Triclocarban
Identification
- Summary
Triclocarban is an antibacterial agent used in liquid soaps and body washes.
- Generic Name
- Triclocarban
- DrugBank Accession Number
- DB11155
- Background
Triclocarban, with the chemical formula C13H9Cl3N2O 10 is an antibacterial agent that is particularly effective against Gram-positive bacteria such as Staphylococcus aureus. It is a bacteriostatic compound that has been found in antibacterial soaps and other personal care products. In 2017, the US FDA prohibited the marketing of over-the-counter (OTC) consumer antiseptic wash products containing triclocarban due to negative health effects such as bacterial resistance or hormonal effects 7, 8.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 315.58
Monoisotopic: 313.978046 - Chemical Formula
- C13H9Cl3N2O
- Synonyms
- 1-(3',4'-dichlorophenyl)-3-(4'-chlorophenyl)urea
- 3,4,4'-trichloro carbanilide
- 3,4,4'-trichlorocarbanilide
- 3,4,4'-trichlorodiphenylurea
- N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)urea
- Triclocarban
Pharmacology
- Indication
Triclocarban (TCC), or 3,4,4'-trichlorocarbanilide, is an antibacterial agent used in bar and liquid soaps and body washes 17.
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- Pharmacodynamics
The antimicrobial mechanism underlying the bacteriostatic and bactericidal effects of triclocarban is believed to be an unspecific adsorption to cell membranes and interruption of their function. As a result, the growth of gram-positive as well as gram-negative bacteria is inhibited 15.
- Mechanism of action
Triclocarban is a triclosan analog with an antibacterial activity. Triclocarban exerts its effect by inhibiting the activity of enoyl-(acyl-carrier protein) (ACP) reductase, which is ubiquitously distributed in bacteria, fungi and various plants. ACP reductase catalyzes the last step in each cycle of fatty acid elongation in the type II fatty acid synthase systems. As a result, this agent interrupts cell membrane synthesis and leads to bacterial growth inhibition 17.
Target Actions Organism AEnoyl-[acyl-carrier-protein] reductase [NADPH] FabI antagonistStaphylococcus aureus (strain MRSA252) - Absorption
A human exposure study in a small group of subjects demonstrated that a portion of the TCC present in bar soaps is absorbed through the skin and is excreted in urine as N-glucuronides 2.
Because they are produced and used in large quantities in various products, they are absorbed into the human body of the general population 13.
The absorption of triclocarban during a human pharmacokinetic study was estimated at 0.6% of the 70 + or - 15 mg of triclocarban in the soap used. The triclocarban-N-glucuronide urine concentration varied considerably among the study subjects, and continuous daily use of the soap led to steady-state levels of excretion 17.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Blood levels after parenteral injection are low and comparison of the radioactivity and chemical determinations suggest rapid metabolism of the Triclocarban 17.
Human metabolism of TCC involves direct glucuronidation to form N- and N'- glucuronides as well as ring hydroxylation to 2'-hydroxy-TCC and 6-hydroxy-TCC, which are further metabolized to sulfate and glucuronide conjugates. In human subjects given a single oral dose of TCC, 27% of the dose was excreted in the urine within 80 hours. About 70% of the administered dose was excreted in the feces within 5 days 17.
The major urinary metabolites were N-glucuronides (average levels, 30 ng/mL) and a major plasma metabolite was the sulfate conjugate of 2'-OH-TCC (levels ranged from 0-20 ng/mL 17.
The maximum plasma level occurred 2.8 hr after dosing and was 3.7 nmol-equivalents of TCC per g of plasma (approximately 1.2 ppm). Biotransformation of TCC was rapid but did not appear to involve splitting of the basic TCC structure. The major plasma metabolites were N- and N'-glucuronides of TCC which were eliminated with half-life approximately 2 hr to the urine and 2'-hydroxy-TCC sulfate and 6-hydroxy-TCC sulfate (the o-hydroxy-TCC sulfates) which were removed with half life approximately 20 hr (presumably into the bile) 17.
- Route of elimination
The metabolism of (14)C-TCC (3,4,4'-trichlorocarbanilide) has been investigated in humans following oral exposure to 2.2 mumol/kg. Fecal elimination (70% of dose) was complete at the 120 hour point after administration and the urinary excretion (27% of dose) was complete after 80 hours post-administration 17.
Urinary glucuronides appear to be valuable biomarkers of triclocarban exposure 2.
- Half-life
10 hours 14
- Clearance
After a pharmacokinetic study in man, radioactivity was rapidly cleared from blood after intravenous administrations of (14)C-triclocarban in propylene glycol with a blood clearance half-life measured to be 8.6 hours 17.
