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Chlorhexidine

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Chlorhexidine
Clinical data
ATC code
Pharmacokinetic data
Protein binding87%
Identifiers
  • N',N'''''-hexane-1,6-diylbis[N-(4-chlorophenyl)(imidodicarbonimidic diamide)]
CAS Number
PubChem CID
DrugBank
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.000.217 Edit this at Wikidata
Chemical and physical data
FormulaC22H30Cl2N10
Molar mass505.446 g/mol g·mol−1
3D model (JSmol)
  • Clc2ccc(NC(=N/C(=N/CCCCCC/N=C(/N=C(N)Nc1ccc(Cl)cc1)N)N)N)cc2
  (verify)

Chlorhexidine is a chemical antiseptic.[1] It kills (is bactericidal too) both gram-positive and gram-negative microbes, although it is less effective with some gram-negative microbes.[2] It is also bacteriostatic.

The mechanism of action is membrane disruption, and not ATPase inactivation as previously thought.[3]

It also shows activity with enveloped viruses, though this has not been extensively investigated.

Products containing chlorhexidine in high concentrations must be kept away from eyes and the ears, due to the risk of damage to those organs. However, chlorhexidine is safely used in very low concentrations in some contact lens solutions.

Availability

Chlorhexidine is present in oral rinses and skin cleansers, and in small quantities it is used as a preservative.

It is sometimes marketed under the brand names Peridex, Periochip, Perichlor or Periogard Oral Rinse. In the UK it is mainly marketed under the brand name Corsodyl (or Chlorohex); in Germany as Chlorhexamed; in Australia and New Zealand as Savacol; in India as Suthol (G. D. Pharmaceuticals), Clohex or Dejavu-MW (QUADRA); in Venezuela as Perioxidina or Peridont, and in some Central American countries as Clorexil.

As a skin cleanser, it is marketed under brand names such as Hibiclens, Hibiscrub, or Dexidin mainly as a surgical scrub, and is also available as a wound wash. It is also used in some acne skin washes. In some countries, it is available by prescription only.

Dental

File:Chlorhexidine mouthrinse.png
OTC mouthwash containing chlorhexidine from Mexico.

It is often used as an active ingredient in mouthwash designed to reduce dental plaque and oral bacteria. Chlorhexidine can thus be used to improve bad breath.[4] It has been shown to have an immediate bactericidal action and a prolonged bacteriostatic action due to adsorption onto the pellicle-coated enamel surface.[5]

Chlorhexidine-based products are usually utilized to combat or prevent gum diseases such as gingivitis. According to Colgate,[6] chlorhexidine gluconate has not been proven to reduce subgingival calculus and in some studies actually increased deposits. When combined with xylitol, a synergistic effect has been observed.[7]

Chlorhexidine's role in preventing tooth decay (dental caries) is controversial.[8] Continued use of products containing chlorhexidine for long periods can cause stains on teeth, especially on silicate and resin restorations; prolonged use can also alter taste sensation - this latter symptom can be reversed by ceasing use of chlorhexidine.[9] A version which stains the teeth less has been developed.[10] Chlorhexidine is neutralized by common toothpaste additives such as sodium lauryl sulfate (SLS) and sodium monofluorophosphate (MFP). Although data is limited, in order to maximize effectiveness it may be best to keep a 30-minute to 2-hour interval between brushing and using the mouthwash.[11]

Topical

OTC topical scrub containing chlorhexidine available in the United States.
OTC topical scrub containing chlorhexidine available in the United States.

Chlorhexidine is also used in non-dental applications, most notably under the brand names Oronine, Avagard, Hibiclens, Hibiscrub, ChloraPrep, ChloraScrub, BIOPATCH, SOLU-I.V. and Exidine. It is also a component of the household antiseptic Savlon. It is used for general skin cleansing, a surgical scrub, and a pre-operative skin preparation. Due to other chemicals listed as inactive ingredients, the cleanser solution is not suitable for use as mouthwash. It is often used as a rubbing agent prior to the use of hypodermic or intravenous needles in place of iodine. Chlorhexidine is contraindicated for use near the meninges, in body cavities, and near the eyes and ears. At the 2% concentration, it can cause serious and permanent injury with prolonged contact with the eye or if instilled through a perforated eardrum. Nevertheless, a topical solution of 0.02% chlorhexidine is recommended by the US Centers for Disease Control and Prevention (CDC) as treatment for keratitis caused by Acanthamoeba. As a scrub, chlorhexidine is not recommended on persons under two months of age.

