Hexamidine (CED0013394)

Record Information
Version1.0
Creation Date2016-06-03 11:27:04 UTC
Update Date2026-08-20 06:21:53 UTC
Accession NumberCHEM043929
Identification
Common NameHexamidine
ClassSmall Molecule
Description
Hexamidine is an organic compound with the chemical formula C20H26N4O2 and an average molecular weight of 354.45 g/mol. Hexamidine belongs to the phenol ethers, a class of benzenoids within the organic compounds. In industrial applications, this compound serves as a preservative. It is found in or released from nine recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is utilized in antiinfectives, nasal preparations, throat preparations, ophthalmological and otological preparations, as well as antiseptics and disinfectants. In the realm of electrical and electronic equipment, it is associated with television systems and magnets. Additionally, it is found in household cleaning and consumer products, specifically in soap dispensers and non-electric simulated smoking devices. The recorded route of exposure for this substance is topical. Regarding its biological activity, there is one recorded protein target: the HTH-type transcriptional regulator QacR (qacR).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4,4'-(1,6-Hexanediylbis(oxy))bis-benzenecarboximidamideChEBI
4,4'-(Hexamethylenedioxy)dibenzamidineChEBI
HexamidinaChEBI
HexamidinumChEBI
OphtamedineMeSH
1,6-Di(para-amidinophenoxy)hexaneMeSH
1,6-Di-(4-amidinophenoxy)hexaneMeSH
HexaseptineMeSH
HexomedinMeSH
Rhône-poulenc rorer brand name OF hexamidine isetionateMeSH
Hexamidine diisethionateMeSH
Hexamidine isethionateMeSH
DésomédineMeSH
Hexomedin NMeSH
HexomedineMeSH
Laryngomedin NMeSH
Hexamidine dihydrochlorideMeSH
Chemical FormulaC20H26N4O2
Average Molecular Mass354.446 g/mol
Monoisotopic Mass354.206 g/mol
CAS Registry Number3811-75-4
IUPAC Name4-{[6-(4-carbamimidoylphenoxy)hexyl]oxy}benzene-1-carboximidamide
Traditional Namehexamidine
SMILESNC(=N)C1=CC=C(OCCCCCCOC2=CC=C(C=C2)C(N)=N)C=C1
InChI IdentifierInChI=1S/C20H26N4O2/c21-19(22)15-5-9-17(10-6-15)25-13-3-1-2-4-14-26-18-11-7-16(8-12-18)20(23)24/h5-12H,1-4,13-14H2,(H3,21,22)(H3,23,24)
InChI KeyOQLKNTOKMBVBKV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Carboximidamide
  • Ether
  • Carboxylic acid amidine
  • Amidine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP1.77ALOGPS
logP2.77ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)12.13ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.2 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity125.13 m³·mol⁻¹ChemAxon
Polarizability40.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000i-0921000000-e1defb75714a63dcce8cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0119000000-3ccc09d09906f24dea1dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05n0-1659000000-f2a4952ff2b24d34e923Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-4900000000-22cccc3886b79c886515Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0309000000-36f82c865ed142473849Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f79-0904000000-373f732954247ed655ffNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-3900000000-5dc637a46ed221466446Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
444.0Log mg/kg[250:790]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
312Antiseptics and disinfectantsHealthcare, pharmaceuticals & veterinary productsNot Available
389Nasal preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
390Throat preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
395AntiinfectivesHealthcare, pharmaceuticals & veterinary productsNot Available
407Ophthalmological and otological preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
490Personal care & cosmeticsNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
602MolluscicidesAgriculture & land managementNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
653SewingTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Hexamidine Drug Metabolism Action Pathway
Hexamidine Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Suppressor of tumorigenicity 14 protein structureClick to view 3D structureSuppressor of tumorigenicity 14 proteinQ9Y5Y6HumansPredicted (SEA)0.856341
Click to view 3D structureAcrosinP08001Sus scrofaPredicted (SEA)0.0778492
Diamine acetyltransferase 1 structureClick to view 3D structureDiamine acetyltransferase 1P21673HumansPredicted (SEA)0.0778492
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)4.9045
Protein S100-B structureClick to view 3D structureProtein S100-BP04271HumansPredicted (SEA)0.0778492
Transmembrane protease serine 2 structureClick to view 3D structureTransmembrane protease serine 2O15393HumansPredicted (SEA)0.856341
Plasminogen structureClick to view 3D structurePlasminogenP00747HumansPredicted (SEA)7.47353
Click to view 3D structureProthrombinP00735Bos taurusPredicted (SEA)3.42537
Click to view 3D structureSerine protease 1P00760Bos taurusPredicted (SEA)10.6653
UDP-3-O-acyl-N-acetylglucosamine deacetylase structureClick to view 3D structureUDP-3-O-acyl-N-acetylglucosamine deacetylaseO67648Aquifex aeolicus (strain VF5)Predicted (SEA)1.47914
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)65.8604
Click to view 3D structureGlandular kallikreinP00752Sus scrofaPredicted (SEA)0.233548
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)44.9968
Click to view 3D structureProtein S100-BP04631Rattus norvegicusPredicted (SEA)0.0778492
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)101.36
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)23.0434
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)95.9102
Click to view 3D structureCoagulation factor XP00743Bos taurusPredicted (SEA)3.97031
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)28.415
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)86.8797
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)27.7922
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)13.6236
Urokinase-type plasminogen activator structureClick to view 3D structureUrokinase-type plasminogen activatorP00749HumansPredicted (SEA)9.9647
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)82.7537
Diamine oxidase [copper-containing] structureClick to view 3D structureDiamine oxidase [copper-containing]P19801HumansPredicted (SEA)0.0778492
Concentrations
Not Available
External Links
DrugBank IDDB03808
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHexamidine
Chemspider IDNot Available
ChEBI ID87184
PubChem Compound ID65130
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=25169145
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25779009
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26235920