CHLORHEXIDINE GLUCONATE


Chlorhexidine Gluconate (CHG) Solution has been used in more than 60 different pharmaceuticals and medical devices. 
Its wide application is due to its broad-spectrum efficacy, safety-profile and substantivity on the skin with low irritation. 
Chlorhexidine Gluconate has been found to possess a high level of antimicrobial activity and strong affinity for binding to skin and mucous membranes.

EC / List no.: 242-354-0
CAS no.: 18472-51-0
Mol. formula: C34H54Cl2N10O14


CHG is a broad-spectrum antimicrobial agent active against both Gram-positive and -negative bacteria, and has been successfully assessed as an effective skin antiseptic since the early 1970s.
Chlorhexidine Gluconate can be applied directly as solution by clean wipes or as an ingredient in soaps and gels.


Chlorhexidine Gluconate is the gluconate salt form of chlorhexidine, a biguanide compound used as an antiseptic agent with topical antibacterial activity. 
Chlorhexidine gluconate is positively charged and reacts with the negatively charged microbial cell surface, thereby destroying the integrity of the cell membrane. 
Subsequently, chlorhexidine gluconate penetrates into the cell and causes leakage of intracellular components leading to cell death. 
Since gram positive bacteria are more negatively charged, they are more sensitive to this agent.

CAS Number: 55-56-1 


Chlorhexidine is an antiseptic effective against a wide variety of gram-negative and gram-positive organisms, facultative anaerobes, aerobes, and yeast. Chlorhexidine is used as an ingredient of bacteriostatic and bacteriocidal by the activity of membrane disruption in a general purpose skin general skin cleansers, surgical scrub, germicidal hand rinses and animal disinfection products. It is used as a topical antiinfective for mucous membranes and as a preservative for eye drops. Chlorhexidine is also used as an antiseptic ingredient used in mouthwash to prevent oral plaque, oral bacteria and in treating gingivitis. Its salts for commercial uses include:
Chlorhexidine salt    
CAS RN

Chlorhexidine diacetate    CAS Number:56-95-1
Chlorhexidine dihydrochloride CAS Number: 3697-42-5
Chlorhexidine digluconate CAS Number:18472-51-0
Chlorhexidine phosphanilate CAS Number:    77146-42-0
Chlorhexidine gluconate CAS Number: 55-56-1 

Chlorhexidine gluconate 0.12% oral solution (Peridex or Periogard oral rinse) is a mouthwash that has been shown to reduce the incidence, duration, and discomfort of RAUs


Chlorhexidine gluconate has been shown to reduce plaque in the oral cavity and around dental implants.
Long-term use of antimicrobials, including chlorhexidine gluconate 0.1% (United States) or 0.2% (Europe) or cetylpyridinium chloride, may be used with brushes and floss to minimize staining. 
With newer generations of chlorhexidine, it is significant to note that alcohol in chlorhexidine serves to preserve and stabilize the solution.
Studies have shown a decrease of antimicrobial benefits in preparations that are alcohol free.

Chlorhexidine gluconate (Hibiclens), for example, is a widely-used broad-spectrum antiseptic, which has faster and longer-acting antiseptic action and capability than the iodophors

Chlorhexidine gluconate is an antiseptic agent that has been shown to decrease microbial flora on the skin and prevent infection risk in various settings, including as a skin preparatory agent for surgical procedures and for insertion of vascular access devices, as a surgical hand scrub, and for oral hygiene

Currently there is interest in the use of chlorhexidine-impregnated wipes as an alternative to bathing or showering with chlorhexidine soap. 
Although the wipes only contain 2 % chlorhexidine, they have been shown to achieve higher chlorhexidine concentrations on the skin than the 4 % chlorhexidine soap, and may represent an attractive alternative for patients who are unable to shower or bathe thoroughly. 
Preoperative chlorhexidine bathing may be considered if other measures have been instituted and SSI rates remain high.

Chlorhexidine gluconate is an organochlorine compound and a D-gluconate adduct. 
Chlorhexidine gluconate has a role as an antibacterial agent. 
Chlorhexidine gluconate derives from a chlorhexidine.

CAS    18472-51-0
EINECS    242-354-0
English    D-gluconic acid, compound with N,N''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine (2:1)
Chemical formula    C22H30Cl2N10.2C6H12O7
IUPAC    N',N'''''-hexane-1,6-diylbis[N-(4-chlorophenyl)(imidodicarbonimidic diamide)] - D-gluconic acid (1:2)
Mol.Wt.    897.7572  
synonyms: 
D-Gluconic acid, compd. with N,N''-bis(4-chlorophenyl) -3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)
D-Gluconic acid, compd. with N,N''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)

Chlorhexidine digluconate, 20 % soln.
CAS name: D-Gluconic acid, compd. with N,N''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)
CAS number: 18472-51-0
Formula: C22H30Cl2N10 x 2 C6H12O7
Product Groups: Amino Acids for Pharma
Markets: Pharma & Healthcare
Applications: Anti-parasitic
Dermatological Products
Code: Chlorhexidine digluconate
Synonyms: 2,4,11,13-Tetraazatetradecanediimidamide, N,N''-bis(4-chlorophenyl)-3,12-diimino-, di-D-gluconate
Biguanide, 1,1'-hexamethylenebis[5-(p-chlorophenyl)-, di-D-gluconate D-Gluconic acid, compd. with 1,1'-hexamethylenebis[5-(p-chlorophenyl)biguanide] (2:1) Gluconic acid, compd. with 1,1'-hexamethylenebis[5-(p-chlorophenyl)biguanide] (2:1), D- 1,1'-Hexamethylenebis[5-(p-chlorophenyl)biguanide] digluconate 
1,6-Bis(4-chlorophenyldiguanino)hexane digluconate 
1,6-Bis(p-chlorophenyldiguanido)hexane digluconate 
1,6-Bis[N5-(p-chlorophenyl)biguanido]hexane digluconate 
4-Chlorhexidine digluconate 
Bis(p-chlorophenyl)diguanidohexane digluconate 
Chlorhexidine bigluconate 
Chlorhexidine di-D-gluconate 
Chlorhexidine digluconate 
Chlorhexidine gluconate
Molecular weight: 897.77 g/mol 

