chlorhexidine diacetate
1,1'-hexamethylenebis(5-(p-chlorophenyl)biguanide)diacetate
 
Notes:
a disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque.
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      C2511 Chlorhexidine Diacetate >98.0%(T)
       
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aceticacid;(1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine (Click)
CAS Number: 56-95-1Picture of molecule
ECHA EINECS - REACH Pre-Reg: 200-302-4
FDA UNII: 5908ZUF22Y
MDL: MFCD00012532
Molecular Weight: 625.55966000
Formula: C26 H38 Cl2 N10 O4
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic agents
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 699.30 °C. @ 760.00 mm Hg (est)
Flash Point: 710.00 °F. TCC ( 376.70 °C. ) (est)
logP (o/w): 4.931 (est)
Soluble in:
 water, 564.5 mg/L @ 25 °C (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antimicrobial agents
oral care agents
preservatives
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Suppliers:
American International Chemical
Chlorhexidine Acetate
George Uhe Company
Chlorhexidine Diacetate
Santa Cruz Biotechnology
For experimental / research use only.
Chlorhexidine Diacetate Salt Hydrate
Sigma-Aldrich: Sigma
For experimental / research use only.
Chlorhexidine diacetate salt hydrate bis(biguanide) antimicrobial
TCI AMERICA
For experimental / research use only.
Chlorhexidine Diacetate >98.0%(T)
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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  38 mg/kg
British Journal of Pharmacology and Chemotherapy. Vol. 9, Pg. 192, 1954.

intravenous-mouse LD50  25 mg/kg
British Journal of Pharmacology and Chemotherapy. Vol. 9, Pg. 192, 1954.

oral-mouse LD50  2000 mg/kg
British Journal of Pharmacology and Chemotherapy. Vol. 9, Pg. 192, 1954.

Dermal Toxicity:
subcutaneous-mouse LD50 325 mg/kg
British Journal of Pharmacology and Chemotherapy. Vol. 9, Pg. 192, 1954.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: cosmetic agents
Recommendation for chlorhexidine diacetate usage levels up to:
 not for fragrance use.
 
Recommendation for chlorhexidine diacetate flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
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EPA ACToR: Toxicology Data
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Laboratory Chemical Safety Summary : 9562059
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 aceticacid;(1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine
Chemidplus: 0000056951
RTECS: DU1930000 for cas# 56-95-1
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References:
 aceticacid;(1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 56-95-1
Pubchem (cid): 9562059
Pubchem (sid): 134970536
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Other Information:
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(IUPAC): Atomic Weights of the Elements 2009 (pdf)
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
 preservatives 
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
 aceticacid;(1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine
 arlacide A
 bactigras
 chlorasept 2000
 chlorhexidinediacetate
1,6-bis(5-(p-chlorophenyl)biguandino)hexane diacetate
1,6-bis(p-chlorophenylbiguanido)hexane diacetate
1,6-di(4'-chlorophenyldiguanidino)hexane diacetate
1,1'-hexamethylene bis(5-(p-chlorophenyl)biguanide) diacetate
1,1'-hexamethylenebis(5-(p-chlorophenyl)biguanide) diacetate
1,1'-hexamethylenebis(5-(p-chlorophenyl)biguanide), diacetate
1,1'-hexamethylenebis(5-(p-chlorophenyl)biguanide)diacetate
2,2'-hexane-1,6-diylbis(1-{(E)-amino[(4-chlorophenyl)amino]methylidene}guanidine) acetate (1:2)
N,N''''-hexane-1,6-diylbis[N'-(4-chlorophenyl)(imidodicarbonimidic diamide)] acetate (1:2)
N,N''''-1,6-hexanediylbis[N'-(4-chlorophenyl)(imidodicarbonimidic diamide)] acetate (1:2)
 imidodicarbonimidic diamide, N,N''''-1,6-hexanediylbis[N'-(4-chlorophenyl)-, acetate (1:2)
 nolvasan
2,4,11,13-tetraazatetradecanediimidamide, N,N''-bis(4-chlorophenyl)-3,12-diimino-, diacetate
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Articles:
PubMed: Effect of antimicrobial agents incorporated into resilient denture relines on the Candida albicans biofilm.
PubMed: Antibacterial activity, surface roughness, flexural strength, and solubility of conventional luting cements containing chlorhexidine diacetate/cetrimide mixtures.
PubMed: Allergic contact dermatitis to chlorhexidine.
PubMed: Antibacterial properties of cyclodextrin-antiseptics-complexes determined by microplate laser nephelometry and ATP bioluminescence assay.
