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Wikipedia

Chlorhexidine

November 02, 2023

Chlorhexidine[1] is a disinfectant and antiseptic with the molecular formula C22H30Cl2N10, which is used for skin disinfection before surgery and to sterilize surgical instruments.[2] 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 a powder.[2][3] It is commonly used in salt form, either the gluconate[4] or the acetate.[5]

Chlorhexidine
Clinical data
Pronunciationklɔː(r)ˈhɛksɪdiːn
Trade namesBetasept, ChloraPrep, Chlorostat, others
Other namesCHX, CHG, 1,6-bis(4-chloro-phenylbiguanido)hexane
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: A
Routes of
administration		Topical
ATC code
Legal status
Legal status
  • AU: S5, S6, S7
  • US: OTC / Rx-only
Identifiers
  • N,N′′′′1,6-Hexanediylbis[N′-(4-chlorophenyl)(imidodicarbonimidic diamide)]
CAS Number
  • 55-56-1 Y
PubChem CID
  • 9552079
DrugBank
  • DB00878 Y
ChemSpider
  • 2612 Y
UNII
  • R4KO0DY52L
KEGG
  • D07668 Y
ChEBI
  • CHEBI:3614 Y
ChEMBL
  • ChEMBL790 Y
CompTox Dashboard (EPA)
  • DTXSID2033314
ECHA InfoCard100.000.217
Chemical and physical data
FormulaC22H30Cl2N10
Molar mass505.45 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point134 to 136 °C (273 to 277 °F)
Solubility in water0.8
  • Clc1ccc(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc2ccc(Cl)cc2)cc1
  • InChI=1S/C22H30Cl2N10/c23-15-5-9-17(10-6-15)31-21(27)33-19(25)29-13-3-1-2-4-14-30-20(26)34-22(28)32-18-11-7-16(24)8-12-18/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34) Y
  • Key:GHXZTYHSJHQHIJ-UHFFFAOYSA-N Y
  (verify)

Side effects may include skin irritation, tooth discoloration, and allergic reactions,[3] although the risk appears to be the same as other topical antiseptics.[6][7] Chlorhexidine rinse is also known to have a bitter metallic aftertaste. Rinsing with water is not recommended as it is known to increase the bitterness.[8] It may cause eye problems if direct contact occurs.[9] Use in pregnancy appears to be safe.[10] Chlorhexidine may come mixed in alcohol,[11][12][13] 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.[14] Chlorhexidine is available over the counter in the United States.[9] It is on the World Health Organization's List of Essential Medicines.[15][16] In 2020, it was the 273rd most commonly prescribed medication in the United States, with more than 1 million prescriptions.[17][18]

Uses edit

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).[19] A 2019 Cochrane review concluded that based on very low certainty evidence in those who are critically ill "it is not clear whether bathing with chlorhexidine reduces hospital-acquired infections, mortality, or length of stay in the ICU, or whether the use of chlorhexidine results in more skin reactions."[20]

In endodontics, chlorhexidine has been used for root canal irrigation and as an intracanal dressing[21][22] but has been replaced by the use of sodium hypochlorite bleach in much of the developed world.[citation needed]

Antiseptic edit

Chlorhexidine is active against Gram-positive and Gram-negative organisms, facultative anaerobes, aerobes, and yeasts.[23] 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.[24]

There is strong evidence that chlorhexidine is more effective than povidone-iodine for clean surgery.[25][26] Evidence shows that it is an effective antiseptic for upper limb surgery.[6]

Meta-data spanning several decades shows that the efficacy of chlorhexidine (against organisms that cause surgical site infection) has not changed,[27] dispelling concerns over emerging resistance.

Dental use edit

 
Perichlor brand 0.12% chlorhexidine gluconate solution

Use of a chlorhexidine-based mouthwash in combination with normal tooth care can help reduce the build-up of plaque and improve mild gingivitis.[28] There is not enough evidence to determine the effect in moderate to severe gingivitis.[28] Its use as a mouthwash has a number of adverse effects including damage to the mouth lining, tooth discoloration, tartar build-up, and impaired taste.[28] Extrinsic tooth staining occurs when chlorhexidine rinse has been used for 4 weeks or longer.[28]

Mouthwashes containing chlorhexidine which stain teeth less than the classic solution have been developed, many of which contain chelated zinc.[29][30][31]

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 reduced 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".[32]

Topical edit

Chlorhexidine gluconate is used as a skin cleanser for surgical scrubs, as a cleanser for skin wounds, for preoperative skin preparation, and for germicidal hand rinses.[23] Chlorhexidine eye drops have been used as a treatment for eyes affected by Acanthamoeba keratitis.[33]

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 neonatal mortality by 12%.[34]

Side effects edit

Chlorhexidine is ototoxic (toxic to the inner ear). If put into an ear canal which has a ruptured eardrum, it can lead to deafness.[35]

Chlorhexidine 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.[24] 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.[36]

Whether prolonged exposure over many years may have carcinogenic potential is still not clear. The US Food and Drug Administration recommendation is to limit the use of a chlorhexidine gluconate mouthwash to a maximum of six months.[37]

When ingested, chlorhexidine is poorly absorbed in the gastrointestinal tract and can cause stomach irritation or nausea.[38][39] 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.[39][40]

Mechanism of action edit

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.[23]

Chemistry edit

It is a cationic polybiguanide (bisbiguanide).[41]

Deactivation edit

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.[42]

Synthesis edit

The structure is based on two molecules of proguanil, linked with a hexamethylenediamine spacer.

 
Two routes for chlorhexidine synthesis:[43] U.S. Patent 2,684,924 (1954 to I.C.I.). The compounds designated (...)2 are substituted hexanes.

Society and culture edit

Brands edit

Chlorhexidine topical is sold as Betasept, Biopatch, Calgon Vesta, ChloraPrep One-Step, Dyna-Hex, Hibiclens, Hibistat Towelette, Scrub Care Exidine, Spectrum-4 among others.[44]

Chlorhexidine gluconate mouthwash is sold as Dentohexin, Paroex, Peridex, PerioChip, Corsodyl and Periogard, among others.[45]

Veterinary medicine edit

In animals, chlorhexidine is used for topical disinfection of wounds,[46] and to manage skin infections.[47] Chlorhexidine-based disinfectant products are used in the dairy farming industry.[48]

Post-surgical respiratory problems have been associated with the use of chlorhexidine products in cats.[49]