Chlorhexidine (commonly known by the salt forms chlorhexidine gluconate and chlorhexidine digluconate (CHG) or chlorhexidine acetate), is a disinfectant and antiseptic that is used for skin disinfection before surgery and to sterilize surgical instruments.
It may be used both to disinfect the skin of the patient and the hands of the healthcare providers.
It is also used for cleaning wounds, preventing dental plaque, treating yeast infections of the mouth, and to keep urinary catheters from blocking.
It is used as a liquid or powder.

Side effects may include skin irritation, teeth discoloration, and allergic reactions.
It may cause eye problems if direct contact occurs.
Use in pregnancy appears to be safe.
Chlorhexidine may come mixed in alcohol, water, or surfactant solution.
It is effective against a range of microorganisms, but does not inactivate spores.

Chlorhexidine came into medical use in the 1950s.
Chlorhexidine is available over the counter (OTC) in the United States.
It is on the World Health Organization's List of Essential Medicines.
In 2017, it was the 286th most commonly prescribed medication in the United States, with more than one million prescriptions.


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).
A 2019 Cochrane review concluded that based on very low certainty evidence in those who are critically ill "it is not clear whether bathing with chlorhexidine reduces hospital‐acquired infections, mortality, or length of stay in the ICU, or whether the use of chlorhexidine results in more skin reactions."

In endodontics, chlorhexidine is used for root canal irrigation and as an intracanal dressing, but has been replaced by the use of sodium hypochlorite bleach in much of the developed world.

Antiseptic
There is strong evidence that it is more effective than povidone-iodine and is it proved to kill 99.9% of germs in 30 sec.

CHG 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. 
The effectiveness against Covid-19 viruses has been established. 
The effectiveness against herpes viruses has not yet been established unequivocally.

Chlorhexidine, like other cation-active compounds, remains on the skin.
It is frequently combined with alcohols (ethanol and isopropyl alcohol).


chlorhexidine digluconate
chlorhexidine D-digluconate
chlorhexidine di-D-gluconate
Hibiclens
Peridex
1,1'-hexamethylene bis(5-(p-chlorophenyl)biguanide), digluconate

Peridex®; Periochip®, Periogard Oral Rinse®;

1,1'-Hexam ethylene bis(5- (p-chlorophenyl) biguanide) digluconate; 1,6-Bis(5-(p- chlorophenyl) biguandino)hexane digluconate; Arlacide G; Bacticlens; Hibitane 5; Orahexal; Peridex; D-Gluconsäure, N,N''-Bis (4-chlorphenyl) -3,12-diimino-2,4,11,13- tetraazatetradecan diamidin (German); ácido D-glucónico, N,N''-bis (4-clorofenil)- 3,12-diimino-2,4,11,13- tetraazatetradecanodiamidina (Spanish), Acide D-gluconique, N,N''-bis(4-chlorophényl)- 3,12-diimino-2,4,11,13- tétraazatétradécanediamidine (French); D-Gluconic acid, N,N''-bis(4-chlorophenyl)-3,12- diimino-2,4,11,13- tetraaza tetradecanediimidamide (2:1);

Dental use

Perichlor brand 0.12% chlorhexidine gluconate solution
Use of a CHG-based mouthwash in combination with normal tooth care can help reduce the build-up of plaque and improve mild gingivitis.
There is not enough evidence to determine the effect in moderate to severe gingivitis.
About 20 mL twice a day of concentrations of 0.1% to 0.2% is recommended for mouth-rinse solutions with a duration of at least 30 seconds.
Such mouthwash also has a number of adverse effects including damage to the mouth lining, tooth discoloration, tartar build-up, and impaired taste.
Extrinsic tooth staining occurs when chlorhexidine rinse has been used for 4 weeks or longer.

Mouthwashes containing chlorhexidine which stain teeth less than the classic solution have been developed, many of which contain chelated zinc.

Using chlorhexidine as a supplement to everyday mechanical oral hygiene procedures for 4 to 6 weeks and 6 months leads to a moderate reduction in gingivitis compared to placebo, control or mechanical oral hygiene alone.

Chlorhexidine is a cation which interacts with anionic components of toothpaste, such as sodium lauryl sulfate and sodium monofluorophosphate, and forms salts of low solubility and antibacterial activity. 
Hence, to enhance the antiplaque effect of chlorhexidine, "it seems best that the interval between toothbrushing and rinsing with CHX [chlorhexidine] be more than 30 minutes, cautiously close to 2 hours after brushing.".

Topical
Nepal was the first country in the world to use chlorhexidine to treat the umbilical cord of newborn babies, and received a USAID Pioneers Prize for reducing the neonatal death rate.
Chlorhexidine is very effective for poor countries like Nepal and its use is growing in the world 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 also neonatal mortality by 12%.
Chlorhexidine gluconate is used as a skin cleanser for surgical scrubs, as a cleanser for skin wounds, for preoperative skin preparation, and for germicidal hand rinses.
Chlorhexidine eye drops have been used as a treatment for eyes affected by Acanthamoeba keratitis.

Side effects
CHG is ototoxic; if put into an ear canal which has a ruptured eardrum, it can lead to deafness.

