chlorhexidine

General Material Information

Preferred name	chlorhexidine
Trivial Name	Chlorhexidine
Short Description	1,6-bis[N'-(p-chlorophenyl)-N5-biguanido]hexane
Formula	C22 H30 Cl2 N10
CAS Number	55-56-1
ECHA Number	200-238-7
FDA UNII	R4KO0DY52L
Beilstein Number	2826432
MDL	MFCD00009673
Bio Activity Summary	External link
NMR Predictor	External link
Synonyms	bioscrub chlorhexidine, free base 1,6-bis[N'-(p- chlorophenyl)-N5-biguanido]hexane {[(4-chlorophenyl)amino]iminomethyl}{[(6-{[({[(4-chlorophenyl)amino]iminomethy l}amino)iminomethyl]amino}hexyl)amino]iminomethyl}amine {[(4-chlorophenyl)amino]iminomethyl}{[(6-{[({[(4-chlorophenyl)amino]iminomethyl}amino)iminomethyl]amino}hexyl)amino]iminomethyl}amine 1,6-bis(5-(p- chlorophenyl)biguandino)hexane 1,6-bis(5-(p- chlorophenyl)biguanidino)hexane 1,6-bis(p- chlorophenyldiguanido)hexane 1,6-di(4'-chlorophenyldiguanido)hexane 1,6-di(N-p-chlorophenyldiguanido)hexane exidine 1,1'- hexamethylene bis(5-(p-chlorophenyl)biguanide) 1,1'- hexamethylenebis(5-(p-chlorophenyl)biguanide 1,1'- hexamethylenebis(5-(p-chlorophenyl)biguanide) 1,1'- hexamethylenebis[5-(4-chlorophenyl)biguanide] 1,1'- hexamethylenebis[5-(p-chlorophenyl)biguanide] N,N''''- hexane-1,6-diylbis[N'-(4-chlorophenyl)(imidodicarbonimidic diamide)] N,N''''-1,6-hexanediylbis[N'-(4-chlorophenyl)(imidodicarbonimidic diamide)] hibispray imidodicarbonimidic diamide, N,N''''-1,6-hexanediylbis[N'-(4-chlorophenyl)- microderm oro-clense periochip periogard pharmaseal scrub care prevacare R savloclens steri-stat 2,4,11,13-tetraazatetradecanediimidamide, N,N''-bis(4-chlorophenyl)-3,12-diimino- (1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine 2,4,11,13-Tetraazatetradecanediimidamide, N1,N14-bis(4-chlorophenyl)-3,12-diimino- Biguanide, 1,1′-hexamethylenebis[5-(p-chlorophenyl)- 2,4,11,13-Tetraazatetradecanediimidamide, N,N′′-bis(4-chlorophenyl)-3,12-diimino- N1,N14-Bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide 1,6-Bis[5-(p-chlorophenyl)biguanidino]hexane Nolvasan 1,1′-Hexamethylenebis[5-(p-chlorophenyl)biguanide] Soretol Chlorohex Fimeil Hexadol Chlorohexidine Tubulicid 1,6-Di(N-p-chlorophenylbiguanidino)hexane Promax Eburos Hexident Chlorhexamed forte Consepsis Dezin Dentosan Chlorohexidene Prevora MeSH ID: D002710 Curasept ADS 350

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Literature & References

	(1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	9552079
Pubchem (sid):	134972280

Publications by PubMed
The staining effect of different mouthwashes containing nanoparticles on dental enamel.
Intervention to Reduce Ventilator-Associated Pneumonia in Individuals on Long-Term Ventilation by Introducing a Customized Bundle.
Assessment of susceptibility of mould isolates towards biocides.
Root Caries in Older Adults.
Antibacterial paperboard packaging using microfibrillated cellulose.
Correlation between antibiotic and biocide resistance in mesophilic and psychrotrophic Pseudomonas spp. isolated from slaughterhouse surfaces throughout meat chain production.
Disinfectant choices in veterinary practices, shelters and households: ABCD guidelines on safe and effective disinfection for feline environments.
Evaluation of the Effect of Enterococcus faecalis Biofilm on the 2% Chlorhexidine Substantivity: An In Vitro Study.
Survival and susceptibility of Burkholderia cepacia complex in chlorhexidine gluconate and benzalkonium chloride.
Aphthous ulcers (recurrent).
Inhibited biofilm formation and improved antibacterial activity of a novel nanoemulsion against cariogenic Streptococcus mutans in vitro and in vivo.
Effect of the hand antiseptic agents benzalkonium chloride, povidone-iodine, ethanol, and chlorhexidine gluconate on atopic dermatitis in NC/Nga mice.
A randomized clinical trial compared the effect of intra-alveolar 0.2 % Chlorohexidine bio-adhesive gel versus 0.12% Chlorohexidine rinse in reducing alveolar osteitis following molar teeth extractions.
Comparative efficacy of alcohol-based surgical scrubs: the importance of formulation.
Characteristics of qacA/B-positive Staphylococcus aureus isolated from patients and a hospital environment in China.
Antimicrobial Effect of Lactobacillus reuteri on Cariogenic Bacteria Streptococcus gordonii, Streptococcus mutans, and Periodontal Diseases Actinomyces naeslundii and Tannerella forsythia.
Prospective evaluation of 2% (w/v) alcoholic chlorhexidine gluconate as an antiseptic agent for blood donor arm preparation.
Comparative analysis of Salmonella susceptibility and tolerance to the biocide chlorhexidine identifies a complex cellular defense network.
Role of EfrAB efflux pump in biocide tolerance and antibiotic resistance of Enterococcus faecalis and Enterococcus faecium isolated from traditional fermented foods and the effect of EDTA as EfrAB inhibitor.
Evaluation of Melia azedarach extracts against Streptococcus mutans.
Microscopic and spectroscopic analyses of chlorhexidine tolerance in Delftia acidovorans biofilms.
In silico identification of novel kinase inhibitors targeting wild-type and T315I mutant ABL1 from FDA-approved drugs.
Quantitative microbial risk assessment of antibacterial hand hygiene products on risk of shigellosis.
Effects of an orabase formulation with ethanolic extract of Malva sylvestris L. in oral wound healing in rats.
Effects of food colouring added to 2% chlorhexidine gluconate and 70% alcohol for surgical site antisepsis.
Nonsurgical management of inflammatory periimplant disease caused by food impaction: a clinical report.
Analysis of triclosan-selected Salmonella enterica mutants of eight serovars revealed increased aminoglycoside susceptibility and reduced growth rates.
Recurrent epistaxis in children.
Biocide and copper tolerance in enterococci from different sources.
Synergistic interaction and mode of action of Citrus hystrix essential oil against bacteria causing periodontal diseases.
Effect of subinhibitory concentrations of four commonly used biocides on the conjugative transfer of Tn916 in Bacillus subtilis.
Lethal and sub lethal effects of the biocide chlorhexidine on aquatic organisms.
Action of food preservatives on 14-days dental biofilm formation, biofilm vitality and biofilm-derived enamel demineralisation in situ.
Involvement of leptin in the progression of experimentally induced peritoneal fibrosis in mice.
Influence of disinfectant solutions on test materials used for the determination of masticatory performance.
Comparative analysis of the susceptibility to triclosan and three other biocides of avian Salmonella enterica isolates collected 1979 through 1994 and 2004 through 2010.
Combined treatments of enterocin AS-48 with biocides to improve the inactivation of methicillin-sensitive and methicillin-resistant Staphylococcus aureus planktonic and sessile cells.
Surgical hand hygiene: scrub or rub?
Assessment of the susceptibility of lactic acid bacteria to biocides.
