関: chlorhexidine、chlorhexidine hydrochloride

WordNet

a long-lasting liquid antiseptic; used by surgeons to wash their hands before performing surgery

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/14 22:59:53」(JST)

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Chlorhexidine is an antibacterial used as an antiseptic and for other applications. It is a cationic polybiguanide (bisbiguanide). It is used primarily as its salts (e.g., the dihydrochloride, diacetate, and digluconate).

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.^[1]

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).^[2]

Antiseptic

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.^[3]

Chlorhexidine is active against Gram-positive and Gram-negative organisms, facultative anaerobes, aerobes, and yeasts.^[3] 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.^[4]

Chlorhexidine, like other cation-active compounds, remains on the skin. It is frequently combined with alcohols (ethanol and isopropyl alcohol).

Dental use

Perichlor brand 0.12% chlorhexidine gluconate solution.

Chlorhexidine is often used as an active ingredient in mouthwash designed to reduce dental plaque and oral bacteria. 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] If it is not deactivated, chlorhexidine lasts longer in the mouth than other mouthwashes, which is partly why it is to be preferred over other treatments for gingivitis.^[6] To treat periodontal pockets equal or greater than 5 mm, chlorhexidine is also available in high concentration (36%) in a gelatin chip.

There are oral pathologic conditions in which the maintenance of oral hygiene with the twice-daily use with 0.12% chlorhexidine gluconate solution (in which a salt of chlorhexidine and gluconic acid has been dissolved) is required for healing and regeneration of the oral tissues. These conditions included gingivitis, periodontitis, dental traumas^[7] (such as subluxation), oral cysts,^[8] and after wisdom tooth extraction. The clinical efficacy of the application of chlorhexidine as a component of oral rinses is well documented by many clinical studies summarized by review articles.^[9]

Continued use of products containing chlorhexidine for long periods can cause stains on teeth, tongue, and gingiva, also on silicate and resin restorations; prolonged use can also reduce bitter and salty taste sensations – this latter symptom can be reversed by ceasing use of chlorhexidine.^[10] The brownish discoloration of teeth and tongue is due to the disintegration of bacterial membranes, leading to the denaturation of bacterial proteins.^[11] At the same time, disulfide functions are reduced to thiol functions^[12] that form dark complexes with iron(III) ions found in saliva.^[13]

Mouthwashes containing chlorhexidine which stain teeth less than the classic solution have been developed, many of which contain chelated zinc.^[14]^[15]^[16]

According to the prescribing information,^[17] chlorhexidine gluconate has not been proven to reduce subgingival calculus and in some studies actually increased deposits.^[18] When combined with xylitol, a synergistic effect has been observed to enhance efficacy.^[19]

Chlorhexidine's role in preventing tooth decay (dental caries) is controversial and "the clinical data are not convincing".^[20]

Chlorhexidine is neutralized by common toothpaste additives such as sodium lauryl sulfate and sodium monofluorophosphate. Although data are limited, to maximize effectiveness, it may be best to keep more than a 30-minute interval between brushing and using the mouthwash, ″cautiously close to 2 hours after brushing".^[21]

Topical

Nepal is 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.^[22] Chlorhexidine is very effective for poor countries like Nepal and its use is growing in the world for treating the umbilical cord. A recent 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%.^[23] Chlorhexidine gluconate is used as a skin cleanser for surgical scrubs, a cleanser for skin wounds, for preoperative skin preparation and germicidal hand rinses.^[3]

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.^[4] 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.^[24]

Other animals

For use in animals, it is used as a topical disinfectant of wounds. Some common brand names are ChlorhexiDerm, ResiChlor, Savinox plus (Bioshields), 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.^[25] Problems^[26] including deafness^[27] have been associated with the use of chlorhexidine products in cats. It is commonly used to manage skin infections in dogs. In addition to this, it is an active ingredient in teat disinfectant products used within the dairy farming industry.

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.^[28] 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 (a topical itself or the residue from a cleanser) is meant to remain on the skin.

Synthesis

This structure is based on Proguanil, 2 molecules linked with a HMDA spacer.

Chlorhexidine synthesis:^[29] eidem, U.S. Patent 2,684,924 (1954 to I.C.I.).

