Chlorhexidine

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
IUPAC name
  • N,N′′′′1,6-Hexanediylbis[N′-(4-chlorophenyl)(imidodicarbonimidic diamide)]
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.217
Chemical and physical data
FormulaC22H30Cl2N10
Molar mass505.45 g·mol−1
3D model (JSmol)
Melting point134 to 136 °C (273 to 277 °F)
Solubility in water0.8
SMILES
  • Clc1ccc(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc2ccc(Cl)cc2)cc1
InChI
  • 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)

Chlorhexidine[1] is a disinfectant and antiseptic which is used for skin disinfection before surgery and to disinfect 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]

Side effects may include skin irritation, tooth discoloration, and allergic reactions,[3] although, apart from discoloration, the risk appears to be the same as that for povidone-iodine.[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][10] Use in pregnancy appears to be safe.[11] Chlorhexidine may come mixed in alcohol,[12][13][14] 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[15] and is available over the counter in the United States.[9] It is on the World Health Organization's List of Essential Medicines.[16] In 2022, it was the 230th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[17][18]

  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.
  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. ^ 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. Archived from the original on 13 January 2017. Retrieved 8 January 2017.
  10. ^ Tabor E, Bostwick DC, Evans CC (January 1989). "Corneal damage due to eye contact with chlorhexidine gluconate". JAMA. 261 (4): 557–558. doi:10.1001/jama.1989.03420040091021. PMID 2909794.
  11. ^ Briggs GG, Freeman RK, Yaffe SJ (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 13 January 2017.
  12. ^ "Prevantics Swab- chlorhexidine gluconate and isopropyl alcohol solution". DailyMed. 26 October 2022. Archived from the original on 24 January 2023. Retrieved 24 January 2023.
  13. ^ "Prevantics Swab- chlorhexidine gluconate and isopropyl alcohol solution". DailyMed. 26 October 2022. Archived from the original on 24 January 2023. Retrieved 24 January 2023.
  14. ^ "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.
  15. ^ Schmalz G, Bindslev DA (2008). Biocompatibility of Dental Materials. Springer Science & Business Media. p. 351. ISBN 9783540777823. Archived from the original on 13 January 2017.
  16. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  17. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  18. ^ "Chlorhexidine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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