Chlorhexidine: Difference between revisions
ElectroWolf (talk | contribs) Reference only mention skin desinfection solutions as eye damaging. Tags: Mobile edit Mobile web edit |
ElectroWolf (talk | contribs) Added references for eye safety, more examples exist if anyone wishes to contest it. Tags: Mobile edit Mobile web edit |
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Side effects may include skin irritation, teeth discoloration, and [[allergic reactions]].<ref name=BNF69>{{cite book|title=British national formulary : BNF 69|date=2015|publisher=British Medical Association|isbn=9780857111562|pages=568, 791, 839|edition=69}}</ref> Topical solutions may cause eye problems if direct contact occurs.<ref name=AHFS2017/> Use in [[pregnancy]] appears to be safe.<ref>{{cite book|last1=Briggs|first1=Gerald G.|last2=Freeman|first2=Roger K.|last3=Yaffe|first3=Sumner J.|title=Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk|date=2011|publisher=Lippincott Williams & Wilkins|isbn=9781608317080|page=252|url=https://books.google.ca/books?id=OIgTE4aynrMC&pg=PA252|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170113121448/https://books.google.ca/books?id=OIgTE4aynrMC&pg=PA252|archivedate=2017-01-13|df=}}</ref> Chlorhexidine may come mixed in [[ethanol|alcohol]], water, or [[surfactant solution]].<ref name=BNF69/> It is effective against a range of [[microorganisms]], but does not inactivate [[spores]].<ref name=WHO2008/> |
Side effects may include skin irritation, teeth discoloration, and [[allergic reactions]].<ref name=BNF69>{{cite book|title=British national formulary : BNF 69|date=2015|publisher=British Medical Association|isbn=9780857111562|pages=568, 791, 839|edition=69}}</ref> Topical solutions may cause eye problems if direct contact occurs.<ref name=AHFS2017/> Low concentration 0.05% solutions (presumably aqueous)<ref>{{cite web |title=Experimental evaluation of chlorhexidine gluconate for ocular antisepsis |url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC180025/}}</ref> is used preoperatively for eye surgery in Sweden.<ref>{{cite web |title=Preoperative preparation of eye with chlorhexidine solution significantly reduces bacterial load prior to 23-gauge vitrectomy in Swedish health care |url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6042411/}}</ref> Use in [[pregnancy]] appears to be safe.<ref>{{cite book|last1=Briggs|first1=Gerald G.|last2=Freeman|first2=Roger K.|last3=Yaffe|first3=Sumner J.|title=Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk|date=2011|publisher=Lippincott Williams & Wilkins|isbn=9781608317080|page=252|url=https://books.google.ca/books?id=OIgTE4aynrMC&pg=PA252|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170113121448/https://books.google.ca/books?id=OIgTE4aynrMC&pg=PA252|archivedate=2017-01-13|df=}}</ref> Chlorhexidine may come mixed in [[ethanol|alcohol]], water, or [[surfactant solution]].<ref name=BNF69/> It is effective against a range of [[microorganisms]], but does not inactivate [[spores]].<ref name=WHO2008/> |
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Revision as of 17:34, 24 May 2019
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Clinical data | |
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Pronunciation | klɔːˈhɛksɪdiːn |
Trade names | Betasept, ChloraPrep, Chlorostat, others |
Other names | 1,6-bis(4-chloro-phenylbiguanido)hexane |
AHFS/Drugs.com | Monograph |
Routes of administration | topical, mouth wash |
ATC code | |
Legal status | |
Legal status |
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Identifiers | |
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CAS Number | |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.000.217 |
Chemical and physical data | |
Formula | C22H30Cl2N10 |
Molar mass | 505.446 g/mol g·mol−1 |
3D model (JSmol) | |
Melting point | 134 to 136 °C (273 to 277 °F) |
Solubility in water | 0.8 mg/mL (20 °C) |
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Chlorhexidine, also known as chlorhexidine gluconate (CHG), is a disinfectant and antiseptic that is used for skin disinfection before surgery and to sterilize surgical instruments.[2] It may be used both to disinfect the skin of the patient and the hands of the healthcare providers.[3] It is also used for cleaning wounds, preventing dental plaque, treating yeast infections of the mouth, and to keep urinary catheters from blocking.[3] It is used as a liquid or powder.[2][3]
Side effects may include skin irritation, teeth discoloration, and allergic reactions.[3] Topical solutions may cause eye problems if direct contact occurs.[1] Low concentration 0.05% solutions (presumably aqueous)[4] is used preoperatively for eye surgery in Sweden.[5] Use in pregnancy appears to be safe.[6] Chlorhexidine may come mixed in alcohol, water, or surfactant solution.[3] It is effective against a range of microorganisms, but does not inactivate spores.[2]
Chlorhexidine came into medical use in the 1950s.[7] It is on the World Health Organization's List of Essential Medicines, the safest and most effective medicines needed in a health system.[8] Chlorhexidine is available over the counter.[1] The wholesale cost in the developing world is about US$2.20–4.10 per liter of 5% solution.[9] In the United Kingdom this amount costs the NHS about £4.80.[3] In 2016 it was the 230th most prescribed medication in the United States with more than 2 million prescriptions.[10]
Uses
Chlorhexidine is used in disinfectants (disinfection of the skin and hands), cosmetics (additive to creams, toothpaste, deodorants, and antiperspirants), and pharmaceutical products (preservative in eye drops, active substance in wound dressings and antiseptic mouthwashes).[11]
In endodontics, chlorhexidine is used for root canal irrigation and as an intracanal dressing,[12][13][14] but has been replaced by the use of sodium hypochlorite bleach in much of the developed world.
