Chlorhexidine

Chlorhexidine is a disinfectant and antiseptic that is used for skin

Chlorhexidine
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] It may cause eye problems if direct contact occurs.[1] Use in
pregnancy appears to be safe.[4] Chlorhexidine may come mixed in alcohol,
water, or surfactant solution.[3] It is effective against a range of
Clinical data
microorganisms, but does not inactivatespores.[2]
Trade names Betasept, ChloraPrep,
Chlorhexidine came into medical use in the 1950s.[5] It is on the World Chlorostat, others
Health Organization's List of Essential Medicines, the most effective and Synonyms 1,6-bis(4-chloro-
safe medicines needed in ahealth system.[6] Chlorhexidine is availableover
phenylbiguanido)hexane
the counter.[1] The wholesale cost in the developing world is about 2.20 to
AHFS/Drugs.com Monograph
4.10 USD per liter of 5% solution.[7] In the United Kingdom this amount
costs the NHS about £4.80.[3] Pregnancy US: B (No risk in non-human
category
studies) and C[1]

Routes of topical, mouth wash

administration
Contents ATC code A01AB03 (WHO) B05CA02
Uses (WHO), D08AC02 (WHO),
Antiseptic D09AA12 (WHO)
Dental use (dressing), R02AA05
Topical (WHO), S01AX09 (WHO),
Side effects S02AA09 (WHO), S03AA04
Mechanism of action (WHO)
Chemistry Legal status
Deactivation Legal status US: OTC
Synthesis
Identifiers
Brand names
Veterinary medicine IUPAC name
Toxicity N,N′′′′1,6-Hexanediylbis[N′-(4-chlorophenyl)(imidodicarbo

See also nimidic diamide)]

References CAS Number 55-56-1

External links PubChem CID 5353524
DrugBank DB00878

Uses ChemSpider 2612

Chlorhexidine is used in disinfectants (disinfection of the skin and hands), UNII R4KO0DY52L
cosmetics (additive to creams, toothpaste, deodorants, and antiperspirants), KEGG D07668
and pharmaceutical products (preservative in eye drops, active substance in
wound dressings and antiseptic mouthwashes).[8] ChEBI CHEBI:3614
ChEMBL CHEMBL790
In endodontics, chlorhexidine is used for root canal irrigation and as an
intracanal dressing, [9][10][11] but has been replaced by the use of sodium ECHA InfoCard 100.000.217
hypochlorite bleach in much of the developed world.
Chemical and physical data
Formula C22H30Cl2N10
Antiseptic Molar mass 505.446 g/mol
There is tentative evidence that it is more effective than povidone- 3D model Interactive image
iodine.[12] (JSmol)
Melting point 134 to 136 °C (273 to
Chlorhexidine is active against Gram-positive and Gram-negative 277 °F)
organisms, facultative anaerobes, aerobes, and yeasts.[13] It is particularly
Solubility in 0.8 mg/mL (20 °C)
effective against Gram-positive bacteria (in concentrations ≥ 1 µg/l). water
Significantly higher concentrations (10 to more than 73 μg/ml) are required
SMILES
for Gram-negative bacteria and fungi. Chlorhexidine is ineffective against Clc1ccc(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc2cc
polioviruses and adenoviruses. The effectiveness against herpes viruses has c(Cl)cc2)cc1

not yet been established unequivocally.[14] InChI

InChI=1S/C22H30Cl2N10/c23-15-5-9-17(10-6-15)31-21
Chlorhexidine, like other cation-active compounds, remains on the skin. It (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,
is frequently combined with alcohols (ethanol and isopropyl alcohol). 27,29,31,33)(H5,26,28,30,32,34)
Key:GHXZTYHSJHQHIJ-UHFFFAOYSA-N

(verify)
Dental use
Use of a chlorhexidine-based mouthwash in combination with normal tooth care can
help reduce the build-up of plaque and improve mild gingivitis.[15] Such mouthwash
also has a number of adverse effects including damage to the mouth lining, tooth
discoloration, tartar build-up, and impaired taste.[15]

Mouthwashes containing chlorhexidine which stain teeth less than the classic solution
have been developed, many of which containchelated zinc.[16][17][18]

Topical
Nepal is the first country in the world to use chlorhexidine to treat the umbilical cord
Perichlor brand 0.12% chlorhexidine
of newborn babies, and received a USAID Pioneers Prize for reducing the neonatal
gluconate solution.
death rate.[19] 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%.[20] Chlorhexidine gluconate is used as a
skin cleanser for surgical scrubs, a cleanser for skin wounds, for preoperative skin preparation and germicidal hand rinses.[13]
fected by Acanthamoeba keratitis.[21]
Chlorhexidine eye drops have been used as a treatment for eyes af

Side effects
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.[14] 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
[22]
gluconate reduced the risk of hospital-acquired infections.
Whether prolonged exposure over many years may have carcinogenic potential is still not clear. The recent recommendation of the
Federal Drug Administration (FDA) in the USA to limit the use of a chlorhexidine gluconate mouthwash to a maximum of six
months.[23]

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.[13]

Chemistry
It is a cationic polybiguanide (bisbiguanide).[24] It is used primarily as its salts (e.g., the dihydrochloride, diacetate, and digluconate).

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.[25] 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
The structure is based on two molecules ofproguanil, linked with a hexamethylenediaminespacer.

Two routes for chlorhexidine synthesis:[26] U.S. Patent 2,684,924 (1954 to I.C.I.). The compounds designated (...)2 are
substituted hexanes.

Brand names
Betasept, ChloraPrep, Chlorostat, Avagard, XEPI Rub CET, BactoShield CHG, Corsodyl, Dyna-Hex, Hibiclens, Hibistat, Operand
Chlorhexidine Gluconate, Peridex, PerioChip, PerioGard, Riohex.

Veterinary medicine
For use in animals, chlorhexidine is used as a topical disinfectant of wounds. It is also more beneficial to wound healing than using
saline solutions alone.[27] Post-surgical respiratory problems have been associated with the use of chlorhexidine products in cats.
[28] If

the product is put into the ear in the presence of a ruptured eardrum, it can also lead to deafness.[29] It is commonly used to manage
skin infections in dogs. In addition to this, it is an active ingredient in disinfectant products used within the dairy farming industry
.
Toxicity
Genotoxicity study in rats indicate chlorhexidine digluconate is able to induce primary DNA damage in leukocytes, in kidney cells[30]
and in oral mucosal cells, but no chromosome breakage or loss in reticulocytes.[31] Chlorhexidine is highly cytotoxic in vitro being
able to induce apoptotic and autophagic/necrotic cell deaths, disturbance of mitochondrial function, intracellular Ca2+ increase and
oxidative stress.[32]

See also
Polyaminopropyl biguanide
Polyhexanide
Triclosan

References
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External links
FDA Professional Drug Information

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