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Identification
Name Hexachlorophene
Accession Number DB00756 (APRD00722)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Acigena
Almederm
AT-7
Bilevon
Bivelon
Compound G-11
Cotofilm
Dermadex
Distodin
E-Z Scrub
Eleven
Exofene
Fascol
Fesia-Sin
Fomac
Fostril
G-Eleven
G-II
Gamophen
Gamophene
Germa-Medica
Hexa-Germ
Hexabalm
Hexachlorofen
Hexachlorophane
Hexachlorophen
Hexachlorophene, Pharma
Hexafen
Hexascrub
Hexazinone
Hexide
Hexophene
Hexosan
Isobac
Isobac 20
Nabac
Nabac 25 Ec
Neosept V
Phiso-Scrub
Phisodan
Phisohex
Pre-Op
Rcra Waste Number U132
Ritosept
Scrubteam Surgical Spongebrush
Septi-Soft
Septisol
Septofen
Soy-Dome
Ster-Zac
Steral
Steraskin
Surgi-Cen
Surgi-Cin
Surofene
Tersaseptic
Trichlorophene
Turgex
First Prev Next Last
Brand mixtures
Brand Name Ingredients
Fosteen Dermatologic Shampoo Hexachlorophene + Lanolin + Salicylic Acid + Sulfur
Hexaphenyl Hexachlorophene + Isopropyl Alcohol
Categories
  • Anti-Infectives
  • Anti-Infective Agents, Local
CAS number 70-30-4
Weight Average: 406.904
Monoisotopic: 403.849895678
Chemical Formula C13H6Cl6O2
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec show (9.34 KB)
Taxonomy
Kingdom Organic
Classes
  • Diphenylmethanes
Substructures
  • Hydroxy Compounds
  • Phenols and Derivatives
  • Benzene and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Diphenylmethanes
  • Aromatic compounds
  • Phenyl Esters
Pharmacology
Indication For 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.
Pharmacodynamics Hexachlorophene, 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 action The 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.
Absorption Detectable blood levels of hexachlorophene following absorption through intact skin have been found in subjects who regularly scrubbed with hexachlorophene.
Volume of distribution Not Available
Protein binding 92%
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Oral, 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
Pathways Not Available
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
Form Route Strength
Emulsion Topical
Prices
Unit description Cost Unit
Phisohex 148ml Bottle 35.46 USD bottle
Hexachlorophene powder 11.47 USD g
Phisohex 3% cleanser 0.18 USD ml
Phisohex 473ml Bottle 0.13 USD ml
Tersaseptic cleanser 0.05 USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State liquid
Experimental Properties
Property Value Source
melting point 166.5 °C PhysProp
boiling point 479 °C PhysProp
water solubility 140 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 7.54 HANSCH,C ET AL. (1995)
pKa 4.95 HANSCH,C & LEO,AJ (1985)
Predicted Properties
Property Value Source
water solubility 4.33e-04 g/l ALOGPS
logP 6.77 ALOGPS
logP 7.08 ChemAxon
logS -6 ALOGPS
pKa (strongest acidic) 5.15 ChemAxon
pKa (strongest basic) -7.4 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 40.46 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 88.59 ChemAxon
polarizability 34.07 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00859 Link_out
KEGG Compound C08039 Link_out
PubChem Compound 3598 Link_out
PubChem Substance 46505858 Link_out
ChemSpider 3472 Link_out
Therapeutic Targets Database DAP001050 Link_out
PharmGKB PA449871 Link_out
Drug Product Database 2017733 Link_out
RxList http://www.rxlist.com/cgi/generic2/hexchlorph.htm Link_out
Drugs.com http://www.drugs.com/cdi/hexachlorophene.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Hexachlorophene Link_out
ATC Codes
  • D08AE01
AHFS Codes
  • 84:04.92
PDB Entries Not Available
FDA label Not Available
MSDS show (76.8 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. D-lactate dehydrogenase

Pharmacological action: yes
Actions: inhibitor

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

Organism class: bacterial
UniProt ID: P06149 Link_out
Gene: dld
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: inhibitor
Organism class: human
UniProt ID: O14521 Link_out
Gene: SDHD Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: inhibitor

May be involved in learning and memory reactions by increasing the turnover of the excitatory neurotransmitter glutamate

Organism class: human
UniProt ID: P00367 Link_out
Gene: GLUD1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19