2091. Chlorhexidine
Nomenclature
CAS number: 55-56-1
N,N″-Bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide; 1,1′-hexamethylenebis[5-(p-chlorophenyl)biguanide]; 1,6-bis[N′-(p-chlorophenyl)-N5-biguanido]hexane; 1,6-bis(N5-p-chlorophenyl-N′-diguanido)hexane; 1,6-di(4′-chlorophenyldiguanido)hexane; 10040. C22H30Cl2N10; mol wt 505.45.
C 52.28%, H 5.98%, Cl 14.03%, N 27.71%.
Description and references
Bisbiguanide with bacteriostatic activity. Prepn: Rose, Swain, J. Chem. Soc. 1956, 4422; eidem, US 2684924 (1954 to I.C.I.). Antibacterial activity and acute toxicity: G. E. Davies et al., Br. J. Pharmacol. 9, 192 (1954). LC-MS determn in hemolyzed blood: K. Usui et al., J. Chromatogr. B 831, 105 (2006). Review of toxicology and clinical uses: D. M. Foulkes, J. Periodontal Res. 8, Suppl. 12, 55-60 (1973). Series of articles on clinical efficacy in gingivitis and plaque control: ibid. 21, Suppl. 16, 1-89 (1986). Clinical trial in prevention of nosocomial infection: P. Segers et al., J. Am. Med. Assoc. 296, 2460 (2006).
Properties
Crystals from methanol, mp 134°. Strong alkaline reaction. Soly in water at 20°: 0.08% (w/v).Derivative
Dihydrochloride.Nomenclature
CAS number: 3697-42-5
C.E.T. HEXtra (Virbac); Nolvasan (Fort Dodge). C22H30Cl2N10.2HCl; mol wt 578.37.
C 45.69%, H 5.58%, Cl 24.52%, N 24.22%.
Properties
Crystals, dec 260-262°. Soly in water at 20°: 0.06 g/100 ml.Derivative
Diacetate.Nomenclature
CAS number: 56-95-1
Chlorasept 2000 (Baxter). C22H30Cl2N10.2C2H4O2; mol wt 625.55.
C 49.92%, H 6.12%, Cl 11.33%, N 22.39%, O 10.23%.
Properties
Crystals, mp 154-155°. Neutral reaction. Soly in water at 20°: 1.9 g/100 ml. Aq solns dec when heated above 70°. Soluble in alcohol, glycerol, propylene glycol, polyethylene glycols. LD50 orally in mice: 2 g/kg (Davies).Derivative
d-Digluconate.Nomenclature
CAS number: 18472-51-0
Biorgasept (Biorga); Chlorhexamed (GSK); Collunovar (Dexo); Corsodyl (GSK); Diaseptyl (Fabre); Dosiseptive (Gifrer Barbezat); Exoseptoplix (Tonipharm); Hibident (SKB); Hibidil (CSP); Hibiscrub (CSP); Hibisprint (CSP); Hibitane (CSP); Merfene (Novartis); Paroex (CSP); Peridex (Zila); Plurexid (UCB); Prexidine (Expanscience); Secalan (Zyma); Septeal (Fabre); Unisept (Unichem). Properties
Soly in water at 20°: >50% (w/v). LD50 in mice (mg/kg): 22 i.v.; 1800 orally (Foulkes).Use
Ingredient in mouth rinses, contact lens cleaners, burn creams and cosmetics.Therapeutic Category
Antiseptic; disinfectant.
Therapeutic Category (Veterinary)
Antiseptic; disinfectant.Keywords
Antiseptic/Disinfectant; Guanidines