Triclosan

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Triclosan is an antimicrobial agent in clinical setting for disinfection, and prevention of spread and growth of bacteria, fungus, and mildew.

Brand Names
Dermaprot Triclotrex-B, Ting
Generic Name
Triclosan
DrugBank Accession Number
DB08604
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 289.542
Monoisotopic: 287.951162589
Chemical Formula
C12H7Cl3O2
Synonyms
  • 2,4,4'-Trichloro-2'-hydroxydiphenyl ether
  • 5-Chloro-2-(2,4-dichloro-phenoxy)-phenol
  • Triclosán
  • Triclosan
  • Triclosanum
External IDs
  • CH-3565

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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAcneCombination Product in combination with: Octasulfur (DB09353)•••••••••••••••••
Used in combination to preventDental cavityCombination Product in combination with: Sodium fluoride (DB09325)••• •••
Used in combination to preventDental plaqueCombination Product in combination with: Sodium fluoride (DB09325)••• •••
Used in combination to treatDermabrasionCombination Product in combination with: Chloroxylenol (DB11121)••• ••••••••
Used in combination to preventGingivitisCombination Product in combination with: Sodium fluoride (DB09325)••• •••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Triclosan is a biocidal compound with multiple targets in the cytoplasm and membrane. At lower concentrations, however, triclosan appears bacteriostatic and is seen to target bacteria mainly by inhibiting fatty acid synthesis. Triclosan binds to enoyl-acyl carrier protein reductase enzyme (ENR). This complex has increased affinity for NAD+ and forms a ternary complex. This complex is unable to participate in fatty acid synthesis, weakening the cell membrane and causing cell death. 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 AvailableHumans
UAndrogen receptorNot AvailableHumans
UNuclear receptor subfamily 1 group I member 3
inverse agonist
Humans
UPeroxisome proliferator-activated receptor gammaNot AvailableHumans
UThyroid peroxidase
weak inhibitor
Humans
Absorption

A study conducted in 2000 demonstrated that low amounts of triclosan can be absorbed through skin and can enter the bloodstream.4 Triclosan is rapidly absorbed and distributed in the human body.5 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.5

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.4

Half-life

The terminal plasma half life of triclosan is 21 h.5

Clearance

Not Available

Adverse Effects
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Toxicity

Oral LD50, Rat: 3700 mg/kg; Dermal LD50, Rabbit: 9300 mg/kg

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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

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International/Other Brands
DERMAPROT / Stri-Dex cleansing bar
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Dermaprot Triclotrex-BLiquid0.3 mg/100mLTopicalSpai Sons Pharmaceutical International Cosmetics2012-08-30Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
1% Triclosan Anti-microbial Foaming Skin CleanserLiquid1.0 %TopicalDeb Canada Inc.Not applicableNot applicableCanada flag
1% Triclosan Anti-microbial Skin CleanserGel1.0 %TopicalDeb Canada Inc.Not applicableNot applicableCanada flag
1014 Foaming AntimicrobialSoap0.003 mg/1mLTopicalAbc Compounding Co. Inc.2013-05-01Not applicableUS flag
3 in 1 Antibacterial Hair and Body WashSolution11.7 g/100mLTopicalKutol Products Company, Inc.2013-11-062017-10-03US flag
A-Septic AS GelGel0.3 %TopicalHOE PHARMACEUTICALS SDN. BHD.2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Adasept Acne GelTriclosan (0.5 %) + Salicylic acid (2 %) + Sodium thiosulfate (8 %)LotionTopicalOdan Laboratories Ltd1974-12-31Not applicableCanada flag
Anti-bacterial 3pkTriclosan (0.15 g/100g) + Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g)KitTopicalGreenbrier International, Inc.2015-03-152016-10-10US flag
Anti-bacterial 3pkTriclosan (0.15 g/100g) + Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g)KitTopicalGreenbrier International, Inc.2015-03-152016-10-10US flag
Anti-bacterial 3pkTriclosan (0.15 g/100g) + Triclosan (0.15 g/100g) + Triclosan (0.15 g/100g)KitTopicalGreenbrier International, Inc.2015-03-152016-10-10US flag
Anti-bacterial Deep Cleansing Hand SoapTriclosan (0.3 % w/w) + Ethanol (5.0 % w/w)LiquidTopicalBeauty Avenues2010-09-012012-07-16Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Chinese Herb Essence Bacteriostatic Foaming AgentTriclosan (0.11 g/100mL)LiquidTopicalJiangxi Renhetang pharmaceutical chain Co., Ltd.2021-03-16Not applicableUS flag
enMotion Antimicrobial with Moisturizers, Fragrance free, dye freeTriclosan (4.5 mg/1mL)SoapPercutaneousCarroll Company2009-10-022014-02-25US flag
enMotion Antimicrobial, with Moisturizers, Tranquil Aloe, GreenTriclosan (4.5 mg/1mL)SoapPercutaneousCarroll Company2009-10-022014-02-25US flag
Jisberry Antibacterial HandTriclosan (2 g/500mL)LotionExtracorporealHangzhou Xizi Sanitary Disinfection Medical Equipment Co., Ltd2020-04-122020-04-30US flag
Jisberry Antibacterial HandlotionTriclosan (2 g/500mL)LotionExtracorporealHangzhou Xizi Sanitary Disinfection Medical Equipment Co., Ltd2020-04-12Not applicableUS flag