Antiseptic
There is tentative evidence that it is more effective than povidone-iodine.[15]
CHG is active against Gram-positive and Gram-negative organisms, facultative anaerobes, aerobes, and yeasts.[16] It is particularly effective against Gram-positive bacteria (in concentrations ≥ 1 µg/l). Significantly higher concentrations (10 to more than 73 μg/ml) are required for Gram-negative bacteria and fungi. Chlorhexidine is ineffective against polioviruses and adenoviruses. The effectiveness against herpes viruses has not yet been established unequivocally.[17]
Chlorhexidine, like other cation-active compounds, remains on the skin. It is frequently combined with alcohols (ethanol and isopropyl alcohol).
Dental use
![](http://upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Perichlor%2C_0.12%25_chlorhexidine_glucomate_solution_medication.jpg/220px-Perichlor%2C_0.12%25_chlorhexidine_glucomate_solution_medication.jpg)
Use of a CHG-based mouthwash in combination with normal tooth care can help reduce the build-up of plaque and improve mild gingivitis.[18] Such mouthwash also has a number of adverse effects including damage to the mouth lining, tooth discoloration, tartar build-up, and impaired taste.[18] Extrinsic tooth staining occurs when chlorhexidine rinse has been used for 4 weeks or longer.[19]
Mouthwashes containing chlorhexidine which stain teeth less than the classic solution have been developed, many of which contain chelated zinc.[20][21][22]
Using chlorhexidine as a supplement to everyday mechanical oral hygiene procedures for 4 to 6 weeks and 6 months leads to a moderate reduction in gingivitis compared to placebo, control or mechanical oral hygiene alone.[23]
Chlorhexidine is a cation which interacts with anionic components of toothpaste, such as sodium lauryl sulfate and sodium monofluorophosphate, and forms salts of low solubility and antibacterial activity. Hence, to enhance the antiplaque effect of chlorhexidine, "it seems best that the interval between toothbrushing and rinsing with CHX [chlorhexidine] be more than 30 minutes, cautiously close to 2 hours after brushing.".[24]
Topical
Nepal was the first country in the world to use chlorhexidine to treat the umbilical cord of newborn babies, and received a USAID Pioneers Prize for reducing the neonatal death rate.[25] Chlorhexidine is very effective for poor countries like Nepal and its use is growing in the world for treating the umbilical cord. A 2015 Cochrane review has yielded high-quality evidence that within the community setting, chlorhexidine skin or cord care can reduce the incidence of omphalitis (inflammation of the umbilical cord) by 50% and also neonatal mortality by 12%.[26] Chlorhexidine gluconate is used as a skin cleanser for surgical scrubs, a cleanser for skin wounds, for preoperative skin preparation and germicidal hand rinses.[16] Chlorhexidine eye drops have been used as a treatment for eyes affected by Acanthamoeba keratitis.[27]
Side effects
CHG is ototoxic; if put into an ear canal which has a ruptured eardrum, it can lead to deafness.[28]
CHG does not meet current European specifications for a hand disinfectant. Under the test conditions of the European Standard EN 1499, no significant difference in the efficacy was found between a 4% solution of chlorhexidine digluconate and soap.[17] In the U.S., between 2007 and 2009, Hunter Holmes McGuire Veterans Administration Medical Center conducted a cluster-randomized trial and concluded that daily bathing of patients in intensive care units with washcloths saturated with chlorhexidine gluconate reduced the risk of hospital-acquired infections.[29]
Whether prolonged exposure over many years may have carcinogenic potential is still not clear. The Federal Drug Administration (FDA) in the USA recommendation is to limit the use of a chlorhexidine gluconate mouthwash to a maximum of six months.[30]
Once digested CHG is poorly absorbed into gastrointestinal tract.[31][32] If aspirated into the lungs at high enough concentration, as reported in one case, it can be fatal due to the high risk of acute respiratory distress syndrome.[32][33]
