CHLORHEXIDINE ACETATE

chlorhexidine acetate (commonly known by the salt forms chlorhexidine gluconate and chlorhexidine digluconate (CHG) ) is a disinfectant and antiseptic with the molecular formula C22H30Cl2N10, which is used for skin disinfection before surgery and to sterilize surgical instruments.
chlorhexidine acetate may be used both to disinfect the skin of the patient and the hands of the healthcare providers.
chlorhexidine acetate is also used for cleaning wounds, preventing dental plaque, treating yeast infections of the mouth, and to keep urinary catheters from blocking.

CAS Number : 56-95-1
EC  Number : 200-302-4
Molecular Formula :    C26H38Cl2N10O4
Molecular Weight  :     625.5

chlorhexidine acetate is used as a liquid or powder.
Side effects may include skin irritation, teeth discoloration, and allergic reactions, although the risk appears to be the same as other topical antiseptics.
chlorhexidine acetate may cause eye problems if direct contact occurs.
Use in pregnancy appears to be safe.
chlorhexidine acetate may come mixed in alcohol, water, or surfactant solution.

chlorhexidine acetate is effective against a range of microorganisms, but does not inactivate spores.
chlorhexidine acetate came into medical use in the 1950s.
chlorhexidine acetate is available over the counter in the United States.
chlorhexidine acetate is on the World Health Organization's List of Essential Medicines.
In 2020, chlorhexidine acetate was the 273rd most commonly prescribed medication in the United States, with more than 1 million prescriptions.

Uses of chlorhexidine acetate
chlorhexidine acetate 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).
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 acetate results in more skin reactions."
In endodontics, chlorhexidine acetate has been used for root canal irrigation and as an intracanal dressing but has been replaced by the use of sodium hypochlorite bleach in much of the developed world.

Antiseptic of chlorhexidine acetate
chlorhexidine acetate is active against Gram-positive and Gram-negative organisms, facultative anaerobes, aerobes, and yeasts.
chlorhexidine acetate 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 acetate is ineffective against polioviruses and adenoviruses. 
The effectiveness against herpes viruses has not yet been established unequivocally.

There is strong evidence that chlorhexidine acetate is more effective than povidone-iodine for clean surgery.
Evidence shows that it is the most effective antiseptic for upper limb surgery, and there is no data to suggest that alcoholic chlorhexidine increases the risk of tourniquet-related burns, ignition fires or allergic episodes during surgery.

Meta-data spanning several decades shows that the efficacy of chlorhexidine (against organisms that cause surgical site infection) has not changed,[24] dispelling concerns over emerging resistance.
chlorhexidine acetate, like other cation-active compounds, remains on the skin. 
chlorhexidine acetate is frequently combined with alcohols (ethanol and isopropyl alcohol).

Dental use
Use of a chlorhexidine acetate-based mouthwash in combination with normal tooth care can help reduce the build-up of plaque and improve mild gingivitis.
There is not enough evidence to determine the effect in moderate to severe gingivitis.
About 20 mL twice a day of concentrations of 0.1% to 0.2% is recommended for mouth-rinse solutions with a duration of at least 30 seconds.
Such mouthwash also has a number of adverse effects including damage to the mouth lining, tooth discoloration, tartar build-up, and impaired taste.
Extrinsic tooth staining occurs when chlorhexidine acetate rinse has been used for 4 weeks or longer.
Mouthwashes containing chlorhexidine acetate which stain teeth less than the classic solution have been developed, many of which contain chelated zinc.

Using chlorhexidine acetate 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.
chlorhexidine acetate 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 acetate, "it seems best that the interval between toothbrushing and rinsing with chlorhexidine acetate be more than 30 minutes, cautiously close to 2 hours after brushing".

Topical of chlorhexidine acetate
chlorhexidine acetate is used as a skin cleanser for surgical scrubs, as a cleanser for skin wounds, for preoperative skin preparation, and for germicidal hand rinses.
chlorhexidine acetate eye drops have been used as a treatment for eyes affected by Acanthamoeba keratitis.
chlorhexidine acetate 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 acetate skin or cord care can reduce the incidence of omphalitis (inflammation of the umbilical cord) by 50% and neonatal mortality by 12%.

