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Details

Stereochemistry ACHIRAL
Molecular Formula C13H6Cl6O2
Molecular Weight 406.904
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HEXACHLOROPHENE

SMILES

OC1=C(CC2=C(O)C(Cl)=CC(Cl)=C2Cl)C(Cl)=C(Cl)C=C1Cl

InChI

InChIKey=ACGUYXCXAPNIKK-UHFFFAOYSA-N
InChI=1S/C13H6Cl6O2/c14-6-2-8(16)12(20)4(10(6)18)1-5-11(19)7(15)3-9(17)13(5)21/h2-3,20-21H,1H2

HIDE SMILES / InChI

Description

Hexachlorophene, also known as Nabac, is an organochlorine compound that was once widely used as a disinfectant. The compound occurs as a white odorless solid, although commercial samples can be off-white and possess a slightly phenolic odor. It is insoluble in water but dissolves in acetone, ethanol, diethyl ether, and chloroform. Exact mechanism(s) of action unknown, but at low concentrations appears to interrupt bacterial electron transport and inhibit membrane-bound enzymes. Higher concentrations rupture bacterial membranes. It induces leakage, causes protoplast lysis, and inhibits respiration. In medicine, hexachlorophene is a useful as a topical anti-infective, anti-bacterial agent, often used in soaps and toothpaste. It is also used in agriculture as a soil fungicide, plant bactericide, and acaricide.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
59.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PRE-OP

T1/2

ValueDoseCo-administeredAnalytePopulation
21.15 h
3 % unknown, topical
HEXACHLOROPHENE blood
Homo sapiens

Doses

PubMed

Sample Use Guides

In Vivo Use Guide
Apply topically to skin as a 3% emulsion.
Route of Administration: Topical
In Vitro Use Guide
Cells of the asporogenous KM strain of B. megaterium were grown in aerated batch culture. Cells was treated by Hexachlorophene (ethanol solution, up to 400 mkg/ml) for 30 min. Protoplast lysis was proportional to Hexachlorophene concentration up to about 50 mg of cell dry weight per mg.