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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
[Contact allergy to antiseptics: 75 cases analyzed by the dermato-allergovigilance network (Revidal)].
2005 Dec
Simultaneous determination of chlorinated bacteriostats in cosmetic and pharmaceutical products.
2005 May-Jun
Measuring environmental phenols and chlorinated organic chemicals in breast milk using automated on-line column-switching-high performance liquid chromatography-isotope dilution tandem mass spectrometry.
2006 Feb 2
Partitioning, persistence, and accumulation in digested sludge of the topical antiseptic triclocarban during wastewater treatment.
2006 Jun 1
Removal of E. coli from water using surface-modified activated carbon filter media and its performance over an extended use.
2006 Oct 1
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
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.
2008 Oct
Meta-analysis of mass balances examining chemical fate during wastewater treatment.
2008 Sep 1
Toxicology in the fast lane: application of high-throughput bioassays to detect modulation of key enzymes and receptors.
2009 Dec
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
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
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
Quantitative determination of triclocarban in wastewater effluent by stir bar sorptive extraction and liquid desorption-liquid chromatography-tandem mass spectrometry.
2010 Mar 12
Aquatic hazard assessment for pharmaceuticals, personal care products, and endocrine-disrupting compounds from biosolids-amended land.
2010 Oct
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 Fri Dec 16 16:55:01 UTC 2022
Edited
by admin
on Fri Dec 16 16:55:01 UTC 2022
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 Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
NCI_THESAURUS C28394
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
Code System Code Type Description
DRUG CENTRAL
3630
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
MERCK INDEX
M11089
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY Merck Index
INN
2017
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
NCI_THESAURUS
C47770
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
ECHA (EC/EINECS)
202-924-1
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
RXCUI
38609
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY RxNorm
DAILYMED
BGG1Y1ED0Y
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
PUBCHEM
7547
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
WIKIPEDIA
TRICLOCARBAN
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
NSC
72005
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
HSDB
5009
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
RS_ITEM_NUM
1681800
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
CHEBI
48347
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
MESH
C009540
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
FDA UNII
BGG1Y1ED0Y
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
DRUG BANK
DB11155
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
ChEMBL
CHEMBL1076347
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
CAS
101-20-2
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
EVMPD
SUB11271MIG
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
EPA CompTox
DTXSID4026214
Created by admin on Fri Dec 16 16:55:01 UTC 2022 , Edited by admin on Fri Dec 16 16:55:01 UTC 2022
PRIMARY
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Tmax PHARMACOKINETIC ORAL ADMINISTRATION