Benzethonium

Identification

Summary

Benzethonium is a medication used as to clean hands and clean minor cuts and scrapes.

Generic Name
Benzethonium
DrugBank Accession Number
DB11125
Background

Benzethonium is a synthetic quaternary ammonium salt with surfactant, antiseptic, and broad spectrum antimicrobial properties. Its salt form, benzethonium chloride, is primarily used as a skin disinfectant at concentrations of 0.1-0.2 %, which are safe and effective concentrations for the compound specified by the U.S. Food and Drug Administration (FDA). It is additionally found in cosmetics and toiletries such as mouthwashes and anti-itch ointments. It is shown to be effective in mediating its antimicrobial action against bacteria, fungi, mold and viruses. There is evidence that benzethonium acts as a spermatocide but may cause vaginal irritation 2. Benzethonium was identified as a novel cancer-specific compound by cell-based small-molecule screen 1.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 412.637
Monoisotopic: 412.321006017
Chemical Formula
C27H42NO2
Synonyms
Not Available

Pharmacology

Indication

Indicated as an antiseptic agent. No therapeutic indications for clinical use.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatInflammation of mouthCombination Product in combination with: Tyrothricin (DB13503), Benzocaine (DB01086)•••••••••••••••••••
Used in combination to treatMouth ulcersCombination Product in combination with: Tyrothricin (DB13503), Benzocaine (DB01086)•••••••••••••••••••
Used in combination to treatOral infectionCombination Product in combination with: Benzocaine (DB01086), Tyrothricin (DB13503)•••••••••••••••••••
Used in combination to treatStreptococcal sore throatCombination Product in combination with: Tyrothricin (DB13503), Benzocaine (DB01086)•••••••••••••••••••
Used in combination to treatTonsillitisCombination Product in combination with: Tyrothricin (DB13503), Benzocaine (DB01086)•••••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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 1.

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 3. 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 3. 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) 2. 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 2.

Absorption

It is reported that percutaneous absorption of benzethonium is clinically insignificant 4. Benzethonium chloride belongs to the family of

Volume of distribution

Pharmacokinetic studies on benzethonium have not been conducted.

Protein binding

Pharmacokinetic studies on benzethonium have not been conducted.

Metabolism

Pharmacokinetic studies on benzethonium have not been conducted.

Route of elimination

Pharmacokinetic studies on benzethonium have not been conducted.

Half-life

Pharmacokinetic studies on benzethonium have not been conducted.

Clearance

Pharmacokinetic studies on benzethonium have not been conducted.

Adverse Effects
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Toxicity

Acute oral LD50 is 295 mg/kg in rat MSDS. Benzethonium was not shown to be mutagenic in the AMES Test MSDS. In a rat dermal study, there was no evidence of carcinogenic or genotoxic potential 2.

Benzethonium is toxic when orally ingested with 1 g reported to be fatal. The risk of toxicity is related to concentration with cationic detergents. Ingestion may lead to diarrhea, abdominal pain, vomiting, collapse, convulsions, coma 4. Oral exposure to high concentrations of benzethonium may lead to burns of the mouth, pharynx, and esophagus. To a rarer extent, hemorrhagic gastrointestinal (GI) tract necrosis and peritonitis, bronchospasm, aspiration pneumonitis, hypoxemia, and acute lung injury may develop. CNS depression progressing to coma and shock have been observed with severe ingestion or corrosive GI injury with parenteral administration of cationic detergents 4.

