U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Curator's Comment: There were alot of studies were conducted around this compound by many different scientists.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
McKesson Antibacterial Soap

Approved Use

For handwashing to decrease bacteria on the skin.

Launch Date

2017
Primary
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of concentration and biochemical assay on the accuracy of urine dipsticks in hypertensive pregnancies.
2001
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
[Study on separation of epirubicin and doxorubicin isomers by displacement chromatography].
2004 Mar
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
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 Jun
Comparative efficacy of hand hygiene agents in the reduction of bacteria and viruses.
2005 Mar
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
Circulating plasma factors induce tubular and glomerular alterations in septic burns patients.
2008
Reduction of disinfectant bactericidal activities in clinically isolated Acinetobacter species in the presence of organic material.
2008 Mar
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
Clinical significance of EGFR, Her-2 and EGF in oral squamous cell carcinoma: a case control study.
2010 Apr 29
The relative toxicity of compounds used as preservatives in vaccines and biologics.
2010 May
Correlation between reduced susceptibility to disinfectants and multidrug resistance among clinical isolates of Acinetobacter species.
2010 Sep
Patents

Patents

Sample Use Guides

Unknown
Route of Administration: Topical
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:02:33 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:02:33 GMT 2023
WHO-ATC D08AJ08
Created by admin on Fri Dec 15 15:02:33 GMT 2023 , Edited by admin on Fri Dec 15 15:02:33 GMT 2023
WHO-VATC QD08AJ08
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WHO-ATC D08AJ58
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WHO-VATC QD08AJ58
Created by admin on Fri Dec 15 15:02:34 GMT 2023 , Edited by admin on Fri Dec 15 15:02:34 GMT 2023
NCI_THESAURUS C28394
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EPA PESTICIDE CODE 69122
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Code System Code Type Description
DRUG BANK
DBSALT001519
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PRIMARY
ECHA (EC/EINECS)
204-479-9
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PRIMARY
WIKIPEDIA
BENZETHONIUM CHLORIDE
Created by admin on Fri Dec 15 15:02:34 GMT 2023 , Edited by admin on Fri Dec 15 15:02:34 GMT 2023
PRIMARY
DAILYMED
PH41D05744
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PRIMARY
CHEBI
31264
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PRIMARY
FDA UNII
PH41D05744
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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
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PRIMARY
ChEMBL
CHEMBL1182210
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PRIMARY
CAS
121-54-0
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PRIMARY
NCI_THESAURUS
C77025
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PRIMARY
EVMPD
SUB05746MIG
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PRIMARY
EPA CompTox
DTXSID6023810
Created by admin on Fri Dec 15 15:02:33 GMT 2023 , Edited by admin on Fri Dec 15 15:02:33 GMT 2023
PRIMARY
RXCUI
40036
Created by admin on Fri Dec 15 15:02:33 GMT 2023 , Edited by admin on Fri Dec 15 15:02:33 GMT 2023
PRIMARY RxNorm
HSDB
567
Created by admin on Fri Dec 15 15:02:33 GMT 2023 , Edited by admin on Fri Dec 15 15:02:33 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
SALT/SOLVATE -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY