Thonzonium

Identification

Name
Thonzonium
Accession Number
DB09552
Description

Thonzonium is a monocationic surface-active agent with surfactant and detergent properties. It is widely used as an additive to in ear and nasal drops to enhance dispersion and penetration of cellular debris and exudate, thereby promoting tissue contact of the administered medication. A common pharmaceutical formulation of thonzonium bromide is cortisporin-TC ear drops. It is also reported that thonzonium also confers an antifungal property and antiresorptive effect on bone.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 511.818
Monoisotopic: 511.437038827
Chemical Formula
C32H55N4O
Synonyms
  • Tonzonium

Pharmacology

Indication

Used as a monocationic surfactant and detergent to help penetration of active ingredients through cellular debris for its antibacterial action.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Thonzonium bromide causes dispersion and penetration of cellular debris and exudate, thereby promoting tissue contact of the active ingredients contained in the administered medication. It is an inhibitor of vacuolar ATPase that uncouples and blocks the function of the pump without inhibiting ATP hydrolysis.

Mechanism of action

Thonzonium bromide is a suface-active agent added in nasal and ear drops that potentiates and lenghten the time of skin contact with the active compounds and penetration through the cellular debris. Thonzonium bromide uncouples vacuolar ATPase in pathogenic fungi such as Candida albicans and inhibit cell growth in vitro. It interacts with the tether of subunit a (Vph1p) of the membrane-bound V0 subunit that forms the proton transport path. Disruption of the essential pump function prevents redistribution of cytosolic protons into the vacuolar lumen, resulting in acidification of the cytosol and cell death [A19501]. A study reports that thonzonium bromide mediates an antiresorptive action on osteoclasts by inhibiting RANKL-induced osteoclast formation. It is shown to block the RANKL-induced activation of NF-jB, ERK and c-Fos as well as the induction of NFATc1 which is essential for OC formation. It also disrupted F-actin ring formation resulting in disturbances in cytoskeletal structure in mature OCs during bone resorption 1.

TargetActionsOrganism
AV-type proton ATPase subunit C 1
inhibitor
Humans
Absorption
Not Available
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.
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Toxicity

Unwanted effects include irritation and allergic reactions.

Affected organisms
Not Available
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
IngredientUNIICASInChI Key
Thonzonium bromideJI2B19CR0R553-08-2WBWDWFZTSDZAIG-UHFFFAOYSA-M
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Coly-Mycin SThonzonium bromide (0.5 mg/1mL) + Colistin sulfate (3 mg/1mL) + Hydrocortisone acetate (10 mg/1mL) + Neomycin sulfate (3.3 mg/1mL)SuspensionAuricular (otic)Par Pharmaceutical2007-11-012017-06-18US flag
Coly-Mycin SThonzonium bromide (0.5 mg/1mL) + Colistin sulfate (3 mg/1mL) + Hydrocortisone acetate (10 mg/1mL) + Neomycin sulfate (3.3 mg/1mL)SuspensionAuricular (otic)Endo Pharmaceuticals Inc.2016-04-182020-04-30US flag
Coly-Mycin SThonzonium bromide (0.5 mg/1mL) + Colistin sulfate (3 mg/1mL) + Hydrocortisone acetate (10 mg/1mL) + Neomycin sulfate (3.3 mg/1mL)SuspensionAuricular (otic)Physicians Total Care, Inc.2007-11-012012-06-30US flag
Cortisporin TCThonzonium bromide (0.5 mg/1mL) + Colistin sulfate (3 mg/1mL) + Hydrocortisone acetate (10 mg/1mL) + Neomycin sulfate (3.3 mg/1mL)SuspensionAuricular (otic)Endo Pharmaceuticals, Inc.2019-06-03Not applicableUS flag
Cortisporin-TCThonzonium bromide (0.5 mg/1mL) + Colistin sulfate (3 mg/1mL) + Hydrocortisone acetate (10 mg/1mL) + Neomycin sulfate (3.3 mg/1mL)SuspensionAuricular (otic)Physicians Total Care, Inc.2007-05-07Not applicableUS flag
Cortisporin-TCThonzonium bromide (0.5 mg/1mL) + Colistin sulfate (3 mg/1mL) + Hydrocortisone acetate (10 mg/1mL) + Neomycin sulfate (3.3 mg/1mL)SuspensionAuricular (otic)Par Pharmaceutical, Inc.2007-11-012017-05-30US flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Anisoles
Direct Parent
Anisoles
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Dialkylarylamines / Benzylamines / Aminopyrimidines and derivatives / Alkyl aryl ethers / Tetraalkylammonium salts / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
Alkyl aryl ether / Amine / Aminopyrimidine / Anisole / Aromatic heteromonocyclic compound / Azacycle / Benzylamine / Dialkylarylamine / Ether / Heteroaromatic compound
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
Z05ZE98FV8
CAS number
25466-36-8
InChI Key
IOYZYMQFUSNATM-UHFFFAOYSA-N
InChI
InChI=1S/C32H55N4O/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-27-36(2,3)28-26-35(32-33-24-19-25-34-32)29-30-20-22-31(37-4)23-21-30/h19-25H,5-18,26-29H2,1-4H3/q+1
IUPAC Name
hexadecyl(2-{[(4-methoxyphenyl)methyl](pyrimidin-2-yl)amino}ethyl)dimethylazanium
SMILES
CCCCCCCCCCCCCCCC[N+](C)(C)CCN(CC1=CC=C(OC)C=C1)C1=NC=CC=N1