Notes

Antibacterial activity and acute toxicity: G. E. Davies et al., Br. J. Pharmacol. 9, 192 (1954). Review of toxicology and clinical uses: D. M. Foulkes, J. Periodontal Res. 8, Suppl. 12, 55-60 (1973). Series of articles on clinical efficacy in gingivitis and plaque control: ibid. 21, Suppl. 16, 1-89 (1986).

References

^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
^ Thomas Güthner et al. (2007), "Guanidine and Derivatives", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 13
^ ^a ^b ^c Leikin, Jerrold B.; Paloucek, Frank P., eds. (2008), "Chlorhexidine Gluconate", Poisoning and Toxicology Handbook (4th ed.), Informa, pp. 183–184
^ ^a ^b Hans-P. Harke (2007), "Disinfectants", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 10–11
^ Jenkins S, Addy M, Wade W (August 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. PMID 3183067.
^ Gaffar A, Afflitto J, Nabi N (October 1997). "Chemical agents for the control of plaque and plaque microflora: an overview". Eur. J. Oral Sci. 105 (5 Pt 2): 502–07. doi:10.1111/j.1600-0722.1997.tb00237.x. PMID 9395116.
^ Zadik Y (December 2008). "Algorithm of first-aid management of dental trauma for medics and corpsmen". Dent Traumatol 24 (6): 698–701. doi:10.1111/j.1600-9657.2008.00649.x. PMID 19021668.
^ Zadik Y, Yitschaky O, Neuman T, Nitzan DW (July 2011). "On the self-resolution nature of the buccal bifurcation cyst". J. Oral Maxillofac. Surg. 69 (7): e282–4. doi:10.1016/j.joms.2011.02.124. PMID 21571416.
^ Lang N, Brecx MC (1986). "Chlorhexidine digluconate-an agent for chemical plaque control and prevention of gingival inflammation". Journal of Periodontal Research 21: 74–89. doi:10.1111/j.1600-0765.1986.tb01517.x.
^ Helms JA, Della-Fera MA, Mott AE, Frank ME (October 1995). "Effects of chlorhexidine on human taste perception". Arch. Oral Biol. 40 (10): 913–20. doi:10.1016/0003-9969(95)00062-T. PMID 8526801.
^ Hjeljord LG, Rolla G, Bonesvoll P (1973). "Chlorhexidine-protein interactions". J Periodontal Res Suppl 12: 11–6. doi:10.1111/j.1600-0765.1973.tb02158.x. PMID 4269593.
^ Gilbert, Hiram F. (2006). "Molecular and Cellular Aspects of Thiol-Disulfide Exchange". Advances in Enzymology and Related Areas of Molecular Biology. pp. 69–172. doi:10.1002/9780470123096.ch2. ISBN 978-0-470-12309-6.
^ Jocelyn, PC (1972). Biochemistry of the SH Group. London-New York: Academic Press. p. 82. ISBN 0-12-385350-8.
^ 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. doi:10.1111/j.1600-051X.1994.tb00741.x. edit
^ 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. edit
^ "Colgate Periogard Rinse (Rx only)". Colgate. Retrieved 2011-09-12.
^ Fabrício Batistin Zanatta; Raquel Pippi Antoniazzi; Cassiano Kuchenbecker Rösing (October 2010). "Staining and calculus formation after 0.12% chlorhexidine rinses in plaque-free and plaque covered surfaces: a randomized trial". J. Appl. Oral Sci. 18 (5). doi:10.1590/S1678-77572010000500015.
^ Decker EM, Maier G, Axmann D, Brecx M, von Ohle C (January 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.
^ Autio-Gold J (2008). "The role of chlorhexidine in caries prevention". Oper Dent 33 (6): 710–6. doi:10.2341/08-3. PMID 19051866.
^ Kolahi J, Soolari A (September 2006). "Rinsing with chlorhexidine gluconate solution after brushing and flossing teeth: a systematic review of effectiveness". Quintessence Int 37 (8): 605–12. PMID 16922019.
^ "USAID Recognizes the Government of Nepal for their Leadership in Saving Newborn Lives". Embassy of the United States, Katmandu - Nepal. February 26, 2014.
^ Sinha A, Sazawal S, Pradhan A, Ramji S, Opiyo N .; Sazawal; Pradhan; Ramji; Opiyo (2015). "Chlorhexidine skin or cord care for prevention of mortality and infections in neonates". Cochrane Database Syst Rev 3 (3): CD007835. PMID 25739381.
^ "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. Retrieved 2014-04-29.
^ Sanchez IR, Swaim SF, Nusbaum KE, Hale AS, Henderson RA, McGuire JA; Swaim; Nusbaum; Hale; Henderson; McGuire (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.
^ 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. Retrieved 2011-09-11.
^ McDonnell, J. "Deafness in Cats". PetPlace.com. Retrieved 2011-09-11.
^ Denton, Graham W (2000). "Chlorhexidine". In Block, Seymour S. Disinfection, Sterilization, and Preservation (5th ed.). Lippincott Williams & Wilkins. pp. 321–36. ISBN 978-0-683-30740-5.
^ Rose, F. L.; Swain, G. (1956). "850. Bisdiguanides having antibacterial activity". Journal of the Chemical Society (Resumed): 4422. doi:10.1039/JR9560004422. edit