References edit

  1. ^ Varoni E, Tarce M, Lodi G, Carrassi A (September 2012). "Chlorhexidine (CHX) in dentistry: state of the art". Minerva Stomatologica. 61 (9): 399–419. PMID 22976567. from the original on 30 September 2021. Retrieved 30 September 2021.
  2. ^ a b c World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 321–22. hdl:10665/44053. ISBN 9789241547659.
  3. ^ a b c d British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 568, 791, 839. ISBN 9780857111562.
  4. ^ "Chlorhexidine Gluconate". PubChem. Retrieved 1 July 2023.
  5. ^ "Chlorhexidine Acetate". PubChem. Retrieved 1 July 2023.
  6. ^ a b Wade RG, Bourke G, Wormald JC, Totty JP, Stanley GH, Lewandowski A, et al. (November 2021). "Chlorhexidine versus povidone-iodine skin antisepsis before upper limb surgery (CIPHUR): an international multicentre prospective cohort study". BJS Open. 5 (6): zrab117. doi:10.1093/bjsopen/zrab117. PMC 8677347. PMID 34915557.
  7. ^ Wade RG, Burr NE, McCauley G, Bourke G, Efthimiou O (December 2021). "The Comparative Efficacy of Chlorhexidine Gluconate and Povidone-iodine Antiseptics for the Prevention of Infection in Clean Surgery: A Systematic Review and Network Meta-analysis". Annals of Surgery. 274 (6): e481–e488. doi:10.1097/SLA.0000000000004076. PMID 32773627. S2CID 225289226.
  8. ^ "Chlorhexidine (Oral Route) Precautions - Mayo Clinic". www.mayoclinic.org. Retrieved 27 June 2023.
  9. ^ a b "Chlorhexidine Gluconate topical". The American Society of Health-System Pharmacists. from the original on 13 January 2017. Retrieved 8 January 2017.
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  11. ^ "Prevantics Swab- chlorhexidine gluconate and isopropyl alcohol solution". DailyMed. 26 October 2022. from the original on 24 January 2023. Retrieved 24 January 2023.
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  20. ^ Lewis SR, Schofield-Robinson OJ, Rhodes S, Smith AF (August 2019). "Chlorhexidine bathing of the critically ill for the prevention of hospital-acquired infection". The Cochrane Database of Systematic Reviews. 8 (8): CD012248. doi:10.1002/14651858.CD012248.pub2. PMC 6718196. PMID 31476022.
  21. ^ Raab D (July–August 2008). "Preparation of contaminated root canal systems – the importance of antimicrobial irrigants". Dental Inc.: 34–36.
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  23. ^ a b c Leikin JB, Paloucek FP, eds. (2008). "Chlorhexidine Gluconate". Poisoning and Toxicology Handbook (4th ed.). Informa. pp. 183–84.
  24. ^ a b Harke HP (2007). "Disinfectants". Ullman's Encyclopedia of Industrial Chemistry (7th ed.). Wiley. pp. 10–11.
  25. ^ Wade RG, Burr NE, McCauley G, Bourke G, Efthimiou O (December 2021). "The Comparative Efficacy of Chlorhexidine Gluconate and Povidone-iodine Antiseptics for the Prevention of Infection in Clean Surgery: A Systematic Review and Network Meta-analysis". Annals of Surgery. 274 (6): e481–e488. doi:10.1097/SLA.0000000000004076. PMID 32773627.
  26. ^ Dumville JC, McFarlane E, Edwards P, Lipp A, Holmes A, Liu Z (April 2015). "Preoperative skin antiseptics for preventing surgical wound infections after clean surgery". The Cochrane Database of Systematic Reviews. 2015 (4): CD003949. doi:10.1002/14651858.CD003949.pub4. PMC 6485388. PMID 25897764.
  27. ^ Aftab R, Dodhia VH, Jeanes C, Wade RG (January 2023). "Bacterial sensitivity to chlorhexidine and povidone-iodine antiseptics over time: a systematic review and meta-analysis of human-derived data". Scientific Reports. 13 (1): 347. Bibcode:2023NatSR..13..347A. doi:10.1038/s41598-022-26658-1. PMC 9825506. PMID 36611032.
  28. ^ a b c d James P, Worthington HV, Parnell C, Harding M, Lamont T, Cheung A, et al. (March 2017). "Chlorhexidine mouthrinse as an adjunctive treatment for gingival health". The Cochrane Database of Systematic Reviews. 3 (3): CD008676. doi:10.1002/14651858.CD008676.pub2. PMC 6464488. PMID 28362061.
  29. ^ Bernardi F, Pincelli MR, Carloni S, Gatto MR, Montebugnoli L (August 2004). "Chlorhexidine with an Anti Discoloration System. A comparative study". International Journal of Dental Hygiene. 2 (3): 122–126. doi:10.1111/j.1601-5037.2004.00083.x. PMID 16451475.