References

General References
  1. Zhu X, Gao JJ, Landao-Bassonga E, Pavlos NJ, Qin A, Steer JH, Zheng MH, Dong Y, Cheng TS: Thonzonium bromide inhibits RANKL-induced osteoclast formation and bone resorption in vitro and prevents LPS-induced bone loss in vivo. Biochem Pharmacol. 2016 Mar 15;104:118-30. doi: 10.1016/j.bcp.2016.02.013. Epub 2016 Feb 21. [PubMed:26906912]
  2. Deo AA, Kulkarni AS, Meshram SU: Monocationic surfactant induced ultra structural changes in antibiotic resistant Escherichia coli. Indian J Med Res. 2010 Jun;131:825-8. [PubMed:20571174]
  3. Pubchem [Link]
  4. CORTISPORIN-TC Otic Suspension (Monarch) with Neomycin and Hydrocortisone [Link]
PubChem Compound
5456
PubChem Substance
347827878
ChemSpider
5257
BindingDB
59083
RxNav
237058
ChEBI
94514
ChEMBL
CHEMBL1201322
ZINC
ZINC000008035268
Wikipedia
Thonzonium_bromide
MSDS
Download (69.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SuspensionAuricular (otic)
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)91.5MSDS
water solubilitySoluble MSDS
Predicted Properties
PropertyValueSource
Water Solubility1.82e-05 mg/mLALOGPS
logP4.07ALOGPS
logP4.92ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)3.12ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.25 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity171.19 m3·mol-1ChemAxon
Polarizability66.44 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Subunit of the peripheral V1 complex of vacuolar ATPase. Subunit C is necessary for the assembly of the catalytic sector of the enzyme and is likely to have a specific function in its catalytic act...
Gene Name
ATP6V1C1
Uniprot ID
P21283
Uniprot Name
V-type proton ATPase subunit C 1
Molecular Weight
43941.245 Da
References
  1. Chan CY, Prudom C, Raines SM, Charkhzarrin S, Melman SD, De Haro LP, Allen C, Lee SA, Sklar LA, Parra KJ: Inhibitors of V-ATPase proton transport reveal uncoupling functions of tether linking cytosolic and membrane domains of V0 subunit a (Vph1p). J Biol Chem. 2012 Mar 23;287(13):10236-50. doi: 10.1074/jbc.M111.321133. Epub 2012 Jan 3. [PubMed:22215674]

Drug created on November 30, 2015 12:10 / Updated on June 12, 2020 10:52

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