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

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
Effect of handwashing on child health: a randomised controlled trial.	2005 Jul 16-22	16023513
Co-occurrence of triclocarban and triclosan in U.S. water resources.	2005 Mar 15	15819193
Partitioning, persistence, and accumulation in digested sludge of the topical antiseptic triclocarban during wastewater treatment.	2006 Jun 1	16786704
Triclocarban seems to defy wastewater treatment.	2006 Jun 1	16786673
Algal bioaccumulation of triclocarban, triclosan, and methyl-triclosan in a North Texas wastewater treatment plant receiving stream.	2007 May	17275881
Detection of trace triclocarban in water sample using solid-phase extraction-liquid chromatography with stochastic resonance algorithm.	2008 Apr 15	18497155
Snail bioaccumulation of triclocarban, triclosan, and methyltriclosan in a North Texas, USA, stream affected by wastewater treatment plant runoff.	2008 Aug	18380516
Fate of triclosan and evidence for reductive dechlorination of triclocarban in estuarine sediments.	2008 Jun 15	18605588
Growth-inhibiting effects of 12 antibacterial agents and their mixtures on the freshwater microalga Pseudokirchneriella subcapitata.	2008 May	18419195
Ab initio and in situ comparison of caffeine, triclosan, and triclocarban as indicators of sewage-derived microbes in surface waters.	2008 May 1	18522115
Determination of household chemicals using gas chromatography and liquid chromatography with tandem mass spectrometry.	2008 May 9	18374930
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.	2008 Oct	18822043
In vitro biologic activities of the antimicrobials triclocarban, its analogs, and triclosan in bioassay screens: receptor-based bioassay screens.	2008 Sep	18795164
Meta-analysis of mass balances examining chemical fate during wastewater treatment.	2008 Sep 1	18800497
Fate of organohalogens in US wastewater treatment plants and estimated chemical releases to soils nationwide from biosolids recycling.	2009 Dec	20024018
Bioaccumulation of triclocarban in Lumbriculus variegatus.	2009 Dec	19655999
Pharmaceutical and personal care products in tile drainage following surface spreading and injection of dewatered municipal biosolids to an agricultural field.	2009 Jul 1	19394680
Simultaneous determination of parabens, triclosan and triclocarban in water by liquid chromatography/electrospray ionisation tandem mass spectrometry.	2009 Jun	19437429
Comparative microscale analysis of the effects of triclosan and triclocarban on the structure and function of river biofilm communities.	2009 May 1	19275956
Ultra-high-performance liquid chromatography-tandem mass spectrometry for determining the presence of eleven personal care products in surface and wastewaters.	2009 Oct 16	19747689
Fate of triclocarban during soil aquifer treatment: soil column studies.	2010	20371936
Stir-bar-sorptive extraction and ultra-high-performance liquid chromatography-tandem mass spectrometry for simultaneous analysis of UV filters and antimicrobial agents in water samples.	2010 Aug	20428847
Uptake of pharmaceutical and personal care products by soybean plants from soils applied with biosolids and irrigated with contaminated water.	2010 Aug 15	20704212
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
Characterization of the androgen-sensitive MDA-kb2 cell line for assessing complex environmental mixtures.	2010 Jun	20821581
Temperature-controlled ionic liquid dispersive liquid-phase microextraction for the sensitive determination of triclosan and triclocarban in environmental water samples prior to HPLC-ESI-MS/MS.	2010 Jun	20491060
Quantitative gene monitoring of microbial tetracycline resistance using magnetic luminescent nanoparticles.	2010 Jun	20424797
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	20379811
Fate of 14C-triclocarban in biosolids-amended soils.	2010 Jun 1	20363015
Quantitative determination of triclocarban in wastewater effluent by stir bar sorptive extraction and liquid desorption-liquid chromatography-tandem mass spectrometry.	2010 Mar 12	20138283
Some flame retardants and the antimicrobials triclosan and triclocarban enhance the androgenic activity in vitro.	2010 Nov	20943248
Identification of wastewater bacteria involved in the degradation of triclocarban and its non-chlorinated congener.	2010 Nov 15	20727675
Rapid resolution liquid chromatography-tandem mass spectrometry method for the determination of endocrine disrupting chemicals (EDCs), pharmaceuticals and personal care products (PPCPs) in wastewater irrigated soils.	2010 Oct	20818522
Retention-release characteristics of triclocarban and triclosan in biosolids, soils, and biosolids-amended soils.	2010 Sep	20821649
Triclocarban and triclosan biodegradation at field concentrations and the resulting leaching potentials in three agricultural soils.	2010 Sep	20705327
Use of chemical mixtures to differentiate mechanisms of endocrine action in a small fish model.	2010 Sep 1	20573408
Computational thermochemistry of six ureas, imidazolidin-2-one, N,N'-trimethyleneurea, benzimidazolinone, parabanic acid, barbital (5,5'-diethylbarbituric acid), and 3,4,4'-trichlorocarbanilide, with an extension to related compounds.	2010 Sep 2	20681553
Effects of bisphenol A and triclocarban on brain-specific expression of aromatase in early zebrafish embryos.	2011 Oct 25	22006313
Inhibition of soluble epoxide hydrolase contributes to the anti-inflammatory effect of antimicrobial triclocarban in a murine model.	2011 Sep 1	21741984
Triclocarban mediates induction of xenobiotic metabolism through activation of the constitutive androstane receptor and the estrogen receptor alpha.	2012	22761658
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

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