CHG does not meet current European specifications for a hand disinfectant. 
Under the test conditions of the European Standard EN 1499, no significant difference in the efficacy was found between a 4% solution of chlorhexidine digluconate and soap.
In the U.S., between 2007 and 2009, Hunter Holmes McGuire Veterans Administration Medical Center conducted a cluster-randomized trial and concluded that daily bathing of patients in intensive care units with washcloths saturated with chlorhexidine gluconate reduced the risk of hospital-acquired infections.

Whether prolonged exposure over many years may have carcinogenic potential is still not clear. 
The US Food and Drug Administration recommendation is to limit the use of a chlorhexidine gluconate mouthwash to a maximum of six months.

When ingested, CHG is poorly absorbed in the gastrointestinal tract and can cause stomach irritation or nausea.
If aspirated into the lungs at high enough concentration, as reported in one case, it can be fatal due to the high risk of acute respiratory distress syndrome.

Mechanism of action
At physiologic pH, chlorhexidine salts dissociate and release the positively charged chlorhexidine cation. 
The bactericidal effect is a result of the binding of this cationic molecule to negatively charged bacterial cell walls. 
At low concentrations of chlorhexidine, this results in a bacteriostatic effect; at high concentrations, membrane disruption results in cell death.

Chemistry
It is a cationic polybiguanide (bisbiguanide).
It is used primarily as its salts (e.g., the dihydrochloride, diacetate, and digluconate).

Deactivation
Chlorhexidine is deactivated by forming insoluble salts with anionic compounds, including the anionic surfactants commonly used as detergents in toothpastes 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.
For best effectiveness, food, drink, smoking, and mouth rinses should be avoided for at least one hour after use. 
Many topical skin products, cleansers, and hand sanitizers should also be avoided to prevent deactivation when chlorhexidine (as a topical by itself or as a residue from a cleanser) is meant to remain on the skin.

Synthesis
The structure is based on two molecules of proguanil, linked with a hexamethylenediamine spacer.

Trade names    Betasept, ChloraPrep, Chlorostat, others
Other names    1,6-bis(4-chloro-phenylbiguanido)hexane

CHLORHEXIDINE DIGLUCONATE
18472-51-0
Chlorhexidine gluconate
Unisept
Chlorhexidine D-digluconate
Peridex
UNII-MOR84MUD8E
Chlorhexidine di-D-gluconate
Periogard
MOR84MUD8E
Exidine
1,1'-Hexamethylene bis(5-(p-chlorophenyl)biguanide), digluconate
Kleersight
Fight bac
Chlorhexidin glukonatu
MFCD00083599
Prevacare
pHiso-Med
Chlorhexidine digluconate solution
Hibitane gluconate
Hibiclens (TN)
Periogard (TN)
Peridex (TN)
Chlohexidine gluconate
Chlorhexidine gluconate [USAN:USP:JAN]
EC 242-354-0
SCHEMBL34468
CHEMBL4297088
DTXSID5034519
CHEBI:28312
Chx plus concentrate premium chlorhexidine teat dip concentrate
Chlorhexidine gluconate (JP17/USP)
AKOS015896303
AKOS025310696
D-Gluconic acid, compd. with N1,N14-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)
M166
C08038
D00858
Chlorhexidine digluconate solution, 20% in H2O
J-011837
Chlorhexidine digluconate, Pharmaceutical Secondary Standard; Certified Reference Material
1,6-Bis(N5-[p-chlorophenyl]-N1-biguanido)hexane; 1,1'-Hexamethylenebis(5-[p-chlorophenyl]biguanide)
1-(4-chlorophenyl)-3-[N-[6-[[N-[N-(4-chlorophenyl)carbamimidoyl]carbamimidoyl]amino]hexyl]carbamimidoyl]guanidine; (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
2,4,11,13-Tetraazatetradecanediimidamide, N,N''-bis(4-chlorophenyl)-3,12-diimino-, digluconate
D-Gluconic acid, compd with N,N''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)
Gluconic acid, compd. with 1,1'-hexamethylene bis(5-(p-chlorophenyl)biguanide) (2:1), D- (8CI)
N',N'''''-hexane-1,6-diylbis[N-(4-chlorophenyl)(imidodicarbonimidic diamide)]--D-gluconic acid (1/2)


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 Dentohexinm, Paroex, Peridex, PerioChip, Corsodyl and Periogard, among others.

Hexoralettene N contains benzocaine, menthol and chlorhexidine hydrochloride. 
It is used as oral antiseptic candies.

Terminology
The name "Chlorhexidine" breaks down as chlor(o) + hex(ane) + id(e) + (am)ine), is a cationic polybiguanide. 
It is used primarily as its gluconate salt.

Veterinary medicine
In animals, chlorhexidine is used for topical disinfection of wounds, and to manage skin infections.
Chlorhexidine-based disinfectant products are used within the dairy farming industry.

Post-surgical respiratory problems have been associated with the use of chlorhexidine products in cats.


If you have been prescribed chlorhexidine gluconate mouthwash, chances are your dentist has told you that you have a mild form of gum disease called gingivitis. 
It might seem a little scary, but this prescription mouthwash could be a simple solution to getting your smile back on track to health and confidence. 
Chlorhexidine gluconate oral rinse contains a chemical called chlorhexidine, which destroys harmful mouth bacteria, treats gingivitis, and promotes the healing of inflamed gums.

What Do Chlorhexidine Gluconate Mouthwashes Treat?
Chlorhexidine gluconate is used to treat gingivitis, another name for mild gum disease. 
Symptoms can include bad breath and gum redness, swelling and bleeding. 
While brushing your teeth and gums twice per day and flossing once per day help prevent gingivitis, a prescription mouthwash may help reduce the symptoms when you're already in the early stages. 
However, according to the Mayo Clinic, you shouldn't look to chlorhexidine gluconate mouthwash to treat periodontitis, a more advanced form of gum disease.

