Identification
- Summary
Hexachlorophene is a chlorinated bisphenol antiseptic used as a surgical scrub and skin cleanser.
- Generic Name
- Hexachlorophene
- DrugBank Accession Number
- DB00756
- Background
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)
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Hexachlorophene (DB00756)
- Weight
- Average: 406.904
Monoisotopic: 403.849895678 - Chemical Formula
- C13H6Cl6O2
- 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'-methylenebis(3,4,6-trichlorophenol)
- 2,2',3,3',5,5'-hexachloro-6,6'-dihydroxydiphenylmethane
- bis(2-hydroxy-3,5,6-trichlorophenyl)methane
- bis(3,5,6-trichloro-2-hydroxyphenyl)methane
- hexachlorophène
- Hexachlorophene
- Hexachlorophenum
- Hexaclorofeno
- External IDs
- NSC-49115
- RCRA Waste Number U132
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.
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- Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AD-lactate dehydrogenase inhibitorEscherichia coli (strain K12) ASuccinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial inhibitorHumans UGlutamate dehydrogenase 1, mitochondrial inhibitorHumans UEstrogen receptor alpha Not Available Humans - 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
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Acigena / Aknefug (Dr. August Wolff) / Almederm / Armohex / Dermisan (Armoxindo) / Dial / Distodin / E-Z scrub / Exofene / Gamophen / Gamophene / Germa-medica / Hexa-Germ / Hexabalm / Hexafen / Hexascrub / Hexide / Nabac / Phiso-scrub / Phisodan / Pre-Op (Davis and Geck) / Pre-Op II / Septi-soft / Septisol / Septofen / Solu-Heks / Soy-Dome / Staphene O / Ster-Zac / Steral / Steraskin / Surgi-Cen / Surgi-Cin / Surofene / Tersaseptic / Turgex
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Phisohex Emulsion 30 mg/1mL Topical Sanofi Aventis 1976-06-11 2016-04-30 US 
Phisohex Emulsion 3 % Topical Sanofi Aventis 1950-12-31 2017-03-30 Canada 
Phisohex Emulsion 30 mg/1mL Topical Physicians Total Care, Inc. 2003-12-03 2011-06-30 US Phisohex Emulsion 30 mg/1mL Topical Remedy Repack 2013-07-10 2015-07-10 US Sapoderm Liquid 2 % Topical Ingram And Bell Inc. 1952-12-31 1999-08-05 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image เฮกซ่า-คลีน Solution 0.35 ml/100ml ห้างหุ้นส่วนจำกัด สุพงษ์เภสัช 1986-10-22 2020-05-24 Thailand 
Categories
- ATC Codes
- D08AE01 — Hexachlorophene
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- P-chlorophenols / O-chlorophenols / M-chlorophenols / Chlorobenzenes / Aryl chlorides / Organooxygen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- 2-chlorophenol / 2-halophenol / 3-chlorophenol / 3-halophenol / 4-chlorophenol / 4-halophenol / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- polyphenol, trichlorobenzene, bridged diphenyl fungicide (CHEBI:5693)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- IWW5FV6NK2
- CAS number
- 70-30-4
- InChI Key
- 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
References
- Synthesis Reference
U.S. Patent 2,250,480 U.S. Patent 2,435,593 U.S. Patent 2,812,365
- General References
- Authors unspecified: Hexachlorophene. IARC Monogr Eval Carcinog Risk Chem Hum. 1979 Oct;20:241-57. [Article]
- Tyrala EE, Hillman LS, Hillman RE, Dodson WE: Clinical pharmacology of hexachlorophene in newborn infants. J Pediatr. 1977 Sep;91(3):481-6. [Article]
- Zheng Y, Zhu X, Zhou P, Lan X, Xu H, Li M, Gao Z: Hexachlorophene is a potent KCNQ1/KCNE1 potassium channel activator which rescues LQTs mutants. PLoS One. 2012;7(12):e51820. doi: 10.1371/journal.pone.0051820. Epub 2012 Dec 12. [Article]
- External Links
- Human Metabolome Database
- HMDB0014894
- KEGG Drug
- D00859
- KEGG Compound