- Adverse Effects
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- Toxicity
Ld50 of 2100 mg/kg in mice 9.
There has been concern voiced over the endocrine effect of triclocarban ande, in particular, on estrogen 4, 5,6,16.
One study determined that triclocarban by itself stimulates AroB (brain aromatase) gene expression only slightly, but TCC strongly enhances the overexpression of AroB that is induced by exogenous estrogen. TCC has the potential to elevate levels of aromatase enzymes and, thereby, levels of endogenous estrogens in the developing brain 17. The effects of triclocarban on the endocrine system are presently not fully elucidated.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- Cutisan / Nobacter / Solubacter
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 1st Date antibacterial Deodorant (Gold) Soap 0.3 g/100g Topical Guilin Share Friend Daily Use Chemical Co.,Ltd 2015-08-01 Not applicable US 1st Date antibacterial Deodorant (Green) Soap 0.3 g/100g Topical Guilin Share Friend Daily Use Chemical Co.,Ltd 2015-08-01 Not applicable US 1st Date antibacterial Deodorant (White) Soap 0.3 g/100g Topical Guilin Share Friend Daily Use Chemical Co.,Ltd 2015-08-01 Not applicable US a.c.care Bees Foam Cleanser Cream 459 mg/150mL Topical Dong Sung Pharm. Co., Ltd. 2014-09-23 2015-11-30 US a.c.care Bees Foam Cleanser Troubled Skin Care 2 pcs Set Cream 153 mg/50mL Topical Dong Sung Pharm. Co., Ltd. 2014-12-04 2015-11-30 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Zarina Medicated Antiseptic Soap Triclocarban (0.4 %) + Triclosan (0.1 %) Soap Topical Fairtrade International Co. Ltd. Not applicable Not applicable Canada
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Halobenzenes
- Direct Parent
- Dichlorobenzenes
- Alternative Parents
- Aryl chlorides / Isoureas / Propargyl-type 1,3-dipolar organic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- 1,2-dichlorobenzene / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Carboximidic acid derivative / Hydrocarbon derivative / Isourea / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxygen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- ureas, dichlorobenzene, monochlorobenzenes (CHEBI:48347)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- BGG1Y1ED0Y
- CAS number
- 101-20-2
- InChI Key
- ICUTUKXCWQYESQ-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 3-(4-chlorophenyl)-1-(3,4-dichlorophenyl)urea
- SMILES
- ClC1=CC=C(NC(=O)NC2=CC(Cl)=C(Cl)C=C2)C=C1
References
- General References
- Schebb NH, Muvvala JB, Morin D, Buckpitt AR, Hammock BD, Rice RH: Metabolic activation of the antibacterial agent triclocarban by cytochrome P450 1A1 yielding glutathione adducts. Drug Metab Dispos. 2014 Jul;42(7):1098-102. doi: 10.1124/dmd.114.058206. Epub 2014 Apr 14. [Article]
- Schebb NH, Inceoglu B, Ahn KC, Morisseau C, Gee SJ, Hammock BD: Investigation of human exposure to triclocarban after showering and preliminary evaluation of its biological effects. Environ Sci Technol. 2011 Apr 1;45(7):3109-15. doi: 10.1021/es103650m. Epub 2011 Mar 7. [Article]
- Schebb NH, Franze B, Maul R, Ranganathan A, Hammock BD: In vitro glucuronidation of the antibacterial triclocarban and its oxidative metabolites. Drug Metab Dispos. 2012 Jan;40(1):25-31. doi: 10.1124/dmd.111.042283. Epub 2011 Sep 27. [Article]
- Kennedy RC, Menn FM, Healy L, Fecteau KA, Hu P, Bae J, Gee NA, Lasley BL, Zhao L, Chen J: Early life triclocarban exposure during lactation affects neonate rat survival. Reprod Sci. 2015 Jan;22(1):75-89. doi: 10.1177/1933719114532844. Epub 2014 May 6. [Article]
- Chen J, Ahn KC, Gee NA, Ahmed MI, Duleba AJ, Zhao L, Gee SJ, Hammock BD, Lasley BL: Triclocarban enhances testosterone action: a new type of endocrine disruptor? Endocrinology. 2008 Mar;149(3):1173-9. doi: 10.1210/en.2007-1057. Epub 2007 Nov 29. [Article]
- Huang H, Du G, Zhang W, Hu J, Wu D, Song L, Xia Y, Wang X: The in vitro estrogenic activities of triclosan and triclocarban. J Appl Toxicol. 2014 Sep;34(9):1060-7. doi: 10.1002/jat.3012. Epub 2014 Apr 16. [Article]