How Does It Work?
When you rinse with chlorhexidine gluconate mouthwash, the active ingredient chlorhexidine immediately works to destroy harmful mouth bacteria, even after you spit. 
The FDA states that after six months using chlorhexidine gluconate mouthwash, levels of mouth bacteria reduced up to 97 percent. 
The FDA also explains that 30% of the chlorhexidine remains in the mouth after rinsing, so the chemical continues to destroy bacteria between uses.

Are ThereAny Side Effects?
Chlorhexidine gluconate mouthwash has a few possible side effects, like a change in taste, an increase in tartar build-up, and staining of the teeth, gums, and dental appliances. 
Not to worry, though. These side effects are usually very minor.

While severe side effects of using medicated mouthwash are rare, some people can experience swollen neck glands and irritation in the mouth and tip of the tongue. 
Call your dentist immediately if you experience any of these symptoms, or you believe you might be experiencing an allergic reaction to the mouthwash.

Is It Safe?
Only use chlorhexidine gluconate mouthwash if your physician or dentist prescribes it. 
Under the guidance of a healthcare professional, the product is safe when used as directed. 
According to C. S. Mott Children's Hospital, medicated mouthwash is not meant for anyone under the age of 18, so make sure to keep it out of reach from young children.

Though chlorhexidine gluconate mouthwash is effective at killing mouth bacteria in mild cases of gum disease, it's not a substitute for regular brushing and flossing for total oral health. 
Along with daily flossing, try brushing with a toothbrush that has curved, soft outer bristles to clean the gumline and firmer inner bristles to effectively clean teeth.

If you are ready to take steps towards gum health, chlorhexidine gluconate oral rinse could be the perfect first step. 
Talk to your dentist about your options, and they will be able to help you find the solution that fits your smile best.

Chlorhexidine gluconate is a germicidal mouthwash that reduces bacteria in the mouth.

Chlorhexidine gluconate oral rinse is used to treat gingivitis (swelling, redness, bleeding gums). 
Chlorhexidine gluconate is usually prescribed by a dentist.

Chlorhexidine gluconate oral rinse is not for treating all types of gingivitis. 
Use the medication only to treat the condition your dentist prescribed it for. 
Do not share this medication with another person, even if they have the same gum symptoms you have.

Chlorhexidine gluconate may also be used for purposes not listed in this medication guide.


Chlorhexidine gluconate is a prescription germicidal mouthwash that decreases bacteria in your mouth.

A 2017 study Trusted Source suggests chlorhexidine is the most effective antiseptic mouthwash to date. 
Dentists primarily prescribe it to treat the inflammation, swelling, and bleeding that comes with gingivitis.

Chlorhexidine is available in the United States under the brand names:

Paroex (GUM)
Peridex (3M)
PerioGard (Colgate)

Chlorhexidine gluconate is an antiseptic agent that has been shown to decrease microbial flora on the skin and prevent infection risk in various settings, including as a skin preparatory agent for surgical procedures and for insertion of vascular access devices, as a surgical hand scrub, and for oral hygiene. 
Numerous studies have been published regarding its use in preoperative bathing, the hypothesis being that by decreasing overall microbial skin colonization there is less opportunity for the surgical wound to become contaminated by the patient's endogenous flora

Chlorhexidine Gluconate Oral Rinse
Chlorhexidine gluconate is the most effective antiplaque agent currently approved. 
Chlorhexidine is a broad-spectrum antiseptic that is bactericidal and effective against some yeasts and viruses.
The effectiveness of chlorhexidine is documented in many controlled clinical trials showing a 50% to 60% decrease in plaque, a 30% to 45% reduction in gingivitis, and a reduction in the number of oral bacteria.
The efficacy of chlorhexidine stems from its ability to bind to oral tissues and slow release into the oral cavity. 
This characteristic, known as substantivity, provides a continued inhibitory effect on plaque formation for 12 to 14 hours.

In the United States, chlorhexidine is available only by prescription in 0.12% concentration for use twice a day. 
Some components of toothpastes, including sodium lauryl sulfate and calcium, interact with chlorhexidine to reduce its effectiveness; therefore, its use should be delayed for 30 minutes after toothbrushing.
Bitter taste of chlorhexidine and alteration in taste that may last as long as 4 hours are side effects resulting from chlorhexidine use. 
Other side effects include increased calculus formation, irritation of the mucosa, and staining of teeth, tongue, and restorations. 
Consequently, patients using chlorhexidine should be reevaluated every 6 months. 
The use of chlorhexidine for as long as 2 years is not associated with increased microbial resistance or disruption of the ecological balance in the oral cavity.53,58

Patient compliance with prescription medications is usually low and is a potential problem when the use of chlorhexidine is promoted. 
Other barriers to adherence of a chlorhexidine regimen include the inconvenience of obtaining the product by prescription and the associated expense.

Chlorhexidine MouthwashEffective treatment and prevention for oral hygiene. 
Chlorhexidine Gluconate Mouthwash is firmly established as the mouthwash of clinical choice. 
It is the proven, prescribed and recommended treatment for gingivitis and oral hygiene.

In addition to antibacterial activity, chlorhexidine phosphanilate is also used as a spermatocidal agent.

Active ingredients in mouthwash or dental caries prophylactic include;

Ingredient

CAS RN

Amosan    8059-88-9
Benzalkonium chloride    8001-54-5
Cetylpyridinium chloride    123-03-5
Chlorhexidine gluconate    18472-51-0
Chlorhexidine    55-56-1
Dectaflur    36505-83-6
Eucalyptol    470-82-6
Hetaflur    3151-59-5
Hydrogen peroxide    7722-84-1
Ipexidine mesylate    69017-90-9
Listerine    51273-66-6
Meridol    120812-75-1
Metesculetol    52814-39-8
Methyl salicylate    119-36-8
Olaflur    6818-37-7
Rhatany    84775-95-1
Salifluor    78417-90-0
Sanguinarine    2447-54-3
Sodium monofluorophosphate    10163-15-2
Sodium fluoride    7681-49-4
Stannous fluoride    7783-47-3
Thymol    89-83-8
Tiodonium chloride    38070-41-6
Zinc chloride    7646-85-7
Zinc fluoride    7783-49-5
SALES SPECIFICATION
BIBLIOGRAPHY

USP / BP

APPEARANCE    
Colorless to Pale Yellow Clear Liquid

CONTENT

19.0 - 21.0 % (Chlorhexidine Gluconate)
pH (5% SOL.)

5.5 - 7.0
MELTING POINT    132 - 136 C
P-CHLOROANILINE    500ppm max
RESIDUE ON IGNITION

0.1% max

SPECIFIC GRAVITY    
1.06 - 1.07

Chlorhexidine (digluconate)

    
Chlorhexidine (digluconate)

18472-51-0

HY-B0608

Chlorhexidine digluconate, 20% w/v aqueous solution


Chlorhexidine digluconate Chemical Properties,Uses,Production

Description
Chlorhexidine digluconate solution is a bis(biguanide) family cationic broad spectrum antibiotic that is available in a range of concentrations and has been safely used for over 40 years for a variety of health-related applications; but its specific use for umbilical cord care was uniquely tested in three clinical trials in Nepal, Bangladesh, and Pakistan, in the form of 7.1% chlorhexidine digluconate (CHX). 
Given the promising results of the trials, in 2013 the World Health Organization (WHO) added CHX to its Model List of Essential Medicines for Children; and in 2014 the WHO issued a new guideline on umbilical cord care, which included a formal recommendation on the use of chlorhexidine.
Chlorhexidine digluconate is a broad spectrum antiseptic. 
Its mechanism of action involves destabilization of the outer bacterial membrane. 
It is effective on both Gram-positive and Gram-negative bacteria, although it is less effective with some Gram-negative bacteria.
It has both bactericidal and bacteriostatic mechanisms of action, the mechanism of action being membrane disruption, not ATPase inactivation as previously thought.It is also useful against fungi and enveloped viruses, though this has not been extensively investigated. 
Chlorhexidine is harmful in high concentrations, but is used safely in low concentrations in many products, such as mouthwash and contact lens solutions.

Chemical Properties
Almost colourless or pale-yellowish liquid.

Uses
chlorhexidine digluconate is a preservative generally used in concentrations of 0.01 to 0.1 percent to protect against bacteria. 
It is unstable at high temperatures. Chlorhexidine digluconate is more widely used in europe than in the united States.

Uses
Hydrogenolysis of benzyl-nitrogen bonds

Uses
Chlorhexidine is used primarily as a topical antiseptic/disinfectant in wound healing, at catheterization sites, in various dental applications and in surgical scrubs.
The gluconate salt form of chlorhexidine, a biguanide compound used as an antiseptic agent with topical antibacterial activity. 
Chlorhexidine gluconate is positively charged and reacts with the negatively charged microbial cell surface, thereby destroying the integrity of the cell membrane. 
Subsequently, chlorhexidine gluconate penetrates into the cell and causes leakage of intracellular components leading to cell death. 
Since gram positive bacteria are more negatively charged, they are more sensitive to this agent.
Chlorhexidine digluconate 20% solution is a broad spectrum bacteriostatis antiseptic agent, oral care agent, disinfectant, cosmetic biocide, and preservative. 
It is very effective against plaque, oral flora including Candida and is active against gram-positive and gram-negative organisms, facultative anaerobes, aerobes, and yeast. 
It can be used in antiseptic soap, mouthwash that fights plaque, disinfecting wounds and burns, vaginal flushing, hair dyes and bleaches, makeup, and other skin and hair care products.

Manufacturing Process
35 parts of hexamethylene bis-dicyandiamide, 35 parts of p-chloroaniline hydrochloride and 250 parts of β-etoxyethanol are stirred together at 130- 140°C for 2 hours under reflux. 
The mixture is then cooled and filtered. 
The solid is washed with water and crystallised from 50% aqueous acetic acid. 
1,1'-Hexamethylene bis(5-(p-chlorophenyl)biguanide) is obtained as colorless plates, melting point 258-260°C. 
By addition of D-gluconic acid to aqueous solution of chlorhexidine base is prepared 1,1'-hexamethylenebis(5-(pchlorophenyl)biguanide)digluconate (1:2).

brand name
Dyna-Hex (Xttrium); Hibiclens (Regent); Peridex (Zila); Periochip (Dexcel); Periogard (Colgate); Prevacare (Johnson & Johnson).

Therapeutic Function

Antiseptic
Clinical Use
1,6-Di(4 -chlorophenyldiguanido)hexane gluconate (Hibiclens) is the most effective of a series of antibacterial biguanides originallydeveloped in Great Britain.
The antimicrobial properties of the biguanides were discoveredas a result of earlier testing of these compounds aspossible antimalarial agents. 
Although thebiguanides are technically not bisquaternary ammoniumcompounds and, therefore, should probably be classifiedseparately, they share many physical, chemical, and antimicrobialproperties with the cationic surfactants. 
The biguanides are strongly basic, and they exist as dications at physiological pH. 
In chlorhexidine, the positive charges arecounterbalanced by gluconate anions. 
Likecationic surfactants, these undergo inactivation when mixedwith anionic detergents and complex anions such as phosphate,carbonate, and silicate.
Chlorhexidine has broad-spectrum antibacterial activitybut is not active against acid-fast bacteria, spores, orviruses. 
It has been used for such topical uses as preoperativeskin disinfection, wound irrigation, mouthwashes, andgeneral sanitization.
Chlorhexidine is not absorbed through skin or mucous membranes and does not causesystemic toxicity.
Chlorhexidine digluconate Preparation Products And Raw materials

Raw materials
4-Chlorobenzenamine hydrochloride

ChlorhexidineDigluconate,20%Solution
ChlorhexidineGluconate20%SolutionChlorhexidineGluconate20%SolutionBp/Usp/Ep
ChlorhedineGluconate
CHLOROHEXIDINE DIGLUCONATE
CHLOROHEXIDINE GLUCONATE
CHLOROHEXIDINE DIGLUCONATE, SOLUTION
Chlorhexdine digluconate
Chlorhexidin bigluconate
D-Gluconic acid, compd. with N,N-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)
chlorhexidine digluconate solution
CHLORHEIXIDINE GLUCONATE
CHLORHEXIDINE GLUCONATE SOLID
CHLORHEXIDINE GLUCONATE SOLUTION
Chlorhexidindigluconat
1,1'-Hexamethylenebis(5-[p-chlorophenyl]biguanide)
CHLORHEXIDINE DIGLUCONATE 20% SOLUTION IN WATER
Chlorhexidine digluconate, 20% w/v aq. soln.
Chlorhexidine digluconate, 20% wv Aqueous Solution, BP
Chlorhexidine solution digluconate
arlacideg
bacticlens
caswellno.481g
chlorhexidinedi-d-gluconate
chlorhexidinedigluconate20%aqueous*solution
chlorhexidinglukonatu
compd.withn,n’’-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-d-gluconicaci
corsodyl
d-)(2:1
d-gluconicacid,compd.withn,n’’-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-t
disteryl
etraazatetradecanediimidamide(2:1)
gluconicacid,compd.with1,1’-hexamethylenebis(5-(p-chlorophenyl)biguanide
hibiclens
hibidil
hibiscrub
hibitane5
orahexal
peridex(antiseptic)
placout
plurexid
Chlorhexidine digluconate solution,20% in H2O
Chlorhexidine gluconate (jp15/usp)
D00858
Hibiclens (tn)
Peridex (tn)
Periogard
Periogard (tn)
Chlorhexidine digluconate w/v aq. soln.
Chlorhexidine digluconate, 20% w/v aq. soln. (non-sterile)
Chlorhexidini G1uconate solution
2-[amino-[6-[[amino-[[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexylimino]methyl]-1-(4-chlorophenyl)guanidine
Chlorhexidine Digluconate (20% in Water)
CHLORHEXIDINE GLUCONATE 20% SOLUTION
CHLORHEXADINE GLUCONATE 20%
CHLORHEXIDINE DIGLUCONATE 20% AQUEOU
Chlorhexidine digluconate, Non-sterile
D-Digluconate
Glucose acid chloride


Chlorhexidine gluconate
D-gluconic acid, compound with N,N''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine (2:1)
EC Inventory
D-gluconic acid, compound with N,N''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine (2:1)
D-gluconic acid, compound with N,N′′-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine(2:1) (CHDG)
N,N''-bis(4-Chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine digluconate

Translated names
5,5′-bis(4-chlorfenyl)-1,1′-(hexan-1,6-diyl)bis(biguanid)-bis(d-glukonát) (CHDG) (cs)
Acid D-gluconic, compus cu N,N′′-bis(4-clorofenil)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidină (2:1) (CHDG) (ro)
Acide D-gluconique, composé avec N,N″-bis(4-chlorophényl)-3,12-diimino-2,4,11,13-tétraazatétradécanediamidine (2:1) (CHDG) (fr)
Acido D-gluconico, composto con N,N′′- bis(4-clorofenil)-3,12-diimmino-2,4,11,13-tetraazatetradecanodiammidina (2:1) (CHDG) (it)
Aċidu D-glukonik ma' N,N′′-bis(4-klorofenil)-3,12-diimino-2,4,11,13-tetraażatetradekanediammidin (2:1) (CHDG) (mt)
D-glikonskābe, savienojums ar N,N′′-bis(4-hlorfenil)-3,12-diimino-2,4,11,13-tetraazatetradekāndiamidīnu (2:1) (CHDG) (lv)
D-gliukono rūgšties ir N,N′′-bis(4-chlorfenil)-3,12-diimino-2,4,11,13- tetraazatetradekandiamidino junginys (2:1) (CHDG) (lt)
D-gluconic acid, compound with N,N′′-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine (2:1) (CHDG) (no)
D-gluconsyre, forbindelse med N,N″-bis(4-chlorphenyl)-3,12-diimino-2,4,11,13-tetraazatetradecandiamidin (2:1) (CHDG) (da)
D-Gluconsäure, Verbindung mit N,N′′-Bis(4-chlorphenyl)-3,12-diimino-2,4,11,13-tetraazatetradecandiamidin (2:1) (CHDG)) (de)
D-gluconzuur, verbinding met N,N′′-bis(4-chloorfenyl)-3,12-diimino-2,4,11,13-tetraazatetradecaandiamidine (2:1) (CHDG) (nl)
D-glukonihappo, yhdiste N,N′′-bis(4-kloorifenyyli)-3,12-di-imino-2,4,11,13-tetra-atsatetradekaanidiamidiinin kanssa (2:1) (CHDG) (fi)
D-glukonsav reakcióterméke N,N′′-bisz(4-klórfenil)-3,12-diimino-2,4,11,13-tetraaza-tetradekán-diamidinnel (2:1) (CHDG) (hu)
D-glukonska kiselina, spoj s N,N′′-bis(4-klorofenil)-3,12-diimino-2,4,11,13-tetraazatetradekandiamidinom (2:1) (CHDG) (hr)
D-glukonska kislina, spojina z N,N''-bis(4-klorofenil)-3,12-diimino-2,4,11,13-tetraazatetradekandiamidinom (2:1) (CHDG) (sl)
D-glukonsyra, förening med N,N′′-bis(4-klorofenyl)-3,12-diimino-2,4,11,13-tetraazatetradekandiamidin (2:1) (CHDG) (sv)
D-glükoonhappe ja N,N′′-bis(4-klorofenüül)-3,12-diimino-2,4,11,13-tetraasatetradekaandiamidiini ühend (2:1) (CHDG) (et)
D-глюконова киселина, свързана с N,N′′-бис(4-хлорофенил)-3,12-диимино-2,4,11,13-тетраазатетрадекандиамидин (2:1) (CHDG) (bg)
Kwas d-glukonowy, związek z N,N″- bis(4-chlorofenylo)-3,12-diimino- 2,4,11,13-tetraazatetradekanodiamidyną (2:1) (CHDG) (pl)
kyselina D-glukónová, zlúčenina s N,N′′-bis(4-chlórfenyl)-3,12-diimino-2,4,11,13-tetraazatetradekánbis(amidimidom) (2:1) (CHDG) (sk)
Ácido D-glucónico, composto com N,N′′-bis(4-clorofenil)-3,12-diimino-2,4,11,13-tetrazatetradecanodiamidina (2:1) (CHDG) (pt)
Ácido D-glucónico, compuesto con N,N′′-bis(4-clorofenil)-3,12-diimino-2,4,11,13-tetraazatetradecanodiamidina (2:1) (CHDG) (es)
Ένωση D-γλυκονικού οξέος με N,N′′-δις(4-χλωροφαινυλο)-3,12-διιμινο-2,4,11,13-τετραζαδεκατετρανοδιαμιδίνη (2:1) (CHDG) (el)

