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Details

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

SHOW SMILES / InChI
Structure of BENZETHONIUM CHLORIDE

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 ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C27H42NO2
Molecular Weight 412.6279
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Nippon Oil and Fat
4
Curator's Comment: There were alot of studies were conducted around this compound by many different scientists.

Approval Year

1942
36
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8429
McKesson Antibacterial Soap

Approved Use

For handwashing to decrease bacteria on the skin.

Launch Date

1.50664315E12
Primary
Preclinical
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Application of an improved biuret method to the determination of total protein in urine and cerebrospinal fluid without concentration step by use of Hitachi 7170 auto-analyzer.
2001
Effectiveness of manual cleaning and disinfection of gastroendoscopes with 3% glutaraldehyde for decreasing risk of transmission of hepatitis C virus.
2001 Jun
Occupational allergic contact dermatitis from alkylammonium amidobenzoate.
2001 May-Jun
Ketamine and its preservative, benzethonium chloride, both inhibit human recombinant alpha7 and alpha4beta2 neuronal nicotinic acetylcholine receptors in Xenopus oocytes.
2001 Oct
[Resistance of Staphylococcus aureus strains to quaternary ammonium compounds and chlorhexidine].
2002
In vitro evaluation of skin sensitivity of povidone-iodine and other antiseptics using a three-dimensional human skin model.
2002
Steroid-induced polycystic ovaries in rats: effect of electro-acupuncture on concentrations of endothelin-1 and nerve growth factor (NGF), and expression of NGF mRNA in the ovaries, the adrenal glands, and the central nervous system.
2003 Apr 8
An evaluation of protein assays for quantitative determination of drugs.
2003 Jul 31
Cetylpyridinium tetrachlorozincate as standard for tenside titration. Analytical methods with 1,3-dibromo-5,5-dimethylhydantoin (DBH) in respect to environmental and economical concern, part 19.
2004 Aug
Evidence for concurrent effects of exposure to environmental cadmium and lead on hepatic CYP2A6 phenotype and renal function biomarkers in nonsmokers.
2004 Nov
Urine protein estimation in hypertensive pregnancy: which thresholds and laboratory assay best predict clinical outcome?
2005
[Relation between oxygen uptake rate and biosorption of activated sludge against chemical substance].
2005 Feb
Ability of fourteen chemical agents used in dental practice to induce chromosome aberrations in Syrian hamster embryo cells.
2005 Jan
In vitro short-time killing activity of povidone-iodine (Isodine Gargle) in the presence of oral organic matter.
2006
Determination of benzethonium chloride in anthrax vaccine adsorbed by HPLC.
2006 Dec
Ormosil nanocomposite materials as modifiers for acrylic coating systems.
2006 Feb
Development and validation of an HPLC/UV/MS method for simultaneous determination of 18 preservatives in grapefruit seed extract.
2006 May 31
Efficacy of an alcohol-based healthcare hand rub containing synergistic combination of farnesol and benzethonium chloride.
2006 Sep
Benzethonium chloride: a novel anticancer agent identified by using a cell-based small-molecule screen.
2006 Sep 15
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 Feb
Displacement chromatography of proteins on hydrophobic charge induction adsorbent column.
2007 Sep 21
Effects of nonionic and ionic surfactants on survival, oxidative stress, and cholinesterase activity of planarian.
2008 Feb
Reduction of disinfectant bactericidal activities in clinically isolated Acinetobacter species in the presence of organic material.
2008 Mar
Is secondary wavelength always necessary in turbidimetric urine protein measurements?
2008 May
Local anesthetics, antipsychotic phenothiazines, and cationic surfactants shut down intracellular reactions through membrane perturbation in yeast.
2008 Nov
Effect of cationic surfactants on enhancement of firefly bioluminescence in the presence of liposomes.
2008 Sep
Harnessing gene expression to identify the genetic basis of drug resistance.
2009
A facile synthesis of highly water-soluble, core-shell organo-silica nanoparticles with controllable size via sol-gel process.
2009 Dec 15
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009 Dec 2
Estimation of proteinuria as a predictor of complications of pre-eclampsia: a systematic review.
2009 Mar 24
The effect of Bacillus subtilis mouth rinsing in patients with periodontitis.
2009 Nov
Kinin B1 receptors mediate depression-like behavior response in stressed mice treated with systemic E. coli lipopolysaccharide.
2010 Dec 31
Culture-modified bone marrow cells attenuate cardiac and renal injury in a chronic kidney disease rat model via a novel antifibrotic mechanism.
2010 Mar 4
Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride.
2013 Aug
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 Feb
Patents

Patents

US9302011
4

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 Fri Dec 15 15:02:33 UTC 2023
Edited
by admin
on Fri Dec 15 15:02:33 UTC 2023
Record UNII
PH41D05744
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENZETHONIUM CHLORIDE
EP   HSDB   II   INCI   INN   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
INN   INCI  
Official Name English
BENZETHONIUM CHLORIDE [EP MONOGRAPH]
Common Name English
BENZETHONIUM CHLORIDE [EP IMPURITY]
Common Name English
BENZETHONIUM CHLORIDE [MI]
Common Name English
BENZETHONIUM CHLORIDE [INCI]
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
HYAMINE
Brand 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
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
WHO-ATC D08AJ08
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
WHO-VATC QD08AJ08
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
WHO-ATC D08AJ58
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
WHO-VATC QD08AJ58
Created by admin on Fri Dec 15 15:02:34 UTC 2023 , Edited by admin on Fri Dec 15 15:02:34 UTC 2023
NCI_THESAURUS C28394
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
EPA PESTICIDE CODE 69122
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
Code System Code Type Description
DRUG BANK
DBSALT001519
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-479-9
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY
WIKIPEDIA
BENZETHONIUM CHLORIDE
Created by admin on Fri Dec 15 15:02:34 UTC 2023 , Edited by admin on Fri Dec 15 15:02:34 UTC 2023
PRIMARY
DAILYMED
PH41D05744
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY
CHEBI
31264
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY
FDA UNII
PH41D05744
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY
PUBCHEM
8478
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PRIMARY
MERCK INDEX
m2346
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PRIMARY Merck Index
RS_ITEM_NUM
1051500
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PRIMARY
INN
1170
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PRIMARY
SMS_ID
100000091941
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PRIMARY
NSC
20200
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL1182210
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY
CAS
121-54-0
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY
NCI_THESAURUS
C77025
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY
EVMPD
SUB05746MIG
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID6023810
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY
RXCUI
40036
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY RxNorm
HSDB
567
Created by admin on Fri Dec 15 15:02:33 UTC 2023 , Edited by admin on Fri Dec 15 15:02:33 UTC 2023
PRIMARY
Related Record Type Details
Structure of BENZETHONIUM CHLORIDE MONOHYDRATE
SALT/SOLVATE -> SALT/SOLVATE
Structure of BENZETHONIUM
PARENT -> SALT/SOLVATE
Structure of BENZETHONIUM OCTYLOXYACETATE
SALT/SOLVATE -> SALT/SOLVATE
Structure of BENZETHONIUM CHLORIDE MONOHYDRATE
SOLVATE->ANHYDROUS
Related Record Type Details
Structure of BENZETHONIUM
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