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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:40:48 UTC
HMDB IDHMDB0015016
Secondary Accession Numbers
  • HMDB15016
Metabolite Identification
Common NameChlorhexidine
DescriptionChlorhexidine, also known as dentisept or merfen-incolore, belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. It is a disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque. Chlorhexidine is only found in individuals that have used or taken this drug. Chlorhexidine is a drug which is used for reduction of pocket depth in patients with adult periodontitis, used as an adjunct to scaling and root planing procedures. also for prevention of dental caries, oropharyngeal decontamination in critically ill patients, hand hygiene in health-care personnel, general skin cleanser, and catheter site preparation and care. Chlorhexidine is a very strong basic compound (based on its pKa). Because of its positive charge, the chlorhexidine molecule reacts with the microbial cell surface to destroy the integrity of the cell membrane. This novel mechanism of action makes it highly unlikely for the development of bacterial resistance. Chlorhexidine, a topical antimicrobial agent, is bactericidal.
Structure
Data?1582753248
Synonyms
ValueSource
1,1'-Hexamethylene bis(5-(p-chlorophenyl)biguanide)ChEBI
N,N'-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamideChEBI
DentiseptKegg
Merfen-incoloreKegg
CloresidinaHMDB
Chemical FormulaC22H30Cl2N10
Average Molecular Weight505.447
Monoisotopic Molecular Weight504.203196424
IUPAC NameN-(4-chlorophenyl)-1-3-(6-{N-[3-(4-chlorophenyl)carbamimidamidomethanimidoyl]amino}hexyl)carbamimidamidomethanimidamide
Traditional Namechlorhexidine
CAS Registry Number55-56-1
SMILES
ClC1=CC=C(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC2=CC=C(Cl)C=C2)C=C1
InChI Identifier
InChI=1S/C22H30Cl2N10/c23-15-5-9-17(10-6-15)31-21(27)33-19(25)29-13-3-1-2-4-14-30-20(26)34-22(28)32-18-11-7-16(24)8-12-18/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34)
InChI KeyGHXZTYHSJHQHIJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Chlorobenzene
  • Biguanide
  • Aryl halide
  • Aryl chloride
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Imine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.026 g/LNot Available
LogP3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP2.71ALOGPS
logP4.51ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)10.52ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area167.58 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity181.71 m³·mol⁻¹ChemAxon
Polarizability54.6 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1390000000-e2087e07b387187b35e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00yi-2912000000-109a5810a9e5d36f3105Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ufr-2900000000-77fb2c1a85c1b39d8e91Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00yi-2912000000-109a5810a9e5d36f3105Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0624090000-0824436f86a1c2a4784bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0922000000-b6c796459e4397e81075Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-2940000000-ba95a6a3988436fdde57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0825090000-0c29f46fa3cd4527a699Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0hk9-0943010000-331d57f140196db7cca5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2920000000-1106ffe675713cb3aa8bSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00878 details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00878 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00878
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2612
KEGG Compound IDC06902
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorhexidine
METLIN IDNot Available
PubChem Compound2713
PDB IDNot Available
ChEBI ID3614
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in histamine N-methyltransferase activity
Specific function:
Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name:
HNMT
Uniprot ID:
P50135
Molecular weight:
6045.9
References
  1. Harle DG, Baldo BA: Structural features of potent inhibitors of rat kidney histamine N-methyltransferase. Biochem Pharmacol. 1988 Feb 1;37(3):385-8. [PubMed:3337739 ]