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Identification
NameHexachlorophene
Accession NumberDB00756  (APRD00722)
TypeSmall Molecule
GroupsApproved, Withdrawn
DescriptionA 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
2,2'-Dihydroxy-3,3',5,5',6,6'-hexachlorodiphenylmethane
2,2'-Dihydroxy-3,5,6,3',5',6'-hexachlorodiphenylmethane
2,2'-Methanediylbis(3,4,6-trichlorophenol)
2,2',3,3',5,5'-Hexachloro-6,6'-dihydroxydiphenylmethane
Acigena
Almederm
Armohex
Bis(2-hydroxy-3,5,6-trichlorophenyl)methane
Bis(3,5,6-trichloro-2-hydroxyphenyl)methane
Distodin
Esaclorofene
Exofene
Gamophen
Gamophene
Germa-medica
Hexa-germ
Hexabalm
Hexachlorophenum
Hexaclorofeno
Hexafen
Hexascrub
Hexide
Nabac
Phiso-scrub
Phisodan
Septi-soft
Septisol
Septofen
Solu-heks
Soy-dome
Staphene O
Ster-zac
Steral
Steraskin
Surgi-cen
Surgi-cin
Surofene
Tersaseptic
Turgex
External Identifiers
  • RCRA Waste Number U132
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Phisohexemulsion30 mg/mLtopicalSanofi Aventis U.S. Llc1976-06-11Not applicableUs
Phisohexemulsion30 mg/mLtopicalREMEDYREPACK INC.2013-07-05Not applicableUs
Phisohexemulsion3 %topicalSanofi Aventis Canada Inc1950-12-31Not applicableCanada
Sapodermliquid2 %topicalIngram And Bell Inc.1952-12-311999-08-05Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AknefugDr. August Wolff
DermisanArmoxindo
Pre-OpDavis and Geck
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIIWW5FV6NK2
CAS number70-30-4
WeightAverage: 406.904
Monoisotopic: 403.849895678
Chemical FormulaC13H6Cl6O2
InChI KeyInChIKey=ACGUYXCXAPNIKK-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • 4-chlorophenol
  • 2-chlorophenol
  • 3-chlorophenol
  • 2-halophenol
  • 3-halophenol
  • 4-halophenol
  • Phenol
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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.
Related Articles
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%
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9935
Blood Brain Barrier+0.9225
Caco-2 permeable+0.8512
P-glycoprotein substrateNon-substrate0.7211
P-glycoprotein inhibitor INon-inhibitor0.9281
P-glycoprotein inhibitor IINon-inhibitor0.9323
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.7848
CYP450 2D6 substrateNon-substrate0.8885
CYP450 3A4 substrateNon-substrate0.653
CYP450 1A2 substrateInhibitor0.8316
CYP450 2C9 inhibitorInhibitor0.9346
CYP450 2D6 inhibitorNon-inhibitor0.7899
CYP450 2C19 inhibitorInhibitor0.9425
CYP450 3A4 inhibitorNon-inhibitor0.7881
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8559
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.7953
BiodegradationNot ready biodegradable0.9636
Rat acute toxicity2.4031 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7894
hERG inhibition (predictor II)Non-inhibitor0.841
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Emulsiontopical3 %
Emulsiontopical30 mg/mL
Liquidtopical2 %
Prices
Unit descriptionCostUnit
Phisohex 148ml Bottle35.46USD bottle
Hexachlorophene powder11.47USD g
Phisohex 3% cleanser0.18USD ml
Phisohex 473ml Bottle0.13USD ml
Tersaseptic cleanser0.05USD g
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 Solubility0.000433 mg/mLALOGPS
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.34 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

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

General ReferencesNot Available
External Links
ATC CodesD08AE01
AHFS Codes
  • 84:04.92
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (76.8 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on the ch-oh group of donors, quinone or similar compound as acceptor
Specific Function:
First component of the membrane-bound D-lactate oxidase, which is believed to play an important role in the energization of the active transport of a variety of sugars and amino acids.
Gene Name:
dld
Uniprot ID:
P06149
Molecular Weight:
64611.82 Da
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:17139284 ]
  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:17016423 ]
  3. Wang JL, Buhler DR: Inhibition of dehydrogenase enzymes by hexachlorophene. Biochem Pharmacol. 1978;27(24):2947-53. [PubMed:570044 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Ubiquinone binding
Specific Function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:
SDHD
Uniprot ID:
O14521
Molecular Weight:
17042.82 Da
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:10487417 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Nad+ binding
Specific Function:
Mitochondrial glutamate dehydrogenase that converts L-glutamate into alpha-ketoglutarate. Plays a key role in glutamine anaplerosis by producing alpha-ketoglutarate, an important intermediate in the tricarboxylic acid cycle. May be involved in learning and memory reactions by increasing the turnover of the excitatory neurotransmitter glutamate (By similarity).
Gene Name:
GLUD1
Uniprot ID:
P00367
Molecular Weight:
61397.315 Da
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. doi: 10.1074/jbc.M109.020222. Epub 2009 Jun 15. [PubMed:19531491 ]
  2. Wang JL, Buhler DR: Inhibition of dehydrogenase enzymes by hexachlorophene. Biochem Pharmacol. 1978;27(24):2947-53. [PubMed:570044 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23