TRICLOSAN

US Previously Marketed

First approved in 1969

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H7Cl3O2
Molecular Weight	289.542
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC(Cl)=CC=C1OC2=CC=C(Cl)C=C2Cl

InChI

InChIKey=XEFQLINVKFYRCS-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.drugbank.ca/drugs/DB08604
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Triclosan https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=64cdbe15-3355-40f8-8dfd-61f7d6f64dc8

Triclosan was used as a hospital scrub in the 1970s. Since then, it has expanded commercially and is now prevalent in soaps (0.10-1.00%), shampoos, deodorants, toothpastes, mouth washes, cleaning supplies and pesticides. It is part of consumer products, including kitchen utensils, toys, bedding, socks and trash bags. In healthcare, triclosan is used in surgical scrubs and hand washes. Use in surgical units is effective with a minimum contact time of approximately two minutes. More recently, showering with 2% triclosan has become a recommended regimen in surgical units for the decolonization of patients whose skin carries methicillin-resistant Staphylococcus aureus (MRSA). Triclosan is also used in the coatings for some surgical sutures. Triclosan has been employed as a selective agent in molecular cloning. At high concentrations, triclosan acts as a biocide with multiple cytoplasmic and membrane targets. However, at the lower concentrations seen in commercial products, triclosan appears bacteriostatic, and it targets bacteria primarily by inhibiting fatty acid synthesis. Triclosan binds to bacterial enoyl-acyl carrier protein reductase (ENR) enzyme, 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 building and reproducing cell membranes. Humans do not have an ENR enzyme and thus are not affected.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial enoyl-[acyl-carrier-protein] reductase 8 Target ID: CHEMBL2364678 Sources: http://www.drugbank.ca/drugs/DB08604	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=64cdbe15-3355-40f8-8dfd-61f7d6f64dc8	Preventing		Approved 8583	MOIST SURE Approved Use Used as a Surgical Scrub and Healthcare Personnel Handwash in patient care or other high risk settings to reduce transient bacteria and the risk of cross contamination. Used when hands are physically clean. Launch Date 1997

C_max

Value	Dose	Co-administered	Analyte	Population
218 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16952905/	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:		TRICLOSAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
2.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16952905/	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:		TRICLOSAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16952905/	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:		TRICLOSAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429	CYP1A2 1197 CYP2B6 776 CYP2C19 1119 CYP1B1 104 CYP2C18 149 CYP1A1 389 CYP2A6 626 CYP2A13 12 CYP2C8 810 CYP2E1 729 CYP3A5 446 CYP3A7 109 CYP4A11 137 UGT1A3 470 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A4 399 UGT1A10 331 UGT2B4 278 UGT2B7 456 UGT2B15 236

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP19A1 430	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5742433/	yes [IC50 15.81 uM]

Drug as victim

Target	Modality	Activity
CYP2A13 12	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP3A7 109	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP4A11 137	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
UGT1A3 470	substrate 4014 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	major
UGT1A6 343	substrate 4014 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	major
UGT1A7 249	substrate 4014 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	major
UGT1A8 323	substrate 4014 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	major
UGT1A9 423	substrate 4014 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	major
UGT1A10 331	substrate 4014 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	minor
UGT1A4 399	substrate 4014 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	minor
UGT2B15 236	substrate 4014 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	minor
UGT2B4 278	substrate 4014 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	minor
UGT2B7 456	substrate 4014 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	minor
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes
CYP1B1 104	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:164200	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:164200
ChemicalBook	CB6771432	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6771432
eMolecules	517128	https://www.emolecules.com/cgi-bin/more?vid=517128
MolPort	MolPort-003-666-702	https://www.molport.com/shop/molecule-link/MolPort-003-666-702
ZINC	ZINC000000002216	http://zinc15.docking.org/substances/ZINC000000002216