- FDA bans triclosan and triclocarban in consumer soaps [Link]
- FDA issues final rule on safety and effectiveness of antibacterial soaps [Link]
- Triclorcarban ToxNet [Link]
- European Chemicals Agency - Triclorcarban [Link]
- Temporal Development of Gut Microbiota in Triclocarban Exposed Pregnant and Neonatal Rats [Link]
- Binding mechanism of triclocarban with human serum albumin: Effect on the conformation and activity of the model transport protein [Link]
- Triclocarban and Triclosan Inhibit Human Aromatase via Different Mechanisms [Link]
- Triclocarban [Link]
- Investigation of human exposure, metabolism and biological effects of the antibacterial triclocarban [Link]
- Effects of triclocarban on the transcription of estrogen, androgen and aryl hydrocarbon receptor responsive genes in human breast cancer cells [Link]
- Triclocarban, PuBMED [Link]
- Triclocarban [CASRN 101-20-2] [File]
- External Links
- KEGG Drug
- D06223
- PubChem Compound
- 7547
- PubChem Substance
- 347827924
- ChemSpider
- 7266
- BindingDB
- 25730
- 38609
- ChEBI
- 48347
- ChEMBL
- CHEMBL1076347
- ZINC
- ZINC000000121480
- PDBe Ligand
- 9EG
- Wikipedia
- Triclocarban
- PDB Entries
- 5vl2 / 5vm0 / 5vm6
- MSDS
- Download (415 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical 459 mg/150mL Cream Topical 153 mg/50mL Soap Topical 15 mg/1g Soap Topical .1 g/100g Soap Cutaneous 0.3 g/100g Soap Cutaneous 0.16 g/100g Soap Topical 1.5 % Soap Topical 2.6 g/10g Soap Topical 1.3 g/10g Soap Topical 0.6 g/100g Soap Topical 1 % Soap Topical 1.5 mg/100mg Soap Topical 1.5 g / 100 g Soap Topical 0.29 g/100g Soap Topical 1.017 g/339g Soap Topical .339 g/113g Soap Cutaneous 0.60 1/1 Soap Topical 113 g/113g Soap Topical .60 g/100g Soap Topical 6 mg/1g Soap Topical 0.3 g/100g Soap Topical 0.33 mg/100mg Soap Topical 0.744 g/99.225g Soap Cutaneous 0.45 g/90g Soap Topical 1.5 g/100g Soap Topical .67 g/86g Liquid Topical 1.5 mg/1000mL Soap Topical 4 mg/1g Liquid Topical 1.5 mg/1mL Soap Topical 0.3 g/1g Soap Topical 1.356 g/113g Soap Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 491.2- 493 MSDS water solubility Insoluble MSDS - Predicted Properties
Property Value Source Water Solubility 0.0029 mg/mL ALOGPS logP 5.1 ALOGPS logP 4.93 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) 11.42 Chemaxon pKa (Strongest Basic) -4.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 41.13 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 80.47 m3·mol-1 Chemaxon Polarizability 28.19 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 159.8431185 predictedDarkChem Lite v0.1.0 [M-H]- 166.21721 predictedDeepCCS 1.0 (2019) [M+H]+ 166.9204952 predictedDarkChem Lite v0.1.0 [M+H]+ 168.5752 predictedDeepCCS 1.0 (2019) [M+Na]+ 159.6043185 predictedDarkChem Lite v0.1.0 [M+Na]+ 174.66835 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Staphylococcus aureus (strain MRSA252)
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Nadp binding
- Specific Function
- Catalyzes the reduction of a carbon-carbon double bond in an enoyl moiety that is covalently linked to an acyl carrier protein (ACP). Involved in the elongation cycle of fatty acid which are used i...
- Gene Name
- fabI
- Uniprot ID
- Q6GI75
- Uniprot Name
- Enoyl-[acyl-carrier-protein] reductase [NADPH] FabI
- Molecular Weight
- 27991.645 Da
References
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Vitamin d 24-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Effects of triclocarban on the transcription of estrogen, androgen and aryl hydrocarbon receptor responsive genes in human breast cancer cells [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1B1
- Uniprot ID
- Q16678
- Uniprot Name
- Cytochrome P450 1B1
- Molecular Weight
- 60845.33 Da
References
- Effects of triclocarban on the transcription of estrogen, androgen and aryl hydrocarbon receptor responsive genes in human breast cancer cells [Link]
Drug created at December 03, 2015 16:51 / Updated at February 20, 2024 23:55