Hexachlorophene
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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- Approved, Withdrawn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
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prophylaxis of Bacterial infection •••••••••••• - 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 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
- 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 Deutschland Gmb H 1976-06-11 2016-04-30 US 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 Phisohex Emulsion 3 % Topical Sanofi Aventis Deutschland Gmb H 1950-12-31 2017-03-30 Canada 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Prevention Methicillin Resistant Staphylococcus Aureus Skin Infections 1 somestatus stop reason just information to hide Not Available Completed Treatment Human Immunodeficiency Virus (HIV) Infections / Infection caused by staphylococci 1 somestatus stop reason just information to hide Not Available Unknown Status Treatment Aortic Root Dilatation / Coronary Artery Disease (CAD) / Diseases of Mitral Valves / Surgery, Cardiac / Tricuspid valve disease / Valve Disease, Aortic 1 somestatus stop reason just information to hide 4 Completed Prevention Narcotics Use / Postoperative pain / Spine Injuries and Disorders 1 somestatus stop reason just information to hide 3 Unknown Status Treatment Acne Vulgaris 1 somestatus stop reason just information to hide
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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 153.8643785 predictedDarkChem Lite v0.1.0 [M-H]- 157.5563978 predictedDarkChem Lite v0.1.0 [M-H]- 166.75401 predictedDeepCCS 1.0 (2019) [M+H]+ 155.0052785 predictedDarkChem Lite v0.1.0 [M+H]+ 163.0955648 predictedDarkChem Lite v0.1.0 [M+H]+ 169.11201 predictedDeepCCS 1.0 (2019) [M+Na]+ 153.9990785 predictedDarkChem Lite v0.1.0 [M+Na]+ 153.8983785 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.62802 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the oxidation of D-lactate to pyruvate. Electrons derived from D-lactate oxidation are transferred to the ubiquinone/cytochrome electron transfer chain, where they may be used to provide energy for the active transport of a variety of amino acids and sugars across the membrane.
- Specific Function
- D-lactate dehydrogenase (quinone) activity
- 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
- 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) (PubMed:10482792, PubMed:9533030). SDH also oxidizes malate to the non-canonical enol form of oxaloacetate, enol-oxaloacetate (By similarity). Enol-oxaloacetate, which is a potent inhibitor of the succinate dehydrogenase activity, is further isomerized into keto-oxaloacetate (By similarity)
- Specific Function
- electron transfer activity
- 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
- Mitochondrial glutamate dehydrogenase that catalyzes the conversion of L-glutamate into alpha-ketoglutarate. Plays a key role in glutamine anaplerosis by producing alpha-ketoglutarate, an important intermediate in the tricarboxylic acid cycle (PubMed:11032875, PubMed:11254391, PubMed:16023112, PubMed:16959573). Plays a role in insulin homeostasis (PubMed:11297618, PubMed:9571255). May be involved in learning and memory reactions by increasing the turnover of the excitatory neurotransmitter glutamate (By similarity)
- Specific Function
- ADP binding
- 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
- 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 tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol/E2) (By similarity)
- Specific Function
- 14-3-3 protein binding
- 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 October 21, 2024 12:38