Categories

ATC Codes
D08AE04 — TriclosanD09AA06 — Triclosan
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,3-dichlorobenzene / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 3-chlorophenol / 3-halophenol / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Diaryl ether
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aromatic ether, phenols, dichlorobenzene, monochlorobenzenes (CHEBI:164200) / a small molecule (CPD0-1227)
Affected organisms
  • Fungi, yeast and protozoans
  • Bacteria

Chemical Identifiers

UNII
4NM5039Y5X
CAS number
3380-34-5
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

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Sandborgh-Englund G, Adolfsson-Erici M, Odham G, Ekstrand J: Pharmacokinetics of triclosan following oral ingestion in humans. J Toxicol Environ Health A. 2006 Oct;69(20):1861-73. doi: 10.1080/15287390600631706. [Article]
  6. ON THE FATE OF TRICLOSAN IN HUMANS [Link]
Human Metabolome Database
HMDB0061385
KEGG Drug
D06226
KEGG Compound
C12059
PubChem Compound
5564
PubChem Substance
99445075
ChemSpider
5363
BindingDB
8726
RxNav
10795
ChEBI
164200
ChEMBL
CHEMBL849
ZINC
ZINC000000002216
PDBe Ligand
TCL
Wikipedia
Triclosan
PDB Entries
1c14 / 1d7o / 1d8a / 1nhg / 1p45 / 1qg6 / 1qsg / 1uh5 / 2b35 / 2o2s
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MSDS
Download (34.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceHealthy Volunteers (HV)1
4CompletedPreventionGeneralized Aggressive Periodontitis1
4CompletedPreventionInfection; Cesarean Section1
4CompletedPreventionSurgery, Laparoscopic / Surgical Site Infections / Surgical Wounds1
4CompletedSupportive CareSkin Irritation1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
GelTopical1.0 %
SoapTopical0.003 mg/1mL
SolutionTopical11.7 g/100mL
LiquidTopical0.10 %
LotionTopical
SolutionTopical1.15 mg/1mL
LiquidTopical0.3 g/10mL
LiquidTopical0.8 mL/1L
LiquidTopical0.3 g/100g
SolutionTopical0.15 g/100g
Gel; soapTopical.5 %
SolutionTopical2 mg/1mL
SprayTopical0.5 %
LiquidTopical0.50 %
SoapTopical3 mg/1g
SoapTopical0.1 mL/100mL
LiquidTopical0.1 % w/w
LotionTopical3 mg/1g
SoapTopical.3 g/100mL
LotionTopical0.3 g/100mL
LiquidTopical0.58 %
LotionTopical0.30 %
SolutionTopical0.70 g/1mL
LiquidTopical0.70 g/1mL
LiquidTopical0.30 mL/100mL
LiquidTopical0.115 mL/100mL
LiquidTopical0.476 mL/340mL
LiquidTopical1.15 mg/100mL
SoapTopical.1 mL/100mL
SoapTopical.888 mL/444mL
SoapTopical0.15 mL/100L
LiquidTopical2 g/1L
LiquidTopical.04 mL/100mL
SoapTopical0.3 g/100g
GelTopical.55 %
SoapTopical.115 kg/100L
LiquidTopical0.55 %
LiquidTopical0.46 mL/100mL
SolutionTopical0.869 mL/289.82mL
LiquidTopical0.60 mL/100mL
