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:: 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
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Activity and mechanisms of action of selected biocidal agents on Gram-positive and -negative bacteria.
2003
Cyclodextrin solubilization of the antibacterial agents triclosan and triclocarban: formation of aggregates and higher-order complexes.
2005 Jun 13
Co-occurrence of triclocarban and triclosan in U.S. water resources.
2005 Mar 15
Biological degradation of triclocarban and triclosan in a soil under aerobic and anaerobic conditions and comparison with environmental fate modelling.
2007 Dec
Detection of triclocarban and two co-contaminating chlorocarbanilides in US aquatic environments using isotope dilution liquid chromatography tandem mass spectrometry.
2007 Jan
Simultaneous determination of triclocarban and triclosan in municipal biosolids by liquid chromatography tandem mass spectrometry.
2007 Sep 14
Snail bioaccumulation of triclocarban, triclosan, and methyltriclosan in a North Texas, USA, stream affected by wastewater treatment plant runoff.
2008 Aug
Fate of triclosan and evidence for reductive dechlorination of triclocarban in estuarine sediments.
2008 Jun 15
Ab initio and in situ comparison of caffeine, triclosan, and triclocarban as indicators of sewage-derived microbes in surface waters.
2008 May 1
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.
2008 Oct
In vitro biologic activities of the antimicrobials triclocarban, its analogs, and triclosan in bioassay screens: receptor-based bioassay screens.
2008 Sep
Meta-analysis of mass balances examining chemical fate during wastewater treatment.
2008 Sep 1
Fate of organohalogens in US wastewater treatment plants and estimated chemical releases to soils nationwide from biosolids recycling.
2009 Dec
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
Impact of biosolids on the persistence and dissipation pathways of triclosan and triclocarban in an agricultural soil.
2009 Nov 15
Ultra-high-performance liquid chromatography-tandem mass spectrometry for determining the presence of eleven personal care products in surface and wastewaters.
2009 Oct 16
Analysis of triclosan and triclocarban in soil and biosolids using molecularly imprinted solid phase extraction coupled with HPLC-UV.
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
Retention-release characteristics of triclocarban and triclosan in biosolids, soils, and biosolids-amended soils.
2010 Sep
Effects of bisphenol A and triclocarban on brain-specific expression of aromatase in early zebrafish embryos.
2011 Oct 25
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 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
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
URINE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION