Identification

Name
Triclosan
Accession Number
DB08604
Type
Small Molecule
Groups
Approved
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
  • 2,4,4'-Trichloro-2'-hydroxydiphenyl ether
  • 5-Chloro-2-(2,4-dichloro-phenoxy)-phenol
  • Triclosan
  • Triclosanum
External IDs
CH-3565
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Derma MedAerosol1 %TopicalTrillium International Trading Group Ltd.Not applicableNot applicableCanada
Dermaprot Triclotrex-BLiquid.3 mg/100mLTopicalSpai Sons Pharmaceutical International Cosmetics2012-08-30Not applicableUs
Handfresh Antibacterial CleanserLotion0.3 %TopicalScott Paper LimitedNot applicableNot applicableCanada
Myo-ther Antimicrobial Skin CleanserLiquid1 %TopicalAbj Custom PackagingNot applicableNot applicableCanada
Phs GoldLiquid0.3 %TopicalU S Chemical CorporationNot applicableNot applicableCanada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
1% Triclosan Anti-microbial Foaming Skin CleanserLiquid1.0 %TopicalDeb CanadaNot applicableNot applicableCanada
1% Triclosan Anti-microbial Skin CleanserGel1.0 %TopicalDeb CanadaNot applicableNot applicableCanada
1014 Foaming AntimicrobialSoap.003 mg/mLTopicalAbc Compounding Co. Inc.2013-05-01Not applicableUs
3 in 1 Antibacterial Hair and Body WashSolution11.7 g/100mLTopicalKutol Products Company2013-11-06Not applicableUs
Ab HandsoapLiquid0.375 %TopicalEpsilon Chemicals Ltd.2003-03-04Not applicableCanada
Accent Plus Antibacterial Skin CleanserLiquid.3 %TopicalHuntington Laboratories, Ecolab Inc.1996-12-311999-08-10Canada
AcclaimLiquid0.10 %TopicalZep, Inc2000-08-21Not applicableCanada
Acnopur Mousse AssainissanteCream0.3 %TopicalBiotherm Canada2002-03-012009-11-03Canada
Action Chemical Antibac ClearLiquid.3 mg/100mLTopicalDeb Canada2013-09-122020-08-01Us
ActivGel0.3 %TopicalWood Wyant Inc2007-04-112008-10-20Canada
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
PRO-LINK OPTIMUM Foaming Medicated HandwashLiquid.003 mg/mLTopicalPro Link, Inc.2004-05-30Not applicableUs
International/Other Brands
DERMAPROT / Stri-Dex cleansing bar
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Adasept Acne GelTriclosan (0.5 %) + Salicylic acid (2 %) + Sodium thiosulfate (8 %)LotionTopicalOdan Laboratories Ltd1974-12-31Not applicableCanada
Anti-bacterial Deep Cleansing Hand SoapTriclosan (0.3 %) + Ethanol (5.0 %)LiquidTopicalBath & Body Works, Inc.2008-09-042011-07-27Canada
Anti-bacterial Deep Cleansing Hand SoapTriclosan (0.3 %) + Ethanol (5.0 %)LiquidTopicalBeauty Avenues2010-09-012012-07-16Canada
Benzocaine and TriclosanTriclosan (.11 g/85g) + Benzocaine (17 g/85g)Aerosol, sprayTopicalChain Drug Consortium2005-12-07Not applicableUs
Benzocaine and TriclosanTriclosan (.11 g/85g) + Benzocaine (17 g/85g)Aerosol, sprayTopicalPremier Brands of America Inc.2013-01-01Not applicableUs
Clearasil Skin Tone Acne Crm MedicationTriclosan (.1 %) + Resorcinol (2 %) + Sulfur (8 %)CreamTopicalRichardson Vicks, Division Of The Procter & Gamble Company1987-12-311997-10-31Canada
Clearasil Vanishing Acne Crm MedicationTriclosan (.1 %) + Resorcinol (2 %) + Sulfur (3 %)CreamTopicalRichardson Vicks, Division Of The Procter & Gamble Company1987-12-311997-10-31Canada
Colgate Total - Advanced HealthTriclosan (0.3 %) + Sodium fluoride (0.243 %)Paste, dentifriceDentalColgate Palmolive2007-03-05Not applicableCanada
Colgate Total Advance WhiteningTriclosan (3 mg/g) + Sodium fluoride (1.5 mg/g)Paste, dentifriceDentalColgate Palmolive2008-08-09Not applicableUs
Colgate Total Advance WhiteningTriclosan (3 mg/g) + Sodium fluoride (1.5 mg/g)Paste, dentifriceDentalTeam Technologies, Inc2008-08-09Not applicableUs
Categories
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.

Structured Indications
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.

TargetActionsOrganism
UEnoyl-[acyl-carrier-protein] reductase [NADH] FabINot AvailableEscherichia coli (strain K12)
UEnoyl-[acyl-carrier-protein] reductase [NADH]Not AvailableMycobacterium tuberculosis
UEnoyl-[acyl-carrier-protein] reductase [NADH] FabINot AvailableHelicobacter pylori (strain ATCC 700392 / 26695)
UEnoyl-[acyl-carrier-protein] reductase [NADH]Not AvailableBacillus anthracis
UEnoyl-[acyl-carrier-protein] reductase [NADPH] FabINot AvailableStaphylococcus aureus (strain MRSA252)
UNuclear receptor subfamily 1 group I member 2Not AvailableHuman
UAndrogen receptorNot AvailableHuman
UNuclear receptor subfamily 1 group I member 3
inverse agonist
Human
UPeroxisome proliferator-activated receptor gammaNot AvailableHuman
UThyroid peroxidase
weak inhibitor
Human
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

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

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

US20120157302
General References
  1. Russell AD: Whither triclosan? J Antimicrob Chemother. 2004 May;53(5):693-5. Epub 2004 Apr 8. [PubMed:15073159]
  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:10196195]
  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:12384334]
  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:10722890]
  5. ON THE FATE OF TRICLOSAN IN HUMANS [Link]
External Links
KEGG Drug
D06226
KEGG Compound
C12059
PubChem Compound
5564
PubChem Substance
99445075
ChemSpider
5363
BindingDB
8726
ChEBI
164200
ChEMBL
CHEMBL849
HET
TCL
Wikipedia
Triclosan
ATC Codes
D08AE04 — TriclosanD09AA06 — Triclosan
AHFS Codes
  • 84:04.92 — Miscellaneous Local Anti-infectives
PDB Entries
1c14 / 1d7o / 1d8a / 1nhg / 1p45 / 1qg6 / 1qsg / 1uh5 / 2b35 / 2o2s
show 21 more
MSDS
Download (34.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentColorectal Cancers / Hepatic Metastases1
2CompletedTreatmentDental Plaque1
2CompletedTreatmentInfection NOS1
2CompletedTreatmentMetastatic Colorectal Cancers1
2Unknown StatusPreventionAtopic Dermatitis (AD)1
2, 3CompletedTreatmentFemale Genital Diseases1
3CompletedTreatmentActinic Keratosis (AK)1
3CompletedTreatmentDental Plaque9
3CompletedTreatmentDentin Hypersensitivity1
3CompletedTreatmentGingival Diseases5
3CompletedTreatmentGingival Inflammation1
3CompletedTreatmentMucositis1
3CompletedTreatmentOral Bacteria1
3CompletedTreatmentPeriodontal Diseases1
3CompletedTreatmentPeriodontitis1
3CompletedTreatmentSalivary Bacteria Levels1
3RecruitingTreatmentBRAF V600E-mutant Metastatic Colorectal Cancer1
3RecruitingTreatmentIdiopathic Pulmonary Fibrosis (IPF)1
3Unknown StatusTreatmentPeriodontal Diseases1
3WithdrawnTreatmentUrinary Tract Infections (UTIs)1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedTreatmentHyperpigmentation1
4Unknown StatusPreventionComplication of Coronary Artery Bypass Graft / Infection, Postoperative Wound1
4Unknown StatusTreatmentPruritis1
Not AvailableCompletedNot AvailableHealthy Volunteers / Hypertensive1
Not AvailableCompletedTreatmentRadiation Induced Fibrosis to the Head and Neck1
Not AvailableCompletedTreatmentStrokes1
Not AvailableNo Longer AvailableNot AvailableDiabetes, Diabetes Mellitus Type 11
Not AvailableUnknown StatusPreventionDermatitis, Eczematous1
Not AvailableUnknown StatusTreatmentPrepubertal Labial Adhesions1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
GelTopical1.0 %
SolutionTopical11.7 g/100mL
LiquidTopical0.10 %
LotionTopical
SolutionTopical1.15 mg/mL
LiquidTopical.3 g/10mL
LiquidTopical.3 g/100g
SolutionTopical.15 g/100g
Gel; soapTopical.5 %
SoapTopical.003 mL/mL
LiquidTopical0.50 %
Kit
SoapTopical.1 mL/100mL
SoapTopical3 mg/g
LiquidTopical0.58 %
LotionTopical0.30 %
SolutionTopical.7 g/mL
LiquidTopical.7 g/mL
LiquidTopical.476 mL/340mL
LiquidTopical1.15 mg/100mL
SoapTopical.15 mL/100L
SoapTopical.888 mL/444mL
SoapTopical5 mg/mL
LiquidTopical2 g/L
LiquidTopical.04 mL/100mL
GelTopical.55 %
LiquidTopical.15 mL/100mL
SoapTopical.15 mL/100mL
SoapTopical.115 kg/100L
LiquidTopical0.55 %
LiquidTopical.46 mL/100mL
LiquidTopical.6 mL/100mL
SolutionTopical.869 mL/289.82mL
LiquidTopical.15 kg/100L
SoapTopical.15 mL/1000mL
SoapTopical1.5 mg/mL
SolutionTopical.3 g/100mL
SoapTopical.15 g/100g
SolutionTopical.994 mL/331.22mL
Lotion / shampooTopical.115 mL/100mL
LotionTopical.115 mL/100mL
LiquidTopical.115 L/100L
LiquidTopical.115 kg/100L
SolutionTopical.6 mL/100mL
LiquidTopical.15 L/100L
SoapTopical.2 mg/100mL
SolutionTopical.15 mL/100mL
SprayTopical0.5 %
SoapTopical.3 mL/100mL
SwabTopical.2 g/100g
LotionTopical0.3 %
SoapTopical.375 mL/100mL
SoapTopical.375 g/100mL
SoapTopical.8 %
SoapTopical.75 %
LotionTopical.3 %
LiquidTopical0.19 %
LiquidTopical2 mg/mL
KitTopical
LiquidTopical.025 mL/100mL
LiquidTopical3 mL/1000mL
GelTopical2.5 mg/mL
CreamTopical0.3 %
LiquidTopical.25 %
LiquidTopical0.4 %
LotionTopical0.4 %
SoapTopical0.35 %
SprayTopical0.3 %
LiquidTopical.0189 L/3.78L
SolutionTopical3.06 mg/mL
LiquidTopical0.3 %
SolutionTopical0.2 %
SoapTopical.25 g/100g
SoapTopical.2 g/100mL
LiquidTopical.5 mL/100mL
LotionTopical.1 %
LiquidTopical1 g
LotionTopical0.6 %
SoapTopical.16 g/100g
LotionTopical1.7 uL/mL
GelTopical.3 mL/100mL
CreamTopical.3 mL/100mL
GelTopical.3 %
LiquidTopical.3 g/100mL
SoapTopical.3 g/100g
LiquidTopical0.25 %
LiquidTopical.025 g/10mL
LotionTopical.5 %
SuspensionTopical0.3 %
SoapTopical0.76 %
GelTopical.5 mL/125mL
LiquidTopical1 g/100mL
CreamTopical.3 %
Paste, dentifriceOral
Gel, dentifriceDental
Paste, dentifriceDental
LotionTopical0.5 %
SoapTopical1 mg/g
SoapTopical.1 g/100g
LiquidTopical1 mg/mL
SoapTopical25 g/100g
LiquidTopical.3 mg/100mL
LiquidTopical7 mg/100mL
LiquidTopical.7 mL/100mL
LiquidTopical7.57 mL/3.78L
SoapTopical1 mg/mL
AerosolTopical1 %
GelTopical
SoapTopical.03 g/g
LiquidTopical.375 mL/100mL
CreamTopical
LiquidTopical1 %
LiquidTopical3.1 mg/mL
SolutionTopical0.60 %
SprayTopical0.975 %
SolutionTopical.46 g/100mL
SolutionTopical4.6 mg/mL
SolutionTopical.46 mL/1000mL
SolutionTopical.46 mg/1000mL
SolutionTopical0.46 %
SolutionTopical.15 mL/1000mL
Aerosol, foamTopical2.94 ug/mL
LiquidTopical.5 %
LiquidTopical0.30 %
SolutionTopical3 mg/mL
LiquidTopical.2 g/100g
SolutionTopical2.05 mg/mL
SolutionTopical10.35 mg/mL
SolutionTopical10.3 mg/mL
LiquidTopical1.0 %
LotionTopical7.5 mg/mL
SolutionTopical.3 mL/100mL
SolutionTopical18.9 g/100mL
SolutionTopical.15 mg/100mL
LiquidTopical.46 g/100mL
SprayTopical
CreamTopical.5 %
LiquidTopical0.60 %
SoapTopical.46 mL/100mL
SoapTopical.003 mg/mL
LiquidTopical0.46 %
SoapTopical.004 g/g
LotionVaginal.12 g/100g
LiquidTopical5 mg/mL
AerosolTopical3 mg/mL
LiquidTopical0.5 %
ShampooTopical3 mL/1000mL
AerosolTopical
SoapTopical.0057 g/g
SoapTopical1 g/100g
SoapTopical2 g/100g
SolutionTopical.06 g/1000g
Aerosol, sprayTopical
SoapTopical.3 %
GelTopical.15 mg/mL
GelTopical7.5 mg/500mg
SoapTopical3 mg/mL
GelPercutaneous2 mL/100mL
ClothTopical0.5 %
LiquidTopical1.545 mg/mL
LiquidTopical1 mL/100mL
LiquidTopical0.33 %
LiquidTopical.375 g/100mL
LiquidTopical.9 g/300g
SolutionTopical20.8 g/100mL
LiquidTopical0.32 %
LiquidTopical.32 %
SoapTopical.007 g/mL
SoapTopical.003 g/mL
SoapTopical.0005 g/g
LiquidTopical.115 g/100g
LotionTopical1.0 %
SolutionTopical0.5 %
LiquidTopical.75 g/100mL
SolutionTopical.46 mL/100mL
SolutionTopical2.5 g/L
CreamTopical0.2 %
LiquidTopical.115 mL/100mL
LiquidTopical1.15 mg/mL
LiquidTopical.25 g/100mL
GelTopical10 mg/500mg
SolutionTopical.575 mL/500mL
LotionTopical0.55 %
SoapTopical.2 g/100g
LiquidTopical.1 mL/100mL
SoapTopical.15 g/100mL
LiquidTopical1.5 g/L
SoapTopical6 mg/mL
SolutionTopical.1 g/100mL
LiquidTopical.2 mL/100mL
GelTopical0.1 %
SoapTopical.3 g/L
SoapTopical3.75 mg/mL
SoapTopical.375 g/100g
LiquidTopical.5 g/1000mL
LiquidTopical.2 %
LiquidTopical5 mg/g
LiquidTopical7.5 mg/g
GelTopical0.3 %
SoapTopical3 mL/1000mL
LiquidTopical.5 mL/250mL
SoapTopical.003 g/g
GelTopical.55 mL/100mL
LiquidDental
LiquidTopical0.2 %
LiquidTopical3 mg/mL
SoapTopical.46 g/100mL
SoapTopical.1 g/100mL
LiquidTopical.6 %
SoapTopical1 %
SoapTopical318.975 mL/2126.5mL
SoapTopical.3 mg/100mL
SoapTopical4.5 mg/mL
SoapTopical.5 g/100g
LiquidTopical.5 mg/100mL
LiquidTopical.55 mL/100mL
SolutionTopical.1 mg/100mL
LiquidTopical.4 mL/100mL
SoapTopical.2 mL/100mL
ClothTopical0.15 %
SoapTopical.562 mL/562mL
LiquidTopical3 mg/.001L
LiquidTopical.3 kg/100kg
LotionTopical.2 %
CreamTopical1.5 mL/L
LiquidTopical1.5 mL/L
LiquidTopical0.15 %
LiquidTopical.0015 mg/mL
LiquidTopical.003 mg/mL
SolutionTopical.3 mg/100mL
SolutionTopical0.3 %
SwabTopical
SolutionTopical.00025 g/g
SoapTopical.115 g/100g
LiquidTopical3 g/L
SoapTopical.115 mL/100mL
SoapTopical.6 mL/100mL
LiquidTopical.15 mg/100mL
LiquidTopical.46 mg/100mL
LiquidTopical4.6 mg/mL
LiquidTopical3.54 mL/118mL
GelTopical1.5 mg/mL
LotionTopical1 %
SoapCutaneous2 mg/mL
SoapTopical.25 g/100mL
LiquidTopical.15 g/100mL
LiquidTopical.1 %
LiquidTopical1.08 g/L
LiquidTopical1 mg
LiquidTopical0.1 g
GelTopical.15 mL/100mL
LiquidTopical1.5 mg/100mL
SolutionTopical5 g/L
SolutionTopical.25 g/100mL
SolutionTopical0.25 %
SoapTopical0.5 %
LiquidTopical.25 mL/100mL
SolutionTopical.25 %
GelTopical.2 mL/100mL
GelTopical3 mg/mL
SoapTopical4.6 mg/mL
LiquidTopical.46 mg/mL
SoapTopical.3 g/100mL
SoapTopical.5 mL/100mL
SoapTopical.5 mg/100mL
SoapTopical.5 %
LiquidTopical115 mg/100mL
LiquidTopical11.7 g/100mL
LiquidTopical0.375 %
LiquidTopical5 g/L
LiquidTopical.55 g/100mL
LiquidTopical5.5 g/L
LiquidTopical1.15 mL/L
LiquidTopical
SoapTopical.12 mL/100mL
LotionTopical.15 mL/100mL
LotionTopical.79 g/293g
LiquidTopical.2 mg/100mL
LiquidTopical1.5 mg/mL
LiquidTopical.3 %
LotionTopical0.3 g
ShampooTopical
LotionTopical0.2 %
SoapTopical.5 g/100mL
Liquid; shampooTopical0.5 %
SoapTopical2 g/L
CreamTopical.3 g/100mL
CreamCutaneous
LiquidTopical6 mg/mL
LiquidTopical.5 g/100mL
PasteDental
LotionTopical.375 %
SpongeTopical5 mg/mL
LiquidTopical.003 mL/mL
LiquidTopical29 mg/mL
LiquidTopical3.15 g/1000mL
SoapTopical1.15 mg/mL
GelTopical.3 g/100g
LiquidTopical300 mg/100mL
SoapTopical6 1/mL
LotionTopical0.1 %
LotionTopical.15 g/100g
SprayTopical1.2 mL/10mL
LiquidTopical.3 mL/100mL
LotionTopical.4 %
SoapTopical.002 g/mL
SoapTopical3.3 mg/221mL
SoapTopical6.6 1/443mL
GelTopical1 mg/237mg
SoapTopical
LiquidTopical1.5 g/100g
LiquidTopical.01 g/10mL
LiquidTopical0.1 %