Minimizing human infection from Escherichia coli O157:H7 using GUMBOS.
Disinfectant and antibiotic susceptibility profiles of Escherichia coli O157:H7 strains from cattle carcasses, feces, and hides and ground beef from the United States.
Development of antimicrobial resistance in Campylobacter jejuni and Campylobacter coli adapted to biocides.
Prevalence of bacteria resistant to antibiotics and/or biocides on meat processing plant surfaces throughout meat chain production.
Comparative lethality kinetic curves and predictive models of F-value for Listeria monocytogenes using different sanitizers.
Presence of antiseptic resistance genes in porcine methicillin-resistant Staphylococcus aureus.
Effects of efflux-pump inducers and genetic variation of the multidrug transporter cmeB in biocide resistance of Campylobacter jejuni and Campylobacter coli.
Dental disease prevalence among methamphetamine and heroin users in an urban setting: a pilot study.
High-level vancomycin resistant Enterococcus faecium related to humans and pigs found in dust from pig breeding facilities.
Susceptibility of anthocyanins to ex vivo degradation in human saliva.
Double-blinded, placebo-controlled study to evaluate an antipruritic shampoo for dogs with allergic pruritus.
Inspissated oral secretions and a review of their clinical, biological, and physiological significance.
Caregiver acceptability and preferences for preventive dental treatments for young African-American children.
Efficacy of surgical preparation solutions in lumbar spine surgery.
Efficacy of biocides used in the modern food industry to control salmonella enterica, and links between biocide tolerance and resistance to clinically relevant antimicrobial compounds.
Involvement of efflux mechanisms in biocide resistance of Campylobacter jejuni and Campylobacter coli.
An expert panel report of a proposed scientific model demonstrating the effectiveness of antibacterial handwash products.
Neurologic complications after chlorhexidine antisepsis for spinal anesthesia.
Nonfluoride caries-preventive agents: new guidelines.
Effect of enterocin AS-48 in combination with biocides on planktonic and sessile Listeria monocytogenes.
Effects of iodine intake and teat-dipping practices on milk iodine concentrations in dairy cows.
Effects of iodine in microbial control of dental treatment water.
Comparative antibacterial efficacy of endemic satureja khuzistanica jamzad essential oil, sodium hypochlorite and chlorhexidine gluconate solutions as root canal irrigations.
Amoebicidal effects of contact lens disinfecting solutions.
A meta-analysis of the published literature on the effectiveness of antimicrobial soaps.
[Selection and spreading of antibiotic resistance in bacteria].
Food components with anticaries activity.
Strict hand hygiene and other practices shortened stays and cut costs and mortality in a pediatric intensive care unit.
Food-borne enterococci and their resistance to oxidative stress.
MRSA colonisation (eradicating colonisation in people without active/invasive infection).
Characterization of Salmonella enterica isolates from turkeys in commercial processing plants for resistance to antibiotics, disinfectants, and a growth promoter.
Comparative efficacy of seven hand sanitizers against murine norovirus, feline calicivirus, and GII.4 norovirus.
Ask us. White spot lesions: prevention and treatment.
Design of the Prevention of Adult Caries Study (PACS): a randomized clinical trial assessing the effect of a chlorhexidine dental coating for the prevention of adult caries.
[Clinical strains isolation and antibiotic susceptibility of Stenotrophomonas maltophilia].
Clinical and microbiological evaluation of the use of toothpaste containing 1% chlorhexidine and the influence of motivation on oral hygiene in patients with motor deficiency.
Genotoxicity of two mouthwash products in the Drosophila Wing-Spot Test.
Avagard hand antisepsis vs. traditional scrub in 3600 pediatric urologic procedures.
Iodine in enteral and parenteral nutrition.
Cost-effectiveness of an experimental caries-control regimen in a 3.4-yr randomized clinical trial among 11-12-yr-old Finnish schoolchildren.
Clinical management of root caries.
Chemical decontamination of Campylobacter jejuni on chicken skin and meat.
Caregiver acceptability and preferences for early childhood caries preventive treatments for Hispanic children.
Application of the gingival contour plaque index: six-month plaque and gingivitis study.
