CHLORHEXIDINE
Chlorhexidine is an antiseptic effective against various gram-negative and gram-positive organisms.
Chlorhexidine is commonly used in cosmetic and personal care products like skin cleansers.
EC / List no.: 200-238-7
CAS no.: 55-56-1
Mol. formula: C22H30Cl2N10
Synonym(s): 1,1′-Hexamethylenebis[5-(4-chlorophenyl)biguanide], CHX, CHG, 1,6-bis(4-chloro-phenylbiguanido)hexane, CHD-Base
Linear Formula: [-(CH2)3NHC(=NH)NHC(=NH)NHC6H4Cl]2
Molar mass: 505.45 g·mol−1
Chlorhexidine has been widely used in various applications, including wound care, hand washes, preoperative body showers, oral hygiene, and general disinfection.
Chlorhexidine is a germicidal mouthwash that reduces bacteria in the mouth.
Chlorhexidine is effective against plaque oral flora, including Candida, and is active against gram-positive and gram-negative organisms, facultative anaerobes, aerobes, and yeast.
Chlorhexidine can be used in antiseptic soap, a mouthwash that fights plaque, disinfect wounds and burns, vaginal flushing, hair dyes and bleaches, makeup, and other skin and hair care products.
Chlorhexidine is a bis(biguanide) family cationic broad-spectrum antibiotic.
Studies indicate that Chlorhexidine solution functions via destabilization of the outer bacterial membrane, which resulted in the release of periplasmic enzymes in gram-negative bacteria.
Chlorhexidine (CHX) is a low-foaming, broad-spectrum antiseptic. Its mechanism of action involves the destabilization of the outer bacterial membrane.
Chlorhexidine is effective on Gram-positive and Gram-negative bacteria, making it an excellent cationic cosmetic preservative.
In addition, Chlorhexidine solution inhibits oxygen utilization, which leads to a reduction in bacterial ATP.
These studies also indicate that the solution did not affect the inner membrane in gram-negative bacteria.
However, active transport was inhibited for small molecules entering the cell.
Furthermore, Chlorhexidine solution is very effective against bacteria such as Propionibacterium, Selenomonas, and cocci resembling Veillonella.
This gluconate salt is positively charged and disrupts the cell membrane of microbes, thanks to its interaction with their negatively charged surfaces.
By penetrating the microbial cell, Chlorhexidine triggers the release of intracellular components, ultimately leading to the cell’s demise.
Chlorhexidine, also called CHX, is an antibacterial compound C22H30Cl2N10 used as a local antiseptic (as in mouthwash) and disinfectant, especially in the form of its hydrochloride, gluconate, or acetate.
Chlorhexidine is a cationic chlorophenyl-biguanide chemical and has excellent antimicrobial properties.
Chlorhexidine (1,1-hexamethylenebis[5-(P-chlorophenyl) biguanide]) antimicrobial has broad-spectrum coverage, including S. aureus, P. aeruginosa, S. marcescens, and facultative anaerobes.
Chlorhexidine is a cationic surfactant synthetic biguanide with broad-spectrum antibacterial and less pronounced antifungal activity.
Chlorhexidine disrupts microbial cell membranes and coagulates cytoplasmic proteins.
Chlorhexidine is nonirritant, nontoxic, and works in organic debris.
Chlorhexidine was first made available as the low-solubility hydrochloride salt and, subsequently, the acetate salt.
The freely-soluble Chlorhexidine gluconate salt was introduced in 1957.
Most formulations of Chlorhexidine currently available are based on the gluconate salt.
Chlorhexidine is a disinfectant and antiseptic with the molecular formula C22H30Cl2N10, used for skin disinfection before surgery and sterilizing surgical instruments.
Chlorhexidine is also used for cleaning wounds, preventing dental plaque, treating yeast infections of the mouth, and keeping urinary catheters from blocking.
Chlorhexidine (1:6-di[4-chlorophenyldiguanido]-hexane) is a bisbiguanide that consists of two chlorguanide chains linked by a hexamethylene chain.
Chlorhexidine is a strong base and is a di-cation at physiological pH.
Chlorhexidine solutions are colorless, odorless, and have an extremely bitter taste.
Chlorhexidine is known by the salt forms chlorhexidine gluconate (chlorhexidine digluconate) and chlorhexidine acetate (chlorhexidine diacetate).
Chlorhexidine is insoluble in water and is formulated with gluconic or acetic acid to form water-soluble digluconate or diacetate salts.
Chlorhexidine is an incredibly effective antiseptic when combined with alcohol.
Chlorhexidine’s antimicrobial effects persist because it binds strongly to proteins in the skin and mucosa, making it an effective antiseptic ingredient for handwashing, skin
preparation for surgery and the placement of intravascular access.
Catheters impregnated with chlorhexidine and antimicrobial agents can reduce the incidence of catheter-related bloodstream infections.
Side effects may include skin irritation, tooth discoloration, and allergic reactions, although the risk appears to be the same as other topical antiseptics.
Chlorhexidine rinse is also known to have a bitter metallic aftertaste.
Rinsing with water is not recommended as it is known to increase the bitterness.
It may cause eye problems if direct contact occurs.
Chlorhexidine may come mixed in alcohol, water, or surfactant solution.
It is effective against a range of microorganisms but does not inactivate spores.
Uses
Chlorhexidine is used in disinfectants (disinfection of the skin and hands), cosmetics (additive to creams, toothpaste, deodorants, and antiperspirants), and pharmaceutical products (preservative in eye drops, active substance in wound dressings and antiseptic mouthwashes).
Chlorhexidine has been used in human medicine as an antiseptic and disinfectant for over 40 years.
Chlorhexidine has been used extensively for decades as a broad-spectrum antiseptic in hospitals and elsewhere.
Chlorhexidine has also been given as a maternal vaginal lavage, full-body newborn skin cleanser, and umbilical cord cleansing to prevent infection in neonates.
Recent evidence has suggested that these chlorhexidine interventions may have a significant effect on the burden of neonatal infection and mortality in developing countries
Antiseptic
Chlorhexidine is active against Gram-positive and Gram-negative organisms, facultative anaerobes, aerobes, and yeasts.
It is particularly effective against Gram-positive bacteria (in concentrations ≥ 1 μg/L).
Significantly higher concentrations (10 to more than 73 μg/mL) are required for Gram-negative bacteria and fungi.
Chlorhexidine is ineffective against polioviruses and adenoviruses.
The effectiveness against herpes viruses has not yet been established unequivocally.
Evidence shows that it is an effective antiseptic for upper limb surgery.
Meta-data spanning several decades shows that the efficacy of chlorhexidine (against organisms that cause surgical site infection) has not changed, dispelling concerns over emerging resistance.
At concentrations greater than 100 µg/ml, chlorhexidine is bactericidal.
Concentrations in the range 1-100 µg/ml are bacteriostatic.
The mode of action involves rapid attraction to the bacterial cell, absorption of phosphate compounds on the bacterial surface, overcoming the cell wall exclusion mechanisms, attraction towards the cytoplasmic membrane, leakage of low molecular weight cytoplasmic components, and precipitation of the cytoplasm by the formation of complexes with phosphate moieties.
Dental use
CHX, as a mouth rinse and periodontal irrigant, has been used in periodontal therapy, implantology, and cariology for many years to control dental plaque
Chlorhexidine is the most commonly used mouthwash for chemical plaque control.
Chlorhexidine’s use is becoming widespread as an adjuvant treatment of mechanical control, particularly in individuals with compromised oral hygiene.
The use of a chlorhexidine-based mouthwash in combination with ordinary tooth care can help reduce the build-up of plaque and improve mild gingivitis.
There is insufficient evidence to determine the effect of moderate to severe gingivitis.
Its use as a mouthwash has several adverse effects, including damage to the mouth lining, tooth discoloration, tartar build-up, and impaired taste.
Mouthwashes containing chlorhexidine, which stain teeth less than the classic solution, have been developed, many of which contain chelated zinc.
Chlorhexidine is a cation that interacts with anionic components of toothpaste, such as sodium lauryl sulfate and sodium monofluorophosphate, and forms salts of low solubility and reduced antibacterial activity.
Topical
Chlorhexidine gluconate is used as a skin cleanser for surgical scrubs, skin wounds, preoperative skin preparation, and germicidal hand rinses.
Chlorhexidine eye drops have been used to treat eyes affected by Acanthamoeba keratitis.
Chlorhexidine is very effective for poor countries like Nepal, and its use is growing worldwide for treating the umbilical cord.
A 2015 Cochrane review has yielded high-quality evidence that within the community setting, chlorhexidine skin or cord care can reduce the incidence of omphalitis (inflammation of the umbilical cord) by 50% and neonatal mortality by 12%.
Chlorhexidine is usually combined with other ingredients. Some sore throat treatments have a local anesthetic to help numb pain.
Mouth and throat treatments include mouthwashes, tablets, gels, and sprays.
Skin treatments come as creams, ointments, and lotions.
Chlorhexidine is used in hospitals and clinics to clean skin or surgical equipment before surgery.
Chlorhexidine can be used in some bladder procedures, including cleaning catheters.
Mechanism of action
At physiologic pH, chlorhexidine salts dissociate and release the positively charged chlorhexidine cation.
The bactericidal effect results from this cationic molecule’s binding to negatively charged bacterial cell walls.
Low chlorhexidine concentrations result in a bacteriostatic effect; membrane disruption results in cell death at high concentrations.
Chemistry
Chlorhexidine is a cationic polybiguanide (bisbiguanide).
Deactivation
Chlorhexidine is deactivated by forming insoluble salts with anionic compounds, including the anionic surfactants commonly used as detergents in toothpaste and mouthwashes, anionic thickeners such as carbomer, and anionic emulsifiers such as acrylates/C10-30 alkyl acrylate crosspolymer, among many others.
For this reason, chlorhexidine mouth rinses should be used at least 30 minutes after other dental products.
Brands
Chlorhexidine topical is sold as Betasept, Biopatch, Calgon Vesta, ChloraPrep One-Step, Dyna-Hex, Hibiclens, Hibistat Towelette, Scrub Care Exidine, Spectrum-4 among others.