PubMed: Minimizing human infection from Escherichia coli O157:H7 using GUMBOS.
PubMed: Peel bond strength of resilient liner modified by the addition of antimicrobial agents to denture base acrylic resin.
PubMed: Development of antimicrobial resistance in Campylobacter jejuni and Campylobacter coli adapted to biocides.
PubMed: Development of sustained-release antibacterial urinary biomaterials through using an antimicrobial as an organic modifier in polyurethane nanocomposites.
PubMed: Effects of efflux-pump inducers and genetic variation of the multidrug transporter cmeB in biocide resistance of Campylobacter jejuni and Campylobacter coli.
PubMed: Chlorhexidine salt-loaded polyurethane orthodontic chains: in vitro release and antibacterial activity studies.
PubMed: Antibacterial activity of calcium hydroxide and chlorhexidine containing points against Fusobacterium nucleatum and Parvimonas micra.
PubMed: Antimicrobial properties of cyclodextrin-antiseptics-complexes determined by microplate laser nephelometry and ATP bioluminescence assay.
PubMed: Combining in the melt physical and biological properties of poly(caprolactone) and chlorhexidine to obtain antimicrobial surgical monofilaments.
PubMed: 10% chlorhexidine varnish did not reduce caries in an adult population.
PubMed: Incorporation of chlorhexidine diacetate in provisional cements: antimicrobial activity against Streptococcus mutans and the effect on tensile strength in vitro.
PubMed: Effect of chlorhexidine incorporation into dental adhesive resin on durability of resin-dentin bond.
PubMed: Involvement of efflux mechanisms in biocide resistance of Campylobacter jejuni and Campylobacter coli.
PubMed: Efficacy of chlorhexidine varnish for the prevention of adult caries: a randomized trial.
PubMed: Comparison of different treatment modalities for oral halitosis.
PubMed: Presurgical antiseptic efficacy of chlorhexidine diacetate and providone-iodine in the canine preputial cavity.
PubMed: Controlled release of chlorhexidine antiseptic from microporous amorphous silica applied in open porosity of an implant surface.
PubMed: Buccal tablets containing cysteine and chlorhexidine for the reduction of acetaldehyde levels in the oral cavity.
PubMed: Commentary. Antibacterial activity and physical properties of conventional glass-ionomer cements containing chlorhexidine diacetate/cetrimide mixtures.
PubMed: Antibacterial activity and physical properties of conventional glass-ionomer cements containing chlorhexidine diacetate/cetrimide mixtures.
PubMed: Evaluation of the antibacterial and physical properties of glass ionomer cements containing chlorhexidine and cetrimide: an in-vitro study.
PubMed: Cytotoxicity of set polymer nanocomposite resin root-end filling materials.
PubMed: Ethanol wet-bonding challenges current anti-degradation strategy.
PubMed: Fluoride and chlorhexidine release from filled resins.
PubMed: Chlorhexidine release and antibacterial properties of chlorhexidine-incorporated polymethyl methacrylate-based resin cement.
PubMed: Substantivity of chlorhexidine to human dentin.
PubMed: Antibacterial effects of MDPB against anaerobes associated with endodontic infections.
PubMed: Antibacterial polyurethane nanocomposites using chlorhexidine diacetate as an organic modifier.
PubMed: Preparation of novel organovermiculites with antibacterial activity using chlorhexidine diacetate.
PubMed: Global transcriptomic response of Pseudomonas aeruginosa to chlorhexidine diacetate.
PubMed: Characterization of a polyurethane-based controlled release system for local delivery of chlorhexidine diacetate.
PubMed: In vitro drug release study of methacrylate polymer blend system: effect of polymer blend composition, drug loading and solubilizing surfactants on drug release.
PubMed: Controlled release of chlorhexidine from amorphous microporous silica.
PubMed: Engineering a titanium and polycaprolactone construct for a biocompatible interface between the body and artificial limb.
PubMed: Antibacterial effect of experimental chlorhexidine-releasing polymethyl methacrylate-based root canal sealers.
PubMed: Chemical decontamination of Campylobacter jejuni on chicken skin and meat.
PubMed: Superficial distribution and identification of antifungal/antimicrobial agents on a modified tissue conditioner by SEM-EDS microanalysis: a preliminary study.
PubMed: Inhibition of Candida albicans biofilm formation on denture material.
PubMed: Development of remineralizing, antibacterial dental materials.
PubMed: Bio-active restorative materials with antibacterial effects: new dimension of innovation in restorative dentistry.
PubMed: Preparation, in vitro characterization and preliminary in vivo evaluation of buccal polymeric films containing chlorhexidine.