Gastroprotective and blood pressure lowering effects of dietary nitrate are abolished by an antiseptic mouthwash.
Comparison of the efficacy of three different mouthrinse solutions in decreasing the level of streptococcus mutans in saliva.
Investigation of functional and morphological changes in Pseudomonas aeruginosa and Staphylococcus aureus cells induced by Origanum compactum essential oil.
Prevalence and risk factors for allergic contact dermatitis to topical treatment in atopic dermatitis: a study in 641 children.
Efficacy of novel antimicrobial gloves impregnated with antiseptic dyes in preventing the adherence of multidrug-resistant nosocomial pathogens.
Burns (minor thermal).
Chlorhexidine with an anti discoloration system after periodontal flap surgery: a cross-over, randomized, triple-blind clinical trial.
Effects of commonly used food preservatives on biofilm formation of Streptococcus mutans in vitro.
Effect of food preservatives on in situ biofilm formation.
A review of anti-septic agents for pre-operative skin preparation.
Characterization of predominant bacteria isolates from clean rooms in a pharmaceutical production unit.
Susceptibility of Listeria monocytogenes strains isolated from dairy products and frozen vegetables to antibiotics inhibiting murein synthesis and to disinfectants.
Comparative of a new and innovative 2% chlorhexidine gluconate-impregnated cloth with 4% chlorhexidine gluconate as topical antiseptic for preparation of the skin prior to surgery.
Aphthous ulcers (recurrent).
Antimicrobial effect of mastic gum methanolic extract against Porphyromonas gingivalis.
Quantitative mapping of chlorhexidine in natural river biofilms.
In vivo efficacy of an alcohol-based surgical hand disinfectant containing a synergistic combination of ethylhexylglycerin and preservatives.
Lignocaine and chlorhexidine toxicity in children resulting from mouth paint ingestion: a bottling problem.
Assessment of benefits from use of antimicrobial hand products: reduction in risk from handling ground beef.
The impact of periodontal therapy and the adjunctive effect of antiseptics on breath odor-related outcome variables: a double-blind randomized study.
The prevention of plaque re-growth by toothpastes and solutions containing block copolymers with and without polypeptide.
A unique water optional health care personnel handwash provides antimicrobial persistence and residual effects while decreasing the need for additional products.
Residues of spinosad in the tissues of sheep after aerosol treatment of blowfly myiasis.
The use of chlorhexidine/n-propyl gallate as a urine preservative.
Susceptibility of different bacterial species isolated from food animals to copper sulphate, zinc chloride and antimicrobial substances used for disinfection.
A salivary incubation test for evaluation of oral malodor: a pilot study.
Elimination kinetics of chlorhexidine in milk following intramammary infusion to stop lactation in mastitic mammary gland quarters of cows.
Xylitol and dental caries: an overview for clinicians.
Methodology for quantifying residues of chlorhexidine in raw dairy milk.
Effects of high temperature and disinfectants on the viability of Sarcocystis neurona sporocysts.
Tongue brushing and mouth rinsing as basic treatment measures for halitosis.
Risk assessment of hand washing efficacy using literature and experimental data.
Disinfectant and antibiotic resistance of lactic acid bacteria isolated from the food industry.
Diazepam submicron emulsions containing soya-bean oil and intended for oral or rectal delivery.
The effect of toothpaste on the propensity of chlorhexidine and cetyl pyridinium chloride to produce staining in vitro: a possible predictor of inactivation.
Caries risk assessment and prevention: strategies for Head Start, Early Head Start, and WIC.
Site specific delivery of antimicrobial agents for periodontal disease.
New drug approvals in 1998.
A new horizon for the dental hygienist: controlled local delivery of antimicrobials.
Use of infrared thermography to detect inflammation caused by contaminated growth promotant ear implants in cattle.
Efficacy of disinfection of shell eggs externally contaminated with Salmonella enteritidis. Implications for egg testing.
Cost-effectiveness of antiseptic-impregnated central venous catheters for the prevention of catheter-related bloodstream infection.
Different responses of planktonic and attached Bacillus subtilis and Pseudomonas fluorescens to sanitizer treatment.
