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Chlorhexidine gluconate CHG 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 Chlorhexidine gluconate CHG 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 gluconate CHG is a broad spectrum antiseptic.
CAS: 18472-51-0
MF: C22H30Cl2N10.2C6H12O7
MW: 897.76
EINECS: 242-354-0
Synonyms: ChlorhexidineDigluconate,20%Solution;ChlorhexidineGluconate20%SolutionChlorhexidineGluconate20%SolutionBp/Usp/Ep;ChlorhedineGluconate;CHLOROHEXIDINE DIGLUCONATE;CHLOROHEXIDINE GLUCONATE;CHLOROHEXIDINE DIGLUCONATE, SOLUTION;Chlorhexdine digluconate;Chlorhexidin bigluconate;CHLORHEXIDINE DIGLUCONATE;Chlorhexidine gluconate;18472-51-0;Hibiclens;Bioscrub;Hibistat;Microderm;Periochip;Periogard;Exidine;Peridex;Unisept;Chlorhexidine D-digluconate;Dyna-hex;Brian Care;Steri-Stat;Cida-Stat;Bacticlens;Corsodyl;Disteryl;Hibidil;Kleersight;Orahexal;Plurexid;Prevacare;Septeal;Abacil;Pharmaseal Scrub Care;CHG SCRUB;Fight bac;Plac out;Prevacare R;Arlacide G;Hibitane 5;Chlorhexidine di-D-gluconate;Peridex (antiseptic);Chlorhexidin glukonatu;Bactoshield CHG 2%;Caswell No. 481G;UNII-MOR84MUD8E;MOR84MUD8E;Hibitane gluconate;READYPREP CHG;DRG-0091;EINECS 242-354-0;EPA Pesticide Chemical Code 045504;NSC-753971;CHEBI:28312;1,1'-Hexamethylene bis(5-(p-chlorophenyl)biguanide), digluconate;EC 242-354-0;1,1'-Hexamethylenebis(5-(p-chlorophenyl)biguanide) di-D-gluconate;chlorhexidine;NSC 753971;1,6-Bis(5-(p-chlorophenyl)biguandino)hexane digluconate;Chlorhexidine gluconate [USAN:USP:JAN];1,1'-Hexamethylenebis(5-(p-chlorophenyl)biguanide) gluconate;Hibiscrub;Hibitane;1,1'-Hexamethylenebis(5-(p-chlorophenyl)biguanide)digluconate;Biguanide, 1,1'-hexamethylenebis(5-(p-chlorophenyl)-, digluconate;AVAGARD COMPONENT CHLORHEXIDINE GLUCONATE;SOLUPREP COMPONENT CHLORHEXIDINE GLUCONATE;2,4,11,13-Tetraazatetradecanediimidamide, N,N''-bis(4-chlorophenyl)-3,12-diimino-, di-D-gluconate;CHLORAPREP COMPONENT CHLORHEXIDINE GLUCONATE;Chlorhexamed;Hibident;chlorhexidine bigluconate;CHLORHEXIDINE GLUCONATE (MART.);CHLORHEXIDINE GLUCONATE [MART.];Chlorhexidine gluconate (USAN:USP:JAN);CHLORHEXIDINE GLUCONATE (USP IMPURITY);CHLORHEXIDINE GLUCONATE [USP IMPURITY];Dermachlor;Betasept;Otodine;Vetasan;Dental;Paroex;Davis;PwrioChip;Scrub;TrisOphth;ChlorHex;HexaDermMax;TrisDent;Bactoshield Chg;Chloradine Lube;Chlorhexidin glukonatu [Czech];1,6-Bis(N5-[p-chlorophenyl]-N1-biguanido)hexane;Scrub-stat;TrizChlor Flush;BioHexWipesWipes;CeraSootheCHX;gly4Chlor;Ultra HexFlush;Chloradine Scrub;Dermachlor Rinse;Fresh Mouth;MFCD00083599;Scrub Care;Stomodine F;Vital-Chlor;Hexa-Foam;pHiso-Med;Ultra Hex;1,1'-HBCB;Clx Derm;Hex-Wash;Hexi Dip;Max Chlorhexidine;Oris Chx;Sky Oral Rinse;Clx Derm Spot;Major Oral Rinse;TrizChlor 4;Chlorhexidine 4%;Chlorhexidine Lube;Hex-Tra;VetraSeb CeraDerm;Chlordine 55;Chlordine105;ChlorHex 2X;Hibiclens (TN);Periogard (TN);Chlorhexidine Flush;Chlorhexidine Scrub;Davis Chlorhexidine;Dyna-Hex2;Equine Anti-Fungal;Chlordine 110;Chlordine 510;Dyna-hex 2;Dyna-hex 4;Scrub, Scrub-Stat;Dr. Dean;Peridex (TN);Hex-PLUS;TrizChlor 4 Mousse;Chlorhexidine Shampoo;SUFFUSION;TELFATEAT;Chlohexidine gluconate;Bisbiguanide Teat Dip;Chlordine 110 Dip;Chlorhexidine4% scrub;Chorhexidine Gluconate;Hexi-Dip 1%;Max ChlorhexidineFlush;TrizCHLOR 4 Wipes;Zymadent Dental Wipes;CHLORHEIX-LUBE;VETASAN SCRUB;BLUE RIBBON;Chlorhexidine 4%Scrub;Chlorhexidine Scrub4%;Chlordine Barrier Film;SANI-CLING;Stratford Dental Wipes;FS-106Spray;CHG BARRIER DIP;Chlorhexidine Gluconante;CHLORHEXIDINE2%;Hexi Dip 110;MAX Chlorhexidine 4%;Chem-Star Classic Plus;DYNA-HEX CHG;ChlorHex Maxi Scrub4%;Chlorhexidine Scrub 4%;CHLORHEXIDINESolution;Cutania TrisEDTA Wipes;TrizChlor 4 Conditioner;Antiseptic Foam Handwash;Antiseptic Skin Cleanser;Chlordine 55 Teat Dip;Chlorhexidine Solution2%;Glen Haven TrizChlor 4;Tru-Blu Chlor Hex-Wash;Antiseptic Surgical Scrub;Purell Antimicrobial Foam;Bd E-Z Scrub 107;CLX DERM OTO PLUS;Curaseb Chlorhexidine 4%;Tru-Blu C-Hex 110;Chlordine 105 Teat Dip;Chlordine 510 Teat Dip;Scrub CareExidine-2 CHG;Scrub CareExidine-4 CHG;Antiseptic Cleansing Wipes;BLUE RIBBON SPRA Y;Antimicrobial Foam Handwash
Chlorhexidine gluconate CHG's mechanism of action involves destabilization of the outer bacterial membrane.
Chlorhexidine gluconate CHG is effective on both Gram-positive and Gram-negative bacteria, although it is less effective with some Gram-negative bacteria.
Chlorhexidine gluconate CHG has both bactericidal and bacteriostatic mechanisms of action, the mechanism of action being membrane disruption, not ATPase inactivation as previously thought.
Chlorhexidine gluconate CHG is also useful against fungi and enveloped viruses, though this has not been extensively investigated.
Chlorhexidine gluconate CHG is harmful in high concentrations, but is used safely in low concentrations in many products, such as mouthwash and contact lens solutions.
Chlorhexidine gluconate CHG is an organochlorine compound and a D-gluconate adduct.
Chlorhexidine gluconate CHG has a role as an antibacterial agent.
Chlorhexidine gluconate CHG is functionally related to a chlorhexidine.
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 gluconate CHG is a chlorophenyl biguanide with broad antibacterial action against both Gram (+) and (-) bacteria and fungi.
Chlorhexidine gluconate CHG is a broad-spectrum antiseptic and disinfectant.
Chlorhexidine gluconate CHG is effective to prevent and control infectious diseases of the mouth by killing bacteria in saliva and tongue.
Chlorhexidine gluconate CHG is a cytotoxic agent and induces cell necrosis and apoptosis.
Chlorhexidine gluconate CHG is the salt of Chlorhexidine, which is a disinfectant and topical anti-infective agent for reduction of pocket depth in patients with adult periodontitis.
Chlorhexidine gluconate CHG 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 gluconate CHG (18472-51-0)
Uses
Hydrogenolysis of benzyl-nitrogen bonds.
Chlorhexidine gluconate CHG is an antimicrobial irrigant that is used as an antiseptic for the skin in the healthcare industry.
Chlorhexidine gluconate CHG is used in hospitals to prevent infection of patients during surgeries and can also be found in mouthrinses.
Chlorhexidine gluconate CHG 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 gluconate CHG, a biguanide compound used as an antiseptic agent with topical antibacterial activity.
Chlorhexidine gluconate CHG is positively charged and reacts with the negatively charged microbial cell surface, thereby destroying the integrity of the cell membrane.
Subsequently, Chlorhexidine gluconate CHG 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 gluconate CHG is a broad spectrum bacteriostatis antiseptic agent, oral care agent, disinfectant, cosmetic biocide, and preservative.
Chlorhexidine gluconate CHG 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 gluconate CHG 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 CHG is a preservative generally used in concentrations of 0.01 to 0.1 percent to protect against bacteria.
Chlorhexidine gluconate CHG is unstable at high temperatures.
Chlorhexidine gluconate CHG is more widely used in europe than in the united States.
Clinical Use
Chlorhexidine gluconate CHG 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 ammonium compounds 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, 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 gluconate CHG has broad-spectrum antibacterial activitybut is not active against acid-fast bacteria, spores, orviruses.
Chlorhexidine gluconate CHG has been used for such topical uses as preoperativeskin disinfection, wound irrigation, mouthwashes, andgeneral sanitization.
Chlorhexidine gluconate CHG 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 gluconate CHG 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 gluconate CHG's mechanism of action involves destabilization of the outer bacterial membrane.
Chlorhexidine gluconate CHG is used primarily as a topical antiseptic/disinfectant in wound healing, at catheterization sites, in various dental applications and in surgical scrubs.