  30. ^ Sanz M, Vallcorba N, Fabregues S, Müller I, Herkströter F (July 1994). "The effect of a dentifrice containing chlorhexidine and zinc on plaque, gingivitis, calculus and tooth staining". Journal of Clinical Periodontology. 21 (6): 431–437. doi:10.1111/j.1600-051X.1994.tb00741.x. PMID 8089246.
  31. ^ Kumar S, Patel S, Tadakamadla J, Tibdewal H, Duraiswamy P, Kulkarni S (February 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.
  32. ^ Kolahi J, Soolari A (September 2006). "Rinsing with chlorhexidine gluconate solution after brushing and flossing teeth: a systematic review of effectiveness". Quintessence International. 37 (8): 605–612. PMID 16922019.
  33. ^ Alkharashi M, Lindsley K, Law HA, Sikder S (February 2015). "Medical interventions for acanthamoeba keratitis". The Cochrane Database of Systematic Reviews. 2015 (2): CD010792. doi:10.1002/14651858.CD010792.pub2. PMC 4730543. PMID 25710134.
  34. ^ Sinha A, Sazawal S, Pradhan A, Ramji S, Opiyo N (March 2015). "Chlorhexidine skin or cord care for prevention of mortality and infections in neonates". The Cochrane Database of Systematic Reviews. 3 (3): CD007835. doi:10.1002/14651858.CD007835.pub2. PMID 25739381. S2CID 16586836.
  35. ^ Lai P, Coulson C, Pothier DD, Rutka J (December 2011). "Chlorhexidine ototoxicity in ear surgery, part 1: review of the literature". Journal of Otolaryngology - Head & Neck Surgery. 40 (6): 437–440. PMID 22420428.
  36. ^ "Daily Bathing With Antiseptic Agent Significantly Reduces Risk of Hospital-Acquired Infections in Intensive Care Unit Patients". Agency for Healthcare Research and Quality. 23 April 2014. from the original on 13 January 2017. Retrieved 29 April 2014.
  37. ^ Below H, Assadian O, Baguhl R, Hildebrandt U, Jäger B, Meissner K, et al. (February 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". The British Journal of Oral & Maxillofacial Surgery. 55 (2): 150–155. doi:10.1016/j.bjoms.2016.10.007. PMID 27789177.
  38. ^ "Chlorhexidine Adverse Effects". www.poison.org. from the original on 5 July 2018. Retrieved 4 July 2018.
  39. ^ a b "Chlorhexidine". Pubchem. U.S. National Library of Medicine. from the original on 5 July 2018. Retrieved 4 July 2018.
  40. ^ Hirata K, Kurokawa A (April 2002). "Chlorhexidine gluconate ingestion resulting in fatal respiratory distress syndrome". Veterinary and Human Toxicology. 44 (2): 89–91. PMID 11931511. An 80-y-old woman with dementia accidentally ingested approximately 200 mL of Maskin (5% chlorhexidine) in a nursing home and then presumably aspirated gastric contents.
  41. ^ Tanzer JM, Slee AM, Kamay BA (December 1977). "Structural requirements of guanide, biguanide, and bisbiguanide agents for antiplaque activity". Antimicrobial Agents and Chemotherapy. 12 (6): 721–729. doi:10.1128/aac.12.6.721. PMC 430011. PMID 931371.
  42. ^ Denton GW (2000). "Chlorhexidine". In Block SS (ed.). Disinfection, Sterilization, and Preservation (5th ed.). Lippincott Williams & Wilkins. pp. 321–36. ISBN 978-0-683-30740-5. from the original on 12 January 2023. Retrieved 10 October 2016.
  43. ^ Rose FL, Swain G (1956). "850. Bisdiguanides having antibacterial activity". Journal of the Chemical Society (Resumed): 4422. doi:10.1039/JR9560004422.
  44. ^ "Hibiclens Uses, Side Effects & Warnings - Drugs.com". Drugs.com. from the original on 4 August 2018. Retrieved 4 August 2018.
  45. ^ "Chlorhexidine gluconate Uses, Side Effects & Warnings - Drugs.com". Drugs.com. from the original on 28 August 2021. Retrieved 4 August 2018.
  46. ^ van Hengel T, ter Haar G, Kirpensteijn J (2013). "Chapter 2. Wound management: a new protocol for dogs and cats. Chlorhexidine solution". In Kirpensteijn J, ter Haar G (eds.). Reconstructive Surgery and Wound Management of the Dog and Cat. CRC Press. ISBN 9781482261455.
  47. ^ Maddison JE, Page SW, Church DB, eds. (2008). "Antimicrobial agents. Chlorhexidine". Small Animal Clinical Pharmacology. Elsevier Health Sciences. p. 552. ISBN 978-0702028588.
  48. ^ Blowey RW, Edmondson P (2010). Mastitis Control in Dairy Herds. CABI. p. 120. ISBN 9781845937515.
  49. ^ 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. from the original on 27 September 2011. Retrieved 11 September 2011.