CAS names
D-Gluconic acid, compd. with N1,N14-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)

IUPAC names
(1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine;(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
(1E)-2-[6-[[amino-[[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine; (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
1,1′-(hexane-1,6-diyl)bis[5-(4-chlorophenyl)biguanide] di-d-gluconate
bis((2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid); N-(4-chlorophenyl)-1-3-(6-{N-[3-(4-chlorophenyl)carbamimidamidomethanimidoyl]amino}hexyl)carbamimidamidomethanimidamide
Chlorhexidin digluconat

Chlorhexidine digluconate
D-gluconic acid, compound with N,N''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine (2:1)
Chlorhexidine gluconate
Chlorhexidine gluconate solution
Chlorohexidine gluconate 20% (CHG)

Clariant product trade name:Vivhex-G
D-Gluconic acid, compd. with N1,N14-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)
D-Gluconic acid, compound with N,N''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine (2:1)
D-gluconic acid, compound with N,N''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine (2:1)
N',N'''''-hexane-1,6-diylbis[N-(4-chlorophenyl)(imidodicarbonimidic diamide)] - D-gluconic acid (1:2)
N,N''-Bis(4-chlorphenyl)-3,12-diimino-2,4,11,13-tetraazatetradecandiimidamid compound with D-Gluconic acid (1:2)
Spectradyne
Trade names
CHDG
Registration dossier


Synonyms:
     arlacide G
     betasept
     chloraprep
     chlorhexamed
     chlorhexidine bigluconate
     chlorhexidine D-digluconate
     chlorhexidine di-D-gluconate
4-    chlorhexidine digluconate
     chlorhexidine gluconate
N,N''-bis(4-    chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide di-D-gluconate
1,6-bis(5-(p-    chlorophenyl)biguandino)hexane digluconate
     corsodyl
     disteryl
D-    gluconic acid compd. with N,N''-Bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)
1,1'-    hexamethylene bis(5-(p-chlorophenyl)biguanide), digluconate
1,1'-    hexamethylenebis(5-(p-chlorophenyl)biguanide) di-D-gluconate
1,1'-    hexamethylenebis(5-(p-chlorophenyl)biguanide)digluconate
N',N'''''-    hexane-1,6-diylbis[N-(4-chlorophenyl)(imidodicarbonimidic diamide)] - D-gluconic acid (1:2)
N,N''''-    hexane-1,6-diylbis[N'-(4-chlorophenyl)(imidodicarbonimidic diamide)] - D-gluconic acid (1:2)
N,N''''-1,6-    hexanediylbis[N'-(4-chlorophenyl)(imidodicarbonimidic diamide)] - D-gluconic acid (1:2)
     hexidine
     hibident
     hibisol
     imidodicarbonimidic diamide, N,N''''-1,6-hexanediylbis[N'-(4-chlorophenyl)-, compd. with D-gluconic acid (1:2)
     manusan
     maskin R
     orahexal
(2R,3S,4R,5R)-2,3,4,5,6-    pentahydroxyhexanoic acid - N',N'''''-hexane-1,6-diylbis[N-(4-chlorophenyl)(imidodicarbonimidic diamide)] (2:1)
(2R,3S,4R,5R)-2,3,4,5,6-    pentahydroxyhexans�ure--N,N''''-hexan-1,6-diylbis[N'-(4-chlorphenyl)(imidodicarbonimidic diamid)](2:1)
     phiso-med
     plurexid
     rotersept
     sterilon
2,4,11,13-    tetraazatetradecanediimidamide, N,N''-bis(4-chlorophenyl)-3,12-diimino-, di-D-gluconate
2,4,11,13-    tetraazatetradecanediimidamide, N,N''-bis(4-chlorophenyl)-3,12-diimino-, digluconate
     unisept


English    chlorhexidine digluconate
French    digluconate de chlorhexidine
Spanish    digluconato de clorhexidina
German    Chlorhexidindigluconat
Dutch    chlorhexidinedigluconaat

EINECS    242-354-0
CAS    18472-51-0
Chemical formula    C22H30Cl2N10.2C6H12O7
English    D-gluconic acid, compound with N,N''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine (2:1)
French    acide D-gluconique, composé avec N,N''-bis(4-chlorophényl)-3,12-diimino-2,4,11,13-tétraazatétradécanediamidine (2:1)
Spanish    ácido D-glucónico, composto con N,N''-bis(4-clorofenil)-3,12-diimino-2,4,11,13-tetraazatetradecanodiamidina (2:1)
German    D-Gluconsäure, Verbindung mit N,N''-Bis(4-chlorphenyl)-3,12-diimino-2,4,11,13-tetraazatetradecandiamidin (2:1)

Chlorhexidine is a bactericidal antiseptic effective against a large range of vegetative gram positive and gram negative bacteria, but it is more effective against gram positive bacteria. 
Some species of Pseudomonas and Proteus are relatively less susceptible. 
Chlorhexidine is ineffective against acidfast bacteria, bacterial spores, fungi and viruses.
As a cationic material chlorhexidine is incompatible with soaps and other anionic materials.
Chlorhexidine is incompatible with borates, bicarbonates, carbonates, chlorides, citrates, phosphates and sulfates, forming salts of low solubility which may precipitate from solution after standing.
Chlorhexidine is most active at a neutral pH; its activity is reduced by organic matter (blood, serum, etc.) and by phospholipids.

INDICATIONS AND CLINICAL USE
Baxedin® 20% must always be diluted before use.
Baxedin® 20% only contains 20% chlorhexidine (w/v) without any surfactant.

Hospital setting

General disinfection and skin cleansing.
Preoperative skin preparation.
Preoperative hand scrub.
Prolonged storage of sterile instruments.
Emergency disinfection of clean medical and surgical instruments.
Disinfection of respiratory and anesthetic equipment.

Chlorhexidine is a bisbiguanide antisep-tic and disinfectant that is bactericidal or bacteriostatic against a wide range of gram-positive and gram-negative bacteria. 
It inhibits mycobacteria, fungi and some viruses. Chlorhexidine is most active at a neutral or slightly acidic pH. 
It is used for disinfection of skin, clean instruments and hard surfaces in a concentration of 0.05 to 0.5% in water or 70% alcohol.

Chlorhexidine Gluconate 20% is a high-quality antiseptic for a wide range of indications. 
Chlorhexidine is used for its antiseptic action above all in dentistry and dental care, as well as for cleaning and disinfection of wounds. 

It can be used as a preservative in cosmetics at a maximum concentration of 0.3%. 
Worked into hair and skin care products or into nappy or intimate care products, Chlorhexidine Gluconate 20% has a conserving effect that protects the formulation against microbial spoiling. 
Chlorhexidine is an attractively priced raw material that can even be used as the sole preservative in a formulation. 


Chlorhexidine Gluconate 20% Solution is a broad spectrum bacteriostatis antiseptic agent, oral care agent, disinfectant, cosmetic biocide, and preservative.

Chlorhexidine Gluconate 20% is very effective against plaque, oral flora including Candida and is active against gram-positive and gram- negative organisms, facultative anaerobes, aerobes, and yeast. 
It can be used in antiseptic soap, mouthwash that fights plaque, disinfecting wounds and burns, vaginal flushing, hair dyes and bleaches, makeup, and other skin and hair care products.

Chlorhexidine Gluconate is mainly available in OTC products to clean and prepare the skin before surgery and before injections in order to help reduce bacteria that potentially can cause skin infections. 
These products are available as solutions, washes, sponges, and swabs and under many different brand names.


Definition of Antiseptic (Anti-Infective Agents, Local)
Substances used on humans and animals that destroy harmful microorganisms or inhibit their activity.

Topical use

Surgical scrub and antiseptic hand rinse for healthcare personnel
Skin cleanser for preoperative skin preparation, skin wound and general skin cleanser for patients
Oral use

Oral rinse: 0.12% Antibacterial dental rinse for gingivitis treatment
Periodontal chip: Adjunctive therapy to reduce pocket depth in patients with periodontitis
Veterinary use

Effective protection against Mastitis by cows
Used in the general dairy hygiene of milk producing animals
Typical concentration as antiseptic is 0,5 – 4% of Chlorhexidine Di Gluconate

 

Chlorhexidine is an antiseptic that is mainly used to prevent plaque and gingivitis in dental medicinal products like toothpaste, liquid dental care product or mouth rinses and sprays. 
Chlorhexidine is also used on plasters, in ointments or powders and as an effective preservative against bacteria and fungi in cosmetics.


CHLORHEXIDINE SALTS have a very wide range of applications in the fields of human health and personal care, food handling and animal health. 
Proven effective against both gram-positive and gram-negative organisms, they also have a fungicidal and sporicidal effect.

Although one of Chlorhexidine’s primary benefits is its tremendous ability to kill bacteria on contact, it has an additional benefit that is perhaps more important – a residual effect that prevents microbial regrowth after application. 
This gives Chlorhexidine a clear advantage over other products such as Triclosan, PCMX or alcohols.

AS A RESULT Chlorhexidine is one of the strongest, most effective antimicrobials available. 
From its importance in surgical procedures…to its effectiveness in animal disinfection…to its role in treating gingivitis, Chlorhexidine is widely used in today’s marketplace.

ATAMAN CHEMICALS is your preferred partner for Chlorhexidine and it’s salts produced under GMP and supported by DMF’s, a CEP and the ECHA authorization to sell Chlorhexidine digluconate as a biocidal active product.


General surgery and clinical use: preoperative skin preparation, disinfection of instruments (except those containing cemented glass), surface disinfection (e.g. operating tables).


 

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