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chlorhexidine(CAS No. 55-56-1)

chlorhexidine C22H30Cl2N10 (cas 55-56-1) Molecular Structure

55-56-1 Structure

Identification and Related Records

【Name】
chlorhexidine
【CAS Registry number】
55-56-1
【Synonyms】
Chlorhexidine Base
5,5-bis(4-chlorophenyl)-1,1-hexamethylenedibiguanide
Chlorohexidine base
【EINECS(EC#)】
200-238-7
【Molecular Formula】
C22H30Cl2N10 (Products with the same molecular formula)
【Molecular Weight】
505.45
【Inchi】
InChI=1/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
【Isomers smiles】
C1=CC(=CC=C1N/C(=N/C(=NCCCCCCN=C(/N=C(/NC2=CC=C(C=C2)Cl)\N)N)N)/N)Cl
【MOL File】
55-56-1.mol

Chemical and Physical Properties

【Appearance】
white powder
【Density】
1.39 g/cm3
【Melting Point】
132-136℃
【Boiling Point】

Vapour density:
【Flash Point】
312
【Water】
0.08 g/100 mL (20℃)
【Solubilities】
slightly
【Color/Form】
Crystals from methanol
Solid
【Stability】
Stable. Incompatible with strong oxidizing agents.
【Storage temp】
Keep tightly closed.
【Computed Properties】
Molecular Weight:505.4466 [g/mol]
Molecular Formula:C22H30Cl2N10
XLogP3:0.1
H-Bond Donor:6
H-Bond Acceptor:2
Rotatable Bond Count:13
Tautomer Count:36
Exact Mass:504.203196
MonoIsotopic Mass:504.203196
Topological Polar Surface Area:178
Heavy Atom Count:34
Formal Charge:0
Complexity:649
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:2
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Donor Count:6
Feature 3D Cation Count:4
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:2
Effective Rotor Count:13
Conformer Sampling RMSD:1.2
CID Conformer Count:149

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38;R51/53
【Safety Statements 】
S26;S36/37;S60;S61
【HazardClass】
9
【PackingGroup 】
III
【Skin, Eye, and Respiratory Irritations】
Causes moderate eye irritation. /0.01% Chlorhexidine diacetate, from Cougar product label/
Irritating to eye and mucous membranes. /Nolvasan-S, Chlorhexidine diacetate/
Chlorhexidine diacetate ...is highly acutely toxic when applied to the eye. /Chlorhexidine diacetate/
【Transport】
UN 3077
【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.
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription and over-the-counter drug products, incl chlorhexidine gluconate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Chlorhexidine gluconate/
Ophthalmic and topical dosage form new animal drugs. Chlorhexidine ointment. The product contains 1% chlorhexidine acetate in an ointment base. Indications for use: use as a topical antiseptic ointment for surface wounds on dogs, cats, and horses. Limitations: Not for use in horses intended for food.
Certain other dosage form new animal drugs. chlorhexidine tablets and suspension. Each tablet and each 28-mL syringe of suspension contain 1 g of chlorhexidine dihydrochloride. Indications for use: for prevention or treatment of metritis and vaginitis in cows and mares when caused by pathogens sensitive to chlorhexidine dihydrochloride.
Tolerances for residues of new animal drugs in food. A tolerance of zero is established for residues of chlorhexidine in the uncooked edible tissues of calves.
【Reactivities and Incompatibilities】
Strong alkaline reaction.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Protective Equipment and Clothing】
Causes moderate eye irritation. /0.01% Chlorhexidine diacetate, from Cougar product label/
Irritating to eye and mucous membranes. /Nolvasan-S, Chlorhexidine diacetate/
Chlorhexidine diacetate ...is highly acutely toxic when applied to the eye. /Chlorhexidine diacetate/
【Octanol/Water Partition Coefficient】
log Kow = 0.080 @ pH 5
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

It can be prepared ... from 1,6-hexamethylenebis(dicyandiamide) and 4-chloroaniline hydrochloride.
【Usage】