November 02, 2023
chlorhexidine, disinfectant, antiseptic, with, molecular, formula, c22h30cl2n10, which, used, skin, disinfection, before, surgery, sterilize, surgical, instruments, also, used, cleaning, wounds, preventing, dental, plaque, treating, yeast, infections, mouth, k. Chlorhexidine 1 is a disinfectant and antiseptic with the molecular formula C22H30Cl2N10 which is used for skin disinfection before surgery and to sterilize surgical instruments 2 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 a powder 2 3 It is commonly used in salt form either the gluconate 4 or the acetate 5 ChlorhexidineClinical dataPronunciationklɔː r ˈhɛksɪdiːnTrade namesBetasept ChloraPrep Chlorostat othersOther namesCHX CHG 1 6 bis 4 chloro phenylbiguanido hexaneAHFS Drugs comMonographLicense dataUS DailyMed ChlorhexidinePregnancycategoryAU ARoutes ofadministrationTopicalATC codeA01AB03 WHO B05CA02 WHO D08AC02 WHO D09AA12 WHO dressing R02AA05 WHO S01AX09 WHO S02AA09 WHO S03AA04 WHO Legal statusLegal statusAU S5 S6 S7 US OTC Rx onlyIdentifiersIUPAC name N N 1 6 Hexanediylbis N 4 chlorophenyl imidodicarbonimidic diamide CAS Number55 56 1 YPubChem CID9552079DrugBankDB00878 YChemSpider2612 YUNIIR4KO0DY52LKEGGD07668 YChEBICHEBI 3614 YChEMBLChEMBL790 YCompTox Dashboard EPA DTXSID2033314ECHA InfoCard100 000 217Chemical and physical dataFormulaC 22H 30Cl 2N 10Molar mass505 45 g mol 13D model JSmol Interactive imageMelting point134 to 136 C 273 to 277 F Solubility in water0 8SMILES Clc1ccc NC N NC N NCCCCCCNC N NC N Nc2ccc Cl cc2 cc1InChI InChI 1S C22H30Cl2N10 c23 15 5 9 17 10 6 15 31 21 27 33 19 25 29 13 3 1 2 4 14 30 20 26 34 22 28 32 18 11 7 16 24 8 12 18 h5 12H 1 4 13 14H2 H5 25 27 29 31 33 H5 26 28 30 32 34 YKey GHXZTYHSJHQHIJ UHFFFAOYSA N Y verify Side effects may include skin irritation tooth discoloration and allergic reactions 3 although the risk appears to be the same as other topical antiseptics 6 7 Chlorhexidine rinse is also known to have a bitter metallic aftertaste Rinsing with water is not recommended as it is known to increase the bitterness 8 It may cause eye problems if direct contact occurs 9 Use in pregnancy appears to be safe 10 Chlorhexidine may come mixed in alcohol 11 12 13 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 14 Chlorhexidine is available over the counter in the United States 9 It is on the World Health Organization s List of Essential Medicines 15 16 In 2020 it was the 273rd most commonly prescribed medication in the United States with more than 1 million prescriptions 17 18 Contents 1 Uses 1 1 Antiseptic 1 2 Dental use 1 3 Topical 2 Side effects 3 Mechanism of action 4 Chemistry 5 Deactivation 6 Synthesis 7 Society and culture 7 1 Brands 8 Veterinary medicine 9 ReferencesUses editChlorhexidine 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 19 A 2019 Cochrane review concluded that based on very low certainty evidence in those who are critically ill it is not clear whether bathing with chlorhexidine reduces hospital acquired infections mortality or length of stay in the ICU or whether the use of chlorhexidine results in more skin reactions 20 In endodontics chlorhexidine has been used for root canal irrigation and as an intracanal dressing 21 22 but has been replaced by the use of sodium hypochlorite bleach in much of the developed world citation needed Antiseptic edit Chlorhexidine is active against Gram positive and Gram negative organisms facultative anaerobes aerobes and yeasts 23 It is particularly effective against Gram positive bacteria in concentrations 1 mg L Significantly higher concentrations 10 to more than 73 mg 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 24 There is strong evidence that chlorhexidine is more effective than povidone iodine for clean surgery 25 26 Evidence shows that it is an effective antiseptic for upper limb surgery 6 Meta data spanning several decades shows that the efficacy of chlorhexidine against organisms that cause surgical site infection has not changed 27 dispelling concerns