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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyTriclosan
Identification
- Name
- Triclosan
- Accession Number
- DB08604
- Type
- Small Molecule
- Groups
- Approved, Investigational
- 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.
- Structure
Structure for Triclosan (DB08604)
- Synonyms
- 2,4,4'-Trichloro-2'-hydroxydiphenyl ether
- 5-Chloro-2-(2,4-dichloro-phenoxy)-phenol
- Triclosán
- Triclosan
- Triclosanum
- External IDs
- CH-3565
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Derma Med Aerosol 1 % Topical Trillium International Trading Group Ltd. Not applicable Not applicable Canada 
Handfresh Antibacterial Cleanser Lotion 0.3 % Topical Scott Paper Limited Not applicable Not applicable Canada Phs Gold Liquid 0.3 % Topical U S Chemical Corporation Not applicable Not applicable Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End 1% Triclosan Anti-microbial Foaming Skin Cleanser Liquid 1.0 % Topical Deb Canada Not applicable Not applicable Canada 1% Triclosan Anti-microbial Skin Cleanser Gel 1.0 % Topical Deb Canada Not applicable Not applicable Canada 1014 Foaming Antimicrobial Soap 0.003 mg/1mL Topical Abc Compounding Co. Inc. 2013-05-01 Not applicable US 
3 in 1 Antibacterial Hair and Body Wash Solution 11.7 g/100mL Topical Kutol Products Company 2013-11-06 Not applicable US Ab Handsoap Liquid 0.375 % Topical Epsilon Chemicals Ltd. 2003-03-04 Not applicable Canada Accent Plus Antibacterial Skin Cleanser Liquid .3 % Topical Huntington Laboratories, Ecolab Inc. 1996-12-31 1999-08-10 Canada Acclaim Liquid 0.10 % Topical Zep, Inc 2000-08-21 Not applicable Canada Acnopur Mousse Assainissante Cream 0.3 % Topical Biotherm Canada 2002-03-01 2009-11-03 Canada Action Chemical Antibac Clear Liquid 0.30 mg/100mL Topical Deb Canada 2013-09-12 2020-08-01 US Activ Gel 0.3 % Topical Wood Wyant Inc 2007-04-11 2008-10-20 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Adasept Acne Gel Triclosan (0.5 %) + Salicylic acid (2 %) + Sodium thiosulfate (8 %) Lotion Topical Odan Laboratories Ltd 1974-12-31 Not applicable Canada Anti-bacterial 3pk Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g) Kit Greenbrier International, Inc. 2015-03-15 2016-10-10 US Anti-bacterial 3pk Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g) Kit Greenbrier International, Inc. 2015-03-15 2016-10-10 US Anti-bacterial 3pk Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g) Kit Greenbrier International, Inc. 2015-03-15 2016-10-10 US Anti-bacterial Deep Cleansing Hand Soap Triclosan (0.3 %) + Ethanol (5.0 %) Liquid Topical Beauty Avenues 2010-09-01 2012-07-16 Canada Anti-bacterial Deep Cleansing Hand Soap Triclosan (0.3 %) + Ethanol (5.0 %) Liquid Topical Bath & Body Works, Inc. 2008-09-04 2011-07-27 Canada Antimicrobial Triclosan (0.06 g/100mL) + Chloroxylenol (0.45 g/100mL) Soap Topical Sky Systems Co., Inc 1990-12-10 Not applicable US Antiseptic Hand Soap Triclosan (0.6 %) + Bronopol (0.1 %) Liquid Topical Dustbane Products Ltd 1983-12-31 Not applicable Canada APRIL Bath and Shower Anti-bacterial Hand 3 Pack Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g) Kit Topical Greenbrier International, Inc. 2013-06-06 2015-11-01 US APRIL Bath and Shower Anti-bacterial Hand 3 Pack Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g) Kit Topical Greenbrier International, Inc. 2013-06-06 2015-11-01 US - International/Other Brands
- DERMAPROT / Stri-Dex cleansing bar
- Categories
- Anti-Infective Agents
- Anti-Infective Agents, Local
- Antiseptics and Disinfectants
- Benzene Derivatives
- Dermatologicals
- Ethers
- Fatty Acid Synthesis Inhibitors
- Hypolipidemic Agents
- Lipid Regulating Agents
- Medicated Dressings
- Medicated Dressings With Antiinfectives
- Miscellaneous Local Anti-infectives
- Noxae
- Phenol and Derivatives
- Phenols
- Phenyl Ethers
- Toxic Actions
- UNII
- 4NM5039Y5X
- CAS number
- 3380-34-5
- Weight
- Average: 289.542
Monoisotopic: 287.951162589 - Chemical Formula
- C12H7Cl3O2
- InChI Key
- XEFQLINVKFYRCS-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
Pharmacology
- Indication
Triclosan 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.