Mechanism of action
At physiologic pH, chlorhexidine salts dissociate and release the positively charged chlorhexidine cation. The bactericidal effect is a result of the binding of this cationic molecule to negatively charged bacterial cell walls. At low concentrations of chlorhexidine, this results in a bacteriostatic effect; at high concentrations, membrane disruption results in cell death.[16]
Chemistry
It is a cationic polybiguanide (bisbiguanide).[34] It is used primarily as its salts (e.g., the dihydrochloride, diacetate, and digluconate).[citation needed]
Deactivation
Chlorhexidine is deactivated by forming insoluble salts with anionic compounds, including the anionic surfactants commonly used as detergents in toothpastes and mouthwashes, anionic thickeners such as carbomer, and anionic emulsifiers such as acrylates/C10-30 alkyl acrylate crosspolymer, among many others. For this reason, chlorhexidine mouth rinses should be used at least 30 minutes after other dental products.[35] For best effectiveness, food, drink, smoking, and mouth rinses should be avoided for at least one hour after use. Many topical skin products, cleansers, and hand sanitizers should also be avoided to prevent deactivation when chlorhexidine (as a topical by itself or as a residue from a cleanser) is meant to remain on the skin.[citation needed]
Synthesis
The structure is based on two molecules of proguanil, linked with a hexamethylenediamine spacer.
![](http://upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Chlorhexidine_synthesis.png/700px-Chlorhexidine_synthesis.png)
Brands
Chlorhexidine topical is sold as Betasept, Biopatch, Calgon Vesta, ChloraPrep One-Step, Dyna-Hex, Hibiclens, Hibistat Towelette, Scrub Care Exidine, Spectrum-4 among others.[37]
Chlorhexidine gluconate mouth rinse is sold as Paroex, Peridex, PerioChip, Periogard among others.[38]
Terminology
Chlorhexidine breaks down as chlor(o) + hex(ane) + id(e) + (am)ine), is a cationic polybiguanide. It is used primarily as its gluconate salt.
Veterinary medicine
In animals, chlorhexidine is used for topical disinfection of wounds,[39] and to manage skin infections.[40] Chlorhexidine-based disinfectant products are used within the dairy farming industry.[41]
Post-surgical respiratory problems have been associated with the use of chlorhexidine products in cats.[42]
See also
References
- ^ a b c "Chlorhexidine Gluconate topical". The American Society of Health-System Pharmacists. Archived from the original on 13 January 2017. Retrieved 8 January 2017.
{{cite web}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ a b c WHO Model Formulary 2008 (PDF). World Health Organization. 2009. pp. 321–22. ISBN 9789241547659. Archived from the original (PDF) on 13 December 2016. Retrieved 8 January 2017.
{{cite book}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ a b c d e f British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 568, 791, 839. ISBN 9780857111562.
- ^ "Experimental evaluation of chlorhexidine gluconate for ocular antisepsis".
- ^ "Preoperative preparation of eye with chlorhexidine solution significantly reduces bacterial load prior to 23-gauge vitrectomy in Swedish health care".
- ^ Briggs, Gerald G.; Freeman, Roger K.; Yaffe, Sumner J. (2011). Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk. Lippincott Williams & Wilkins. p. 252. ISBN 9781608317080. Archived from the original on 2017-01-13.
{{cite book}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ Schmalz, Gottfried; Bindslev, Dorthe Arenholt (2008). Biocompatibility of Dental Materials. Springer Science & Business Media. p. 351. ISBN 9783540777823. Archived from the original on 2017-01-13.
{{cite book}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived from the original (PDF) on 13 December 2016. Retrieved 8 December 2016.
{{cite web}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ "Chlorhexidine Gluconate". International Drug Price Indicator Guide. Archived from the original on 10 May 2017. Retrieved 8 December 2016.