Latest FDA approvals for dentistry.
The time and ease of placement of the chlorhexidine chip local delivery system.
Evaluation of potential disinfectants for preslaughter broiler crop decontamination.
High-performance liquid chromatographic analysis of chlorhexidine in saliva after mouthrinsing.
Development and evaluation of a new alcohol-based surgical hand scrub formulation with persistent antimicrobial characteristics and brushless application.
Nonaqueous capillary electrophoresis--its applicability in the analysis of food, pharmaceuticals and biological fluids.
Clinical efficacy of a chlorous acid preoperative skin antiseptic.
Decontaminating beef for Escherichia coli O157:H7.
Potential hypersensitivity reactions to chlorhexidine-impregnated medical devices.
Prevention of early childhood caries.
From the Food and Drug Administration.
The role of local drug delivery in the management of periodontal diseases: a comprehensive review.
Formation of nitrosamines during consumption of nitrate- and amine-rich foods, and the influence of the use of mouthwashes.
The comparative effect of acidified sodium chlorite and chlorhexidine mouthrinses on plaque regrowth and salivary bacterial counts.
The propensity of different brands of tea and coffee to cause staining associated with chlorhexidine.
FDA panel finds insufficient data to approve antimicrobial glove.
Gradient liquid chromatographic method for determination of chlorhexidine and its degradation products in bulk material.
Erosive and ulcerative skin disease.
Caries diagnosis and risk assessment. A review of preventive strategies and management.
Susceptibility of suspended and surface-attached Salmonella enteritidis to biocides and elevated temperatures.
Dietary staining in vitro by mouthrinses as a comparative measure of antiseptic activity and predictor of staining in vivo.
Glucose uptake by Listeria monocytogenes Scott A and inhibition by pediocin JD.
Identification and isolation of chlorhexidine digluconate impurities.
Efficacy evaluations on five chlorhexidine teat dip formulations.
Evaluation of 57 teat sanitizers using excised cow teats.
Inhibition of plaque formation and gingivitis in beagle dogs by topical use of a degradable controlled-release system containing chlorhexidine.
Evaluation of the repeatability and reproducibility of European suspension test methods for antimicrobial activity of disinfectants and antiseptics.
[Individual risk assessment of caries].
Bioluminescent Listeria monocytogenes provide a rapid assay for measuring biocide efficacy.
How the FDA and the ADA affect development of prescription drugs for oral care.
Quantitative relationship between oral nitrate-reducing activity and the endogenous formation of N-nitrosoamino acids in humans.
Problems affecting the liquid chromatographic quantitation of chlorhexidine digluconate in ophthalmic solutions.
Importance of neutralizers in the stripping fluid in a simulated healthcare personnel handwash.
Fermentable simple sugars in self-administered medications as aetiologic agents in rampant caries. Case report.
In vivo bioluminescence: a cellular reporter for research and industry.
[Plaque and plaque control].
Evaluation of the skin disinfecting activity and cumulative effect of chlorhexidine and triclosan handwash preparations on hands artificially contaminated with Serratia marcescens.
Experts discuss development of spermicides.
[Contraceptive development--the view from the U.S.A. in the mid 80s].
Extrinsic tooth discoloration by metals and chlorhexidine. I. Surface protein denaturation or dietary precipitation?
Chemical plaque control and extrinsic tooth discoloration. A review of possible mechanisms.
An in vitro and in vivo study of the effect of incorporation of chlorhexidine into autopolymerizing acrylic resin plates upon the growth of Candida albicans.
Comparison of the in vivo and in vitro antibacterial properties of antiseptic mouthrinses containing chlorhexidine, alexidine, cetyl pyridinium chloride and hexetidine. Relevance to mode of action.
An in vitro study of the role of dietary factors in the aetiology of tooth staining associated with the use of chlorhexidine.
[Control of the effectiveness of chlorhexidine and a sulfamide compound in nasal carriers of pathogenic Staphylococcus].
[Caries prophylaxis].
Binding of dyes to chlorhexidine-treated hydroxyapatite.
[Plaque formation and its prevention].
Intrinsic and extrinsic discoloration of the dentition (a literature review).