LiquidTopical0.4600 mL/100mL
LiquidTopical0.10 % w/v
LiquidTopical0.1 % w/v
SoapTopical3.0 mg/1mL
SolutionTopical0.46 mL/100mL
LiquidTopical0.15 kg/100L
SoapTopical.886 mL/443mL
SoapTopical0.15 mg/1000mL
SoapTopical1.5 mg/1mL
SoapTopical0.15 g/100g
SolutionTopical0.994 mL/331.22mL
Lotion / shampooTopical0.1150 mL/100mL
LotionTopical0.1150 mL/100mL
LiquidTopical0.115 L/100L
LiquidExtracorporeal2.5 mg/500mL
LiquidTopical.115 kg/100L
LiquidTopical0.4 % w/w
LotionTopical0.4 % w/w
SolutionTopical0.6 mL/100mL
LiquidTopical0.1500 mL/100mL
SoapTopical3.0 g/946mL
SoapTopical0.75 g/237mL
SoapTopical0.3000 mL/100.0000mL
LiquidTopical0.15 L/100L
SoapTopical0.2 mg/100mL
SolutionTopical0.15 mL/100mL
SprayTopical0.5 % w/w
SwabTopical0.2 g/100g
LotionTopical0.3 %
SolutionTopical0.3 % w/w
SoapTopical0.375 g/100mL
SoapTopical0.375 mg/100mL
SoapTopical.8 %
SoapTopical.75 %
LotionTopical.3 %
LiquidTopical0.19 %
CreamTopical0.3 g/100g
LiquidTopical0.15 g/100g
LiquidTopical0.025 mL/100mL
LotionTopical0.15 g/100g
SoapTopical25 g/100g
SoapTopical3 mL/1000mg
LiquidTopical3 mL/1000mL
PowderTopical0.3 g
GelTopical2.5 mg/1mL
CreamTopical0.3 %
LiquidTopical.25 %
LiquidTopical0.4 %
LotionTopical0.4 %
SoapTopical0.35 %
SprayTopical0.3 %
LiquidTopical0.0189 L/3.78L
LiquidTopical0.3 %
SolutionTopical3.06 mg/1mL
SolutionTopical0.2 %
SoapTopical0.25 g/100g
SoapTopical0.2 g/100mL
LiquidTopical0.5 mL/100mL
SolutionTopical0.15 mL/1000mL
LotionTopical0.1 %
LotionTopical.1 %
LiquidTopical1 g / 100 g
LotionTopical0.6 % w/v
SoapTopical0.16 g/100g
LotionTopical1.7 mg/1mL
LiquidTopical1.545 mg/1mL
CreamTopical0.30 mL/100mL
LiquidTopical.30 mL/100mL
GelTopical0.30 mL/100mL
GelTopical.3 %
LiquidTopical0.003 mL/1mL
LiquidTopical3 mg/1mL
LiquidTopical0.11 g/100mL
SolutionTopical0.25 %
LiquidTopical0.25 %
LiquidTopical0.025 g/10mL
SolutionTopical0.3 mg/100mL
SoapTopical.15 g/100mL
LotionTopical.5 %
SuspensionTopical0.3 %
SoapTopical0.76 %
GelTopical0.5 mL/125mL
LiquidTopical1 g/100mL
CreamTopical.3 %
Paste, dentifriceOral
Gel, dentifriceDental
Paste, dentifriceDental
LiquidTopical0.2 mg/100mL
LiquidTopical2 mg/100mL
LotionTopical0.5 %
SoapTopical0.46 mL/100mL
SoapTopical1 mg/1g
SoapTopical0.1 g/100g
LiquidTopical1 mg/1mL
LiquidTopical.70 mL/100mL
LiquidTopical7 mg/100mL
LiquidTopical0.70 mL/100mL
LiquidTopical7.57 mL/3.78L
SoapTopical1.0 mg/1mL
AerosolTopical1 %
GelTopical
SoapTopical.03 g/1g
LiquidTopical0.375 mL/100mL
LiquidTopical0.3 mg/100mL
CreamTopical
LiquidTopical1 %
Shampoo; solutionTopical0.5 % w/w
LiquidTopical3.1 mg/1mL
SolutionTopical0.15 g/100mL
SolutionTopical0.60 %
SprayTopical0.975 %
SolutionTopical0.46 g/100mL