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

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Product Ingredients
IngredientUNIICASInChI Key
Benzethonium chloridePH41D05744121-54-0UREZNYTWGJKWBI-UHFFFAOYSA-M
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
(Qiqing) Skin DisinfectantLiquid1.8 g/1000mLTopicalQINGDAO PRECISION MEDICAL TECHNOLOGY CO.,LTD. ZIBO BRANCH2020-06-21Not applicableUS flag
3 in 1 First Aid Wound CareSolution1.3 mg/1gTopicalRite Aid Corporation2018-12-01Not applicableUS flag
99 Plus Hand SanitizerLiquid2 mg/1mLTopicalMomar Incorporated2017-12-20Not applicableUS flag
AcclaymCream0.5 % w/wTopicalAustin Research Labs CorpNot applicableNot applicableCanada flag
Alpha Foaming E-2Soap12.5 mg/1mLTopicalWhisk Products, Inc.2007-11-292013-11-30US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4125 First Aid KitBenzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Menthol (0.33 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)Inhalant; Kit; Liquid; Ointment; Spray; SwabOphthalmic; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4125 First Aid KitBenzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Menthol (0.33 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)Inhalant; Kit; Liquid; Ointment; Spray; SwabOphthalmic; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4129 First Aid KitBenzethonium chloride (0.2 g/100g) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Benzocaine (20 g/100g) + Ethanol (0.5 mL/1mL) + Hydrocortisone acetate (1 g/100g) + Hydrocortisone acetate (1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Povidone-iodine (10 mg/1mL)KitRespiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4142 First Aid KitBenzethonium chloride (0.2 g/100g) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Benzocaine (10 g/100g) + Lidocaine hydrochloride (2 g/100g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4209 First Aid KitBenzethonium chloride (0.2 g/100g) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzocaine (20 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
(Qiqing) Skin DisinfectantBenzethonium chloride (1.8 g/1000mL)LiquidTopicalQINGDAO PRECISION MEDICAL TECHNOLOGY CO.,LTD. ZIBO BRANCH2020-06-21Not applicableUS flag
4125 First Aid KitBenzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Menthol (0.33 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)Inhalant; Kit; Liquid; Ointment; Spray; SwabOphthalmic; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4125 First Aid KitBenzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Menthol (0.33 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)Inhalant; Kit; Liquid; Ointment; Spray; SwabOphthalmic; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4129 First Aid KitBenzethonium chloride (0.2 g/100g) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Benzocaine (20 g/100g) + Ethanol (0.5 mL/1mL) + Hydrocortisone acetate (1 g/100g) + Hydrocortisone acetate (1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Povidone-iodine (10 mg/1mL)KitRespiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4142 First Aid KitBenzethonium chloride (0.2 g/100g) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Benzocaine (10 g/100g) + Lidocaine hydrochloride (2 g/100g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag

Categories

ATC Codes
D08AJ58 — Benzethonium chloride, combinationsR02AA09 — BenzethoniumD08AJ08 — Benzethonium chloride
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropanes
Direct Parent
Phenylpropanes
Alternative Parents
Phenylmethylamines / Phenoxy compounds / Phenol ethers / Benzylamines / Aralkylamines / Alkyl aryl ethers / Tetraalkylammonium salts / Dialkyl ethers / Organopnictogen compounds / Organic salts
show 2 more
Substituents
Alkyl aryl ether / Amine / Aralkylamine / Aromatic homomonocyclic compound / Benzylamine / Dialkyl ether / Ether / Hydrocarbon derivative / Organic cation / Organic nitrogen compound
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
1VU15B70BP
CAS number
10172-60-8
InChI Key
SIYLLGKDQZGJHK-UHFFFAOYSA-N
InChI
InChI=1S/C27H42NO2/c1-26(2,3)22-27(4,5)24-13-15-25(16-14-24)30-20-19-29-18-17-28(6,7)21-23-11-9-8-10-12-23/h8-16H,17-22H2,1-7H3/q+1
IUPAC Name
benzyldimethyl(2-{2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy}ethyl)azanium
SMILES
CC(C)(C)CC(C)(C)C1=CC=C(OCCOCC[N+](C)(C)CC2=CC=CC=C2)C=C1

References

General References
  1. Yip KW, Mao X, Au PY, Hedley DW, Chow S, Dalili S, Mocanu JD, Bastianutto C, Schimmer A, Liu FF: Benzethonium chloride: a novel anticancer agent identified by using a cell-based small-molecule screen. Clin Cancer Res. 2006 Sep 15;12(18):5557-69. doi: 10.1158/1078-0432.CCR-06-0536. [Article]
  2. Authors unspecified: NTP Toxicology and Carcinogenesis Studies of Benzethonium Chloride (CAS No. 121-54-0) in F344/N Rats and B6C3F1 Mice (Dermal Studies). Natl Toxicol Program Tech Rep Ser. 1995 Jul;438:1-220. [Article]
  3. McBain AJ, Ledder RG, Moore LE, Catrenich CE, Gilbert P: Effects of quaternary-ammonium-based formulations on bacterial community dynamics and antimicrobial susceptibility. Appl Environ Microbiol. 2004 Jun;70(6):3449-56. doi: 10.1128/AEM.70.6.3449-3456.2004. [Article]
  4. BENZETHONIUM CHLORIDE - National Library of Medicine HSDB Database [Link]
PubChem Compound
2335
PubChem Substance
347827906
ChemSpider
2245
BindingDB
50203812
RxNav
1390
ChEBI
94725
ChEMBL
CHEMBL1182210
ZINC
ZINC000001571009
Wikipedia
Benzethonium_chloride
MSDS
Download (46.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LiquidTopical1.8 g/1000mL
KitRespiratory (inhalation); Topical
KitOphthalmic; Oral; Respiratory (inhalation); Topical
Inhalant; kit; liquid; ointment; spray; swab; tabletOphthalmic; Oral; Respiratory (inhalation); Topical
Inhalant; kit; liquid; ointment; spray; swabOphthalmic; Respiratory (inhalation); Topical
Kit; liquid; ointment; spray; swabOphthalmic; Topical
KitOphthalmic; Respiratory (inhalation); Topical
Cream; kit; liquid; ointment; spray; tabletOphthalmic; Oral; Topical
Cream; gel; kit; liquid; ointment; spray; swabOphthalmic; Topical
CreamTopical0.5 % w/w
SoapTopical12.5 mg/1mL
ClothTopical0.1 % w/w
ClothTopical0.1 g/100mL
SwabTopical0.115 g/100g
SwabTopical0.3 g/100g
SwabTopical0.2 g/100g
LiquidTopical0.2 g/100g
LotionCutaneous2 mg/1mL
SoapTopical0.13 mg/1mg
SolutionTopical1 mg/1mL
LiquidTopical0.14 %
CreamTopical1 mg / g
SolutionTopical0.2 1/100g
SolutionTopical0.12 g/100g
CreamTopical0.5 %
ShampooTopical1 mL/1000mL
ShampooTopical100 mg/100mL
LiquidTopical1 mL/1L
SprayTopical30 mg/30mL
SolutionTopical.1 g/100mL
SolutionTopical.2 g/100mL
SolutionTopical0.2 g/100mL
SoapCutaneous0.1 g/100g
SoapTopical0.1 g/100g
PowderTopical
SolutionAuricular (otic)
SolutionTopical0.12 g/100mL
CreamTopical0.2 g/100g
ClothTopical0.05 g/1g
LiquidTopical0.1 mL/100mL
Lotion / shampooTopical0.1 g/100g
SoapTopical0.1 g/100mL
LiquidTopical0.13 %
SolutionTopical0.15 %
LiquidTopical1.3 mg/1mL
SoapTopical0.09 g/100g
SprayTopical1.3 g/981mL
GelTopical0.15 % v/v
LiquidTopical0.1 g/100mL
SoapTopical1 mg/1mL
OintmentTopical0.2 g/100g
LiquidTopical200 mg/1000mg
CreamTopical0.2 % w/w
CreamTopical195 mg/100mL
LiquidTopical0.2 % w/w
GelTopical50 mg/50mL
