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Identification
NameHexachlorophene
Accession NumberDB00756  (APRD00722)
TypeSmall Molecule
GroupsApproved, Withdrawn
Description

A chlorinated bisphenol antiseptic with a bacteriostatic action against Gram-positive organisms, but much less effective against Gram-negative organisms. It is mainly used in soaps and creams and is an ingredient of various preparations used for skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p797)

Structure
Thumb
Synonyms
SynonymLanguageCode
2,2'-Dihydroxy-3,3',5,5',6,6'-hexachlorodiphenylmethaneNot AvailableNot Available
2,2'-Dihydroxy-3,5,6,3',5',6'-hexachlorodiphenylmethaneNot AvailableNot Available
2,2'-Methanediylbis(3,4,6-trichlorophenol)Not AvailableNot Available
2,2',3,3',5,5'-Hexachloro-6,6'-dihydroxydiphenylmethaneNot AvailableNot Available
AcigenaNot AvailableNot Available
AlmedermNot AvailableNot Available
ArmohexNot AvailableNot Available
Bis(2-hydroxy-3,5,6-trichlorophenyl)methaneNot AvailableNot Available
Bis(3,5,6-trichloro-2-hydroxyphenyl)methaneNot AvailableNot Available
DistodinNot AvailableNot Available
EsaclorofeneNot AvailableNot Available
ExofeneNot AvailableNot Available
GamophenNot AvailableNot Available
GamopheneNot AvailableNot Available
Germa-medicaNot AvailableNot Available
Hexa-germNot AvailableNot Available
HexabalmNot AvailableNot Available
HexachlorophenumNot AvailableNot Available
HexaclorofenoNot AvailableNot Available
HexafenNot AvailableNot Available
HexascrubNot AvailableNot Available
HexideNot AvailableNot Available
NabacNot AvailableNot Available
Phiso-scrubNot AvailableNot Available
PhisodanNot AvailableNot Available
Septi-softNot AvailableNot Available
SeptisolNot AvailableNot Available
SeptofenNot AvailableNot Available
Solu-heksNot AvailableNot Available
Soy-domeNot AvailableNot Available
Staphene ONot AvailableNot Available
Ster-zacNot AvailableNot Available
SteralNot AvailableNot Available
SteraskinNot AvailableNot Available
Surgi-cenNot AvailableNot Available
Surgi-cinNot AvailableNot Available
SurofeneNot AvailableNot Available
TersasepticNot AvailableNot Available
TurgexNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
AknefugDr. August Wolff
DermisanArmoxindo
pHisoHexSanofi
Pre-OpDavis and Geck
Brand mixturesNot Available
Categories
CAS number70-30-4
WeightAverage: 406.904
Monoisotopic: 403.849895678
Chemical FormulaC13H6Cl6O2
InChI KeyACGUYXCXAPNIKK-UHFFFAOYSA-N
InChI
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
IUPAC Name
3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol
SMILES
OC1=C(CC2=C(O)C(Cl)=CC(Cl)=C2Cl)C(Cl)=C(Cl)C=C1Cl
Mass Specshow(9.34 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassDiphenylmethanes
Direct parentDiphenylmethanes
Alternative parentsp-Chlorophenols; m-Chlorophenols; o-Chlorophenols; Chlorobenzenes; Aryl Chlorides; Enols; Polyamines; Organochlorides
Substituents4-chlorophenol; 3-chlorophenol; 2-chlorophenol; 4-halophenol; 2-halophenol; 3-halophenol; chlorobenzene; phenol derivative; aryl halide; aryl chloride; enol; polyamine; organochloride; organohalogen
Classification descriptionThis compound belongs to the diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Pharmacology
IndicationFor use as a surgical scrub and a bacteriostatic skin cleanser. It may also be used to control an outbreak of gram-positive infection where other infection control procedures have been unsuccessful.
PharmacodynamicsHexachlorophene, a detergent cleanser, is an antibacterial sudsing emulsion for topical administration. It is a bacteriostatic cleansing agent. It cleanses the skin thoroughly and has bacteriostatic action against staphylococci and other gram-positive bacteria. Cumulative antibacterial action develops with repeated use. Cleansing with alcohol or soaps containing alcohol removes the antibacterial residue.
Mechanism of actionThe primary mechanism of action of hexachlorophene, based on studies with Bacillus megatherium, is to inhibit the membrane-bound part of the electron transport chain, respiratory D-lactate dehydrogenase. It induces leakage, causes protoplast lysis, and inhibits respiration.
AbsorptionDetectable blood levels of hexachlorophene following absorption through intact skin have been found in subjects who regularly scrubbed with hexachlorophene.
Volume of distributionNot Available
Protein binding92%
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral, rat LD50: 66 mg/kg. Signs of overdose include anorexia, vomiting, abdominal cramps, diarrhea, dehydration, convulsions, hypotension, and shock, and in several reported instances, fatalities.
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9935
Blood Brain Barrier + 0.9225
Caco-2 permeable + 0.8512
P-glycoprotein substrate Non-substrate 0.7211
P-glycoprotein inhibitor I Non-inhibitor 0.9281
P-glycoprotein inhibitor II Non-inhibitor 0.9323
Renal organic cation transporter Non-inhibitor 0.8178
CYP450 2C9 substrate Non-substrate 0.7848
CYP450 2D6 substrate Non-substrate 0.8885
CYP450 3A4 substrate Non-substrate 0.653
CYP450 1A2 substrate Inhibitor 0.8316
CYP450 2C9 substrate Inhibitor 0.9346
CYP450 2D6 substrate Non-inhibitor 0.7899
CYP450 2C19 substrate Inhibitor 0.9425
CYP450 3A4 substrate Non-inhibitor 0.7881
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8559
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.7953
Biodegradation Not ready biodegradable 0.9636
Rat acute toxicity 2.4031 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7894
hERG inhibition (predictor II) Non-inhibitor 0.841
Pharmacoeconomics
Manufacturers
  • Vestal laboratories div chemed corp
  • Xttrium laboratories inc
  • Huntington laboratories inc
  • Sanofi aventis us llc
  • Bayer pharmaceuticals corp
  • Arbrook inc
  • Dial corp div greyhound co
  • Calgon corp div merck and co inc
  • Becton dickinson and co
  • Professional disposables inc
  • Davis and geck div american cyanamid co
  • 3m co
Packagers
Dosage forms
FormRouteStrength
EmulsionTopical
Prices
Unit descriptionCostUnit
Phisohex 148ml Bottle35.46USDbottle
Hexachlorophene powder11.47USDg
Phisohex 3% cleanser0.18USDml
Phisohex 473ml Bottle0.13USDml
Tersaseptic cleanser0.05USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point161-163U.S. Patent 2,435,593.
boiling point479 °CPhysProp
water solubility140 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP7.54HANSCH,C ET AL. (1995)
pKa4.95HANSCH,C & LEO,AJ (1985)
Predicted Properties
PropertyValueSource
Water Solubility0.000433ALOGPS
logP6.77ALOGPS
logP7.08ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)5.15ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.59 m3·mol-1ChemAxon
Polarizability34.07 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