Side effects of chlorhexidine acetate
chlorhexidine acetate is ototoxic; if put into an ear canal which has a ruptured eardrum, it can lead to deafness.
chlorhexidine acetate 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.
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 acetate reduced the risk of hospital-acquired infections.

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 acetate mouthwash to a maximum of six months.
When ingested, chlorhexidine acetate is poorly absorbed in the gastrointestinal tract and can cause stomach irritation or nausea.
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.

Mechanism of action of chlorhexidine acetate
At physiologic pH, chlorhexidine acetate 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 acetate, this results in a bacteriostatic effect; at high concentrations, membrane disruption results in cell death.

Chemistry of chlorhexidine acetate
chlorhexidine acetate is a cationic polybiguanide (bisbiguanide).
chlorhexidine acetate is used primarily as its salts (e.g., the dihydrochloride, diacetate, and digluconate)

Deactivation of chlorhexidine acetate
chlorhexidine acetate 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 acetate mouth rinses should be used at least 30 minutes after other dental products.
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.

Brands
chlorhexidine acetate topical is sold as Betasept, Biopatch, Calgon Vesta, ChloraPrep One-Step, Dyna-Hex, Hibiclens, Hibistat Towelette, Scrub Care Exidine, Spectrum-4 among others.
chlorhexidine acetate gluconate mouthwash is sold as Dentohexin, Paroex, Peridex, PerioChip, Corsodyl and Periogard, among others.
Hexoralettene N contains benzocaine, menthol and chlorhexidine acetate. 
chlorhexidine acetate is used as oral antiseptic candies.

Veterinary medicine of chlorhexidine acetate
In animals, chlorhexidine acetate is used for topical disinfection of wounds, and to manage skin infections.
chlorhexidine acetate-based disinfectant products are used in the dairy farming industry.
Post-surgical respiratory problems have been associated with the use of chlorhexidine acetate products in cats.

chlorhexidine acetate is a broad-spectrum antimicrobial biguanide used as a topical antiseptic and in dental practice for the treatment of inflammatory dental conditions caused by microorganisms.
chlorhexidine acetate is one of the most common skin and mucous membrane antiseptic agents in use today.
The molecule itself is a cationic bis-guanide consisting of two 4-chlorophenyl rings and two biguanide groups joined by a central hexamethylene chain.
Topical chlorhexidine acetate for disinfection, as well as oral rinses for dental use, carries activity against a broad range of pathogens including bacteria, yeasts, and viruses.

chlorhexidine acetate was developed in the UK  in the early 1950s9 and was introduced to the US in the 1970s.
The FDA withdrew its approval for the use of chlorhexidine acetate topical tincture 0.5%, due to a significant number of reports concerning chemical and thermal burns associated with the use of this product.
Other formulations of chlorhexidine acetate continue to be available.

chlorhexidine acetate is used as a general antiseptic. 
chlorhexidine acetate is used for the cleaning and disinfecting of wounds and the antiseptic treatment of burns.
chlorhexidine acetate is an antiseptic effective against a wide variety of gram-negative and gram-positive organisms, facultative anaerobes, aerobes, and yeast.
chlorhexidine acetate is used as an ingredient of bacteriostatic and bacteriocidal products to provide the activity of membrane disruption.

Applications of chlorhexidine acetate
chlorhexidine acetate is a salt of Chlorhexidine (C335045), an antiseptic used in the treatment of fungal and bacterial infections. 
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package.

chlorhexidine acetate and the related compound chlorhexidine digluconate are used as antiseptics and disinfectants.
chlorhexidine acetate has been used in research on gingivitis and plaque control.
chlorhexidine acetate can be used for prevention of microbial growth in chromatography resins such as cross-linked dextran at a concentration of 0.002%. 
However, chlorhexidine acetate is not recommended for use with beaded agarose.
Information on the compatibility of chlorhexidine acetate with different solutions has been published.