- Associated Conditions
- Associated Therapies
- Pharmacodynamics
- Not Available
- Mechanism of action
At 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.
Target Actions Organism UEnoyl-[acyl-carrier-protein] reductase [NADH] FabI Not Available Escherichia coli (strain K12) UEnoyl-[acyl-carrier-protein] reductase [NADH] Not Available Mycobacterium tuberculosis UEnoyl-[acyl-carrier-protein] reductase [NADH] FabI Not Available Helicobacter pylori (strain ATCC 700392 / 26695) UEnoyl-[acyl-carrier-protein] reductase [NADH] Not Available Bacillus anthracis UEnoyl-[acyl-carrier-protein] reductase [NADPH] FabI Not Available Staphylococcus aureus (strain MRSA252) UNuclear receptor subfamily 1 group I member 2 Not Available Humans UAndrogen receptor Not Available Humans UNuclear receptor subfamily 1 group I member 3 inverse agonistHumans UPeroxisome proliferator-activated receptor gamma Not Available Humans UThyroid peroxidase weak inhibitorHumans - Absorption
A 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 distribution
- Not Available
- Protein binding
- Not 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 elimination
In 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 life
The terminal plasma half life of triclosan is 21 h (Sandborgh-Englund et al., 2006).
- Clearance
- Not Available
- Toxicity
Oral LD50, Rat: 3700 mg/kg; Dermal LD50, Rabbit: 9300 mg/kg
- Affected organisms
- Fungi, yeast and protozoans
- Bacteria
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
References
- Synthesis Reference
Michael A. Mitchell, "Process For Producing Triclosan-Coated Superabsorbents." U.S. Patent US20120157302, issued June 21, 2012.
US20120157302- General References
- Russell AD: Whither triclosan? J Antimicrob Chemother. 2004 May;53(5):693-5. Epub 2004 Apr 8. [PubMed:15073159]
- 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:10196195]
- 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:12384334]
- 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:10722890]
- ON THE FATE OF TRICLOSAN IN HUMANS [Link]
- External Links
- ATC Codes
- D08AE04 — Triclosan
- D08AE — Phenol and derivatives
- D08A — ANTISEPTICS AND DISINFECTANTS
- D08 — ANTISEPTICS AND DISINFECTANTS
- D — DERMATOLOGICALS
- AHFS Codes
- 84:04.92 — Miscellaneous Local Anti-infectives
- PDB Entries
- 1c14 / 1d7o / 1d8a / 1nhg / 1p45 / 1qg6 / 1qsg / 1uh5 / 2b35 / 2o2s … show 22 more
- MSDS
- Download (34.7 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
