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Thonzonium

HCID 5456
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Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
25466-36-8
Standard SMILES
CCCCCCCCCCCCCCCC[N+](C)(C)CCN(Cc1ccc(OC)cc1)c1ncccn1
InChIKey
IOYZYMQFUSNATM-UHFFFAOYSA-N
Molecular formula
C32H55N4O+
Average molar mass
511.8 g/mol
Monoisotopic mass
511.43758739

Overview

Hexadecyl-[2-[(4-methoxyphenyl)methyl-(2-pyrimidinyl)amino]ethyl]-dimethylammonium is a member of methoxybenzenes.

Names & identifiers

Preferred name
Thonzonium
IUPAC
hexadecyl-[2-[(4-methoxyphenyl)methyl-pyrimidin-2-ylamino]ethyl]-dimethylazanium

Names & synonyms

thonzoniumTonzoniumThonzonium ionThonzonium cationZ05ZE98FV825466-36-8TONZONIUM [WHO-DD]N-(2-((4-Methoxybenzyl)(pyrimidin-2-yl)amino)ethyl)-N,N-dimethylhexadecan-1-aminiumDTXSID8048232hexadecyl(2-{[(4-methoxyphenyl)methyl](pyrimidin-2-yl)amino}ethyl)dimethylazaniumhexadecyl(2-(((4-methoxyphenyl)methyl)(pyrimidin-2-yl)amino)ethyl)dimethylazaniumRefChem:897992
Show more names
DTXCID9028207UNII-Z05ZE98FV8NCGC00016507-01CAS-553-08-2ThonizidePrestwick0_000925Prestwick1_000925Prestwick2_000925

Database identifiers

CAS
25466-36-8
PubChem CID
5456
DTXSID
DTXSID8048232
ChEMBL
CHEMBL1201322
ChEBI
CHEBI:94514
UNII
Z05ZE98FV8
Nikkaji
J238.511B

Properties

Computed structural properties

XLogP
9.9
Topological polar surface area
38.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
22
Heavy atoms
37
Formal charge
1
Complexity
515

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
SolubilitySoluble

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

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 · 1 item

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. 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.

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Compound notes

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