DrugBank ID:

DB00878

Description:

Chlorhexidine is a broad-spectrum antimicrobial biguanide used as a topical antiseptic and in dental practice for the treatment of inflammatory dental conditions caused by microorganisms.It is one of the most common skin and mucous membrane antiseptic agents in use today.The molecule itself is a cationic bis-guanide consisting of two 4-chlorophenyl rings and two biguanide groups joined by a central hexamethylene chain.Topical chlorhexidine for disinfection, as well as oral rinses for dental use, carries activity against a broad range of pathogens including bacteria, yeasts, and viruses.Chlorhexidine was developed in the UK by Imperial Chemical Industries in the early 1950sand was introduced to the US in the 1970s. [DrugBank]

Targets:

Bacterial outer membrane (Bacteria) [DrugBank]

Pharmacodynamics:

Chlorhexidine is a broad-spectrum antimicrobial with demonstrated activity against both gram-positive and gram-negative bacteria, yeasts, and viruses.2 Antimicrobial activity is dose-dependent - chlorhexidine is bacteriostatic at lower concentrations (0.02%-0.06%) and bactericidal at higher concentrations (>0.12%).2 Pharmacokinetic studies of oral chlorhexidine rinses indicate that approximately 30% of the active ingredient is retained in the mouth following rinsing, which is subsequently slowly released into oral fluids.11 This ability to adsorb to dentine, shared with tetracycline antibiotics such as doxycycline, is known as "substantivity" and is the result of chlorhexidine's positive charge - it is likely that this substantivity plays at least some role in chlorhexidine's antimicrobial activity, as its persistence on surfaces such as dentine prevent microbial colonization.7 [DrugBank]

SMILES:

NC(=N\CCCCCC/N=C(N)/N=C(\N)Nc1ccc(Cl)cc1)/N=C(\N)Nc1ccc(Cl)cc1

2D structures:  

3D structures: