Dequalinium
Identification
- Name
- Dequalinium
- Accession Number
- DB04209
- Description
Dequalinium is a quaternary ammonium cation that contains two quaternary quinolinium units linked by an N-decylene chain. It is an antiseptic and disinfectant agent with a broad bactericidal and fungicidal activity. It is most commonly available as a dichloride salt but is available as other various salts as well. It is used in wound dressings and mouth infections and may also have antifungal action, but may associate with skin ulceration. Dequalinium chloride is used as an active ingredient in tablets as Fluomizin for vaginal bacterial infections and in topical bacteriostat formulation as Dequadin. It has been studied for use in treatment of malaria and acute promyelocytic leukemia. Its multiple mode of action is thought to reduce the risk of resistance of pathogens.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Dequalinium (DB04209)
- 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
Effective local treatment as vaginal tablets for infections such as fluor vaginalis, bacterial vaginosis, aerobic vaginitis, vulvo-vaginal candidiasis and trichomoniasis. Used as a topical antimicrobial agent.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Dequalinium is an antimicrobial against Gram negative and positive bacteria, yeast and protozoa. It primarily mediates this action by increasing the cell permeability with subsequent loss of enzyme activity under a rapid bactericidal and fungicidal action. The enzymatic inactivation initially might be reversible but becomes irreversible after a longer contact time between the drug and bacteria 1. The bactericidal and fungicidal effect of dequalinium chloride has been demonstrated to occur within 30–60 min 7. Dequalinium targets a broad spectrum of microorganisms including aerobic and anaerobic bacteria, as well as Candida species.
- Mechanism of action
Dequalinium has a multiple mode of action. It disrupts the cell permeability of the bacteria by absorbing onto the bacterial cell surface and diffusing across the membrane. It also binds to the cytoplasmic membrane with subsequent formation of complexes and protein precipitation and lyses the membrane in adequate concentrations, perturbing osmotic exchange. Loss of normal enzymatic activity is achieved through several different processes. Denaturation of proteins results in inhibition of bacterial cell metabolism. Disruption of bacterial energy production is mediated through inhibition of glucose metabolism and inhibition of mitochondrial ATP synthesis via inhibition of bacterial F1-ATPase. Protein synthesis is also terminated at the level of ribosomes. Bacterial nucleic acids are also affected through direct binding of the drug to DNA in vitro, and precipitation of cytoplasmic material with nucleic acids being the most sensitive 1. The cationic form of dequalinium accumulates in the mitochondria and promotes anticancer activity in human leukemia cells. It mediates a cytotoxic effect by altering redox balance in cells and downregulating Raf/MEK/ERK1/2 and PI3K/Akt signaling pathways in these cells which leads to cell death by apoptosis and/or necrosis 3,4,5. Dequalinium inhibits mycothiol ligase activity in Mycobacterium tuberculosis strains 9.
Target Actions Organism UAcriflavine resistance protein B Not Available Escherichia coli (strain K12) AE3 ubiquitin-protein ligase XIAP antagonistinhibitorHumans UcGMP-gated cation channel alpha-1 blockerHumans UCalcium-activated potassium channel subunit alpha-1 inhibitorHumans UHTH-type transcriptional regulator QacR Not Available Staphylococcus aureus - Absorption
The degree of absorption is minimal in case of topical or vaginal administration thus systemic exposure is negligible. <0.1 % is absorbed systemically after oral administration.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
The oral LD50 value of dequalinium chloride for mouse is 300mg/kg. Lethal dose (LD50) of a single intraperitoneal administration in a murine model system is 18.3 mg/kg. The majority of the adverse reactions of vaginal dequalinium tablets in clinical studies (about 90 %) were local reactions, particularly vaginal discharge, vulvovaginal pruritus, and a vaginal burning sensation. Dequalinuim is not reported to possess embryo-foetal toxicity at clinically relevant doses.
