Basic information
- CAS
10172-60-8- Standard SMILES
CC(C)(C)CC(C)(C)c1ccc(OCCOCC[N+](C)(C)Cc2ccccc2)cc1- InChIKey
SIYLLGKDQZGJHK-UHFFFAOYSA-N- Molecular formula
- C27H42NO2+
- Average molar mass
- 412.6 g/mol
- Monoisotopic mass
- 412.32155458
Overview
Dimethyl-(phenylmethyl)-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethyl]ammonium is an alkylbenzene.
Names & identifiers
- Preferred name
- Benzethonium
- IUPAC
- benzyl-dimethyl-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethyl]azanium
Names & synonyms
benzethoniumBenzethonium ionBenzethonium cation10172-60-8Benzothonium1VU15B70BPDTXSID5046984Benzyldimethyl(2-(2-(p-(1,1,3,3-tetramethylbutyl)phenoxy)ethoxy)ethyl)ammoniumAmmonium, benzyldimethyl(2-(2-(p-(1,1,3,3-tetramethylbutyl)phenoxy)ethoxy)ethyl)-Benzenemethanaminium, N,N-dimethyl-N-(2-(2-(4-(1,1,3,3-tetramethylbutyl)phenoxy)ethoxy)ethyl)benzyl-dimethyl-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethyl]azaniumPuriClens
Show more names
Formula MagicPuri ClensMagic, Formulabenzyl-dimethyl-(2-(2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)ethoxy)ethyl)azaniumRefChem:54480DTXCID3026984benzyldimethyl(2-(2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)ethoxy)ethyl)azanium498-77-1
Database identifiers
- CAS
10172-60-8、121-54-0、498-77-1- PubChem CID
- 2335
- DTXSID
DTXSID5046984- ChEMBL
CHEMBL1182210- ChEBI
CHEBI:94725- UNII
- 1VU15B70BP
- EC Number
- 684-540-8
- Nikkaji
- J193.052D
Properties
Computed structural properties
- XLogP
- 6.7
- Topological polar surface area
- 18.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 12
- Heavy atoms
- 30
- Formal charge
- 1
- Complexity
- 466
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
SolubilitySoluble
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point158-163
Collision Cross Section
208.1 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID6023810]
209.09 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Corr. 1B (100%)
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
QR - Respiratory system
Protein BindingPharmacokinetic studies on benzethonium have not been conducted.
Pharmacodynamics
Benzethonium belongs to the family of compounds known as cationic detergents that act by disrupting lipid bilayers. It demonstrated antitumor activity against cancer cell lines in vitro. The effective dose required to decrease cell viability by 50% after 48 hours (ED50) of benzethonium for FaDu (hypopharyngeal squamous cancer) and C666-1 (nasopharyngeal cancer) cell lines were approximately 3.8 and 5.3 μmol/L, respectively.
Mechanism of Action
While exact mechanism of benzethonium is not fully understood, it is proposed that benzethonium acts similarly to other structurally-related quaternary ammonium compounds in disrupting cytoplasmic and outer membrane lipid bilayers of microorganisms. The positively charged quaternary nitrogen associates with the polar head groups of acidic membrane phospholipids, followed by the hydrophobic tail interacting with the hydrophobic membrane core. Benzethonium is thought to form mixed-micelle aggregates with hydrophobic membrane components that solubilize membrane and lyse the cells, leading to leakage of cytoplasmic contents. Based on findings in vitro cell assays, its mode of action on cancer cells may involve cancer cell apoptosis via dysregulating mitochondria or rough endoplasmic reticulum (rER). It is proposed that intracellular cationic molecules such as benzethonium will create swelling of the rER and damage the organelle. Ultimately, there is a loss in cell membrane integrity and cytosolic Ca2+ levels increase. Dysregulation of mitochondria and rER leads to the activation of caspase-2, caspase-8, caspase-9, and caspase-3.
Biological Half-LifePharmacokinetic studies on benzethonium have not been conducted.
Metabolism/MetabolitesPharmacokinetic studies on benzethonium have not been conducted.
MeSH Pharmacological ClassificationSubstances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.
Absorption, Distribution and Excretion
It is reported that percutaneous absorption of benzethonium is clinically insignificant. Benzethonium chloride belongs to the family of
Pharmacokinetic studies on benzethonium have not been conducted.
Pharmacokinetic studies on benzethonium have not been conducted.
Pharmacokinetic studies on benzethonium have not been conducted.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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