BENZETHONIUM CHLORIDE

First approved in 1942

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H42NO2.Cl
Molecular Weight	448.081
Optical Activity	NONE
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Cl-].CC(C)(C)CC(C)(C)C1=CC=C(OCCOCC[N+](C)(C)CC2=CC=CC=C2)C=C1

InChI

InChIKey=UREZNYTWGJKWBI-UHFFFAOYSA-M

InChI=1S/C27H42NO2.ClH/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;1H/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula	C27H42NO2
Molecular Weight	412.6279
Charge	1
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0a6c9eee-ddbf-5cf5-e054-00144ff8d46c
Curator's Comment: description was created based on several sources, including: http://www.news-medical.net/news/2007/12/04/33135.aspx https://en.wikipedia.org/wiki/Benzethonium_chloride

Benzethonium chloride, also known as hyamine, is a synthetic quaternary ammonium salt. It has surfactant, antiseptic, and anti-infective properties and it is used as a topical antimicrobial agent in first aid antiseptics. It is also found in cosmetics and toiletries such as mouthwashes, anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride exhibits a broad spectrum of microbiocidal activity against bacteria, fungi, mold and viruses. The US Food and Drug Administration (FDA) specifies that the safe and effective concentrations for benzethonium chloride are 0.1-0.2% in first aid products. Aqueous solutions of benzethonium chloride are not absorbed through the skin. It is not approved in the US or Europe for use as a food additive. Being a quaternary ammonium salt, it is more toxic than negatively charged surfactants. However, in a two-year study on rats, there was no evidence of carcinogenic activity. Benzethonium chloride was characterized as a novel anticancer compound possessing both in vitro and in vivo efficacy justifying further investigation.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Bacterial Infections 63 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=58892abf-e0b9-83d9-e053-2a91aa0ad035	Preventing	Approved 8583	McKesson Antibacterial Soap Approved Use For handwashing to decrease bacteria on the skin. Launch Date 2017
Head and neck cancer 50 Sources: http://clincancerres.aacrjournals.org/content/12/18/5557.full.pdf+html	Primary	Preclinical	Unknown Approved Use Unknown
Skin infections 59 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0a6c9eee-ddbf-5cf5-e054-00144ff8d46c	Curative	Basic research	Unknown Approved Use Unknown
Methicillin-resistant Staphylococcus aureus 6 Sources: http://www.news-medical.net/news/2007/12/04/33135.aspx	Curative	Basic research	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2E1 1060 OATP1B1 1079 CYP2C19 2057 OATP1B3 961 CYP2A6 879 BSEP 550	CYP 303 P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIyMTc1MyJ9fQ==	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIyMTc1MyJ9fQ==	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIyMTc1MyJ9fQ==	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjIxNzUzIn19	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IiBDSEVNQkwyMjE3NTMifX0=	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17468864/	yes [IC50 15 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17468864/	yes [IC50 23 uM]
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32703874/	yes [IC50 29 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IiBDSEVNQkwyMjE3NTMifX0=	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIyMTc1MyJ9fQ==	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 Sources: https://jpet.aspetjournals.org/content/385/S3/175.abstract	yes
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2335#section=Biological-Test-Results Page: 81.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjIxNzUzIn19