Analytical standard for pharmaceuticals.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.
- Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley's Condensed Chemical Dictionary, 11th ed)
- Solutions for rinsing the mouth, possessing cleansing, germicidal, or palliative properties. (From Boucher's Clinical Dental Terminology, 4th ed)
【Therapeutic Uses】
Antiseptic; disinfectant. (Vet): antiseptic; disinfectant.
Chlorhexidine is indicated for use between dental visits for the treatment of gingivitis that is characterized by redness and swelling of the gingivae or gingival bleeding upon probing. /Included in US product labeling/
Chlorhexidine is used along with other measures in the treatment of acute necrotizing ulcerative gingivitis (ANUG). /NOT included in US product labeling/
Chlorhexidine is used in the treatment of mouth infections in cancer patients who are being prepared for bone marrow transplants. Chlorhexidine is also used in the management of oral complications that occur in leukemia patients. /NOT included in US product labeling/
Chlorhexidine is also used following periodontal surgery to promote healing by minimizing mouth infections and plaque that may lead to increased inflammation and infection during the healing process. /NOT included in US product labeling/
Chlorhexidine is used in the treatment of inflammation of the oral mucosa caused by bacterial or fungal actions associated with the wearing of dentures but should not be used when inflammation is caused by poor fit or other mechanical factors associated with dentures. /NOT included in US product labeling/
Chlorhexidine is used in the management of minor aphthous ulcers. /NOT included in US product labeling/
Chlorhexidine is used for reduction of dental plaque. /NOT included in US product labeling/
/EXPTL Therapy:/ Rats were injected with 10 mg/kg azoxymethane sc weekly for 12 weeks to induce colorectal cancers. At 20 weeks, subtotal colectomies were performed on rats with colorectal tumors and without peritoneal implants or liver metastases. At the time of surgery, a cut portion of the tumor was placed in the abdomen for 30 minutes; the rats then randomly received peritoneal irrigation with chlorhexidine, or sterile water (control). Eight weeks postoperatively a necropsy was performed. At that time, obvious and suspected recurrences and the anastomotic area were sampled for histologic evaluation. Significant differences were seen with chlorhexidine vs. water for gross tumor (P=0.05) and microscopic tumor (P<0.05).
【Biomedical Effects and Toxicity】
Chlorhexidine is absorbed poorly from the GI tract and is absorbed poorly following topical application to the skin. Systemic absorption does not appear to occur following subgingival administration as ... biodegradable pellets ... or topical oral solution as mouth wash or rinse.
Following adminstration of chlorhexidine gluconate 0.12% topical topical oral solution as a mouth wash or rinse, approximately 30% of the drug is retained in the oral cavity. Chlorhexidine is bound to phosphate groups principally on the coatings of mucous membrane surfaces and is then gradually released into oral fluids for up to 24 hours.
...Chlorhexidine gluconate topical oral solution should not be swallowed, results of a pharmacokinetic study indicate that peak plasma chlorhexidine concentrations of 0.206 ug/mL are attained 30 minutes after ingestion of a 300 mg dose of chlorhexidine gluconate; however, the drug is undetectable 12 hours after the dose.
In clinical studies in adults who received chlorhexidine inserted into 4 periodontal pockets, there were no detectable plasma or urine concentrations of the drug (limits of detection 30 ng/mL).
Results of a pharmacokinetic study indicate that following the ingestion of a 300-mg dose of chlorhexidine gluconate, approximately 90% of the dose is excreated in feces via biliary elimination and less than 1% is eliminated in the urine.
Percutaneous absorption of the antimicrobial agent chlorhexidine (labelled with carbon-14) was studied in rats. Less than 5% of the topically applied chlorhexidine was absorbed during a 5-day period. Excretion of absorbed radioactivity occurred mainly in the feces.
The percutaneous absorption of chlorhexidine gluconate (chlorhexidine digluconate; Hibitane) through hairless rat skin with or without stratum corneum was studied. For tests carried out on whole skin, storage in cutaneous structures after 48 hr was more important than diffusion; the reverse was observed for stripped skin. When the skin was stripped, the amount absorbed was multiplied by approximately 100, and the amount stored in skin by approximately 10. The difference in chlorhexidine diffusion observed between whole and stripped skin was related to the physicochemical characteristics of chlorhexidine. /Chlorhexidine gluconate/
To evaluate the elimination kinetics of chlorhexidine in milk when used as an intramammary infusion to stop lactation in cows. ... The study was performed in 2 phases. Three cows were studied in each phase. All cows were treated with chlorhexidine suspension by infusion into a mastitic mammary gland quarter after 2 milkings 24 hours apart. Foremilk samples (100 mL) were collected from treated and untreated (controls) mammary gland quarters of each cow. Chlorhexidine was extracted from raw milk, and residue concentrations were quantified by use of high-performance liquid chromatography. Foremilk samples from days 2, 5, and 8 were analyzed in phase I, and samples from time 0 and days 3, 7, 14, 21, 28, 35, and 42 were analyzed in phase II. In phases I and II, there was no quantifiable transference of chlorhexidine to milk in untreated mammary gland quarters. Measurable chlorhexidine residues were found in milk from treated mammary gland quarters of 2 cows throughout the 42-day sample period in phase II. Estimated mean elimination half-life for chlorhexidine in milk was 11.5 days. [Middleton JR et al; J Am Vet Med Assoc 222 (12): 1746-9 (2003)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 26(SRC), determined from a log Kow of 0.08(2) and a regression-derived equation(3), indicates that chlorhexidine is expected to have very high mobility in soil(SRC). However, the pKa of chlorhexidine is 10.78(4), indicating that this compound will primarily exist in the protonated form in the environment and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(5). Volatilization of chlorhexidine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-30 atm-cu m/mole(SRC), using a fragment constant estimation method(6). Chlorhexidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.0X10-14 mm Hg(SRC), determined from a fragment constant method(7). Chlorhexidine, present at 12 ppm (dissolved in a specific mineral salts medium), did not degrade in 21 days using a soil extract inoculum(8); therefore, biodegradation may not be an important environmental fate process in soil.
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 28(SRC), determined from a log Kow of 0.08(2) and a regression-derived equation(3), indicates that chlorhexidine is not expected to adsorb to suspended solids and sediment(SRC). However, the pKa of chlorhexidine is 10.78(4), indicating that this compound will primarily exist in the protonated form in the environment and cations generally adsorb more strongly to suspended solids and sediment than their neutral counterparts(5). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.1X10-30 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). According to a classification scheme(7), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Chlorhexidine was reported as non-biodegradable under sewage treatment conditions(9); therefore, biodegradation may not be an important environmental fate process in water.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorhexidine, which has an estimated vapor pressure of 2.0X10-14 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase chlorhexidine may be removed from the air by wet and dry deposition(SRC). Chlorhexidine absorbs light in the environmental range (>290 nm)(3) and therefore may be susceptible to direct photolysis.

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