Form Route Strength Gel Topical 1.0 % Soap Topical 0.003 mg/1mL Solution Topical 11.7 g/100mL Liquid Topical 0.10 % Lotion Topical Solution Topical 1.15 mg/1mL Liquid Topical .3 g/10mL Liquid Topical 0.8 mL/1L Liquid Topical 0.3 g/100g Solution Topical 0.15 g/100g Gel; soap Topical .5 % Solution Topical 2 mg/1mL Liquid Topical 0.50 % Soap Topical 0.1 mL/100mL Soap Topical 3 mg/1g Lotion Topical 3 mg/1g Soap Topical .3 g/100mL Lotion Topical 0.3 g/100mL Liquid Topical 0.58 % Lotion Topical 0.30 % Solution Topical 0.70 g/1mL Liquid Topical 0.70 g/1mL Liquid Topical 0.30 mL/100mL Liquid Topical 0.115 mL/100mL Liquid Topical 0.476 mL/340mL Liquid Topical 1.15 mg/100mL Soap Topical .1 mL/100mL Soap Topical .888 mL/444mL Soap Topical 0.15 mL/100L Liquid Topical 2 g/1L Liquid Topical .04 mL/100mL Soap Topical 0.3 g/100g Gel Topical .55 % Soap Topical .115 kg/100L Liquid Topical 0.55 % Liquid Topical 0.46 mL/100mL Solution Topical 0.869 mL/289.82mL Liquid Topical 0.60 mL/100mL Liquid Topical 0.4600 mL/100mL Soap Topical 3.0 mg/1mL Solution Topical 0.46 mL/100mL Liquid Topical 0.15 kg/100L Soap Topical .886 mL/443mL Soap Topical 0.15 mg/1000mL Soap Topical 1.5 mg/1mL Soap Topical 0.15 g/100g Solution Topical 0.994 mL/331.22mL Lotion / shampoo Topical 0.1150 mL/100mL Lotion Topical 0.1150 mL/100mL Liquid Topical 0.115 L/100L Liquid Topical .115 kg/100L Solution Topical 0.6 mL/100mL Liquid Topical 0.1500 mL/100mL Soap Topical 3.0 g/946mL Soap Topical 0.75 g/237mL Soap Topical 0.3000 mL/100.0000mL Liquid Topical 0.15 L/100L Soap Topical 0.2 mg/100mL Solution Topical 0.15 mL/100mL Spray Topical 0.5 % Swab Topical 0.2 g/100g Lotion Topical 0.3 % Soap Topical 0.375 g/100mL Soap Topical 0.375 mL/100mL Soap Topical .8 % Soap Topical .75 % Lotion Topical .3 % Liquid Topical 0.19 % Cream Topical 0.3 g/100g Kit Topical Liquid Topical 0.15 g/100g Liquid Topical 0.025 mL/100mL Lotion Topical 0.15 g/100g Soap Topical 25 g/100g Soap Topical 3 mL/1000mL Liquid Topical 3 mL/1000mL Gel Topical 2.5 mg/1mL Cream Topical 0.3 % Liquid Topical .25 % Liquid Topical 0.4 % Lotion Topical 0.4 % Soap Topical 0.35 % Spray Topical 0.3 % Liquid Topical 0.0189 L/3.78L Solution Topical 3.06 mg/1mL Liquid Topical 0.3 % Solution Topical 0.2 % Soap Topical 0.25 g/100g Soap Topical 0.2 g/100mL Cream Topical 0.3 g/100mL Liquid Topical 0.5 mL/100mL Solution Topical 0.15 mL/1000mL Lotion Topical .1 % Liquid Topical 1 g Lotion Topical 0.6 % Soap Topical 0.16 g/100g Lotion Topical 1.7 uL/1mL Liquid Topical 1.545 mg/1mL Cream Topical 0.30 mL/100mL Liquid Topical .30 mL/100mL Gel Topical 0.30 mL/100mL Gel Topical .3 % Liquid Topical 3 mg/1mL Liquid Topical 0.25 % Liquid Topical 0.025 g/10mL Soap Topical .15 g/100mL Lotion Topical .5 % Suspension Topical 0.3 % Soap Topical 0.76 % Gel Topical 0.5 mL/125mL Liquid Topical 1 g/100mL Cream Topical .3 % Paste, dentifrice Dental Paste, dentifrice Oral Gel, dentifrice Dental Lotion Topical 0.5 % Soap Topical 0.46 mL/100mL Soap Topical 1 mg/1g Soap Topical 0.1 g/100g Liquid