PubMed

Title	Date	PubMed
A dynamic mechanical method for determining the silicone elastomer solubility of drugs and pharmaceutical excipients in silicone intravaginal drug delivery rings.	2002-09	12109683
Aquatic toxicity of triclosan.	2002-07	12109732
Fate and effects of triclosan in activated sludge.	2002-07	12109731
Measurement of triclosan in wastewater treatment systems.	2002-07	12109730
Occurrence and environmental behavior of the bactericide triclosan and its methyl derivative in surface waters and in wastewater.	2002-06-01	12075785
Methyl triclosan found in Swiss lakes.	2002-06-01	12075779
Crystallization and preliminary X-ray crystallographic analysis of enoyl-acyl carrier protein reductase from Helicobacter pylori.	2002-06	12037321
An in vitro oral biofilm model for comparing the efficacy of antimicrobial mouthrinses.	2002-05-31	12037365
The antimicrobial properties of a urea-based handwash lotion with triclosan.	2002-05-25	12024756
In vitro antioxidant activities of mouthrinses and their components.	2002-05	12060430
Determination of triclosan in personal health care products by liquid chromatography (HPLC).	2002-05	12058811
Inhibitors of fatty acid synthesis as antimicrobial chemotherapeutics.	2002-05	12021787
Effect of a triclosan-containing toothpaste supplemented with 10% xylitol on mutans streptococci in saliva and dental plaque. A 6-month clinical study.	2002-04-19	11961328
Structural elucidation of the specificity of the antibacterial agent triclosan for malarial enoyl acyl carrier protein reductase.	2002-04-12	11792710
Effect of an amine-fluoride-triclosan mouthrinse on plaque regrowth and biofilm vitality.	2002-04	11966934
Evaluation of the effectiveness of a pre-brushing rinse in plaque removal: a meta-analysis.	2002-04	11966927
Pseudomonas aeruginosa cells adapted to benzalkonium chloride show resistance to other membrane-active agents but not to clinically relevant antibiotics.	2002-04	11909837
Triclosan: release from transdermal adhesive formulations and in vitro permeation across human epidermal membranes.	2002-03-20	11879757
Pharmaceuticals, hormones, and other organic wastewater contaminants in U.S. streams, 1999-2000: a national reconnaissance.	2002-03-15	11944670
Efficacy of two antiplaque and antigingivitis treatments in a group of young mentally retarded patients.	2002-03-12	11887021
Triclosan, a commonly used bactericide found in human milk and in the aquatic environment in Sweden.	2002-03	12002480
Triclosan inhibits enoyl-reductase of type I fatty acid synthase in vitro and is cytotoxic to MCF-7 and SKBr-3 breast cancer cells.	2002-03	11935210
Clinical effect of a new liquid dentifrice containing triclosan/copolymer on existing plaque and gingivitis.	2002-02	11868841
Paradigm shifts in malaria parasite biochemistry and anti-malarial chemotherapy.	2002-02	11835284
Comparative analysis of some mouthrinses on the production of volatile sulfur-containing compounds.	2002-01	11902607
Evaluation of an antimicrobial-impregnated continuous ambulatory peritoneal dialysis catheter for infection control in rats.	2002-01	11774116
The antibacterial activity of triclosan-impregnated storage boxes against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Bacillus cereus and Shewanella putrefaciens in conditions simulating domestic use.	2002-01	11751771
Experimental gingivitis studies: effects of triclosan and triclosan-containing dentifrices on dental plaque and gingivitis in three-week randomized controlled clinical trials.	2002	12116726
Triclosan/pyrophosphate dentifrice: dental plaque and gingivitis effects in a 6-month randomized controlled clinical study.	2002	12116725
Susceptibility of antibiotic-resistant cocci to biocides.	2002	12000624
Quantitative assessment of risk reduction from hand washing with antibacterial soaps.	2002	12000622
Introduction of biocides into clinical practice and the impact on antibiotic-resistant bacteria.	2002	12000621
Biofilms in vitro and in vivo: do singular mechanisms imply cross-resistance?	2002	12000619
Active efflux, a common mechanism for biocide and antibiotic resistance.	2002	12000614
Mechanisms of bacterial biocide and antibiotic resistance.	2002	12000613
Effectiveness of some recent antimicrobial packaging concepts.	2002	11962704
A six-week clinical study to compare the stain removal efficacy of three dentifrices.	2002	11695214
The clinical efficacy of a new tooth whitening dentifrice formulation: a six-month study in adults.	2002	11695213
Clinical efficacy of a new tooth whitening dentifrice.	2002	11695212
A study to assess the tooth whitening efficacy of a new dentifrice formulation variant containing a special grade of silica: a six-week study on adults.	2002	11695211
The clinical efficacy of Colgate Total Plus Whitening Toothpaste containing a special grade of silica and Colgate Total Toothpaste for controlling breath odor twelve hours after toothbrushing: a single-use clinical study.	2002	11695210
A clinical study to compare the anticalculus efficacy of three dentifrice formulations.	2002	11695209
A clinical study to assess the anticalculus efficacy of a new dentifrice containing a special grade of silica (Colgate Total Plus Whitening Toothpaste): a clinical trial on adults.	2002	11695208
Kinetic determinants of the interaction of enoyl-ACP reductase from Plasmodium falciparum with its substrates and inhibitors.	2001-12-14	11735121
Antibacterial efficacy of polymers containing triclosan and other antimicrobial additives.	2001-12	11743492
Bacterial adaptation to biocides: the possible role of 'alarmones'.	2001-12	11740885
[Can disinfectants contribute to antibiotic resistance?].	2001-11-10	11876147
Allergic contact dermatitis from triclosan in antibacterial handwashes.	2001-11	11722499
[Effect of a new triclosan-containing mouth rinse on oral infection].	2001-07	11718017
The benefits of toothpaste--real or imagined? The effectiveness of toothpaste in the control of plaque, gingivitis, periodontitis, calculus and oral malodour.	2001-04	11819975

Patents

Sample Use Guides

In Vivo Use Guide

0.3% for hand washing

Route of Administration: Other

In Vitro Use Guide

Twenty bacterial strains (proposed by the FDA) were exposed to plain and antibacterial soaps (the same formulation as plain soap, but containing 0.3% triclosan) for 20 s at 22°C (room temperature) and 40°C (warm temperature). The temperature and time were selected to simulate the hand washing conditions and procedures used by consumers. The triclosan concentration of 0.3% is the maximum allowed by law. Antibacterial soap containing triclosan (0.3%) was no more effective than plain soap at reducing bacterial contamination when used under 'real-life' conditions.

Name

Type

Language

STRI-DEX CLEANSING BAR

Preferred Name

English

TRICLOSAN

Official Name

English

NSC-759151

Code

English

TRICLOSAN [MI]

Common Name

English

triclosan [INN]

Common Name

English

2,4,4'-TRICHLORO-2'-HYDROXYDIPHENYL ETHER

Common Name

English

TRICLOSAN [USP MONOGRAPH]

Common Name

English

DNDI1246774

Code

English

TRICLOSAN [USP-RS]

Common Name

English

COLGATE TOTAL COMPONENT TRICLOSAN

Common Name

English

PHENOL, 5-CHLORO-2-(2,4-DICHLOROPHENOXY)-

Systematic Name

English

CH-3565

Code

English

TRICLOSAN [USAN]

Common Name

English

TRICLOSAN [VANDF]

Common Name

English

TRICLOSAN [MART.]

Common Name

English

TRICLOSAN [HSDB]

Common Name

English

CH 3565

Code

English

TRICLOSAN [ORANGE BOOK]

Common Name

English

Triclosan [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

D09AA06