Chemical Properties
Almost colourless or pale-yellowish liquid.
Originator
Abacil,Polfa-Lodz SA,Poland
Definition
ChEBI: Chlorhexidine gluconate is an organochlorine compound and a D-gluconate adduct. It has a role as an antibacterial agent. It is functionally related to a chlorhexidine.
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
General Description
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.
Flammability and Explosibility
Notclassified
Biochem/physiol Actions
Cationic broad-spectrum antimicrobial agent belonging to the bis(biguanide) family. Its mechanism of action involves destabilization of the outer bacterial membrane. It is used primarily as a topical antiseptic/disinfectant in wound healing, at catheterization sites, in various dental applications and in surgical scrubs.
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. Thebiguanides 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 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 absorbedthrough skin or mucous membranes and does not causesystemic toxicity.