SolutionTopical4.6 mg/1mL
SolutionTopical0.46 mL/1000mL
SolutionTopical0.46 mg/1000mL
SolutionTopical0.46 % w/w
SolutionTopical0.46 %
Aerosol, foamTopical2.94 ug/1mL
LiquidTopical0.15 mL/100mL
LiquidTopical.5 %
LiquidTopical0.30 %
SolutionTopical0.3 mL/100mL
SolutionTopical10 mg/1mL
KitTopical
LiquidTopical0.2 g/100g
SolutionTopical2.05 mg/1mL
SolutionTopical10.35 mg/1mL
SolutionTopical10.3 mg/1mL
LiquidTopical1.0 %
LiquidTopical.46 g/100mL
SoapTopical4.5 mg/1mL
LotionTopical7.5 mg/1mL
LiquidTopical0.46 mg/100mL
SoapTopical0.15 g/100mL
LiquidTopical0.46 g/100mL
CreamTopical.5 %
LiquidTopical0.5 mg/100mL
SolutionTopical
LiquidTopical0.6 mL/100mL
LiquidTopical0.60 %
SoapTopical0.4600 mL/100.0000mL
SoapTopical0.6000 mL/100mL
LiquidTopical0.46 % w/w
LiquidTopical.46 mg/1mL
LiquidTopical6 mg/1mL
SoapTopical0.004 g/1g
LiquidTopical0.3 g/100mL
SoapTopical.003 g/1g
LotionVaginal0.12 g/100g
LiquidTopical5 mg/1mL
AerosolTopical3 mg/1mL
LiquidTopical0.5 %
LiquidTopical0.3 % w/w
ShampooTopical3 mg/1mL
AerosolTopical
SoapTopical0.0057 g/1g
SoapTopical1.0 g/100g
SoapTopical2.0 g/100g
SolutionTopical0.06 g/1000g
LiquidTopical0.003 mg/1mL
Aerosol, sprayTopical
Cream
SoapTopical.3 %
GelTopical0.15 mg/1mL
GelTopical7.5 mg/500mg
SoapTopical0.5 mg/100mL
GelPercutaneous2 mL/100mL
ClothTopical0.5 %
LiquidTopical1 mL/100mL
SolutionTopical0.15 mg/100mL
LiquidTopical0.33 %
LiquidTopical0.375 g/100mL
LiquidTopical.9 g/300g
LiquidTopical3.15 g/1000mL
SolutionTopical20.8 g/100mL
LiquidTopical0.32 %
LiquidTopical.32 %
SoapTopical0.007 g/1mL
SoapTopical0.003 g/1mL
SoapTopical0.1500 mL/100.0000mL
ShampooTopical1 g
SoapTopical0.0005 g/1g
LiquidTopical.01 g/10mL
LotionExtracorporeal2 g/500mL
LotionTopical1.0 %
SolutionTopical0.5 %
LiquidTopical7.5 mg/1mL
LiquidTopical0.75 g/100mL
LiquidTopical0.2 g/100mL
SolutionTopical0.5 % w/w
SolutionTopical2.5 g/1L
SolutionTopical0.005 g/0.001L
LiquidExtracorporeal0.176 mg/80mL
LiquidExtracorporeal0.176 mg/100mL
SolutionTopical1 %
CreamTopical0.2 % w/w
LiquidTopical.2 mL/100mL
LiquidTopical0.25 g/100mL
LiquidTopical0.25 % w/w
GelTopical10 mg/500mg
SolutionTopical0.575 mL/500mL
LotionTopical0.55 %
SoapTopical0.2 g/100g
LiquidTopical0.1 mL/100mL
LiquidTopical1.5 g/1L
SoapTopical6 mg/1mL
SolutionTopical0.3 g/100mL
SolutionTopical0.1 g/100mL
LotionTopical0.2 %
GelTopical0.1 % w/w
SoapTopical3.75 mg/1mL
SoapTopical0.375 g/100g
LiquidTopical0.5 g/1000mL
LiquidTopical.2 %
SolutionTopical1 g
LiquidTopical5 mg/1g
LiquidTopical7.5 mg/1g
GelTopical0.3 %
SolutionTopical80 g
SoapTopical3 mL/1000mL
LiquidTopical0.5 mL/250mL
LiquidTopical0.2 % w/w
LiquidTopical2 mg/1mL
SoapTopical3 mg/1mL
SoapTopical0.003 g/1g
