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Identification
NameTriclosan
Accession NumberDB08604
Typesmall molecule
Groupsapproved
Description

An aromatic ether that is phenol which is substituted at C-5 by a chloro group and at C-2 by a 2,4-dichlorophenoxy group. It is widely used as a preservative and antimicrobial agent in personal care products such as soaps, skin creams, toothpaste and deodorants as well as in household items such as plastic chopping boards, sports equipment and shoes. [ChEBI]

Structure
Thumb
Synonyms
SynonymLanguageCode
2,4,4'-Trichloro-2'-hydroxydiphenyl etherNot AvailableNot Available
5-Chloro-2-(2,4-dichloro-phenoxy)-phenolNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
DERMAPROTNot Available
Stri-Dex cleansing barNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number3380-34-5
WeightAverage: 289.542
Monoisotopic: 287.951162589
Chemical FormulaC12H7Cl3O2
InChI KeyXEFQLINVKFYRCS-UHFFFAOYSA-N
InChI
InChI=1S/C12H7Cl3O2/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6,16H
IUPAC Name
5-chloro-2-(2,4-dichlorophenoxy)phenol
SMILES
OC1=CC(Cl)=CC=C1OC1=C(Cl)C=C(Cl)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassEthers
SubclassDiarylethers
Direct parentDiarylethers
Alternative parentsm-Chlorophenols; Dichlorobenzenes; Phenol Ethers; Aryl Chlorides; Enols; Polyamines; Organochlorides
Substituents3-chlorophenol; 1,3-dichlorobenzene; phenol ether; 3-halophenol; phenol derivative; chlorobenzene; benzene; aryl halide; aryl chloride; polyamine; enol; organochloride; organohalogen
Classification descriptionThis compound belongs to the diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
Pharmacology
IndicationTriclosan is used in a variety of common household products, including soaps, mouthwashes, dish detergents, toothpastes, deodorants, and hand sanitizers. It is also used in health care settings in surgical scrubs and personnel hand washes.
PharmacodynamicsNot Available
Mechanism of actionAt in-use concentrations, triclosan acts as a biocide, with multiple cytoplasmic and membrane targets. At lower concentrations, however, triclosan appears bacteriostatic and is seen to target bacteria mainly by inhibiting fatty acid synthesis. Triclosan binds to bacterial enoyl-acyl carrier protein reductase enzyme (ENR), which is encoded by the gene FabI. This binding increases the enzyme's affinity for nicotinamide adenine dinucleotide (NAD+). This results in the formation of a stable ternary complex of ENR-NAD+-triclosan, which is unable to participate in fatty acid synthesis. Fatty acids are necessary for reproducing and building cell membranes. Humans do not have an ENR enzyme, and thus are not affected.
AbsorptionA study conducted in 2000 demonstrated that low amounts of triclosan can be absorbed through skin and can enter the bloodstream. [PMID: 10722890] Triclosan is rapidly absorbed and distributed in the human body (Sandborgh-Englund et al., 2006). Maximum concentrations are reached within three hours after oral intake. However, the metabolism and excretion of the compound is fast.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Triclosan is prone to phase II metabolism via sulfotransferase and glucuronosyltransferase enzymes (Wang et al., 2004). In humans the resulting conjugates are excreted primarily in urine (Sandborgh-Englund et al., 2006).