External links

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UpToDate Contents

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4. 熱傷の局所治療：外用抗菌薬と被覆材 local treatment of burns topical antimicrobial agents and dressings
5. Methicillin-resistant Staphylococcus aureus in adults: Prevention and control

English Journal

Chlorhexidine bathing in a tertiary care neonatal intensive care unit: impact on central line-associated bloodstream infections.

Quach C, Milstone AM, Perpête C, Bonenfant M, Moore DL, Perreault T.Author information Division of Infection Control, Department of Pediatrics, Montreal Children's Hospital, McGill University Health Centre, Montreal, Quebec, Canada.AbstractBackground. Despite implementation of recommended best practices, our central line-associated bloodstream infection (CLABSI) rates remained high. Our objective was to describe the impact of chlorhexidine gluconate (CHG) bathing on CLABSI rates in neonates. Methods. Infants with a central venous catheter (CVC) admitted to the neonatal intensive care unit from April 2009 to March 2013 were included. Neonates with a birth weight of 1,000 g or less, aged less than 28 days, and those with a birth weight greater than 1,000 g were bathed with mild soap until March 31, 2012 (baseline), and with a 2% CHG-impregnated cloth starting on April 1, 2012 (intervention). Infants with a birth weight of 1,000 g or less, aged 28 days or more, were bathed with mild soap during the entire period. Neonatal intensive care unit nurses reported adverse events. Adjusted incidence rate ratios (aIRRs), using Poisson regression, were calculated to compare CLABSIs/1,000 CVC-days during the baseline and intervention periods. Results. Overall, 790 neonates with CVCs were included in the study. CLABSI rates decreased during the intervention period for CHG-bathed neonates (6.00 vs 1.92/1,000 CVC-days; aIRR, 0.33 [95% confidence interval (CI), 0.15-0.73]) but remained unchanged for neonates with a birth rate of 1,000 g or less and aged less than 28 days who were not eligible for CHG bathing (8.57 vs 8.62/1,000 CVC-days; aIRR, 0.86 [95% CI, 0.17-4.44]). Overall, 195 infants with a birth weight greater than 1,000 g and 24 infants with a birth weight of 1,000 g or less, aged 28 days or more, were bathed with CHG. There was no reported adverse event. Conclusions. We observed a decrease in CLABSI rates in CHG-bathed neonates in the absence of observed adverse events. CHG bathing should be considered if CLABSI rates remain high, despite the implementation of other recommended measures.
Infection control and hospital epidemiology : the official journal of the Society of Hospital Epidemiologists of America.Infect Control Hosp Epidemiol.2014 Feb;35(2):158-63. doi: 10.1086/674862. Epub 2013 Dec 24.
Background. Despite implementation of recommended best practices, our central line-associated bloodstream infection (CLABSI) rates remained high. Our objective was to describe the impact of chlorhexidine gluconate (CHG) bathing on CLABSI rates in neonates. Methods. Infants with a central venous
PMID 24442078

Influence of several root canal disinfection methods on pushout bond strength of self-etch post and core systems.

