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
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)
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 |
DescriptionCurator'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
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
T1/2
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: |
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... Other AEs: Skin irritation (grade 1) Sources: |
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: |
healthy, 21 to 65 years old n = 10 Health Status: healthy Age Group: 21 to 65 years old Sex: M Population Size: 10 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
[Contact allergy to antiseptics: 75 cases analyzed by the dermato-allergovigilance network (Revidal)]. | 2005 Dec |
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Simultaneous determination of chlorinated bacteriostats in cosmetic and pharmaceutical products. | 2005 May-Jun |
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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 |
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Partitioning, persistence, and accumulation in digested sludge of the topical antiseptic triclocarban during wastewater treatment. | 2006 Jun 1 |
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Removal of E. coli from water using surface-modified activated carbon filter media and its performance over an extended use. | 2006 Oct 1 |
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Simultaneous determination of triclocarban and triclosan in municipal biosolids by liquid chromatography tandem mass spectrometry. | 2007 Sep 14 |
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Snail bioaccumulation of triclocarban, triclosan, and methyltriclosan in a North Texas, USA, stream affected by wastewater treatment plant runoff. | 2008 Aug |
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Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography. | 2008 Oct |
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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 |
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Fate of triclocarban during soil aquifer treatment: soil column studies. | 2010 |
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The antimicrobial triclocarban stimulates embryo production in the freshwater mudsnail Potamopyrgus antipodarum. | 2010 Apr |
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Electrochemistry-mass spectrometry unveils the formation of reactive triclocarban metabolites. | 2010 Dec |
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Occurrence and loss over three years of 72 pharmaceuticals and personal care products from biosolids-soil mixtures in outdoor mesocosms. | 2010 Dec |
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Pharmaceuticals and personal care products in archived U.S. biosolids from the 2001 EPA National Sewage Sludge Survey. | 2010 Jan |
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Occurrence and risks of triclosan and triclocarban in the Pearl River system, South China: from source to the receiving environment. | 2010 Jul 15 |
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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 |
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Quantitative determination of triclocarban in wastewater effluent by stir bar sorptive extraction and liquid desorption-liquid chromatography-tandem mass spectrometry. | 2010 Mar 12 |
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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
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=12534815
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
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EPA PESTICIDE CODE |
27901
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NCI_THESAURUS |
C28394
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M11089
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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