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

Details

Stereochemistry ACHIRAL
Molecular Formula C13H9Cl3N2O
Molecular Weight 315.582
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRICLOCARBAN

SMILES

ClC1=CC=C(NC(=O)NC2=CC=C(Cl)C(Cl)=C2)C=C1

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 315.582
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
National and regional assessment of the antibacterial soap market: a step toward determining the impact of prevalent antibacterial soaps.
2001 Oct
Activity and mechanisms of action of selected biocidal agents on Gram-positive and -negative bacteria.
2003
Removal of E. coli from water using surface-modified activated carbon filter media and its performance over an extended use.
2006 Oct 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
Runoff of pharmaceuticals and personal care products following application of dewatered municipal biosolids to an agricultural field.
2009 Aug 1
Adsorption and degradation of triclosan and triclocarban in soils and biosolids-amended soils.
2009 Jun 10
Ultra-high-performance liquid chromatography-tandem mass spectrometry for determining the presence of eleven personal care products in surface and wastewaters.
2009 Oct 16
Pharmaceuticals and personal care products in archived U.S. biosolids from the 2001 EPA National Sewage Sludge Survey.
2010 Jan
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
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
Aquatic hazard assessment for pharmaceuticals, personal care products, and endocrine-disrupting compounds from biosolids-amended land.
2010 Oct
Retention-release characteristics of triclocarban and triclosan in biosolids, soils, and biosolids-amended soils.
2010 Sep
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
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 Wed Jul 05 22:52:51 UTC 2023
Edited
by admin
on Wed Jul 05 22:52:51 UTC 2023
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 [WHO-DD]
Common Name English
TRICLOCARBAN [INCI]
Common Name English
triclocarban [INN]
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 Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
NCI_THESAURUS C28394
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
Code System Code Type Description
DRUG CENTRAL
3630
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
MERCK INDEX
M11089
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY Merck Index
INN
2017
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
NCI_THESAURUS
C47770
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
ECHA (EC/EINECS)
202-924-1
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
RXCUI
38609
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY RxNorm
DAILYMED
BGG1Y1ED0Y
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
PUBCHEM
7547
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
WIKIPEDIA
TRICLOCARBAN
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
NSC
72005
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
HSDB
5009
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
RS_ITEM_NUM
1681800
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
CHEBI
48347
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
MESH
C009540
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
FDA UNII
BGG1Y1ED0Y
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
DRUG BANK
DB11155
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
SMS_ID
100000077518
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
ChEMBL
CHEMBL1076347
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
CAS
101-20-2
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
EVMPD
SUB11271MIG
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID4026214
Created by admin on Wed Jul 05 22:52:51 UTC 2023 , Edited by admin on Wed Jul 05 22:52:51 UTC 2023
PRIMARY
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