U.S. Patent 2,250,480
U.S. Patent 2,435,593
U.S. Patent 2,812,365

General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00859
KEGG CompoundC08039
PubChem Compound3598
PubChem Substance46505858
ChemSpider3472
Therapeutic Targets DatabaseDAP001050
PharmGKBPA449871
Drug Product Database2017733
RxListhttp://www.rxlist.com/cgi/generic2/hexchlorph.htm
Drugs.comhttp://www.drugs.com/cdi/hexachlorophene.html
WikipediaHexachlorophene
ATC CodesNot Available
AHFS Codes
  • 84:04.92
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(76.8 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. D-lactate dehydrogenase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
D-lactate dehydrogenase P06149 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Wang JL, Buhler DR: Inhibition of dehydrogenase enzymes by hexachlorophene. Biochem Pharmacol. 1978;27(24):2947-53. Pubmed

2. Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial O14521 Details

References:

  1. Lokanatha V, Sailaja P, Rajendra W: In vitro kinetics of the rat brain succinate dehydrogenase inhibition by hexachlorophene. J Biochem Mol Toxicol. 1999;13(6):303-6. Pubmed

3. Glutamate dehydrogenase 1, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Glutamate dehydrogenase 1, mitochondrial P00367 Details

References:

  1. Li M, Smith CJ, Walker MT, Smith TJ: Novel inhibitors complexed with glutamate dehydrogenase: allosteric regulation by control of protein dynamics. J Biol Chem. 2009 Aug 21;284(34):22988-3000. Epub 2009 Jun 15. Pubmed
  2. Wang JL, Buhler DR: Inhibition of dehydrogenase enzymes by hexachlorophene. Biochem Pharmacol. 1978;27(24):2947-53. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on April 28, 2014 16:27