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 60	CYP1A1 349 CYP1B1 92 UGT1A9 380	CYP1A1 108 CYP1B1 51

Drug as perpetrator

Target	Modality	Activity
CYP19A1 60	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5742433/	yes [IC50 15.81 uM]
CYP1A1 218	inducer 1573 Sources: https://www.sciencedirect.com/science/article/pii/S0887233313000672 Page: 8.0	yes
CYP1B1 67	inducer 1573 Sources: https://www.sciencedirect.com/science/article/pii/S0887233313000672 Page: 8.0	yes

Drug as victim

Target	Modality	Activity
CYP1A1 349	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3522462/	likely
CYP1B1 92	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3522462/	likely
UGT1A9 380	substrate 3367 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
Activity and mechanisms of action of selected biocidal agents on Gram-positive and -negative bacteria.	2003	12534815
Simultaneous determination of chlorinated bacteriostats in cosmetic and pharmaceutical products.	2005 May-Jun	16116523
Detection of triclocarban and two co-contaminating chlorocarbanilides in US aquatic environments using isotope dilution liquid chromatography tandem mass spectrometry.	2007 Jan	16678153
Snail bioaccumulation of triclocarban, triclosan, and methyltriclosan in a North Texas, USA, stream affected by wastewater treatment plant runoff.	2008 Aug	18380516
Growth-inhibiting effects of 12 antibacterial agents and their mixtures on the freshwater microalga Pseudokirchneriella subcapitata.	2008 May	18419195
Determination of household chemicals using gas chromatography and liquid chromatography with tandem mass spectrometry.	2008 May 9	18374930
Runoff of pharmaceuticals and personal care products following application of dewatered municipal biosolids to an agricultural field.	2009 Aug 1	19464726
Fate of organohalogens in US wastewater treatment plants and estimated chemical releases to soils nationwide from biosolids recycling.	2009 Dec	20024018
Adsorption and degradation of triclosan and triclocarban in soils and biosolids-amended soils.	2009 Jun 10	19441835
Effect of triclosan and triclocarban biocides on biodegradation of estrogens in soils.	2009 Nov	19804895
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	19875124
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
Analysis of triclosan and triclocarban in soil and biosolids using molecularly imprinted solid phase extraction coupled with HPLC-UV.	2010 Jul-Aug	20922967
Quantitative gene monitoring of microbial tetracycline resistance using magnetic luminescent nanoparticles.	2010 Jun	20424797
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
Triclocarban and triclosan biodegradation at field concentrations and the resulting leaching potentials in three agricultural soils.	2010 Sep	20705327
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 15 15:22:17 GMT 2023` Edited by `admin` on `Fri Dec 15 15:22:17 GMT 2023`
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