TRICLOCARBAN

US Previously Marketed

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 Search

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
Sources: http://www.cosmeticsinfo.org/triclocarban-information
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

Condition	Modality	Targets	Highest Phase	Product
Skin bacterial infections 4 Sources: http://www.dialsoap.com/products/spring-water-all-day-freshness-antibacterial-deodorant-bar-soap https://www.ncbi.nlm.nih.gov/pubmed/21131331	Preventing		Withdrawn	Dial® soap Approved Use Antibacterial Soap used to protect skin from bacterial infections

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1109279/	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

Dose	Population	Adverse 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: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_016.pdf https://pubmed.ncbi.nlm.nih.gov/743875/	healthy, 21 to 65 years old n = 10 Health Status: healthy Age Group: 21 to 65 years old Sex: M Population Size: 10 Sources: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_016.pdf https://pubmed.ncbi.nlm.nih.gov/743875/	Other AEs: Skin irritation... Other AEs: Skin irritation (grade 1) Sources: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_016.pdf https://pubmed.ncbi.nlm.nih.gov/743875/

AEs

AE	Significance	Dose	Population
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: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_016.pdf https://pubmed.ncbi.nlm.nih.gov/743875/	healthy, 21 to 65 years old n = 10 Health Status: healthy Age Group: 21 to 65 years old Sex: M Population Size: 10 Sources: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_016.pdf https://pubmed.ncbi.nlm.nih.gov/743875/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 58	CYP1A1 344 CYP1B1 90 UGT1A9 378	CYP1A1 103 CYP1B1 50

Drug as perpetrator

Target	Modality	Activity
CYP19A1 58	inhibitor 3185 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5742433/	yes [IC50 15.81 uM]
CYP1A1 206	inducer 1515 Sources: https://www.sciencedirect.com/science/article/pii/S0887233313000672 Page: 8.0	yes
CYP1B1 66	inducer 1515 Sources: https://www.sciencedirect.com/science/article/pii/S0887233313000672 Page: 8.0	yes

Drug as victim

Target	Modality	Activity
CYP1A1 344	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3522462/	likely
CYP1B1 90	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3522462/	likely
UGT1A9 378	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3250046/	likely

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:48347	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48347
ChemicalBook	CB7193925	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7193925
MolPort	MolPort-001-012-487	https://www.molport.com/shop/molecule-link/MolPort-001-012-487
ZINC	ZINC000000121480	http://zinc15.docking.org/substances/ZINC000000121480
eMolecules	478039	https://www.emolecules.com/cgi-bin/more?vid=478039

PubMed

Title	Date	PubMed
[Contact allergy to antiseptics: 75 cases analyzed by the dermato-allergovigilance network (Revidal)].	2005 Dec	16446637
Simultaneous determination of chlorinated bacteriostats in cosmetic and pharmaceutical products.	2005 May-Jun	16116523
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	16377264
Partitioning, persistence, and accumulation in digested sludge of the topical antiseptic triclocarban during wastewater treatment.	2006 Jun 1	16786704
Removal of E. coli from water using surface-modified activated carbon filter media and its performance over an extended use.	2006 Oct 1	17051805
Simultaneous determination of triclocarban and triclosan in municipal biosolids by liquid chromatography tandem mass spectrometry.	2007 Sep 14	17692856
Snail bioaccumulation of triclocarban, triclosan, and methyltriclosan in a North Texas, USA, stream affected by wastewater treatment plant runoff.	2008 Aug	18380516
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.	2008 Oct	18822043
Meta-analysis of mass balances examining chemical fate during wastewater treatment.	2008 Sep 1	18800497
Toxicology in the fast lane: application of high-throughput bioassays to detect modulation of key enzymes and receptors.	2009 Dec	20049205
Fate of triclocarban during soil aquifer treatment: soil column studies.	2010	20371936
The antimicrobial triclocarban stimulates embryo production in the freshwater mudsnail Potamopyrgus antipodarum.	2010 Apr	20821527
Electrochemistry-mass spectrometry unveils the formation of reactive triclocarban metabolites.	2010 Dec	20861155
Occurrence and loss over three years of 72 pharmaceuticals and personal care products from biosolids-soil mixtures in outdoor mesocosms.	2010 Dec	20728197
Pharmaceuticals and personal care products in archived U.S. biosolids from the 2001 EPA National Sewage Sludge Survey.	2010 Jan	20106500
Occurrence and risks of triclosan and triclocarban in the Pearl River system, South China: from source to the receiving environment.	2010 Jul 15	20303651
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	20646273
Quantitative determination of triclocarban in wastewater effluent by stir bar sorptive extraction and liquid desorption-liquid chromatography-tandem mass spectrometry.	2010 Mar 12	20138283
Aquatic hazard assessment for pharmaceuticals, personal care products, and endocrine-disrupting compounds from biosolids-amended land.	2010 Oct	20872647
Effects of triclocarban on the transcription of estrogen, androgen and aryl hydrocarbon receptor responsive genes in human breast cancer cells.	2013 Aug	23524099

Patents

Sample Use Guides

In Vivo Use Guide

Use Dial® soap containing 0.30% triclocarban for hand and body wash

Route of Administration: Other

In Vitro Use Guide

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

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Name

Type

Language

TRICLOCARBAN

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