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

Details

Stereochemistry ACHIRAL
Molecular Formula C13H9Cl3N2O
Molecular Weight 315.5827
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRICLOCARBAN

SMILES

c1cc(ccc1Cl)NC(=Nc2ccc(c(c2)Cl)Cl)O

InChI

InChIKey=ICUTUKXCWQYESQ-UHFFFAOYSA-N
InChI=1S/C13H9Cl3N2O/c14-8-1-3-9(4-2-8)17-13(19)18-10-5-6-11(15)12(16)7-10/h1-7H,(H2,17,18,19)

HIDE SMILES / InChI

Molecular Formula C13H9Cl3N2O
Molecular Weight 315.5827
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created using several sources including: http://www.fda.gov/newsevents/newsroom/pressannouncements/ucm517478.htm; http://www.fda.gov/downloads/aboutfda/reportsmanualsforms/reports/economicanalyses/ucm519798.pdf; https://www.ncbi.nlm.nih.gov/pubmed/22626523; https://www.ncbi.nlm.nih.gov/pubmed/21131331; http://www.ncbi.nlm.nih.gov/pubmed/?term=12534815

Triclocarban is a triclosan analogue with an antibmicrobial property. It has been used in a wide range of personal cleansing products including deodorant and bar soaps, deodorants, detergents, cleansing lotions, and wipes. In US triclocarban was approved for marketing of over-the-counter (OTC) consumer antiseptic wash products. But on September 2, 2016 U.S. Food and Drug Administration banned containing triclocarban and triclosan consumer antiseptic wash products from further marketing in USA because of a potential damage to human health, resulting from extended exposure to antiseptic active ingredients on a regular bases. However the new rule does not not affect consumer hand “sanitizers” or wipes, or antibacterial products used in health care settings. Triclocarban is a limited spectrum antibacterial agent effective in vitro against some strains of staphylococcus, streptococcus, and enterococcus bacteria. The minimum inhibitory concentration has been found to range from 0.5 to 8 mg/L for these various strains. Triclocarban can act by non-specific membrane-destabilizing mechanism; also was suggested, that similar to triclosan, Triclocarban exerts its effect by inhibiting the activity of enoyl-(acyl-carrier protein) (ACP) reductase, widely distributed in bacteria, fungi and plants. As a result, this agent interrupts cell membrane synthesis and leads to bacterial growth inhibition.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Dial® soap

Approved Use

Antibacterial Soap used to protect skin from bacterial infections
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.6 h
103 μg single, intravenous
dose: 103 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
TRICLOCARBAN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
9 % 1 times / day multiple, topical
Highest studied dose
Dose: 9 %, 1 times / day
Route: topical
Route: multiple
Dose: 9 %, 1 times / day
Sources:
healthy, 21 to 65 years old
n = 10
Health Status: healthy
Age Group: 21 to 65 years old
Sex: M
Population Size: 10
Sources:
Other AEs: Skin irritation...
AEs