Katalinić I, Glockner K, Anić I.Author information Dentist in a private office, Zagreb, Croatia.AbstractAIM: To determine the effect of four root canal disinfection protocols (2.5% sodium hypochlorite, 0.2% chlorhexidine gluconate, gaseous ozone and Nd : YAG laser) on the pushout bond strength of a self-etch post and core system.
International endodontic journal.Int Endod J.2014 Feb;47(2):140-6. doi: 10.1111/iej.12124. Epub 2013 May 24.
AIM: To determine the effect of four root canal disinfection protocols (2.5% sodium hypochlorite, 0.2% chlorhexidine gluconate, gaseous ozone and Nd : YAG laser) on the pushout bond strength of a self-etch post and core system.METHODOLOGY: Sixty anterior single-rooted permanent human teeth were us
PMID 23701197

Nonsurgical management of inflammatory periimplant disease caused by food impaction: A clinical report.

Bidra AS.Author information Assistant Professor and Assistant Program Director, Post-Graduate Prosthodontics, University of Connecticut Health Center, Farmington, Conn; Private practice, Meriden, Conn. Electronic address: avinashbidra@yahoo.com.AbstractThe incidence, etiology, diagnosis, and management of infections and inflammatory disease around dental implants continue to be controversial. Although various researchers have described different etiologies and their ensuing treatments, none have proven to be definitive. Terms such as periimplant mucositis and periimplantitis have gained popularity. Food impaction into the periimplant sulcus and its role in inflammatory periimplant disease has not been previously reported in the literature. This article describes the nonsurgical management of a patient with a maxillary implant-supported overdenture, a recent history of pain, and suppuration around one of the implants. A detailed analysis of the patient's history and clinical findings indicated a differential diagnosis of impaction of husks of masticated sunflower seeds into the periimplant sulcus. The situation was successfully resolved in 1 week by local irrigation with 0.12% chlorhexidine gluconate and the use of systemic antibiotics.
The Journal of prosthetic dentistry.J Prosthet Dent.2014 Feb;111(2):96-100. doi: 10.1016/j.prosdent.2013.06.017. Epub 2013 Nov 15.
The incidence, etiology, diagnosis, and management of infections and inflammatory disease around dental implants continue to be controversial. Although various researchers have described different etiologies and their ensuing treatments, none have proven to be definitive. Terms such as periimplant m
PMID 24246371

Japanese Journal

クロルヘキシジンの殺菌活性を阻害するアルコールジェル手指消毒薬の簡易識別法

曽川芳郎,小林寛伊,梶浦工
医療関連感染 4(1), 14-18, 2011-07
NAID 40018938993

クロルヘキシジングルコン酸塩水溶液とアニオン系物質を混合した際の性状変化と殺菌活性の変化

曽川芳郎,小林寛伊,梶浦工
医療関連感染 4(1), 9-13, 2011-07
NAID 40018938992

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★リンクテーブル★

リンク元	「クロルヘキシジン」「chlorhexidine hydrochloride」
拡張検索	「chlorhexidine gluconate solution」
関連記事	「chlorhexidine」

「クロルヘキシジン」

Chlorhexidine
Systematic (IUPAC) name
	N,N′′′′1,6-Hexanediylbis[N′-(4-chlorophenyl)(imidodicarbonimidic diamide)]
Clinical data
Trade names	Avagard, BactoShield CHG, Betasept, ChloraPrep, Chlorostat, Corsodyl, Dyna-Hex, Hibiclens, Hibistat, Operand Chlorhexidine Gluconate, Peridex, PerioChip, PerioGard
AHFS/Drugs.com	FDA Professional Drug Information
Legal status	US: OTC;
Identifiers
CAS Registry Number	55-56-1
ATC code	A01AB03 B05CA02, D08AC02, D09AA12 (dressing), R02AA05, S01AX09, S02AA09, S03AA04
PubChem	CID: 5353524
DrugBank	DB00878
ChemSpider	2612
UNII	R4KO0DY52L
KEGG	D07668
ChEBI	CHEBI:3614
ChEMBL	CHEMBL790
Synonyms	1,6-bis(4-chloro-phenylbiguanido)hexan
Chemical data
Formula	C22H30Cl2N10
Molecular mass	505.446 g/mol
	SMILES Clc2ccc(NC(=N/C(=N/CCCCCC/N=C(/N=C(N)Nc1ccc(Cl)cc1)N)N)N)cc2;
	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) ; Key:GHXZTYHSJHQHIJ-UHFFFAOYSA-N ;
Physical data
Solubility in water	0.0008 mg/mL (20 °C)
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