PubMed

Title	Date	PubMed
Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride.	2013-08	23792315
A repurposing approach identifies off-patent drugs with fungicidal cryptococcal activity, a common structural chemotype, and pharmacological properties relevant to the treatment of cryptococcosis.	2013-02	23243064
Kinin B1 receptors mediate depression-like behavior response in stressed mice treated with systemic E. coli lipopolysaccharide.	2010-12-31	21194425
Benzethonium increases the cytotoxicity of S(+)-ketamine in lymphoma, neuronal, and glial cells.	2010-12	20889936
Arginine metabolism in Trichomonas vaginalis infected with Mycoplasma hominis.	2010-12	20656780
Caspase-1 is involved in the genesis of inflammatory hypernociception by contributing to peripheral IL-1β maturation.	2010-10-04	20920345
Correlation between reduced susceptibility to disinfectants and multidrug resistance among clinical isolates of Acinetobacter species.	2010-09	20576639
The relative toxicity of compounds used as preservatives in vaccines and biologics.	2010-05	20424565
Clinical significance of EGFR, Her-2 and EGF in oral squamous cell carcinoma: a case control study.	2010-04-29	20429940
Presence of chemical additives and microbial inhibition capacity in grapefruit seed extracts used in apiculture.	2010-04-23	20411504
Culture-modified bone marrow cells attenuate cardiac and renal injury in a chronic kidney disease rat model via a novel antifibrotic mechanism.	2010-03-04	20209052
Effects of high-dose major components in oral disinfectants on the cell cycle and apoptosis in primary human gingival fibroblasts in vitro.	2010-01	20379016
Sugar alcohols, caries incidence, and remineralization of caries lesions: a literature review.	2010	20339492
A facile synthesis of highly water-soluble, core-shell organo-silica nanoparticles with controllable size via sol-gel process.	2009-12-15	19783256
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.	2009-12-02	19956587
The effect of Bacillus subtilis mouth rinsing in patients with periodontitis.	2009-11	19649665
Suppression of experimental uveitis by a recombinant adeno-associated virus vector encoding interleukin-1 receptor antagonist.	2009-08-08	19693263
A study of the relationship between albuminuria, proteinuria and urinary reagent strips.	2009-05	19264826
Estimation of proteinuria as a predictor of complications of pre-eclampsia: a systematic review.	2009-03-24	19317889
Harnessing gene expression to identify the genetic basis of drug resistance.	2009	19888205
Central sympatholytics prolong survival in experimental sepsis.	2009	19196475
Local anesthetics, antipsychotic phenothiazines, and cationic surfactants shut down intracellular reactions through membrane perturbation in yeast.	2008-11	18997430
The enhancement effect of three sugar alcohols on the fungicidal effect of benzethonium chloride toward Candida albicans.	2008-11	18778883
Effect of cationic surfactants on enhancement of firefly bioluminescence in the presence of liposomes.	2008-09	18781021
Validation of a quantitative NMR method for suspected counterfeit products exemplified on determination of benzethonium chloride in grapefruit seed extracts.	2008-08-05	18456447
Rapid antibacterial activity of 2 novel hand soaps: evaluation of the risk of development of bacterial resistance to the antibacterial agents.	2008-08	18616390
[Case of serious renal failure induced by ingesting large volume of MAKIRON].	2008-07	18712075
Is secondary wavelength always necessary in turbidimetric urine protein measurements?	2008-05	18249194
Reduction of disinfectant bactericidal activities in clinically isolated Acinetobacter species in the presence of organic material.	2008-03	18192683
Effects of nonionic and ionic surfactants on survival, oxidative stress, and cholinesterase activity of planarian.	2008-02	17905407
Actinomycetes from sediments in the Trondheim fjord, Norway: diversity and biological activity.	2008-01-23	18648671
FMRFamide-like immunoreactivity in the central nervous system and alimentary tract of the non-hematophagous blow fly, Phormia regina, and the hematophagous horse fly, Tabanus nigrovittatus.	2008	20302523
Circulating plasma factors induce tubular and glomerular alterations in septic burns patients.	2008	18364044
Displacement chromatography of proteins on hydrophobic charge induction adsorbent column.	2007-09-21	17692858
Simultaneous identification and quantification by liquid chromatography of benzethonium chloride, methyl paraben and triclosan in commercial products labeled as grapefruit seed extract.	2007-08	17867553
Assessment using human dental pulp cells of clastogenicity of antiseptics used in dental practice and agents for root canal enlargement and cleaning.	2007-07	17660979
Adverse effects by artificial grapefruit seed extract products in patients on warfarin therapy.	2007-06	17468864
Evaluation of an alcohol-based surgical hand disinfectant containing a synergistic combination of farnesol and benzethonium chloride for immediate and persistent activity against resident hand flora of volunteers and with a novel in vitro pig skin model.	2007-02	17265401
Cationic surfactants induce apoptosis in normal and cancer cells.	2007-01	17404011
Strong interference of hemoglobin concentration on CSF total protein measurement using the trichloroacetic acid precipitation method.	2007	17243927
Determination of benzethonium chloride in anthrax vaccine adsorbed by HPLC.	2006-12	16492397
Benzethonium chloride: a novel anticancer agent identified by using a cell-based small-molecule screen.	2006-09-15	17000693
Hexadecyl-phosphorylcholine ointment for treatment of cutaneous leishmaniasis: an animal trial.	2006-09	17333810
Efficacy of an alcohol-based healthcare hand rub containing synergistic combination of farnesol and benzethonium chloride.	2006-09	16750419
[Properties of benzethonium chloride in micellar solutions and the effect of added sodium chloride].	2006-07	16921736
Development and validation of an HPLC/UV/MS method for simultaneous determination of 18 preservatives in grapefruit seed extract.	2006-05-31	16719494
Ormosil nanocomposite materials as modifiers for acrylic coating systems.	2006-02	16573033
In vitro short-time killing activity of povidone-iodine (Isodine Gargle) in the presence of oral organic matter.	2006	16490985
Susceptibilities to antiseptic agents and distribution of antiseptic-resistance genes qacA/B and smr of methicillin-resistant Staphylococcus aureus isolated in Asia during 1998 and 1999.	2005-06	15888465
Urine protein estimation in hypertensive pregnancy: which thresholds and laboratory assay best predict clinical outcome?	2005	16263601