PubMed: Concentration dependent aggregation properties of chlorhexidine salts.
PubMed: Chlorhexidine release and water sorption characteristics of chlorhexidine-incorporated hydrophobic/hydrophilic resins.
PubMed: Antimicrobial activity and local release characteristics of chlorhexidine diacetate loaded within the dental copolymer matrix, ethylene vinyl acetate.
PubMed: Characterization of chlorhexidine-releasing, fast-setting, brushite bone cements.
PubMed: Drug release from injectable biodegradable polymeric adhesives for bone repair.
PubMed: Long-term antibacterial effects and physical properties of a chlorhexidine-containing glass ionomer cement.
PubMed: Retention and marginal leakage of provisional crowns cemented with provisional cements enriched with chlorhexidine diacetate.
PubMed: Characterization of the physicochemical, antimicrobial, and drug release properties of thermoresponsive hydrogel copolymers designed for medical device applications.
PubMed: Wound dressings based on chitosans and hyaluronic acid for the release of chlorhexidine diacetate in skin ulcer therapy.
PubMed: Release of antimicrobial and antiviral drugs from methacrylate copolymer system: effect of copolymer molecular weight and drug loading on drug release.
PubMed: Novel chlorhexidine releasing system developed from thermosensitive vinyl ether-based hydrogels.
PubMed: Influence of additives and storage temperature on physicochemical and microbiological properties of eye drops containing ceftazidime.
PubMed: Controlled release of chlorhexidine diacetate from a porous methacrylate system: supercritical fluid assisted foaming and impregnation.
PubMed: Physicochemical and microbiological properties of eye drops containing cefuroxime.
PubMed: Characterisation of some experimental silicones.
PubMed: Effects of solubilizing surfactants and loading of antiviral, antimicrobial, and antifungal drugs on their release rates from ethylene vinyl acetate copolymer.
PubMed: Controlled release of chlorhexidine from UDMA-TEGDMA resin.
PubMed: Antimicrobial effect, in vitro, of gutta-percha points containing root canal medications against yeasts and Enterococcus faecalis.
PubMed: Chlorhexidine-containing chewing gum. Clinical documentation.
PubMed: Influence of additives and storage temperature on physicochemical and microbiological properties of eye drops containing cefazolin.
PubMed: Acanthamoeba keratitis in a 5-year-old boy without a history of contact lens usage.
PubMed: Bacteria and cell cytocompatibility studies on coated medical grade titanium surfaces.
PubMed: Poly(ethylene-co-vinyl acetate) copolymer matrix for delivery of chlorhexidine and acyclovir drugs for use in the oral environment: effect of drug combination, copolymer composition and coating on the drug release rate.
PubMed: Drug release from cast films of ethylene vinyl acetate (EVA) copolymer: Stability of drugs by 1H NMR and solid state 13C CP/MAS NMR.
PubMed: Chlorhexidine-releasing methacrylate dental composite materials.
PubMed: Antimicrobial activity of chlorhexidine diacetate and benzalkonium chloride against Pseudomonas aeruginosa and its response to biocide residues.
PubMed: NMR imaging of the diffusion of water at 310 K into semi-IPNs of PEM and poly(HEMA-co-THFMA) with and without chlorhexidine diacetate.
PubMed: Biguanide-induced changes in Acanthamoeba castellanii: an electron microscopic study.
PubMed: Resistance, biguanide sorption and biguanide-induced pentose leakage during encystment of Acanthamoeba castellanii.
PubMed: Heterodera glycines Cyst Components and Surface Disinfestants Affect H. glycines Hatching.
PubMed: A polymeric device for delivery of anti-microbial and anti-fungal drugs in the oral environment: effect of temperature and medium on the rate of drug release.
PubMed: Technology of eye drops containing aloe (Aloe arborescens Mill.--Liliaceae) and eye drops containing both aloe and neomycin sulphate.
PubMed: Effects of ortho-phthalaldehyde, glutaraldehyde and chlorhexidine diacetate on Mycobacterium chelonae and Mycobacterium abscessus strains with modified permeability.
PubMed: Antibacterial and physical properties of resin modified glass-ionomers combined with chlorhexidine.
PubMed: Formulation and in vivo evaluation of chlorhexidine buccal tablets prepared using drug-loaded chitosan microspheres.
PubMed: A polymeric system for the intra-oral delivery of an anti-fungal agent.
PubMed: Encystation in Acanthamoeba castellanii: development of biocide resistance.
PubMed: Development of resistance to chlorhexidine diacetate in Pseudomonas aeruginosa and the effect of a "residual" concentration.
