Chlorhexidine
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Basic Info
| Common Name | Chlorhexidine(F05967) |
| 2D Structure | |
| FRCD ID | F05967 |
| CAS Number | 55-56-1 |
| PubChem CID | 9552079 |
| Formula | C22H30Cl2N10 |
| IUPAC Name | (1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine |
| InChI Key | GHXZTYHSJHQHIJ-UHFFFAOYSA-N |
| InChI | 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) |
| Canonical SMILES | C1=CC(=CC=C1NC(=NC(=NCCCCCCN=C(N)N=C(N)NC2=CC=C(C=C2)Cl)N)N)Cl |
| Isomeric SMILES | C1=CC(=CC=C1N/C(=N/C(=NCCCCCCN=C(/N=C(/NC2=CC=C(C=C2)Cl)\N)N)N)/N)Cl |
| Synonyms |
Chlorhexidinum
Soretol
chlorhexidine
55-56-1
Chlorhexidin
Nolvasan
Rotersept
Tubulicid
Fimeil
Hexadol
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Halobenzenes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Chlorobenzenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Biguanide - Chlorobenzene - Aryl chloride - Aryl halide - Guanidine - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Organohalogen compound - Imine - Organic nitrogen compound - Hydrocarbon derivative - Organochloride - Organonitrogen compound - Organopnictogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 505.452 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 13 |
| Complexity | 649 |
| Monoisotopic Mass | 504.203 |
| Exact Mass | 504.203 |
| XLogP | 0.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 34 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8353 |
| Human Intestinal Absorption | HIA+ | 0.8424 |
| Caco-2 Permeability | Caco2- | 0.5134 |
| P-glycoprotein Substrate | Substrate | 0.5623 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8182 |
| Inhibitor | 0.7755 | |
| Renal Organic Cation Transporter | Inhibitor | 0.8271 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4774 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7758 |
| CYP450 2D6 Substrate | Non-substrate | 0.6111 |
| CYP450 3A4 Substrate | Non-substrate | 0.6613 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9107 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8362 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8932 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5683 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8709 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5298 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.6699 |
| Non-inhibitor | 0.6467 | |
| AMES Toxicity | Non AMES toxic | 0.6199 |
| Carcinogens | Non-carcinogens | 0.8605 |
| Fish Toxicity | High FHMT | 0.9677 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9983 |
| Honey Bee Toxicity | Low HBT | 0.8089 |
| Biodegradation | Not ready biodegradable | 0.9963 |
| Acute Oral Toxicity | III | 0.3911 |
| Carcinogenicity (Three-class) | Non-required | 0.6172 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.0328 | LogS |
| Caco-2 Permeability | 0.6883 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2479 | LD50, mol/kg |
| Fish Toxicity | 1.3540 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.8514 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Other Terrestrial Mammals,Edible Offal | Japan | 0.5ppm | |||
| Milk | Japan | 0.05ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.5ppm | |||
| Other Terrestrial Mammals,Liver | Japan | 0.5ppm | |||
| Other Terrestrial Mammals,Fat | Japan | 0.5ppm | |||
| Other Terrestrial Mammals,Muscle | Japan | 0.5ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Susceptibility of Methicillin-Resistant and -Susceptible Staphylococcus aureusIsolates of Various Clonal Lineages from Germany to Eight Biocides. | Appl Environ Microbiol | 2018 Jun 18 | 29728378 |
| Chlorhexidine sustained-release varnishes for catheter coating - Dissolutionkinetics and antibiofilm properties. | Eur J Pharm Sci | 2018 Jan 15 | 29104066 |
| Study of the Interactions Between Bacteriophage phiIPLA-RODI and Four ChemicalDisinfectants for the Elimination of Staphylococcus aureus Contamination. | Viruses | 2018 Feb 28 | 29495568 |
| Importance of the RpoE Regulon in Maintaining the Lipid Bilayer during Antimicrobial Treatment with the Polycationic Agent, Chlorhexidine. | Proteomics | 2018 Feb | 29280319 |
| Antibacterial potency and fluoride release of a glass ionomer restorativematerial containing different concentrations of natural and chemical products: Anin-vitro comparative study. | J Clin Exp Dent | 2018 Apr 1 | 29750090 |
| A broad-spectrum bactericidal lipopeptide with anti-biofilm properties. | Sci Rep | 2017 May 19 | 28526864 |
| Comparative analysis of the susceptibility to biocides and heavy metals ofextended-spectrum β-lactamase-producing Escherichia coli isolates of human andavian origin, Germany. | Diagn Microbiol Infect Dis | 2017 May | 28256291 |
| Effects of exposure to quaternary-ammonium-based biocides on antimicrobialsusceptibility and tolerance to physical stresses in bacteria from organic foods. | Food Microbiol | 2017 May | 28040182 |
| Antiseptics for burns. | Cochrane Database Syst Rev | 2017 Jul 12 | 28700086 |
| Effects of Extended Storage of Chlorhexidine Gluconate and Benzalkonium Chloride Solutions on the Viability of Burkholderia cenocepacia. | J Microbiol Biotechnol | 2017 Dec 28 | 29032643 |
| Susceptibility of vancomycin-resistant and -sensitive Enterococcus faeciumobtained from Danish hospitals to benzalkonium chloride, chlorhexidine andhydrogen peroxide biocides. | J Med Microbiol | 2017 Dec | 29134935 |
| Prevention of ventilator-associated pneumonia. | Curr Opin Infect Dis | 2017 Apr | 28118221 |
| Antibacterial and antifungal activities of 2,3-pyrrolidinedione derivativesagainst oral pathogens. | Bioorg Med Chem Lett | 2016 Mar 1 | 26860735 |
| A pilot study comparing in vitro efficacy of topical preparations againstveterinary pathogens. | Vet Dermatol | 2016 Jun | 27109449 |
| Disinfectant and Antimicrobial Susceptibility Profiles of the Big Six Non-O157 Shiga Toxin-Producing Escherichia coli Strains from Food Animals and Humans. | J Food Prot | 2016 Aug | 27497123 |
| Characteristics of qacA/B-positive Staphylococcus aureus isolated from patients and a hospital environment in China. | J Antimicrob Chemother | 2015 Mar | 25429780 |
| Disinfectant choices in veterinary practices, shelters and households: ABCD guidelines on safe and effective disinfection for feline environments. | J Feline Med Surg | 2015 Jul | 26101311 |
| Aphthous ulcers (recurrent). | BMJ Clin Evid | 2015 Feb 26 | 25720501 |
| Evaluation of Melia azedarach extracts against Streptococcus mutans. | J Med Food | 2015 Feb | 25069066 |
| The Effects of Chronic Nitrate Supplementation and the Use of Strong and WeakAntibacterial Agents on Plasma Nitrite Concentration and Exercise Blood Pressure. | Int J Sports Med | 2015 Dec | 26332900 |