over emerging resistance Dental use edit nbsp Perichlor brand 0 12 chlorhexidine gluconate solutionUse of a chlorhexidine based mouthwash in combination with normal tooth care can help reduce the build up of plaque and improve mild gingivitis 28 There is not enough evidence to determine the effect in moderate to severe gingivitis 28 Its use as a mouthwash has a number of adverse effects including damage to the mouth lining tooth discoloration tartar build up and impaired taste 28 Extrinsic tooth staining occurs when chlorhexidine rinse has been used for 4 weeks or longer 28 Mouthwashes containing chlorhexidine which stain teeth less than the classic solution have been developed many of which contain chelated zinc 29 30 31 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 reduced 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 32 Topical edit Chlorhexidine gluconate is used as a skin cleanser for surgical scrubs as a cleanser for skin wounds for preoperative skin preparation and for germicidal hand rinses 23 Chlorhexidine eye drops have been used as a treatment for eyes affected by Acanthamoeba keratitis 33 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 neonatal mortality by 12 34 Side effects editChlorhexidine is ototoxic toxic to the inner ear If put into an ear canal which has a ruptured eardrum it can lead to deafness 35 Chlorhexidine 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 24 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 36 Whether prolonged exposure over many years may have carcinogenic potential is still not clear The US Food and Drug Administration recommendation is to limit the use of a chlorhexidine gluconate mouthwash to a maximum of six months 37 When ingested chlorhexidine is poorly absorbed in the gastrointestinal tract and can cause stomach irritation or nausea 38 39 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 39 40 Mechanism of action editAt 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 23 Chemistry editIt is a cationic polybiguanide bisbiguanide 41 Deactivation editChlorhexidine 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 42 Synthesis editThe structure is based on two molecules of proguanil linked with a hexamethylenediamine spacer nbsp Two routes for chlorhexidine synthesis 43 U S Patent 2 684 924 1954 to I C I The compounds designated 2 are substituted hexanes Society and culture editBrands edit Chlorhexidine topical is sold as Betasept Biopatch Calgon Vesta ChloraPrep One Step Dyna Hex Hibiclens Hibistat Towelette Scrub Care Exidine Spectrum 4 among others 44 Chlorhexidine gluconate mouthwash is sold as Dentohexin Paroex Peridex PerioChip Corsodyl and Periogard among others 45 Veterinary medicine editIn animals chlorhexidine is used for topical disinfection of wounds 46 and to manage skin infections 47 Chlorhexidine based disinfectant products are used in the dairy farming industry 48 Post surgical respiratory problems have been associated with the use of chlorhexidine products in cats 49 References edit Varoni E Tarce M Lodi G Carrassi A September 2012 Chlorhexidine CHX in dentistry state of the art Minerva Stomatologica 61 9 399 419 PMID 22976567 Archived from the original on 30 September 2021 Retrieved 30 September 2021 a b c World Health Organization 2009 Stuart MC Kouimtzi M Hill SR eds WHO Model Formulary 2008 World Health Organization pp 321 22 hdl 10665 44053 ISBN 9789241547659 a b c d British national formulary BNF 69 69 ed British Medical Association 2015 pp 568 791 839 ISBN 9780857111562 Chlorhexidine Gluconate PubChem Retrieved 1 July 2023 Chlorhexidine Acetate PubChem Retrieved 1 July 2023 a b Wade RG Bourke G Wormald JC Totty JP Stanley GH Lewandowski A et al November 2021 Chlorhexidine versus povidone iodine skin antisepsis before upper limb surgery CIPHUR an international multicentre prospective cohort study BJS Open 5 6 zrab117 doi 10 1093 bjsopen zrab117 PMC 8677347 PMID 34915557 Wade RG Burr NE McCauley G Bourke G Efthimiou O December 2021 The Comparative