Route of eliminationIn one study, after in vivo topical application of a 64.5mM alcoholic solution of [(3)H]triclosan to rat skin, 12% radioactivity was recovered in the faeces, 8% in the carcass 1% in the urine, 30% in the stratum corneum and 26% was rinsed from the skin surface at 24 hours after application. [PMID: 10722890]
Half lifeThe terminal plasma half life of triclosan is 21 h (Sandborgh-Englund et al., 2006).
ClearanceNot Available
ToxicityOral LD50, Rat: 3700 mg/kg; Dermal LD50, Rabbit: 9300 mg/kg
Affected organisms
  • Fungi, yeast and protozoans
  • Bacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9941
Blood Brain Barrier + 0.9653
Caco-2 permeable + 0.8461
P-glycoprotein substrate Non-substrate 0.7545
P-glycoprotein inhibitor I Non-inhibitor 0.8094
P-glycoprotein inhibitor II Non-inhibitor 0.8656
Renal organic cation transporter Non-inhibitor 0.8261
CYP450 2C9 substrate Non-substrate 0.7708
CYP450 2D6 substrate Non-substrate 0.8807
CYP450 3A4 substrate Non-substrate 0.6205
CYP450 1A2 substrate Inhibitor 0.8668
CYP450 2C9 substrate Inhibitor 0.6565
CYP450 2D6 substrate Non-inhibitor 0.8851
CYP450 2C19 substrate Inhibitor 0.8943
CYP450 3A4 substrate Non-inhibitor 0.8979
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7195
Ames test Non AMES toxic 0.9413
Carcinogenicity Non-carcinogens 0.7864
Biodegradation Not ready biodegradable 0.9368
Rat acute toxicity 2.0589 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.906
hERG inhibition (predictor II) Non-inhibitor 0.8289
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point55-57 °CMSDS
boiling point120 °CMSDS
pKa7.9Merck Index 12:3, 2000
Predicted Properties
PropertyValueSource
water solubility6.05e-03 g/lALOGPS
logP5.53ALOGPS
logP4.98ChemAxon
logS-4.7ALOGPS
pKa (strongest acidic)7.68ChemAxon
pKa (strongest basic)-6.7ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area29.46ChemAxon
rotatable bond count2ChemAxon
refractivity68.69ChemAxon
polarizability25.92ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Michael A. Mitchell, “Process For Producing Triclosan-Coated Superabsorbents.” U.S. Patent US20120157302, issued June 21, 2012.

US20120157302
General Reference
  1. Russell AD: Whither triclosan? J Antimicrob Chemother. 2004 May;53(5):693-5. Epub 2004 Apr 8. Pubmed
  2. Heath RJ, Rubin JR, Holland DR, Zhang E, Snow ME, Rock CO: Mechanism of triclosan inhibition of bacterial fatty acid synthesis. J Biol Chem. 1999 Apr 16;274(16):11110-4. Pubmed
  3. Fan F, Yan K, Wallis NG, Reed S, Moore TD, Rittenhouse SF, DeWolf WE Jr, Huang J, McDevitt D, Miller WH, Seefeld MA, Newlander KA, Jakas DR, Head MS, Payne DJ: Defining and combating the mechanisms of triclosan resistance in clinical isolates of Staphylococcus aureus. Antimicrob Agents Chemother. 2002 Nov;46(11):3343-7. Pubmed
  4. Moss T, Howes D, Williams FM: Percutaneous penetration and dermal metabolism of triclosan (2,4, 4’-trichloro-2’-hydroxydiphenyl ether). Food Chem Toxicol. 2000 Apr;38(4):361-70. Pubmed
  5. ON THE FATE OF TRICLOSAN IN HUMANS
External Links
ResourceLink
KEGG DrugD06226
KEGG CompoundC12059
ChEBI164200
ChEMBL
HETTCL
WikipediaTriclosan
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(34.7 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Enoyl-[acyl-carrier-protein] reductase [NADH] FabI

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Enoyl-[acyl-carrier-protein] reductase [NADH] FabI P0AEK4 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Enoyl-[acyl-carrier-protein] reductase [NADH]

Kind: protein

Organism: Mycobacterium tuberculosis

Pharmacological action: unknown

Components

Name UniProt ID Details
Enoyl-[acyl-carrier-protein] reductase [NADH] P0A5Y6 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

3. Enoyl-[acyl-carrier-protein] reductase [NADH] FabI

Kind: protein

Organism: Helicobacter pylori (strain ATCC 700392 / 26695)

Pharmacological action: unknown

Components

Name UniProt ID Details
Enoyl-[acyl-carrier-protein] reductase [NADH] FabI O24990 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

4. Enoyl-[acyl-carrier-protein] reductase [NADH]

Kind: protein

Organism: Bacillus anthracis str. A0193

Pharmacological action: unknown

Components

Name UniProt ID Details
Enoyl-[acyl-carrier-protein] reductase [NADH] B0Q840 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

5. Enoyl-[acyl-carrier-protein] reductase [NADPH] FabI

Kind: protein

Organism: Staphylococcus aureus (strain MRSA252)

Pharmacological action: unknown

Components

Name UniProt ID Details
Enoyl-[acyl-carrier-protein] reductase [NADPH] FabI Q6GI75 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

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Drug created on September 15, 2010 15:33 / Updated on December 16, 2013 23:33