- C08039
- PubChem Compound
- 3598
- PubChem Substance
- 46505858
- ChemSpider
- 3472
- BindingDB
- 31712
- 5293
- ChEBI
- 5693
- ChEMBL
- CHEMBL496
- ZINC
- ZINC000001530968
- Therapeutic Targets Database
- DAP001050
- PharmGKB
- PA449871
- PDBe Ligand
- H3P
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Hexachlorophene
- PDB Entries
- 3ete
- MSDS
- Download (76.8 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Narcotics Use / Postoperative pain / Spine Injuries and Disorders 1 3 Unknown Status Treatment Acne Vulgaris 1 2 Completed Treatment Dental Pain 1 2, 3 Terminated Treatment Analgesia / Inguinal Hernias / Pain 1 Not Available Completed Prevention Methicillin Resistant Staphylococcus Aureus Skin Infections 1 Not Available Completed Treatment Human Immunodeficiency Virus (HIV) Infections / Infection caused by staphylococci 1 Not Available Unknown Status Treatment Aortic Root Dilatation / Aortic Valve Disorder / Coronary Artery Disease (CAD) / Diseases of Mitral Valves / Surgery, Cardiac / Tricuspid valve disease 1
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
- Bayer Healthcare
- Doak Dermatologics
- Physicians Total Care Inc.
- Sanofi-Aventis Inc.
- Spectrum Pharmaceuticals
- Dosage Forms
Form Route Strength Emulsion Topical 3 % Emulsion Topical 30 mg/1mL Liquid Topical 2 % Powder Topical Solution 0.35 ml/100ml - Prices
Unit description Cost Unit Phisohex 148ml Bottle 35.46USD bottle Hexachlorophene powder 11.47USD g Phisohex 3% cleanser 0.18USD ml Phisohex 473ml Bottle 0.13USD ml Tersaseptic cleanser 0.05USD 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 (°C) 161-163 U.S. Patent 2,435,593. boiling point (°C) 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 0.000433 mg/mL 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 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 88.59 m3·mol-1 Chemaxon Polarizability 34.29 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Inhibitor 0.9346 CYP450 2D6 inhibitor Non-inhibitor 0.7899 CYP450 2C19 inhibitor Inhibitor 0.9425 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Download (9.34 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-0udl-0902800000-eab954bdd46ef95ea0e6 LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-0006-0903000000-af7e51011b8ac55a0b9c
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- 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
- Uniprot Name
- D-lactate dehydrogenase
- Molecular Weight
- 64611.82 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Wang JL, Buhler DR: Inhibition of dehydrogenase enzymes by hexachlorophene. Biochem Pharmacol. 1978;27(24):2947-53. [Article]
- Kind
- Protein
- Organism
- Humans
- 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...
- Gene Name
- SDHD
- Uniprot ID
- O14521
- Uniprot Name
- Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial
- Molecular Weight
- 17042.82 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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 th...
- Gene Name
- GLUD1
- Uniprot ID
- P00367
- Uniprot Name
- Glutamate dehydrogenase 1, mitochondrial
- Molecular Weight
- 61397.315 Da
References
- 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. [Article]
- Wang JL, Buhler DR: Inhibition of dehydrogenase enzymes by hexachlorophene. Biochem Pharmacol. 1978;27(24):2947-53. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Curator comments
- competitive antagonist
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- Jung J, Ishida K, Nishihara T: Anti-estrogenic activity of fifty chemicals evaluated by in vitro assays. Life Sci. 2004 May 7;74(25):3065-74. [Article]
Drug created at June 13, 2005 13:24 / Updated at March 03, 2023 17:39