AEs

AESignificanceDosePopulation
Skin irritation grade 1
9 % 1 times / day multiple, topical
Highest studied dose
Dose: 9 %, 1 times / day
Route: topical
Route: multiple
Dose: 9 %, 1 times / day
Sources:
healthy, 21 to 65 years old
n = 10
Health Status: healthy
Age Group: 21 to 65 years old
Sex: M
Population Size: 10
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Effect of handwashing on child health: a randomised controlled trial.
2005 Jul 16-22
Cyclodextrin solubilization of the antibacterial agents triclosan and triclocarban: formation of aggregates and higher-order complexes.
2005 Jun 13
Triclocarban seems to defy wastewater treatment.
2006 Jun 1
Algal bioaccumulation of triclocarban, triclosan, and methyl-triclosan in a North Texas wastewater treatment plant receiving stream.
2007 May
Simultaneous determination of triclocarban and triclosan in municipal biosolids by liquid chromatography tandem mass spectrometry.
2007 Sep 14
Detection of trace triclocarban in water sample using solid-phase extraction-liquid chromatography with stochastic resonance algorithm.
2008 Apr 15
Growth-inhibiting effects of 12 antibacterial agents and their mixtures on the freshwater microalga Pseudokirchneriella subcapitata.
2008 May
Determination of household chemicals using gas chromatography and liquid chromatography with tandem mass spectrometry.
2008 May 9
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.
2008 Oct
Toxicology in the fast lane: application of high-throughput bioassays to detect modulation of key enzymes and receptors.
2009 Dec
Fate of organohalogens in US wastewater treatment plants and estimated chemical releases to soils nationwide from biosolids recycling.
2009 Dec
Pharmaceutical and personal care products in tile drainage following surface spreading and injection of dewatered municipal biosolids to an agricultural field.
2009 Jul 1
Simultaneous determination of parabens, triclosan and triclocarban in water by liquid chromatography/electrospray ionisation tandem mass spectrometry.
2009 Jun
Adsorption and degradation of triclosan and triclocarban in soils and biosolids-amended soils.
2009 Jun 10
Effect of triclosan and triclocarban biocides on biodegradation of estrogens in soils.
2009 Nov
On-line solid-phase extraction of large-volume injections coupled to liquid chromatography-tandem mass spectrometry for the quantitation and confirmation of 14 selected trace organic contaminants in drinking and surface water.
2009 Nov 27
Ultra-high-performance liquid chromatography-tandem mass spectrometry for determining the presence of eleven personal care products in surface and wastewaters.
2009 Oct 16
Fate of triclocarban during soil aquifer treatment: soil column studies.
2010
The antimicrobial triclocarban stimulates embryo production in the freshwater mudsnail Potamopyrgus antipodarum.
2010 Apr
Stir-bar-sorptive extraction and ultra-high-performance liquid chromatography-tandem mass spectrometry for simultaneous analysis of UV filters and antimicrobial agents in water samples.
2010 Aug
Uptake of pharmaceutical and personal care products by soybean plants from soils applied with biosolids and irrigated with contaminated water.
2010 Aug 15
Electrochemistry-mass spectrometry unveils the formation of reactive triclocarban metabolites.
2010 Dec
Occurrence and loss over three years of 72 pharmaceuticals and personal care products from biosolids-soil mixtures in outdoor mesocosms.
2010 Dec
Mass loadings of triclosan and triclocarbon from four wastewater treatment plants to three rivers and landfill in Savannah, Georgia, USA.
2010 Feb
Pharmaceuticals and personal care products in archived U.S. biosolids from the 2001 EPA National Sewage Sludge Survey.
2010 Jan
Occurrence and risks of triclosan and triclocarban in the Pearl River system, South China: from source to the receiving environment.
2010 Jul 15
Self-reported chemicals exposure, beliefs about disease causation, and risk of breast cancer in the Cape Cod Breast Cancer and Environment Study: a case-control study.
2010 Jul 20
Analysis of triclosan and triclocarban in soil and biosolids using molecularly imprinted solid phase extraction coupled with HPLC-UV.
2010 Jul-Aug
Transformation of triclosan and triclocarban in soils and biosolids-applied soils.
2010 Jul-Aug
Characterization of the androgen-sensitive MDA-kb2 cell line for assessing complex environmental mixtures.
2010 Jun
Temperature-controlled ionic liquid dispersive liquid-phase microextraction for the sensitive determination of triclosan and triclocarban in environmental water samples prior to HPLC-ESI-MS/MS.
2010 Jun
Quantitative gene monitoring of microbial tetracycline resistance using magnetic luminescent nanoparticles.
2010 Jun
Trace determination of triclosan and triclocarban in environmental water samples with ionic liquid dispersive liquid-phase microextraction prior to HPLC-ESI-MS-MS.
2010 Jun
Measured physicochemical characteristics and biosolids-borne concentrations of the antimicrobial Triclocarban (TCC).
2010 Jun 1
Fate of 14C-triclocarban in biosolids-amended soils.
2010 Jun 1
Triclocarban, triclosan, polybrominated diphenyl ethers, and 4-nonylphenol in biosolids and in soil receiving 33-year biosolids application.
2010 Mar
Quantitative determination of triclocarban in wastewater effluent by stir bar sorptive extraction and liquid desorption-liquid chromatography-tandem mass spectrometry.
2010 Mar 12
Some flame retardants and the antimicrobials triclosan and triclocarban enhance the androgenic activity in vitro.
2010 Nov
Personal care products and endocrine disruption: A critical review of the literature.
2010 Nov
Identification of wastewater bacteria involved in the degradation of triclocarban and its non-chlorinated congener.
2010 Nov 15
Aquatic hazard assessment for pharmaceuticals, personal care products, and endocrine-disrupting compounds from biosolids-amended land.
2010 Oct
Rapid resolution liquid chromatography-tandem mass spectrometry method for the determination of endocrine disrupting chemicals (EDCs), pharmaceuticals and personal care products (PPCPs) in wastewater irrigated soils.
2010 Oct
Retention-release characteristics of triclocarban and triclosan in biosolids, soils, and biosolids-amended soils.
2010 Sep
Triclocarban and triclosan biodegradation at field concentrations and the resulting leaching potentials in three agricultural soils.
2010 Sep
Use of chemical mixtures to differentiate mechanisms of endocrine action in a small fish model.
2010 Sep 1
Computational thermochemistry of six ureas, imidazolidin-2-one, N,N'-trimethyleneurea, benzimidazolinone, parabanic acid, barbital (5,5'-diethylbarbituric acid), and 3,4,4'-trichlorocarbanilide, with an extension to related compounds.
2010 Sep 2
Effects of bisphenol A and triclocarban on brain-specific expression of aromatase in early zebrafish embryos.
2011 Oct 25
Inhibition of soluble epoxide hydrolase contributes to the anti-inflammatory effect of antimicrobial triclocarban in a murine model.
2011 Sep 1
Triclocarban mediates induction of xenobiotic metabolism through activation of the constitutive androstane receptor and the estrogen receptor alpha.
2012
Effects of triclocarban on the transcription of estrogen, androgen and aryl hydrocarbon receptor responsive genes in human breast cancer cells.
2013 Aug
Patents

Sample Use Guides

Use Dial® soap containing 0.30% triclocarban for hand and body wash
Route of Administration: Other
To study effects of antimicrobial agents on the growth of P. aeruginosa at 37°C triclocarban at concentrations of 0 - 5 ug/ml were used
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:19:41 UTC 2021
Edited
by admin
on Sat Jun 26 11:19:41 UTC 2021
Record UNII
BGG1Y1ED0Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRICLOCARBAN
HSDB   INCI   INN   MART.   MI   USAN   USP-RS   WHO-DD  
INCI   INN   USAN  
Official Name English
UREA, N-(4-CHLOROPHENYL)-N'-(3,4-DICHLOROPHENYL)-
Systematic Name English
1-(4-CHLOROPHENYL)-3-(3,4-DICHLOROPHENYL)UREA
Systematic Name English
NSC-72005
Code English
TRICLOCARBAN [MI]
Common Name English
TRICLOCARBAN [USP-RS]
Common Name English
TRICLOCARBAN [HSDB]
Common Name English
TRICLOCARBAN [USP MONOGRAPH]
Common Name English
TRICLOCARBAN [INCI]
Common Name English
TRICLOCARBAN [INN]
Common Name English
TRICLOCARBAN [WHO-DD]
Common Name English
3,4,4'-TRICHLOROCARBANILIDE
Common Name English
TRICLOCARBAN [USAN]
Common Name English
TRICLOCARBAN [MART.]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 27901
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
NCI_THESAURUS C28394
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
Code System Code Type Description
DRUG CENTRAL
3630
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
MERCK INDEX
M11089
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY Merck Index
INN
2017
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
NCI_THESAURUS
C47770
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
ECHA (EC/EINECS)
202-924-1
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
USP_CATALOG
1681800
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY USP-RS
RXCUI
38609
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY RxNorm
PUBCHEM
7547
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
WIKIPEDIA
TRICLOCARBAN
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
HSDB
5009
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
MESH
C009540
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
FDA UNII
BGG1Y1ED0Y
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
DRUG BANK
DB11155
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
ChEMBL
CHEMBL1076347
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
CAS
101-20-2
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
EVMPD
SUB11271MIG
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
EPA CompTox
101-20-2
Created by admin on Sat Jun 26 11:19:42 UTC 2021 , Edited by admin on Sat Jun 26 11:19:42 UTC 2021
PRIMARY
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