U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of TRICLOSAN

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

Molecular Formula C12H7Cl3O2
Molecular Weight 289.542
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
MOIST SURE

Cmax

ValueDoseCo-administeredAnalytePopulation
218 ng/mL
4 mg single, oral
TRICLOSAN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
2.6 ng × h/mL
4 mg single, oral
TRICLOSAN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
21 h
4 mg single, oral
TRICLOSAN plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

PubMed

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.
Substance Class Chemical
Record UNII
4NM5039Y5X
Record Status Validated (UNII)
Record Version