Efficacy of Chlorhexidine Gluconate and Povidone iodine Antiseptics for the Prevention of Infection in Clean Surgery A Systematic Review and Network Meta analysis Annals of Surgery 274 6 e481 e488 doi 10 1097 SLA 0000000000004076 PMID 32773627 S2CID 225289226 Chlorhexidine Oral Route Precautions Mayo Clinic www mayoclinic org Retrieved 27 June 2023 a b Chlorhexidine Gluconate topical The American Society of Health System Pharmacists Archived from the original on 13 January 2017 Retrieved 8 January 2017 Briggs GG Freeman RK Yaffe SJ 2011 Drugs in Pregnancy and Lactation A Reference Guide to Fetal and Neonatal Risk Lippincott Williams amp Wilkins p 252 ISBN 9781608317080 Archived from the original on 13 January 2017 Prevantics Swab chlorhexidine gluconate and isopropyl alcohol solution DailyMed 26 October 2022 Archived from the original on 24 January 2023 Retrieved 24 January 2023 Prevantics Swab chlorhexidine gluconate and isopropyl alcohol solution DailyMed 26 October 2022 Archived from the original on 24 January 2023 Retrieved 24 January 2023 Prevantics Maxi Swabstick chlorhexidine gluconate and isopropyl alcohol solution DailyMed 26 October 2022 Archived from the original on 24 January 2023 Retrieved 24 January 2023 Schmalz G Bindslev DA 2008 Biocompatibility of Dental Materials Springer Science amp Business Media p 351 ISBN 9783540777823 Archived from the original on 13 January 2017 World Health Organization 2019 World Health Organization model list of essential medicines 21st list 2019 Geneva World Health Organization hdl 10665 325771 WHO MVP EMP IAU 2019 06 License CC BY NC SA 3 0 IGO World Health Organization 2021 World Health Organization model list of essential medicines 22nd list 2021 Geneva World Health Organization hdl 10665 345533 WHO MHP HPS EML 2021 02 The Top 300 of 2020 ClinCalc Archived from the original on 12 February 2021 Retrieved 7 October 2022 Chlorhexidine Drug Usage Statistics ClinCalc Archived from the original on 8 July 2020 Retrieved 7 October 2022 Thomas Guthner et al 2007 Guanidine and Derivatives Ullman s Encyclopedia of Industrial Chemistry 7th ed Wiley p 13 Lewis SR Schofield Robinson OJ Rhodes S Smith AF August 2019 Chlorhexidine bathing of the critically ill for the prevention of hospital acquired infection The Cochrane Database of Systematic Reviews 8 8 CD012248 doi 10 1002 14651858 CD012248 pub2 PMC 6718196 PMID 31476022 Raab D July August 2008 Preparation of contaminated root canal systems the importance of antimicrobial irrigants Dental Inc 34 36 Raab D 2010 Die Bedeutung chemischer Spulungen in der Endodontie PDF Endodontie Journal 2 22 23 permanent dead link a b c Leikin JB Paloucek FP eds 2008 Chlorhexidine Gluconate Poisoning and Toxicology Handbook 4th ed Informa pp 183 84 a b Harke HP 2007 Disinfectants Ullman s Encyclopedia of Industrial Chemistry 7th ed Wiley pp 10 11 Wade RG Burr NE McCauley G Bourke G Efthimiou O December 2021 The Comparative Efficacy of Chlorhexidine Gluconate and Povidone iodine Antiseptics for the Prevention of Infection in Clean Surgery A Systematic Review and Network Meta analysis Annals of Surgery 274 6 e481 e488 doi 10 1097 SLA 0000000000004076 PMID 32773627 Dumville JC McFarlane E Edwards P Lipp A Holmes A Liu Z April 2015 Preoperative skin antiseptics for preventing surgical wound infections after clean surgery The Cochrane Database of Systematic Reviews 2015 4 CD003949 doi 10 1002 14651858 CD003949 pub4 PMC 6485388 PMID 25897764 Aftab R Dodhia VH Jeanes C Wade RG January 2023 Bacterial sensitivity to chlorhexidine and povidone iodine antiseptics over time a systematic review and meta analysis of human derived data Scientific Reports 13 1 347 Bibcode 2023NatSR 13 347A doi 10 1038 s41598 022 26658 1 PMC 9825506 PMID 36611032 a b c d James P Worthington HV Parnell C Harding M Lamont T Cheung A et al March 2017 Chlorhexidine mouthrinse as an adjunctive treatment for gingival health The Cochrane Database of Systematic Reviews 3 3 CD008676 doi 10 1002 14651858 CD008676 pub2 PMC 6464488 PMID 28362061 Bernardi F Pincelli MR Carloni S Gatto MR Montebugnoli L August 2004 Chlorhexidine with an Anti Discoloration System A comparative study International Journal of Dental Hygiene 2 3 122 126 doi 10 1111 j 1601 5037 2004 00083 x PMID 16451475 Sanz M Vallcorba N Fabregues S Muller I Herkstroter F July 1994 The effect of a dentifrice containing chlorhexidine and zinc on plaque gingivitis calculus and tooth staining Journal of Clinical Periodontology 21 6 431 437 doi 10 1111 j 1600 051X 1994 tb00741 x PMID 8089246 Kumar S Patel S Tadakamadla J Tibdewal H Duraiswamy P Kulkarni S February 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 Kolahi J Soolari A September 2006 Rinsing with chlorhexidine gluconate solution after brushing and flossing teeth a systematic review of effectiveness Quintessence International 37 8 605 612 PMID 16922019 Alkharashi M Lindsley K Law HA Sikder S February 2015 Medical interventions for acanthamoeba keratitis The Cochrane Database of Systematic Reviews 2015 2 CD010792 doi 10 1002 14651858 CD010792 pub2 PMC 4730543 PMID 25710134 Sinha A Sazawal S Pradhan A Ramji S Opiyo N March 2015 Chlorhexidine skin or cord care for prevention of mortality and infections in neonates The Cochrane Database of Systematic Reviews 3 3 CD007835 doi 10 1002 14651858 CD007835 pub2 PMID 25739381 S2CID 16586836 Lai P Coulson C Pothier DD Rutka J December 2011 Chlorhexidine ototoxicity in ear surgery part 1 review of the literature Journal of Otolaryngology Head amp Neck Surgery 40 6 437 440 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 23 April 2014 Archived from the original on 13 January 2017 Retrieved 29 April 2014 Below H Assadian O Baguhl R Hildebrandt U Jager B Meissner K et al February 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 The British Journal of Oral amp Maxillofacial Surgery 55 2 150 155 doi 10 1016 j bjoms 2016 10 007 PMID 27789177 Chlorhexidine Adverse Effects www poison org Archived from the original on 5 July 2018 Retrieved 4 July 2018 a b Chlorhexidine Pubchem U S National Library of Medicine Archived from the original on 5 July 2018 Retrieved 4 July 2018 Hirata K Kurokawa A April 2002 Chlorhexidine gluconate ingestion resulting in fatal respiratory distress syndrome Veterinary and Human Toxicology 44 2 89 91 PMID 11931511 An 80 y old woman with dementia accidentally ingested approximately 200 mL of Maskin 5 chlorhexidine in a nursing home and then presumably aspirated gastric contents Tanzer JM Slee AM Kamay BA December 1977 Structural requirements of guanide biguanide and bisbiguanide agents for antiplaque activity Antimicrobial Agents and Chemotherapy 12 6 721 729 doi 10 1128 aac 12 6 721 PMC 430011 PMID 931371 Denton GW 2000 Chlorhexidine In Block SS ed Disinfection Sterilization and Preservation 5th ed Lippincott Williams amp Wilkins pp 321 36 ISBN 978 0 683 30740 5 Archived from the original on 12 January 2023 Retrieved 10 October 2016 Rose FL Swain G 1956 850 Bisdiguanides having antibacterial activity Journal of the Chemical Society Resumed 4422 doi 10 1039 JR9560004422 Hibiclens Uses Side Effects amp Warnings Drugs com Drugs com Archived from the original on 4 August 2018 Retrieved 4 August 2018 Chlorhexidine gluconate Uses Side Effects amp Warnings Drugs com Drugs com Archived from the original on 28 August 2021 Retrieved 4 August 2018 van Hengel T ter Haar G Kirpensteijn J 2013 Chapter 2 Wound management a new protocol for dogs and cats Chlorhexidine solution In Kirpensteijn J ter Haar G eds Reconstructive Surgery and Wound Management of the Dog and Cat CRC Press ISBN 9781482261455 Maddison JE Page SW Church DB eds 2008 Antimicrobial agents Chlorhexidine Small Animal Clinical Pharmacology Elsevier Health Sciences p 552 ISBN 978 0702028588 Blowey RW Edmondson P 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 27 September 2011 Retrieved 11 September 2011 Portal nbsp Medicine Retrieved from https en wikipedia org w index php title 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