Topical 1 mg/1mL Soap Topical .20 g/100g Liquid Topical .70 mL/100mL Liquid Topical 7 mg/100mL Liquid Topical 0.70 mL/100mL Liquid Topical 7.57 mL/3.78L Soap Topical 1.0 mg/1mL Aerosol Topical 1 % Soap Topical .03 g/1g Liquid Topical 0.375 mL/100mL Liquid Topical 0.3 mg/100mL Liquid Topical 1 % Liquid Topical 3.1 mg/1mL Solution Topical 0.15 g/100mL Solution Topical 0.60 % Spray Topical 0.975 % Solution Topical 0.46 g/100mL Solution Topical 4.6 mg/1mL Solution Topical 0.46 mL/1000mL Solution Topical 0.46 mg/1000mL Solution Topical 0.46 % Aerosol, foam Topical 2.94 ug/1mL Liquid Topical 0.15 mL/100mL Liquid Topical .5 % Liquid Topical 0.30 % Solution Topical 0.3 mL/100mL Solution Topical 10 mg/1mL Kit Liquid Topical 0.2 g/100g Solution Topical 2.05 mg/1mL Solution Topical 10.35 mg/1mL Solution Topical 10.3 mg/1mL Liquid Topical 1.0 % Soap Topical 4.5 mg/1mL Soap Percutaneous 0.82 mg/25mL Liquid Topical .46 g/100mL Lotion Topical 7.5 mg/1mL Liquid Topical 0.46 mg/100mL Soap Topical 0.15 g/100mL Liquid Topical 0.46 g/100mL Cream Topical .5 % Liquid Topical 0.3 mL/100mL Liquid Topical 0.6 mL/100mL Liquid Topical 0.60 % Soap Topical 0.4600 mL/100.0000mL Soap Topical 0.6000 mL/100mL Liquid Topical 0.46 % Liquid Topical .46 mg/1mL Liquid Topical 6 mg/1mL Soap Topical 0.004 g/1g Liquid Topical .2 mg/100mL Liquid Topical 0.3 g/100mL Soap Topical .003 g/1g Lotion Vaginal 0.12 g/100g Liquid Topical 5 mg/1mL Aerosol Topical 3 mg/1mL Liquid Topical 0.5 % Shampoo Topical 3 mg/1mL Aerosol Topical Soap Topical 0.0057 g/1g Soap Topical 1.0 g/100g Soap Topical 2.0 g/100g Solution Topical 0.06 g/1000g Liquid Topical 0.003 mg/1mL Aerosol, spray Topical Soap Topical .3 % Gel Topical 0.15 mg/1mL Gel Topical 7.5 mg/500mg Soap Topical 0.5 mg/100mL Gel Percutaneous 2 mL/100mL Cloth Topical 0.5 % Liquid Topical 1 mL/100mL Solution Topical 0.15 mg/100mL Liquid Topical 0.33 % Liquid Topical 0.375 g/100mL Liquid Topical .9 g/300g Liquid Topical 3.15 g/1000mL Solution Topical 20.8 g/100mL Liquid Topical 0.32 % Liquid Topical .32 % Soap Topical 0.007 g/1mL Soap Topical 0.003 g/1mL Soap Topical 0.1500 mL/100.0000mL Soap Topical 0.0005 g/1g Liquid Topical .01 g/10mL Lotion Topical 1.0 % Solution Topical 0.5 % Liquid Topical 0.75 g/100mL Liquid Topical 0.2 g/100mL Solution Topical 2.5 g/1L Solution Topical 0.005 g/0.001L Cream Topical 0.2 % Liquid Topical 0.25 g/100mL Gel Topical 10 mg/500mg Solution Topical 0.575 mL/500mL Soap Topical 0.20 g/100mL Lotion Topical 0.55 % Soap Topical 0.2 g/100g Liquid Topical 0.1 mL/100mL Liquid Topical 1.5 g/1L Soap Topical 6.0 mg/1mL Solution Topical 0.3 g/100mL Solution Topical 0.1 g/100mL Liquid Topical 0.2 mL/100mL Gel Topical 0.1 % Soap Topical 3.75 mg/1mL Soap Topical 0.375 g/100g Liquid