{{cite web}}
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- ^ Thomas Güthner; et al. (2007), "Guanidine and Derivatives", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 13
- ^ Raab D: Preparation of contaminated root canal systems – the importance of antimicrobial irrigants. DENTAL INC 2008: July / August 34–36.
- ^ Raab D, Ma A: Preparation of contaminated root canal systems – the importance of antimicrobial irrigants. 经感染的根管系统的修复 – 化学冲洗对根管治疗的重要性DENTAL INC Chinese Edition 2008: August 18–20.
- ^ Raab D: "Die Bedeutung chemischer Spülungen in der Endodontie". Endodontie Journal 2010: 2; 22–23. http://www.oemus.com/archiv/pub/sim/ej/2010/ej0210/ej0210_22_23_raab.pdf
- ^ Dumville, JC; McFarlane, E; Edwards, P; Lipp, A; Holmes, A; Liu, Z (21 April 2015). "Preoperative skin antiseptics for preventing surgical wound infections after clean surgery". The Cochrane Database of Systematic Reviews (4): CD003949. doi:10.1002/14651858.CD003949.pub4. PMID 25897764.
- ^ a b c Leikin, Jerrold B.; Paloucek, Frank P., eds. (2008), "Chlorhexidine Gluconate", Poisoning and Toxicology Handbook (4th ed.), Informa, pp. 183–84
- ^ a b Hans-P. Harke (2007), "Disinfectants", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 10–11
- ^ a b James P, Worthington HV, Parnell C, Harding M, Lamont T, Cheung A, Whelton H, Riley P (2017). "Chlorhexidine mouthrinse as an adjunctive treatment for gingival health". Cochrane Database Syst Rev. 3: CD008676. doi:10.1002/14651858.CD008676.pub2. PMID 28362061.
- ^ James, Patrice; Worthington, Helen V; Parnell, Carmel; Harding, Maireas; Lamont, Thomas; Cheung, Andrea; Whelton, Helen; Riley, Philip (31 March 2017). "Chlorhexidine mouthrinse as an adjunctive treatment for gingival health". Cochrane Database of Systematic Reviews. 3: CD008676. doi:10.1002/14651858.CD008676.pub2. PMID 28362061.
- ^ Bernardi F, Pincelli MR, Carloni S, Gatto MR, Montebugnoli L (August 2004). "Chlorhexidine with an Anti Discoloration System. A comparative study". Int J Dent Hyg. 2 (3): 122–26. doi:10.1111/j.1601-5037.2004.00083.x. PMID 16451475.
- ^ Sanz, M.; Vallcorba, N.; Fabregues, S.; Muller, I.; Herkstroter, F. (1994). "The effect of a dentifrice containing chlorhexidine and zinc on plaque, gingivitis, calculus and tooth staining". Journal of Clinical Periodontology. 21 (6): 431–37. doi:10.1111/j.1600-051X.1994.tb00741.x. PMID 8089246.
- ^ Kumar, S; Patel, S; Tadakamadla, J; Tibdewal, H; Duraiswamy, P; Kulkarni, S (2013). "Effectiveness of a mouthrinse containing active ingredients in addition to chlorhexidine and triclosan compared with chlorhexidine and triclosan rinses on plaque, gingivitis, supragingival calculus and extrinsic staining". International Journal of Dental Hygiene. 11 (1): 35–40. doi:10.1111/j.1601-5037.2012.00560.x. PMID 22672130.
- ^ James, Patrice; Worthington, Helen V; Parnell, Carmell; Harding, Mairead; Lamont, Thomas; Cheung, Andrea; Whelton, Helen; Riley, Philip (31 March 2017). "Chlorhexidine mouthrinse as an adjunctive treatment for gingival". Cochrane Database of Systematic Reviews. 3: CD008676. doi:10.1002/14651858.CD008676.pub2. PMID 28362061.
- ^ Kolahi, J; Soolari, A (September 2006). "Rinsing with chlorhexidine gluconate solution after brushing and flossing teeth: a systematic review of effectiveness". Quintessence International (Berlin, Germany : 1985). 37 (8): 605–12. PMID 16922019.
- ^ "USAID Recognizes the Government of Nepal for their Leadership in Saving Newborn Lives". Embassy of the United States, Kathmandu – Nepal. February 26, 2014. Archived from the original on December 28, 2014.