LotionTopical0.2 g/100g
LiquidTopical0.2 g/100mL
GelTopical0.095 g/100mL
GelTopical0.105 g/100mL
LiquidTopical0.2 mg/100mL
SprayTopical0.2 % w/v
LotionTopical0.2 % w/w
GelTopical0.2 g/100mL
Aerosol, foamTopical0.002 g/1mL
LiquidTopical2 mg/1mL
SwabTopical0.3 g/1001
Lotion / shampooTopical
LotionTopical
LiquidTopical0.2 %
LiquidTopical0.20 %
CreamTopical
LiquidTopical0.02 g/10mL
GelCutaneous2 mg/1mL
LiquidTopical0.13 % w/w
SolutionTopical0.13 g/100mL
LotionTopical.2 mg/1mg
SolutionTopical0.13 % w/w
PowderTopical100 mg
LiquidTopical0.1 mg/100mL
LotionTopical1.98 mg/1g
ClothTopical30 mL/1000mL
GelTopical0.1 mg/100mL
LiquidTopical0.06 mg/1mL
LiquidTopical1.8 mg/1mL
SprayTopical60 mg/1g
SprayTopical
SolutionTopical0.001 mL/1mL
LiquidTopical0.13 g/100mL
LiquidTopical1 mg/50mL
KitTopical
SolutionTopical7.56 g/100mL
ClothTopical2 mg/1g
LiquidTopical0.09 mg/9mL
LiquidTopical50 mg/50mL
PatchTopical
SprayTopical0.13 g/100g
LiquidTopical0.1 g/100g
LotionTopical0.1 g/100mL
SolutionTopical
SprayTopical1.3 ug/1mL
SprayTopical1.3 mg/1mL
SprayTopical1.3 mg/1L
SprayTopical.013 1/1mL
SprayTopical0.013 1/1mL
SolutionTopical2 mg/1mL
LiquidTopical2.5 g/1L
SprayTopical0.13 mL/1mL
SprayTopical1 mg/13mL
LiquidTopical0.1 %
LiquidTopical
LiquidTopical2.66 mg/1mL
LiquidTopical0.2 mL/100mL
AerosolTopical0.19 mg / mL
LiquidTopical0.1 % w/w
GelTopical
PatchTopical0.0018 g/1g
OintmentTopical
SprayTopical2 mg/1mL
CreamTopical0.00192 g/1mL
SprayTopical0.001212 g/1mL
SoapTopical.33 mL/251mL
ClothTopical
ClothTopical0.001 mg/1
LotionTopical0.12 g/100g
LiquidTopical2.0 g/1.0L
PowderTopical0.5 %
ClothTopical0.13 % w/w
SolutionTopical1.3 mg/1g
ClothTopical0.3 % w/w
ClothTopical0.3 %
ClothTopical.009 g/3g
ClothTopical0.03 g/100g
ClothTopical0.3 g/1
SwabTopical0.3 mL/1
SwabTopical0.3 1/1001
SwabTopical0.45 g/150g
GelTopical0.15 % w/w
SprayTopical0.15 % w/w
SwabTopical3 mg/100mg
Aerosol, sprayTopical
SolutionTopical0.2 %
LotionTopical2 mg/1mL
SoapTopical2 mg/1mL
LotionTopical192.3 mg/1000mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)158-163MSDS
water solubilitySolubleBudavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 167
Predicted Properties
PropertyValueSource
Water Solubility7.49e-06 mg/mLALOGPS
logP3.13ALOGPS
logP2.37Chemaxon
logS-7.8ALOGPS
pKa (Strongest Acidic)17.31Chemaxon
pKa (Strongest Basic)-4.1Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area18.46 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity139 m3·mol-1Chemaxon
Polarizability50.78 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000f-3914000000-bbc993e61a3cade86016
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.05946
predicted
DeepCCS 1.0 (2019)
[M+H]+207.41747
predicted
DeepCCS 1.0 (2019)
[M+Na]+214.11833
predicted
DeepCCS 1.0 (2019)

Drug created at December 03, 2015 16:51 / Updated at March 19, 2024 11:06