Topical 0.5 g/1000mL Liquid Topical .2 % Liquid Topical 5 mg/1g Liquid Topical 7.5 mg/1g Gel Topical 0.3 % Liquid Topical 0.5 mL/250mL Soap Topical 0.003 g/1g Gel Topical 0.55 mL/100mL Liquid Topical 0.25 mL/100mL Soap Topical 0.3 mg/100mL Liquid Dental Liquid Topical 0.2 % Solution Topical .46 g/100mL Soap Topical .46 g/100mL Liquid Topical .6 % Soap Topical 1 % Soap Topical 318.975 mL/2126.5mL Gel Topical 1.5 mg/1mL Soap Topical 0.5 g/100g Liquid Topical 0.50 mg/100mL Liquid Topical .55 mL/100mL Gel Topical Soap Topical 0.115 g/100g Solution Topical 0.1 mg/100mL Liquid Topical 0.4 mL/100mL Soap Topical 0.2 mL/100mL Cloth Topical 0.15 % Liquid Topical 0.115 g/100g Solution Topical 18.9 g/100mL Soap Topical .562 mL/562mL Soap Topical 0.15 L/100L Soap Topical 0.003 mL/1mL Liquid Topical 3 mg/0.001L Liquid Topical 0.30 kg/100kg Liquid Topical 0.30 mg/100mL Lotion Topical .2 % Soap Topical 5 mg/1mL Cream Topical 1.5 mL/1L Liquid Topical 0.15 % Liquid Topical 0.0015 mg/1mL Solution Topical 0.3 mg/100mL Soap Topical 0.3 g/1L Solution Topical 0.3 % Spray Topical Swab Topical Solution Topical 0.00025 g/1g Soap Topical 0.002 g/1mL Soap Topical 0.115 mL/100mL Soap Topical 0.6 mL/100mL Soap Topical 0.15 mL/100mL Liquid Topical 0.15 mg/100mL Liquid Topical 1.5 mg/1mL Liquid Topical 3.54 mL/118mL Lotion Topical 1 % Soap Cutaneous 2 mg/1mL Soap Topical 0.25 g/100mL Liquid Topical .15 g/100mL Liquid Topical 2 mg/1mL Liquid Topical .2 mL/100mL Liquid Topical .1 % Liquid Topical 1.08 g/1L Liquid Topical 1 mg Liquid Topical 0.1 g Liquid Topical 1.5 mg/100mL Gel Topical 0.15 mL/100mL Solution Topical 0.25 % Solution Topical 0.25 g/100mL Soap Topical 0.5 % Solution Topical .25 % Gel Topical 0.2 mL/100mL Gel Topical 3 mg/1mL Soap Topical 4.6 mg/1mL Soap Topical 0.46 g/100mL Soap Topical 0.3 g/100mL Liquid Topical 1.15 mg/1mL Soap Topical 0.5 mL/100mL Soap Topical .5 % Liquid Topical 115 mg/100mL Liquid Topical 11.7 g/100mL Liquid Topical 0.375 % Liquid Topical 5 g/1L Liquid Topical 0.55 g/100mL Liquid Topical 5.5 g/1L Solution Topical 5 g/1L Liquid Topical 1.15 g/1L Liquid Topical 1.5 mL/1L Cream Topical Liquid Topical Liquid Topical 0.46 mg/1mL Soap Topical 0.12 mL/100mL Lotion Topical 0.15 mL/100mL Lotion Topical .79 g/293g Liquid Topical .3 % Lotion Topical 0.3 g Shampoo Topical Lotion Topical 0.2 % Soap Topical 0.5 g/100mL Liquid Topical 3 g/1L Gel Topical 1 mg/1mL Liquid; shampoo Topical 0.5 % Soap Topical 2 g/1L Solution Topical 3 mg/1mL Cream Cutaneous Soap Topical 0.6 mL/100.0000mL Liquid Topical 4.6 mg/1mL Liquid Topical 0.5 g/100mL Paste Dental Lotion Topical .375 % Sponge Topical 5 mg/1mL Liquid Topical 0.003 mL/1mL Liquid Topical 29 mg/1mL Soap Topical 1.15 mg/1mL Gel Topical 0.3 g/100g Liquid Topical 300 