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=C(OC2=C(Cl)C=C(Cl)C=C2)C=CC(Cl)=C1

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 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=64cdbe15-3355-40f8-8dfd-61f7d6f64dc8	Preventing		Approved 8429	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 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 60	CYP1A2 1054 CYP2B6 664 CYP2C19 991 CYP1B1 92 CYP2C18 138 CYP1A1 349 CYP2A6 543 CYP2A13 12 CYP2C8 693 CYP2E1 667 CYP3A5 395 CYP3A7 110 CYP4A11 119 UGT1A3 422 UGT1A6 307 UGT1A7 236 UGT1A8 283 UGT1A9 380 UGT1A4 347 UGT1A10 291 UGT2B4 249 UGT2B7 389 UGT2B15 203

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP19A1 60	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5742433/	yes [IC50 15.81 uM]

Drug as victim

Target	Modality	Activity
CYP2A13 12	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP3A5 395	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP3A7 110	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
CYP4A11 119	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	little or no
UGT1A3 422	substrate 3367 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	major
UGT1A6 307	substrate 3367 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	major
UGT1A7 236	substrate 3367 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	major
UGT1A8 283	substrate 3367 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	major
UGT1A9 380	substrate 3367 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	major
UGT1A10 291	substrate 3367 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	minor
UGT1A4 347	substrate 3367 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	minor
UGT2B15 203	substrate 3367 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	minor
UGT2B4 249	substrate 3367 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	minor
UGT2B7 389	substrate 3367 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.27.1_supplement.892.11	minor
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes
CYP1B1 92	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes
CYP2C18 138	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27896399/	yes
CYP2D6 1217	substrate 3367 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
MolPort	MolPort-003-666-702	https://www.molport.com/shop/molecule-link/MolPort-003-666-702
ZINC	ZINC000000002216	http://zinc15.docking.org/substances/ZINC000000002216
eMolecules	517128	https://www.emolecules.com/cgi-bin/more?vid=517128

PubMed

Title	Date	PubMed
Percutaneous treatment of chronic MRSA osteomyelitis with a novel plant-derived antiseptic.	2001	11368798
Antibacterial efficacy of triclosan-incorporated polymers.	2001 Apr	11287882
New agents to combat malaria.	2001 Feb	11175835
A study to assess the plaque inhibitory action of a newly formulated triclosan toothpaste.	2001 Jan	11142672
[Effect of a new triclosan-containing mouth rinse on oral infection].	2001 Jul	11718017
Membranotropic effects of the antibacterial agent Triclosan.	2001 Jun 1	11368524
The acute phase response following implantation of triclosan-bonded vascular prostheses.	2001 Mar	11467400
Determination of phenolic disinfectant agents in commercial formulations by liquid chromatography.	2001 May-Jun	11417646
[Can disinfectants contribute to antibiotic resistance?].	2001 Nov 10	11876147
Sustained drug delivery system based on a cationic polymer and an anionic drug/cyclodextrin complex.	2001 Sep	11594000
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
Biofilms in vitro and in vivo: do singular mechanisms imply cross-resistance?	2002	12000619
Mechanisms of bacterial biocide and antibiotic resistance.	2002	12000613
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
The clinical efficacy of Colgate Total Plus Whitening Toothpaste containing a special grade of silica and Colgate Total Fresh Stripe Toothpaste in the control of plaque and gingivitis: a six-month clinical study.	2002	11695207
Hexametaphosphate effects on tooth surface conditioning film chemistry--in vitro and in vivo studies.	2002	11507931
Laboratory studies on the chemical whitening effects of a sodium hexametaphosphate dentifrice.	2002	11507927
Evaluation of the effectiveness of a pre-brushing rinse in plaque removal: a meta-analysis.	2002 Apr	11966927
Pseudomonas aeruginosa cells adapted to benzalkonium chloride show resistance to other membrane-active agents but not to clinically relevant antibiotics.	2002 Apr	11909837
Clinical effect of a new liquid dentifrice containing triclosan/copolymer on existing plaque and gingivitis.	2002 Feb	11868841
Comparative analysis of some mouthrinses on the production of volatile sulfur-containing compounds.	2002 Jan	11902607
Effect of a triclosan-containing toothpaste supplemented with 10% xylitol on mutans streptococci in saliva and dental plaque. A 6-month clinical study.	2002 Jan-Feb	11961328
Fate and effects of triclosan in activated sludge.	2002 Jul	12109731
Crystallization and preliminary X-ray crystallographic analysis of enoyl-acyl carrier protein reductase from Helicobacter pylori.	2002 Jun	12037321
An in vitro oral biofilm model for comparing the efficacy of antimicrobial mouthrinses.	2002 Mar-Apr	12037365
Efficacy of two antiplaque and antigingivitis treatments in a group of young mentally retarded patients.	2002 Mar-Apr	11887021

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

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

TRICLOSAN COMPONENT OF COLGATE TOTAL

Common Name

English

STRI-DEX CLEANSING BAR

Brand 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 [INCI]

Common Name

English

TRICLOSAN [ORANGE BOOK]

Common Name

English

Triclosan [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

D09AA06