Chlorhexidine gluconate mouthwash is sold as Dentohexin, Paroex, Peridex, PerioChip, Corsodyl, and Periogard, among others.
Veterinary medicine
Chlorhexidine is used as a general-purpose disinfectant for cleansing wounds, skin, instruments, and equipment in veterinary medicine,
These products usually contain around 1.5% w/v chlorhexidine gluconate and are diluted with water by a factor of 1 in 30 to 1 in 100 before use.
Chlorhexidine is also used in teat dips and sprays as an aid in the control of mastitis.
These products are typically applied post-milking to the whole herd and are diluted to a concentration of 0.425% w/v chlorhexidine gluconate before direct application to the udder.
In animals, chlorhexidine is used for topical disinfection of wounds and to manage skin infections.
Chlorhexidine-based disinfectant products are used in the dairy farming industry.
Post-surgical respiratory problems have been associated with using chlorhexidine products in cats.
Chlorhexidine is indicated for dogs and cats with skin infections and dry to normal skin.
Chlorhexidine is a disinfectant and antiseptic used on dogs to remove unwanted bacterial or fungal growth from the skin.
Chlorhexidine can be used for several reasons, from keeping wounds clean to treating skin infections.
Chlorhexidine is more effective for bacterial infections, particularly Staphylococcus spp, than yeast or dermatophyte infections.
Chlorhexidine is usually added in concentrations between 0.5% and 3%.
Shampoos containing combinations of chlorhexidine and miconazole are available and have superior action against yeast and fungal infections compared to shampoos containing chlorhexidine only.
Chlorhexidine for dogs is also included in many forms to help treat conditions at home.
These forms can include:
Shampoo
Wipes
Mousse
Spray
When included in products, chlorhexidine comes in different concentrations.
At least a 2% concentration is generally used to treat overgrowth or infections on the skin. Most products have a range from 2% to 4%.
How to use chlorhexidine for dogs depends on the form the product comes in:
Chlorhexidine solution may be sent home from the vet to help clean infected areas on the skin. Or, it may be used as foot soaks in the case of wounds or infections of the feet, toes, or nails.
Chlorhexidine wipes are used to clean the paws, nail beds, skin hot spots, or other small areas where killing bacteria or fungus is essential.
A chlorhexidine spray for dogs may be used similarly on smaller areas of concern.
Chlorhexidine shampoo for dogs is often used to reduce bacteria and fungus when multiple areas of the body are affected or when infections affect the hair coat.
Chlorhexidine mousse for dogs can be used on larger areas of the skin and the hair coat.
Chlorhexidine may be used alone or with oral medications as part of a larger treatment approach.
Chlorhexidine
EC Inventory
Chlorhexidine
chlorhexidine
N,N”-bis(4-Chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine
IUPAC names
(1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine
1,1′-Hexamethylenebis[5-(p-chlorophenyl)biguanide]
2,2′-hexane-1,6-diylbis(1-{amino[(4-chlorophenyl)amino]methylidene}guanidine)
CHLORHEXIDINE
Chlorhexidine
chlorhexidine
Chlorhexidine-base
N’,N””’-hexane-1,6-diylbis[N-(4-chlorophenyl)(imidodicarbonimidic diamide)]
N,N'”-BIS(4-CHLOROPHENYL)-3,12-DIIMINO-2,4,11,13-TETRAAZOTETRADECANEDIIMIDAMIDE
N-(4-chlorophenyl)-1-{N-[6-(N-{[N’-(4-chlorophenyl)carbamimidamido]methanimidoyl}amino)hexyl]carbamimidamido}methanimidamide
Trade names: CHD-Base
Registration dossier
CHX is a wide-spectrum antimicrobial agent, active against gram-positive and gram-negative bacteria as well as yeasts.
Owing to its cationic nature, CHX is capable of electrostatically binding to the negatively charged surfaces of bacteria, damaging the outer layers of the cell wall and rendering it permeable.165,178,179
Depending on its concentration, CHX can have both bacteriostatic and bactericidal effects.
At high concentrations, CHX acts as a detergent; damaging the cell membrane causes precipitation of the cytoplasm and thereby exerts a bactericidal effect.
At low sublethal concentrations, CHX is bacteriostatic, causing low molecular weight substances (i.e., potassium and phosphorous) to leak out without the cell being irreversibly damaged.
CHX can also affect bacterial metabolism, such as abolishing sugar phosphotransferase system (PTS) transport activity and inhibiting acid production in some bacteria.
Chlorhexidine is an incredibly effective antiseptic when combined with alcohol.
Chlorhexidine’s antimicrobial effects persist because it binds strongly to proteins in the skin and mucosa, making it an effective antiseptic ingredient for handwashing, skin
preparation for surgery and the placement of intravascular access.
Catheters impregnated with chlorhexidine and antimicrobial agents can reduce the incidence of catheter-related bloodstream infections.
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Blend of quaternaries
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DDMAC 80
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Didecyl dimethyl ammonium carbonate / bicarbonate
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Tertiary Alkylamine
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