mg/100mL Soap Topical 6 1/1mL Liquid Topical 1.2 mL/1L Lotion Topical 0.1 % Spray Topical 1.2 mL/10mL Lotion Topical .4 % Soap Topical .002 g/1mL Soap Topical 6.6 1/443mL Soap Topical 3.3 mg/221mL Gel Topical 1 mg/237mg Soap Topical Liquid Topical 1.5 g/100g Liquid Topical 0.01 g/10mL Soap Topical 0.1 g/100mL Liquid Topical 0.1 % - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 55-57 °C MSDS boiling point (°C) 120 °C MSDS pKa 7.9 Merck Index 12:3, 2000 - Predicted Properties
Property Value Source Water Solubility 0.00605 mg/mL ALOGPS logP 5.53 ALOGPS logP 4.98 ChemAxon logS -4.7 ALOGPS pKa (Strongest Acidic) 7.68 ChemAxon pKa (Strongest Basic) -6.7 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 29.46 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 68.69 m3·mol-1 ChemAxon Polarizability 25.92 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Inhibitor 0.6565 CYP450 2D6 inhibitor Non-inhibitor 0.8851 CYP450 2C19 inhibitor Inhibitor 0.8943 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylethers
- Direct Parent
- Diphenylethers
- Alternative Parents
- Diarylethers / Phenoxy compounds / Phenol ethers / M-chlorophenols / Dichlorobenzenes / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Aryl chlorides / Organochlorides / Hydrocarbon derivatives
- Substituents
- Diphenylether / Diaryl ether / Phenoxy compound / Phenol ether / 1,3-dichlorobenzene / 3-chlorophenol / 3-halophenol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- aromatic ether, phenols, dichlorobenzene, monochlorobenzenes (CHEBI:164200) / a small molecule (CPD0-1227)
Targets
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Identical protein 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
- P0AEK4
- Uniprot Name
- Enoyl-[acyl-carrier-protein] reductase [NADH] FabI
- Molecular Weight
- 27863.645 Da
References
- 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:10592235]
- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- General Function
- Enoyl-ACP reductase of the type II fatty acid syntase (FAS-II) system, which is involved in the biosynthesis of mycolic acids, a major component of mycobacterial cell walls (PubMed:25227413). Catalyzes the NADH-dependent reduction of the double bond of 2-trans-enoyl-[acyl-carrier protein], an essential step in the fatty acid elongation cycle of the FAS-II pathway (PubMed:7599116). Shows preference for long-chain fatty acyl thioester substrates (>C16), and can also use 2-trans-enoyl-CoAs as alternative substrates (PubMed:7599116). The mycobacterial FAS-II system utilizes the products of the FAS-I system as primers to extend fatty acyl chain lengths up to C56, forming the meromycolate chain that serves as the precursor for final mycolic acids (PubMed:25227413).