Other Information

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(IUPAC):	Periodic Table of the Elements
CHEBI:	View
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KEGG (GenomeNet):	C06902
HMDB (The Human Metabolome Database):	HMDB15016
Export Tariff Code:	2925.20.4000
MedlinePlusSupp:	View
ChemSpider:	View
Wikipedia:	View
Formulations/Preparations: •0.12% oral solution: peridex (zila), periogard (colgate oral pharmaceuticals) •pellet extended-release; 2.5 mg periochip (dexcel pharma) •trade names for various chlorhexidine salts and formulations: chlorhexidine: sterilon, hibitane, rotersept; chlorhexidine dihydrochloride: lisium, arlacide h, ay-5312; chlorhexidine diacetate: hibitane diacetate, novalsan; chlorhexidine digluconate: abacil, anti plaque, arlacide g, bacticlens, chlorhexamed, disteryl, orahexal, septeal, unisept, corsodyl, hibiclens, hibidil, hibiscrub, hibitane, larylin, peridex, plac out, plurexid, rotersept, savacol, solvahex.

Suppliers

American International Chemical, LLC.	BOC Sciences
George Uhe Company	Glentham Life Sciences
Sigma-Aldrich: Aldrich

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	505.45510864258
Flash Point TCC Value	311.6 °C TCC
logP (o/w)	0.08
Solubility
water, 564.5 mg/L @ 25 °C (est)	Yes

Potential Uses

Applications	cosmetic agents
Other purposes	Preservatives
Cosmetic purposes	Antimicrobial agents , Oral care agents , Preservatives

Safety Information

Safety information

Preferred SDS: View

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 44 mg/kg VM/SAC, Veterinary Medicine and Small Animal Clinician. Vol. 72, Pg. 1330, 1977. intravenous-mouse LD50 24 mg/kg Journal of Clinical Periodontology. Vol. 4(5), Pg. 66, 1977. oral-mouse LD50 2515 mg/kg LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA International Congress and Symposium Series - Royal Society of Medicine Services Limited. Vol. 23, Pg. 45, 1980. intravenous-rabbit LD > 8 mg/kg VM/SAC, Veterinary Medicine and Small Animal Clinician. Vol. 72, Pg. 1330, 1977. intraperitoneal-rat LD50 60 mg/kg VM/SAC, Veterinary Medicine and Small Animal Clinician. Vol. 72, Pg. 1330, 1977. intravenous-rat LD50 21 mg/kg BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD International Congress and Symposium Series - Royal Society of Medicine Services Limited. Vol. 23, Pg. 45, 1980. oral-rat LD50 9200 uL/kg GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: ATAXIA Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 6, Pg. 2599, 1978.
Dermal Toxicity:
subcutaneous-mouse LD50 632 mg/kg Journal of Clinical Periodontology. Vol. 4(5), Pg. 66, 1977. subcutaneous-rat LD50 > 1000 mg/kg GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS Journal of Clinical Periodontology. Vol. 4(5), Pg. 66, 1977.
Inhalation Toxicity:
Not determined

Safety in use information

Category:
cosmetic agents
Recommendation for chlorhexidine usage levels up to:
	not for fragrance use.

Recommendation for chlorhexidine flavor usage levels up to:
	not for flavor use.