- Affected organisms
- Candida albicans and other yeasts
- Trichomonas vaginalis, Giardia duodenalis, and Entamoeba histolytica
- Bacteria and protozoa
- Bacteroides
- Peptostreptococcus
- 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.Not Available
- Food Interactions
- No interactions found.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Dequalinium acetate P8W4UX112S 4028-98-2 IWYNVAJACBPVLT-UHFFFAOYSA-N Dequalinium bromide Not Available Not Available Not applicable Dequalinium chloride XYS8INN1I6 522-51-0 LTNZEXKYNRNOGT-UHFFFAOYSA-N Dequalinium iodide Not Available Not Available Not applicable Dequalinium undecenoate Not Available Not Available Not applicable - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataDequadin Lozenge Oral Boyd Pharmaceuticals Inc. 1997-04-01 Not applicable Canada 
Dequadin Mint Loz 0.25mg Lozenge Oral Glaxo Canada Inc 1985-12-31 1998-07-30 Canada Dequadin Oral Paint Solution Buccal Boyd Pharmaceuticals Inc. 1995-12-31 Not applicable Canada Dequadin Oral Paint .5% Liquid Oral Glaxo Canada Inc 1958-12-31 1996-09-10 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- D08AH01 — Dequalinium
- D08AH — Quinoline derivatives
- D08A — ANTISEPTICS AND DISINFECTANTS
- D08 — ANTISEPTICS AND DISINFECTANTS
- D — DERMATOLOGICALS
- Drug Categories
- Anti-Infective Agents
- Anti-Infective Agents, Local
- Antiseptics and Disinfectants
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Heterocyclic Compounds, Fused-Ring
- Miscellaneous Anti-infectives
- Quinoline Derivatives
- Quinolines
- Quinolinium Compounds
- Throat Preparations
- 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)
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
- 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. [PubMed:26506926]
- 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. [PubMed:26348470]
- 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. [PubMed:22875343]
- 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. [PubMed:21477862]
- 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. [PubMed:24811390]
- 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. [PubMed:12404886]
- D'Auria FD, Simonetti G, Strippoli V: [Antimicrobial characteristics of a tincture of dequalinium chloride]. Ann Ig. 1989 Sep-Oct;1(5):1227-41. [PubMed:2483904]
- 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. [PubMed:3474661]
- 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. [PubMed:19525487]
- Gamboa-Vujicic G, Emma DA, Liao SY, Fuchtner C, Manetta A: Toxicity of the mitochondrial poison dequalinium chloride in a murine model system. J Pharm Sci. 1993 Mar;82(3):231-5. [PubMed:8450414]
- External Links
- PubChem Compound
- 2993
- PubChem Substance
- 46507206
- ChemSpider
- 2886
- BindingDB
- 50048403
- 3226
- ChEBI
- 41872
- ChEMBL
- CHEMBL333826
- ZINC
- ZINC000001655706
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- DEQ
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Dequalinium
- AHFS Codes
- 52:04.92 — Miscellaneous Anti-infectives
- PDB Entries
- 1jt6 / 1oyd / 3arp / 3art / 3br1 / 3br2 / 3bt9 / 3btj / 3vw0
- MSDS
- Download (348 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Vulvovaginal Candidiasis 1 3 Completed Treatment Bacterial Vaginosis (BV) 1 Not Available Completed Not Available Bacterial Vaginoses 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 15 mg Lozenge 250 mcg Solution Buccal Liquid Oral Lozenge 50 mg Suppository Vaginal 10 mg Tablet Vaginal Tablet Vaginal 10 mg Pastille Oral 0.25 MG Lozenge Oral - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS4946849 No 1990-08-07 2002-10-01 US 
Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) Decomposes at 326ºC MSDS - Predicted Properties
Property Value Source Water Solubility 4.77e-07 mg/mL ALOGPS logP 0.16 ALOGPS logP -3.6 ChemAxon logS -9 ALOGPS pKa (Strongest Basic) -0.34 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 59.8 Å2 ChemAxon Rotatable Bond Count 11 ChemAxon Refractivity 147 m3·mol-1 ChemAxon Polarizability 56.76 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5208 Blood Brain Barrier + 0.924 Caco-2 permeable + 0.5756 P-glycoprotein substrate Substrate 0.6725 P-glycoprotein inhibitor I Non-inhibitor 0.7203 P-glycoprotein inhibitor II Inhibitor 0.7281 Renal organic cation transporter Inhibitor 0.6769 CYP450 2C9 substrate Non-substrate 0.8745 CYP450 2D6 substrate Non-substrate 0.5072 CYP450 3A4 substrate Non-substrate 0.5434 CYP450 1A2 substrate Non-inhibitor 0.6703 CYP450 2C9 inhibitor Non-inhibitor 0.9119 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Inhibitor 0.6677 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5512 Ames test AMES toxic 0.5875 Carcinogenicity Non-carcinogens 0.9063 Biodegradation Not ready biodegradable 0.9969 Rat acute toxicity 2.6736 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.823 hERG inhibition (predictor II) Inhibitor 0.9123
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- 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
- 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. [PubMed:16166543]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AntagonistInhibitor
- 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
- 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. [PubMed:21340509]
- 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
- 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. [PubMed:12508052]
- 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
- 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. [PubMed:8100530]
- Kind
- Protein
- Organism
- Staphylococcus aureus
- Pharmacological action
- Unknown
- 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
- 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. [PubMed:18616285]
- 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. [PubMed:14726520]
Drug created on June 13, 2005 07:24 / Updated on October 21, 2020 01:55
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