- Specific Function
- Enoyl-[acyl-carrier-protein] reductase (nadh) activity
- Gene Name
- inhA
- Uniprot ID
- P9WGR1
- Uniprot Name
- Enoyl-[acyl-carrier-protein] reductase [NADH]
- Molecular Weight
- 28527.55 Da
References
- 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:10592235]
- Kind
- Protein
- Organism
- Helicobacter pylori (strain ATCC 700392 / 26695)
- Pharmacological action
- Unknown
- General Function
- Enoyl-[acyl-carrier-protein] reductase (nadh) activity
- 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
- O24990
- Uniprot Name
- Enoyl-[acyl-carrier-protein] reductase [NADH] FabI
- Molecular Weight
- 29981.18 Da
References
- 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:10592235]
- Kind
- Protein
- Organism
- Bacillus anthracis
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- Enoyl-[acyl-carrier-protein] reductase (nadh) activity
- Gene Name
- fabI
- Uniprot ID
- Q81JF8
- Uniprot Name
- Enoyl-[acyl-carrier-protein] reductase [NADH]
- Molecular Weight
- 27740.225 Da
References
- 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:10592235]
- Kind
- Protein
- Organism
- Staphylococcus aureus (strain MRSA252)
- Pharmacological action
- Unknown
- 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
- 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:10592235]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- Kretschmer XC, Baldwin WS: CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. 2005 Aug 15;155(3):111-28. [PubMed:16054614]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
- Gene Name
- AR
- Uniprot ID
- P10275
- Uniprot Name
- Androgen receptor
- Molecular Weight
- 98987.9 Da
References
- Christen V, Crettaz P, Oberli-Schrammli A, Fent K: Some flame retardants and the antimicrobials triclosan and triclocarban enhance the androgenic activity in vitro. Chemosphere. 2010 Nov;81(10):1245-52. doi: 10.1016/j.chemosphere.2010.09.031. Epub 2010 Oct 12. [PubMed:20943248]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inverse agonist
- General Function
- Zinc ion binding
- Specific Function
- Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital re...
- Gene Name
- NR1I3
- Uniprot ID
- Q14994
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 3
- Molecular Weight
- 39942.145 Da
References
- Paul KB, Thompson JT, Simmons SO, Vanden Heuvel JP, Crofton KM: Evidence for triclosan-induced activation of human and rodent xenobiotic nuclear receptors. Toxicol In Vitro. 2013 Oct;27(7):2049-60. doi: 10.1016/j.tiv.2013.07.008. Epub 2013 Jul 27. [PubMed:23899473]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
- Gene Name
- PPARG
- Uniprot ID
- P37231
- Uniprot Name
- Peroxisome proliferator-activated receptor gamma
- Molecular Weight
- 57619.58 Da
References
- Fang M, Webster TF, Ferguson PL, Stapleton HM: Characterizing the peroxisome proliferator-activated receptor (PPARgamma) ligand binding potential of several major flame retardants, their metabolites, and chemical mixtures in house dust. Environ Health Perspect. 2015 Feb;123(2):166-72. doi: 10.1289/ehp.1408522. Epub 2014 Oct 14. [PubMed:25314719]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Weak inhibitor
- General Function
- Peroxidase activity
- Specific Function
- Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
- Gene Name
- TPO
- Uniprot ID
- P07202
- Uniprot Name
- Thyroid peroxidase
- Molecular Weight
- 102961.63 Da
References
- Leonard JA, Tan YM, Gilbert M, Isaacs K, El-Masri H: Estimating Margin of Exposure to Thyroid Peroxidase Inhibitors Using High-Throughput in vitro Data, High-Throughput Exposure Modeling, and Physiologically Based Pharmacokinetic/Pharmacodynamic Modeling. Toxicol Sci. 2016 May;151(1):57-70. doi: 10.1093/toxsci/kfw022. Epub 2016 Feb 10. [PubMed:26865668]
Drug created on September 15, 2010 15:33 / Updated on January 22, 2019 17:57