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Topical

In Vitro Use Guide

For benzethonium (48 hour incubation), the dose required to reduce cell viability by 50% was 3.8 uM in FaDu (human hypopharyngeal squamous cancer), 42.2 uM in NIH 3T3 (untransformed mouse embryonic fibroblast), 5.3 uM in C666-1 (nasopharyngeal cancer), and 17.0 uM in GM05757 (primary normal human fibroblast) cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:36:23 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:23 GMT 2025`
Record UNII	PH41D05744
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZETHONIUM CHLORIDE

Official Name

English

HYAMINE

Preferred Name

English

BENZETHONIUM CHLORIDE [EP MONOGRAPH]

Common Name

English

BENZETHONIUM CHLORIDE [EP IMPURITY]

Common Name

English

BENZETHONIUM CHLORIDE [MI]

Common Name

English

benzethonium chloride [INN]

Common Name

English

BENZYLDIMETHYL(2-(2-(P-(1,1,3,3-TETRAMETHYLBUTYL)PHENOXY)ETHOXY)ETHYL)AMMONIUM CHLORIDE

Common Name

English

BENZETHONIUM CHLORIDE [USP IMPURITY]

Common Name

English

BENZETHONIUM CHLORIDE [USP-RS]

Common Name

English

BENZETHONIUM CHLORIDE [HSDB]

Common Name

English

PHEMEROL

Brand Name

English

BENZETHONIUM CHLORIDE [JAN]

Common Name

English

BENZETHONIUM CHLORIDE [II]

Common Name

English

BENZETHONIUM CHLORIDE CONCENTRATE [USP MONOGRAPH]

Common Name

English

BENZENEMETHANAMINIUM, N,N-DIMETHYL-N-(2-(2-(4-(1,1,3,3-TETRAMETHYLBUTYL)PHENOXY)ETHOXY)ETHYL)-, CHLORIDE

Systematic Name

English

BENZETHONIUM CHLORIDE [MART.]

Common Name

English

BENZETHONIUM CHLORIDE [VANDF]

Common Name

English

PHEMEROL CHLORIDE

Brand Name

English

BENZENEMETHANAMINIUM, N,N-DIMETHYL-N-(2-(2-(4-(1,1,3,3-TETRAMETHYLBUTYL)PHENOXY)ETHOXY)ETHYL)-, CHLORIDE (1:1)

Systematic Name

English

Benzethonium chloride [WHO-DD]

Common Name

English

NSC-20200

Code

English

NEOSTELIN GREEN

Brand Name

English

Classification Tree Code System Code

Food Contact Sustance Notif, (FCN No.)

FCN NO. 460