LotionTopical0.3 % w/w
GelTopical0.55 mL/100mL
SolutionBuccal; Oropharyngeal
GelBuccal; Oral
LiquidTopical0.25 mL/100mL
SoapTopical0.3 mg/100mL
LiquidDental
LiquidTopical0.2 %
SolutionTopical.46 g/100mL
SoapTopical.46 g/100mL
LiquidTopical.6 %
SoapTopical1 %
SoapTopical318.975 mL/2126.5mL
GelTopical1.5 mg/1mL
SoapPercutaneous4.5 mg/1mL
SoapTopical0.5 g/100g
LiquidTopical0.50 mg/100mL
LiquidTopical.55 mL/100mL
SoapTopical0.115 g/100g
SolutionTopical0.1 mg/100mL
LiquidTopical0.4 mL/100mL
SoapTopical0.2 mL/100mL
ClothTopical0.15 %
LiquidTopical0.115 g/100g
SolutionTopical18.9 g/100mL
SoapTopical.562 mL/562mL
SoapTopical0.15 L/100L
SoapTopical0.003 mL/1mL
LiquidTopical3 mg/0.001L
LiquidTopical0.30 kg/100kg
LiquidTopical0.30 mg/100mL
LotionTopical.2 %
SoapTopical5 mg/1mL
CreamTopical1.5 g/1L
LiquidTopical0.15 %
LiquidTopical0.0015 mg/1mL
LiquidTopical.003 mg/1mL
SoapTopical0.3 g/1L
SprayTopical
SwabTopical
SolutionTopical0.00025 g/1g
LotionTopical6 % w/w
OilCutaneous
SoapTopical0.002 g/1mL
SolutionTopical0.1 %
SoapTopical0.115 mL/100mL
SoapTopical0.6 mL/100mL
SoapTopical0.15 mL/100mL
LiquidTopical0.15 mg/100mL
LiquidTopical1.5 mg/1mL
LiquidTopical3.54 mL/118mL
LotionTopical1 % w/w
SoapCutaneous2 mg/1mL
SoapTopical0.25 g/100mL
LiquidTopical.15 g/100mL
LiquidTopical.1 %
LiquidTopical1.08 g/1L
LiquidTopical1 mg / g
LiquidTopical0.1 g / 100 g
LiquidTopical1.5 mg/100mL
GelTopical0.15 mL/100mL
SolutionTopical0.25 g/100mL
SolutionTopical0.25 % w/w
SoapTopical0.5 %
LiquidTopical2.5 mg/1mL
SolutionTopical.25 %
LiquidTopical0.3 mL/100mL
GelTopical0.2 mL/100mL
GelTopical3 mg/1mL
LiquidTopical3 g/1000mL
SoapTopical4.6 mg/1mL
SoapTopical0.46 g/100mL
SoapTopical0.3 g/100mL
LiquidTopical1.15 mg/1mL
SoapTopical0.5 mL/100mL
LotionTopical1 %
SoapTopical.5 %
LiquidTopical115 mg/100mL
LiquidTopical11.7 g/100mL
LiquidTopical0.375 %
LiquidTopical5 g/1L
LiquidTopical0.55 g/100mL
LiquidTopical5.5 g/1L
LiquidTopical0.55 % w/w
SolutionTopical5 g/1L
LiquidTopical1.15 g/1L
LiquidTopical
LiquidTopical0.46 mg/1mL
SoapTopical0.12 mL/100mL
LotionTopical0.15 mL/100mL
LotionTopical.79 g/293g
LiquidTopical0.5 % w/w
LiquidTopical.3 %
LotionTopical0.3 g / 100 g
LiquidTopical1 % w/w
PowderTopical0.5 g
PowderTopical
PowderTopical0.1 g
ShampooTopical
LotionTopical0.2 % w/w
SoapTopical0.5 g/100mL
LiquidTopical3 g/1L
GelTopical1 mg/1mL
Liquid; shampooTopical0.5 %
SoapTopical2 g/1L
SolutionTopical3 mg/1mL
CreamTopical0.3 g/100mL
CreamCutaneous0.1000 g
CreamCutaneous
SoapTopical0.6 mL/100.0000mL
LiquidTopical4.6 mg/1mL
LiquidTopical0.5 g/100mL
PasteDental
LotionTopical.375 %
SpongeTopical5 mg/1mL
LiquidTopical29 mg/1mL
SoapTopical1.15 mg/1mL
GelTopical0.3 g/100g
LiquidTopical300 mg/100mL
SoapTopical6 1/1mL
LiquidTopical1.2 mL/1L
LotionTopical0.1 % w/w
SprayTopical1.2 mL/10mL
LotionTopical.4 %
SoapTopical.002 g/1mL
SolutionTopical0.3 %
SoapTopical6.6 1/443mL
SoapTopical3.3 mg/221mL
GelTopical1 mg/237mg
PowderTopical0.2 g
SoapTopical
LiquidTopical1.5 g/100g
LiquidTopical0.01 g/10mL
SoapTopical0.1 g/100mL
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)-3.8Chemaxon
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-MSsplash10-0udi-0490000000-dfb0757bfac1ad90e7a4
Mass Spectrum (Electron Ionization)MSsplash10-029g-9780000000-d39624d358bdeff3e131
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-18cca571133d660ee99d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-98f18a3880f73f629cd8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-46c8b5b37da8a0159120
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-25bb70cfd23a58ee5337
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0229-1690000000-1acec0e7549196e58e7b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-797f40c9db6cb07df2a1
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-147.837759
predicted
DarkChem Lite v0.1.0
[M-H]-147.747159
predicted
DarkChem Lite v0.1.0
[M-H]-152.35313
predicted
DeepCCS 1.0 (2019)
[M+H]+148.191059
predicted
DarkChem Lite v0.1.0
[M+H]+148.290759
predicted
DarkChem Lite v0.1.0
[M+H]+154.7454
predicted
DeepCCS 1.0 (2019)
[M+Na]+148.107659
predicted
DarkChem Lite v0.1.0
[M+Na]+148.128859
predicted
DarkChem Lite v0.1.0
[M+Na]+160.80428
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
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. [Article]
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. [Article]
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
A0A6L8PBX8
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. [Article]
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. [Article]
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
  1. Kretschmer XC, Baldwin WS: CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. 2005 Aug 15;155(3):111-28. [Article]
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
  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. [Article]
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
  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. [Article]
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
  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. [Article]
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
  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. [Article]

Drug created at September 15, 2010 21:33 / Updated at March 18, 2024 16:48