{{cite news}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ Sinha A, Sazawal S, Pradhan A, Ramji S, Opiyo N (2015). "Chlorhexidine skin or cord care for prevention of mortality and infections in neonates". Cochrane Database Syst Rev. 3 (3): CD007835. doi:10.1002/14651858.CD007835.pub2. PMID 25739381.
- ^ Alkharashi M, Lindsley K, Law HA, Sikder S (2015). "Medical interventions for acanthamoeba keratitis". Cochrane Database Syst Rev. 2 (2): CD0010792. doi:10.1002/14651858.CD010792.pub2. PMC 4730543. PMID 25710134.
- ^ Lai, P; Coulson, C; Pothier, D. D; Rutka, J (2011). "Chlorhexidine ototoxicity in ear surgery, part 1: Review of the literature". Journal of Otolaryngology - Head & Neck Surgery = le Journal d'Oto-rhino-laryngologie et de Chirurgie Cervico-faciale. 40 (6): 437–40. PMID 22420428.
- ^ "Daily Bathing With Antiseptic Agent Significantly Reduces Risk of Hospital-Acquired Infections in Intensive Care Unit Patients". Agency for Healthcare Research and Quality. 2014-04-23. Archived from the original on 2017-01-13. Retrieved 2014-04-29.
{{cite web}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ Below, H.; Assadian, O.; Baguhl, R.; Hildebrandt, U.; Jäger, B.; Meissner, K.; Leaper, D.J.; Kramer, A. (2017). "Measurements of chlorhexidine, p-chloroaniline, and p-chloronitrobenzene in saliva after mouth wash before and after operation with 0.2% chlorhexidine digluconate in maxillofacial surgery: a randomised controlled trial". British Journal of Oral and Maxillofacial Surgery. 55 (2): 150–155. doi:10.1016/j.bjoms.2016.10.007. PMID 27789177.
- ^ "Chlorhexidine Adverse Effects". www.poison.org. Retrieved 2018-07-04.
- ^ a b Pubchem. "Chlorhexidine". pubchem.ncbi.nlm.nih.gov. Retrieved 2018-07-04.
- ^ Hirata, Kiyotaka; Kurokawa, Akira (April 2002). "Chlorhexidine gluconate ingestion resulting in fatal respiratory distress syndrome". Veterinary and Human Toxicology. 44 (2): 89–91. ISSN 0145-6296. PMID 11931511.
An 80-y-old woman with dementia accidentally ingested approximately 200 ml of Maskin (5% CHG) in a nursing home and then presumably aspirated gastric contents.
- ^ Tanzer JM, Slee AM, Kamay BA (1977). "Structural requirements of guanide, biguanide, and bisbiguanide agents for antiplaque activity". Antimicrob. Agents Chemother. 12 (6): 721–9. doi:10.1128/aac.12.6.721. PMC 430011. PMID 931371.
- ^ Denton, Graham W (2000). "Chlorhexidine". In Block, Seymour S (ed.). Disinfection, Sterilization, and Preservation (5th ed.). Lippincott Williams & Wilkins. pp. 321–36. ISBN 978-0-683-30740-5.
{{cite book}}
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ignored (|chapter-url=
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- ^ "Hibiclens Uses, Side Effects & Warnings - Drugs.com". Drugs.com.
- ^ "Chlorhexidine gluconate Uses, Side Effects & Warnings - Drugs.com". Drugs.com. Retrieved 4 August 2018.
- ^ van Hengel, Tosca; ter Haar, Gert; Kirpensteijn, Jolle (2013). "Chapter 2. Wound management: a new protocol for dogs and cats. Chlorhexidine solution". In Kirpensteijn, Jolle; ter Haar, Gert (eds.). Reconstructive Surgery and Wound Management of the Dog and Cat. CRC Press. ISBN 9781482261455.
- ^ Maddison, Jill E.; Page, Stephen W.; Church, David B., eds. (2008). "Antimicrobial agents. Chlorhexidine". Small Animal Clinical Pharmacology. Elsevier Health Sciences. p. 552. ISBN 978-0702028588.
- ^ Blowey, Roger William; Edmondson, Peter (2010). Mastitis Control in Dairy Herds. CABI. p. 120. ISBN 9781845937515.
- ^
Zeman, D; Mosley, J; Leslie-Steen, P (Winter 1996). "Post-Surgical Respiratory Distress in Cats Associated with Chlorhexidine Surgical Scrubs". ADDL Newsletters. Indiana Animal Disease Diagnostic Laboratory. Archived from the original on 2011-09-27. Retrieved 2011-09-11.
{{cite web}}
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