Use in animals

For use in animals, it is used as a topical disinfectant of wounds. It is more effective in killing bacteria (bactericidal) than both povidone-iodine and saline, and has residual effects up to 6 hours. Some common brand names are ChlorhexiDerm, ResiChlor, Germi-STAT Antimicrobial Skin Cleanser, Nolvasan Skin and Wound Cleaner, and Nolvasan Ointment. It is also more beneficial to wound healing than using saline solutions alone.[12] Note, however, that problems[13] including deafness[14] have been associated with the use of chlorhexidine products in cats. It is commonly used to manage the skin infections suffered by Westie dogs.

Deactivation

Chlorhexidine is deactivated by anionic compounds, including the anionic surfactants commonly used as detergents in toothpastes and mouthwashes. For this reason, chlorhexidine mouth rinses should be used at least 30 minutes after other dental products.[15] For best effectiveness, food, drink, smoking, and mouth rinses should be avoided for at least one hour after use.

Though effective in the presence of blood, soap, and pus, activity is reduced.[16]

References

  1. ^ "Chlorhexidine Official FDA information, side effects and uses". Drug information Online. Drugs.com. Revised 11/2006. Retrieved 2007-10-08. {{cite web}}: Check date values in: |date= (help) Drugs.com states that this information comes directly from the FDA
  2. ^ "THE MOST COMMON TOPICAL ANTIMICROBIALS". Care of the umbilical cord. World Health Organization. 1998. Retrieved 2007-10-08.
  3. ^ Kuyyakanond T, Quesnel LB. (1992-12-15). "The mechanism of action of chlorhexidine". FEMS Microbiol Lett. 79: 211–215. doi:10.1111/j.1574-6968.1991.tb04531.x. PMID 1335944. {{cite journal}}: |access-date= requires |url= (help)
  4. ^ http://www.freshbreath.ca/fbcpubs.html
  5. ^ Jenkins S, Addy M, Wade W (1988). "The mechanism of action of chlorhexidine. A study of plaque growth on enamel inserts in vivo". J. Clin. Periodontol. 15 (7): 415–24. doi:10.1111/j.1600-051X.1988.tb01595.x?cookieSet=1. PMID 3183067. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  6. ^ "Colgate PerioGard chlorhexidine gluconate oral rinse 0.12% (Rx)".
  7. ^ Decker EM, Maier G, Axmann D, Brecx M, von Ohle C (2008). "Effect of xylitol/chlorhexidine versus xylitol or chlorhexidine as single rinses on initial biofilm formation of cariogenic streptococci". Quintessence Int. 39 (1): 17–22. PMID 18551212. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  8. ^ Autio-Gold J (2008). "The role of chlorhexidine in caries prevention". Oper Dent. 33 (6): 710–6. doi:10.2341/08-3. PMID 19051866.
  9. ^ Effects of chlorhexidine on human taste perception. [Arch Oral Biol. 1995] - PubMed Result
  10. ^ Bernardi F, Pincelli MR, Carloni S, Gatto MR, Montebugnoli L (2004). "Chlorhexidine with an Anti Discoloration System. A comparative study". Int J Dent Hyg. 2 (3): 122–6. doi:10.1111/j.1601-5037.2004.00083.x. PMID 16451475. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  11. ^ Kolahi J, Soolari A (2006). "Rinsing with chlorhexidine gluconate solution after brushing and flossing teeth: a systematic review of effectiveness". Quintessence Int. 37 (8): 605–12. PMID 16922019. {{cite journal}}: Unknown parameter |month= ignored (help)
  12. ^ Sanchez IR, Swaim SF, Nusbaum KE, Hale AS, Henderson RA, McGuire JA (1988). "Effects of chlorhexidine diacetate and povidone-iodine on wound healing in dogs". Vet Surg. 17 (6): 291–5. doi:10.1111/j.1532-950X.1988.tb01019.x. PMID 3232321.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  13. ^ http://www.addl.purdue.edu/newsletters/1996/winter/psrd.shtml
  14. ^ http://www.petplace.com/cats/deafness-in-cats/page2.aspx
  15. ^ Denton W , Chlorhexidine In: Sterilisation and Preservation 5th Edition, Block SS, eds. Lippincott Williams & Williams, Philadelphia, 2001; 321-36.
  16. ^ World Health Organization, Care of the Umbilical Cord/annex, http://www.who.int/reproductive-health/publications/MSM_98_4/MSM_98_4_annex.en.html
  • Drugs.com states that this information comes directly from the FDA.
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