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Chlorhexidine digluconate 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 Chlorhexidine digluconate's 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.
Given the promising results of the trials, in 2013 the World Health Organization (WHO) added Chlorhexidine digluconate 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.
CAS: 18472-51-0
MF: C28H42Cl2N10O7
MW: 701.61
EINECS: 242-354-0
Chlorhexidine digluconate's mechanism of action involves destabilization of the outer bacterial membrane.
Chlorhexidine digluconate is effective on both Gram-positive and Gram-negative bacteria, although it is less effective with some Gram-negative bacteria.
Chlorhexidine digluconate has both bactericidal and bacteriostatic mechanisms of action, the mechanism of action being membrane disruption, not ATPase inactivation as previously thought.
Chlorhexidine digluconate is also useful against fungi and enveloped viruses, though this has not been extensively investigated.
Chlorhexidine digluconate is harmful in high concentrations, but is used safely in low concentrations in many products, such as mouthwash and contact lens solutions.
Chlorhexidine digluconate is a bisbiguanide antiseptic and disinfectant, which is bactericidal or bacteriostatic against a wide range of gram negative and gram positive vegetative bacteria, yeasts, dermatophyte fungi and lipophilic viruses.
The antimicrobial activity covers most of the important species occurring in the oral microflora.
Due to Chlorhexidine digluconate's cationic nature, chlorhexidine digluconate binds strongly to skin, mucosa and other tissues and is thus very poorly absorbed.
No detectable blood levels have been found following oral use.
Chlorhexidine digluconate is an antiseptic agent.
This differs from an antibiotic which targets only specific classes of bacteria.
Chlorhexidine digluconate would fall into a similar category of antiseptic agents such as bleach.
Unlike bleach, Chlorhexidine digluconate is safe to use on the skin and other bodily surfaces.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Chlorhexidine digluconate is an antimicrobial irrigant that is used as an antiseptic for the skin in the healthcare industry.
Chlorhexidine digluconate is used in hospitals to prevent infection of patients during surgeries and can also be found in mouthrinses.
Chlorhexidine digluconate is with purity 20%min; Chlorhexidine digluconate’s an almost colorless or pale-yellow transparent liquid, odorless, miscible with water, sparingly soluble in alcohol and acetone.
Chlorhexidine digluconate is a cationic surface active preservative with broad-spectrum antibacterial effect.
Antiseptic for disinfection.
Chlorhexidine digluconate's mechanism of action is to alter the permeability of bacterial cell membranes.
Chlorhexidine digluconate Chemical Properties
Density: 1.06 g/mL at 25 °C(lit.)
Vapor pressure: 0.005Pa at 25℃
Storage temp.: 2-8°C
Solubility: water: soluble50% (w/v)
Form: Liquid
Color: Colorless
Water Solubility: 750g/L at 20℃
λmax: 257nm(H2O)(lit.)
Sensitive: Light Sensitive
Merck: 14,2091
InChIKey: YZIYKJHYYHPJIB-UUPCJSQJSA-N
LogP: -1.81 at 20.7℃
CAS DataBase Reference: 18472-51-0(CAS DataBase Reference)
EPA Substance Registry System: Chlorhexidine digluconate (18472-51-0)
Chlorhexidine digluconate, a surface active agent type bactericide, has a fairly strong broad-spectrum antibacterial and bactericidal effect, and is effective against both Gram-positive and gram-negative bacteria.
Chlorhexidine digluconate has fast and long-lasting effects, has extremely low toxicity, is hardly absorbed by the body, and is harmless to the human body.
There is no irritation and allergic reaction to various tissues at effective concentrations.
Pharmacological action
Chlorhexidine digluconate is a cationic surface active preservative with a broad-spectrum antibacterial effect.
For disinfection and antiseptic.
The mechanism of action is to change the permeability of the bacterial cell membrane.
Certain Staphylococcus, Streptococcus mutans, Streptococcus salivarius, Candida albicans, Escherichia coli and anaerobic propionic acid bacteria are highly sensitive to it, Streptococcus haemophilus is moderately sensitive, Proteus, Pseudomonas, Klebsiella and Gram-negative cocci (such as Veillonella) are low-sensitive.
Chlorhexidine digluconate's antibacterial effect on Gram-positive and negative bacteria is stronger than disinfectants such as benzalkonium bromide.
Chlorhexidine digluconate is still effective in the presence of serum and blood.
The mechanism of action of Chlorhexidine digluconate is to be adsorbed on the osmotic barrier of the bacterial cytoplasmic membrane, allowing the cell contents to leak out and exert an antibacterial effect.
Low concentration has antibacterial effect, high concentration has bactericidal effect.
Uses
Chlorhexidine digluconate is a preservative generally used in concentrations of 0.01 to 0.1 percent to protect against bacteria.
Chlorhexidine digluconate is unstable at high temperatures.
Chlorhexidine digluconate is more widely used in europe than in the united States.
Hydrogenolysis of benzyl-nitrogen bonds.
Chlorhexidine digluconate is an antimicrobial irrigant that is used as an antiseptic for the skin in the healthcare industry.
Chlorhexidine digluconate is used in hospitals to prevent infection of patients during surgeries and can also be found in mouthrinses.
Chlorhexidine digluconate 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 digluconate is positively charged and reacts with the negatively charged microbial cell surface, thereby destroying the integrity of the cell membrane.
Subsequently, Chlorhexidine digluconate 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 is a broad spectrum bacteriostatis antiseptic agent, oral care agent, disinfectant, cosmetic biocide, and preservative.
Chlorhexidine digluconate is very effective against plaque, oral flora including Candida and is active against gram-positive and gram-negative organisms, facultative anaerobes, aerobes, and yeast.
Chlorhexidine digluconate 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.
Clinical Use
Chlorhexidine digluconate 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 the biguanides 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 atphysiological pH.
In Chlorhexidine digluconate, the positive charges arecounterbalanced by gluconate anions (not shown).
Likecationic surfactants, these undergo inactivation when mixedwith anionic detergents and complex anions such as phosphate,carbonate, and silicate.
Chlorhexidine digluconate has broad-spectrum antibacterial activitybut is not active against acid-fast bacteria, spores, orviruses.
Chlorhexidine digluconate has been used for such topical uses as preoperativeskin disinfection, wound irrigation, mouthwashes, andgeneral sanitization.
Chlorhexidine digluconate is not absorbedthrough skin or mucous membranes and does not causesystemic toxicity.
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).
Biochem/physiol Actions
Cationic broad-spectrum antimicrobial agent belonging to the bis(biguanide) family.
Chlorhexidine digluconate's mechanism of action involves destabilization of the outer bacterial membrane.
Chlorhexidine digluconate is used primarily as a topical antiseptic/disinfectant in wound healing, at catheterization sites, in various dental applications and in surgical scrubs.
Synonyms
CHLORHEXIDINE DIGLUCONATE
18472-51-0
Chlorhexidine gluconate
Hibiclens
Peridex
Dyna-hex
Bioscrub
Chlorhexidine D-digluconate
Exidine
Microderm
Periochip
Periogard
Unisept
Brian Care
Steri-Stat
Cida-Stat
Hibistat
Pharmaseal Scrub Care
CHG SCRUB
Prevacare
Chlorhexidine di-D-gluconate
MOR84MUD8E
NSC-753971
Hibiscrub
Hibitane
1,1'-Hexamethylene bis(5-(p-chlorophenyl)biguanide), digluconate
1,1'-Hexamethylenebis(5-(p-chlorophenyl)biguanide) di-D-gluconate
Bacticlens
Chlorhexamed
Kleersight
Corsodyl
Disteryl
Hibident
Hibidil
Orahexal
Plurexid
Septeal
Abacil
Fight bac
Plac out
Prevacare R
Arlacide G
Hibitane 5
2,4,11,13-Tetraazatetradecanediimidamide, N,N''-bis(4-chlorophenyl)-3,12-diimino-, di-D-gluconate
Chlorhexidin glukonatu
Peridex (antiseptic)
Bactoshield CHG 2%
Caswell No. 481G
UNII-MOR84MUD8E
PwrioChip
Chlorhexidin glukonatu [Czech]
1,6-Bis(N5-[p-chlorophenyl]-N1-biguanido)hexane
pHiso-Med
Hibitane gluconate
Hibiclens (TN)
Periogard (TN)
DRG-0091
EINECS 242-354-0
Peridex (TN)
MFCD00083599
Chlohexidine gluconate
EPA Pesticide Chemical Code 045504
READYPREP CHG
Chlorhexidine gluconate [USAN:USP:JAN]
EC 242-354-0
SCHEMBL34468
1,6-Bis(5-(p-chlorophenyl)biguandino)hexane digluconate
CHEMBL4297088
DTXSID5034519
CHEBI:28312
1,1'-Hexamethylenebis(5-(p-chlorophenyl)biguanide) gluconate
1,1'-Hexamethylenebis(5-(p-chlorophenyl)biguanide)digluconate
Biguanide, 1,1'-hexamethylenebis(5-(p-chlorophenyl)-, digluconate
Chlorhexidine gluconate (JP17/USP)
CHLORHEXIDINE GLUCONATE [JAN]
CHLORHEXIDINE GLUCONATE [USAN]
AKOS015896303
AKOS025310696
CHLORHEXIDINE GLUCONATE [MART.]
CHLORHEXIDINE GLUCONATE [VANDF]
NSC 753971
CHLORHEXIDINE D-DIGLUCONATE [MI]
CHLORHEXIDINE DIGLUCONATE [INCI]
CHLORHEXIDINE GLUCONATE [WHO-DD]
D-Gluconic acid, compound with N,N''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine (2:1)
CHLORHEXIDINE GLUCONATE [ORANGE BOOK]
CHLORHEXIDINE GLUCONATE [USP IMPURITY]
AVAGARD COMPONENT CHLORHEXIDINE GLUCONATE
C08038
D00858
SOLUPREP COMPONENT CHLORHEXIDINE GLUCONATE
CHLORAPREP COMPONENT CHLORHEXIDINE GLUCONATE
CHLORHEXIDINE GLUCONATE COMPONENT OF AVAGARD
CHLORHEXIDINE GLUCONATE COMPONENT OF SOLUPREP
J-011837
CHLORHEXIDINE GLUCONATE COMPONENT OF CHLORAPREP
1,1'-Hexamethylenebis[5-(4-chlorophenyl)biguanide] Digluconate
Chlorhexidine digluconate, Pharmaceutical Secondary Standard; Certified Reference Material
1,1'-Hexamethylenebis[5-(p-chlorophenyl)biguanide] (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid(1:2)
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
2,4,11,13-Tetraazatetradecanediimidamide, N,N'-bis(4-chlorophenyl)-3,12-diimino-, di-D-gluconate
D-Gluconic acid, compd with N,N''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)
N',N'''''-hexane-1,6-diylbis[N-(4-chlorophenyl)(imidodicarbonimidic diamide)]--D-gluconic acid (1/2)