PubMed: Outer membrane changes in Pseudomonas stutzeri resistant to chlorhexidine diacetate and cetylpyridinium chloride.
PubMed: Microbiological aspects of an in situ model to study effects of antimicrobial agents on dental plaque ecology.
PubMed: The minimum inhibitory concentration of oral antibacterial agents against cariogenic organisms.
PubMed: Cytotoxicity and teratogenicity of chlorhexidine diacetate released from hollow nylon fibres.
PubMed: Emergence of resistance to biocides during differentiation of Acanthamoeba castellanii.
PubMed: Effect of antimicrobial agents on livestock waste emissions.
PubMed: Cytological changes in chlorhexidine-resistant isolates of Pseudomonas stutzeri.
PubMed: Chlorhexidine release from room temperature polymerising methacrylate systems.
PubMed: The effect of liquid crystalline structure on chlorhexidine diacetate release.
PubMed: Comparative responses of Pseudomonas stutzeri and Pseudomonas aeruginosa to antibacterial agents.
PubMed: 3He ion-beam analysis of water uptake and drug delivery.
PubMed: Development of resistance to chlorhexidine diacetate and cetylpyridinium chloride in Pseudomonas stutzeri and changes in antibiotic susceptibility.
PubMed: Rapid evaluation of biocidal activity using a transposon-encoded catechol 2,3-dioxygenase from Pseudomonas putida.
PubMed: In-vitro Assays of Meloidogyne incognita and Heterodera glycines for Detection of Nematode-antagonistic Fungal Compounds.
PubMed: Effect of an antibacterial dental varnish on the levels of prostanoids, leukotriene B4, and interleukin-1 beta in gingival crevicular fluid.
PubMed: X-ray microanalysis of chlorine and phosphorus content in biguanide-treated Acanthamoeba castellanii.
PubMed: Antimicrobial efficacy of biocides tested on skin using an ex-vivo test.
PubMed: Use of the Malthus-AT system to assess the efficacy of permeabilizing agents on the activity of antibacterial agents against Pseudomonas aeruginosa.
PubMed: Effects of chlorhexidine diacetate on ruminal microorganisms.
PubMed: Effect of a chlorhexidine/thymol-containing varnish on prostaglandin E2 levels in gingival crevicular fluid.
PubMed: Effects of biocides on Acanthamoeba castellanii as measured by flow cytometry and plaque assay.
PubMed: Caries and plaque inhibition in rats by five topically applied dentifrices.
PubMed: Aspects of the mechanisms of action of biguanides on trophozoites and cysts of Acanthamoeba castellanii.
PubMed: The lethal effects of biguanides on cysts and trophozoites of Acanthamoeba castellanii.
PubMed: Effects of potentiated chlorhexidine on bacteria and tarsocrural joints in ponies.
PubMed: The possible role of yeast cell walls in modifying cellular response to chlorhexidine diacetate.
PubMed: Protection of bovine enamel and dentine by chlorhexidine and fluoride varnishes in a bacterial demineralization model.
PubMed: Effect of chlorhexidine varnish on Actinomyces naeslundii genospecies in plaque from dental fissures.
PubMed: The efficacy of an anti-gingivitis chewing gum.
PubMed: Potentiation of the effects of chlorhexidine diacetate and cetylpyridinium chloride on mycobacteria by ethambutol.
PubMed: Energy dispersive analysis of X-rays study of the distribution of chlorhexidine diacetate and cetylpyridinium chloride on the Pseudomonas aeruginosa bacteriophage F116.
PubMed: X-ray microanalysis of chlorhexidine-treated cells of Saccharomyces cerevisiae.
PubMed: Gypsum compatibility of antimicrobial alginates after spray disinfection.
PubMed: Effects of 0.05% chlorhexidine lavage on the tarsocrural joints of horses.
PubMed: Glucose uptake by Listeria monocytogenes Scott A and inhibition by pediocin JD.
PubMed: The sensitivity to chlorhexidine and cetyl pyridinium chloride of staphylococci on the hands of dental students and theatre staff exposed to these disinfectants.
PubMed: Effects of intra-articular chlorhexidine diacetate lavage on the stifle in healthy dogs.
PubMed: Effects of chlorhexidine diacetate and cetylpyridinium chloride on whole cells and protoplasts of Saccharomyces cerevisiae.
PubMed: Prevention of excess neonatal morbidity associated with group B streptococci by vaginal chlorhexidine disinfection during labour. The Swedish Chlorhexidine Study Group.
PubMed: Effects of chlorhexidine diacetate on Candida albicans, C. glabrata and Saccharomyces cerevisiae.
