 10. [Article]
Kind
Protein
Organism
Mycobacterium tuberculosis (strain ATCC 25177 / H37Ra)
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Dequalinium inhibits this enzyme, also known as mycothiol ligase (MshC).
General Function
Catalyzes the ATP-dependent condensation of GlcN-Ins and L-cysteine to form L-Cys-GlcN-Ins.
Specific Function
Atp binding
Gene Name
mshC
Uniprot ID
A5U4F6
Uniprot Name
L-cysteine:1D-myo-inositol 2-amino-2-deoxy-alpha-D-glucopyranoside ligase
Molecular Weight
45594.045 Da
References
  1. Gutierrez-Lugo MT, Baker H, Shiloach J, Boshoff H, Bewley CA: Dequalinium, a new inhibitor of Mycobacterium tuberculosis mycothiol ligase identified by high-throughput screening. J Biomol Screen. 2009 Jul;14(6):643-52. doi: 10.1177/1087057109335743. Epub 2009 Jun 12. [Article]

Transporters

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
Actions
Substrate
General Function
Identical protein binding
Specific Function
AcrA-AcrB-AcrZ-TolC is a drug efflux protein complex with broad substrate specificity that uses the proton motive force to export substrates.Involved in contact-dependent growth inhibition (CDI), a...
Gene Name
acrB
Uniprot ID
P31224
Uniprot Name
Multidrug efflux pump subunit AcrB
Molecular Weight
113572.75 Da
References
  1. Bailly C: Medicinal applications and molecular targets of dequalinium chloride. Biochem Pharmacol. 2021 Apr;186:114467. doi: 10.1016/j.bcp.2021.114467. Epub 2021 Feb 10. [Article]
  2. Yu EW, Aires JR, McDermott G, Nikaido H: A periplasmic drug-binding site of the AcrB multidrug efflux pump: a crystallographic and site-directed mutagenesis study. J Bacteriol. 2005 Oct;187(19):6804-15. doi: 10.1128/JB.187.19.6804-6815.2005. [Article]

Drug created at June 13, 2005 13:24 / Updated at September 29, 2022 07:52