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)55-57 °CMSDS
boiling point (°C)120 °CMSDS
pKa7.9Merck Index 12:3, 2000
Predicted Properties
PropertyValueSource
Water Solubility0.00605 mg/mLALOGPS
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 Area29.46 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.69 m3·mol-1ChemAxon
Polarizability25.92 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9941
Blood Brain Barrier+0.9653
Caco-2 permeable+0.8461
P-glycoprotein substrateNon-substrate0.7545
P-glycoprotein inhibitor INon-inhibitor0.8094
P-glycoprotein inhibitor IINon-inhibitor0.8656
Renal organic cation transporterNon-inhibitor0.8261
CYP450 2C9 substrateNon-substrate0.7708
CYP450 2D6 substrateNon-substrate0.8807
CYP450 3A4 substrateNon-substrate0.6205
CYP450 1A2 substrateInhibitor0.8668
CYP450 2C9 inhibitorInhibitor0.6565
CYP450 2D6 inhibitorNon-inhibitor0.8851
CYP450 2C19 inhibitorInhibitor0.8943
CYP450 3A4 inhibitorNon-inhibitor0.8979
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7195
Ames testNon AMES toxic0.9413
CarcinogenicityNon-carcinogens0.7864
BiodegradationNot ready biodegradable0.9368
Rat acute toxicity2.0589 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.906
hERG inhibition (predictor II)Non-inhibitor0.8289
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-029g-9780000000-d39624d358bdeff3e131
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-0900000000-58c362c848ddc0ea6b7d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-0900000000-d33e377d9d635f1ce853
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-0900000000-86a497478420de6dd62b
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-01ox-1900000000-3924bb3259de13cc0c32
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-01p9-9500000000-1eea0ef329f1eda65753
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-9000000000-c0811786de4d26d32f19
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0090000000-1e8f398c881d4511de15
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0090000000-1e8f398c881d4511de15
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-0090000000-901f5a26f0a84efe9ab9
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-0190000000-665be7c9535346c9a726

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
  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: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
  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: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
  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: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
  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: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
  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:10592235]
Kind
Protein
Organism
Human
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
  1. 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
Human
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
  1. 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
Human
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
  1. 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
Human
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
  1. 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
Human
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
  1. 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 November 19, 2017 20:34