PubMed: Effects of four preparations of 0.05% chlorhexidine diacetate on wound healing in dogs.
PubMed: The effect of a combination of chlorhexidine diacetate, sodium fluoride and xylitol on plaque wet weight and periodontal index scores in military academy cadets refraining from mechanical tooth cleaning for 7-day experimental periods.
PubMed: Bacterial uptake of 14C-chlorhexidine diacetate and 14C-benzyl alcohol and the influence of phenoxyethanol and azolectin: studies with gram-negative bacteria.
PubMed: Mechanism of action of chlorhexidine diacetate and phenoxyethanol singly and in combination against gram-negative bacteria.
PubMed: Combined effects of Zn(2+)-chlorhexidine and Zn(2+)-cetylpyridinium chloride on caries incidence in partially desalivated rats.
PubMed: Evaluation of surgical scrub and antiseptic solutions for surgical preparation of canine paws.
PubMed: Influence of contact time and concentration of chlorhexidine varnish on mutans streptococci in interproximal dental plaque.
PubMed: In vivo bioluminescence: a cellular reporter for research and industry.
PubMed: Allergic contact dermatitis from chlorhexidine diacetate in a skin swab.
PubMed: Bandages and topical agents.
PubMed: Effects of varnishes containing chlorhexidine on the human dental plaque flora.
PubMed: Development and in vitro evaluation of an intra-oral controlled-release delivery system for chlorhexidine.
PubMed: Uptake of 14C-chlorhexidine diacetate to Escherichia coli and Pseudomonas aeruginosa and its release by azolectin.
PubMed: Effects of sustained-release chlorhexidine acetate on the human dental plaque flora.
PubMed: Effects of chlorhexidine diacetate and povidone-iodine on wound healing in dogs.
PubMed: Chlorhexidine diacetate and povidone-iodine cytotoxicity to canine embryonic fibroblasts and Staphylococcus aureus.
PubMed: Mechanism of resistance of Bacillus subtilis spores to chlorhexidine.
PubMed: Comparative susceptibility of hospital isolates of gram-negative bacteria to antiseptics and disinfectants.
PubMed: Influence of specific growth rate and nutrient limitation upon the sensitivity of Escherichia coli towards chlorhexidine diacetate.
PubMed: Quenching of the antibacterial activity of chlorhexidine and benzalkonium by Letheen broth and Letheen agar in relation to wild-type and envelope mutant strains of gram-negative bacteria.
PubMed: Reversal of the surface effects of chlorhexidine diacetate on cells of Providencia stuartii.
PubMed: Comparison of the potency of d-propranolol, chlorhexidine and nonoxynol-9 in the Sander-Cramer test.
PubMed: Comparison of the action of nonoxynol-9 and chlorhexidine on sperm.
PubMed: Antiseptic-induced changes in the cell surface of a chlorhexidine-sensitive and a chlorhexidine-resistant strain of Providencia stuartii.
PubMed: Correlation of microenvironmental drug concentration with inhibition of growth of microorganisms on surfaces.
PubMed: The sterilizing capacity of propylene oxide and chlorhexidine diacetate solutions upon pre-injection swabs saturated with propan-2-ol.
PubMed: Comparative antimicrobial activity, in vitro and in vivo, of soft N-chloramine systems and chlorhexidine.
PubMed: Stabilization of whole molecules of gastropodan haemocyanins by chlorhexidine.
PubMed: The influence of some monovalent cations, at various concentrations upon the activity of chlorhexidine diacetate and (ethoxy)5 octyl phenol [proceedings].
PubMed: In vitro activity of chlorhexidine diacetate against pseudorabies virus.
PubMed: Gravimetric determination of chlorhexidine using tetraphenylborate ion.
PubMed: Surface-chemical studies on chlorhexidine and related compounds: I. Effects at air-water, n-hexane-water, and hydroxyapatite-water interfaces.
PubMed: Hemolysis of erythrocytes by antibacterial preservatives. IV. Hemolytic activity of chlorhexidine diacetate.
PubMed: CYTOLOGICAL ASPECTS OF THE MODE OF ACTION OF CHLORHEXIDINE DIACETATE.
PubMed: EFFECT OF CHLORHEXIDINE DIACETATE ON "PROTOPLASTS" AND SPHEROPLASTS OF ESCHERICHIA COLI, PROTOPLASTS OF BACILLUS MEGATERIUM AND THE GRAM STAINING REACTION OF STAPHYLOCOCCUS AUREUS.
PubMed: Prevention of urinary tract infections after vaginal surgery.
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