First aid measures of chlorhexidine acetate
-After inhalation: 
Supply fresh air; consult doctor in case of complaints.

-After skin contact:
Immediately wash with water and soap and rinse thoroughly.
If skin irritation continues, consult a doctor.

-After eye contact:
Rinse opened eye for several minutes under running water. 
If symptoms persist, consult a doctor.

-After swallowing:
Rinse mouth. 
Do not induce vomiting.
Seek medical treatment.

Substance identity

EC / List no.: 200-302-4
CAS no.: 56-95-1
Mol. formula: C22H30Cl2N10.2C2H4O2

Hazard classification & labelling of chlorhexidine acetate
Warning! According to the classification provided by companies to ECHA in CLP notifications chlorhexidine acetate is very toxic to aquatic life with long lasting effects, is very toxic to aquatic life, causes serious eye irritation and is harmful if swallowed.

chlorhexidine acetate predicted as likely to meet criteria for category 1A or 1B carcinogenicity, mutagenicity, or reproductive toxicity, or with dispersive or diffuse use(s) where predicted likely to meet any classification criterion for health or environmental hazards, or where there is a nanoform soluble in biological and environmental media.
chlorhexidine acetate indicated, in 2009, as being intended to be registered by at least one company in the EEA.

chlorhexidine acetate for which classification and labeling data have been submitted to ECHA in a registration under REACH or notified by manufacturers or importers under CLP. 
Such notifications are required for hazardous substances, as such or in mixtures, as well as for all substances subject to registration, regardless of their hazard.
chlorhexidine acetate listed in the EINECS, ELINCS, or NLP inventories.

Synonyms:
1,1'-Hexamethylene bis(5-(p-chlorophenyl)biguanide) diacetate
1,6-Bis(5-(p-chlorophenyl)biguandino)hexane diacetate
1,6-Bis(p-chlorophenylbiguanido)hexane diacetate
1,6-Di(4'-chlorophenyldiguanidino)hexane diacetate
10,040 Diacetate
2,4,11,13-Tetraazatetradecanediimidamide, N,N''-bis(4-chlorophenyl)-3,12-diimino-, diacetate (9CI)
2,4,11,13-Tetraazatetradecanediimidamide, N,N'-bis(4-chlorophenyl)-3,12-diimino-, diacetate
Bactigras
Biguanide, 1,1'-hexamethylenebis(5-(p-chlorophenyl)-, diacetate
Bis(p-chlorophenyldiguanidohexane) diacetate
Chlorhexidine acetate
Chlorhexidine acetate (VAN)
Chlorhexidine di(acetate)
Chlorhexidine di(acetate)
chlorhexidine di(acetate)
Chlorhexidine diacetate
Chlorohexidine diacetate
Hibitane diacetate
N,N''-bis(4-Chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine diacetate
N,N'-Bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradeca-nediimidamide, diacetate
Nolvasan
acetic acid; (1E)-2-[6-[[amino-[[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine
chlorhexidine di(acetate)
Chlorhexidine di(acetate) hydrate
Chlorhexidine Diacetate
N',N'''''-hexane-1,6-diylbis[N-(4-chlorophenyl)(imidodicarbonimidic diamide)] diacetate
N-(4-chlorophenyl)-1-3-(6-{N-[3-(4-chlorophenyl)carbamimidamidomethanimidoyl]amino}hexyl)carbamimidamidomethanimidamide; bis(acetic acid)
Chlorhexidine diacetate
56-95-1
Chlorhexidine acetate
Bactigras
Hibitane diacetate
206986-79-0
MFCD00012532
Chlorhexidine Acetate,(S)
Chlorhexidine Gluconate 20%
CHLORHEXIDINE DIACATATE
BCP13778
BCP18752
SY036251
FT-0686552
5-PHENYL-2,4-PYRROLIDINEDICARBOXYLICACID
Q27261630
Hibitane diacetate; MK 412A;MK-412A;MK412A;Sebidin A
Acetate, Chlorhexidine;MK 412A;MK412A;MK-412A;Sebidin A
Chlorhexidine [INN] [Wiki]
1,1'-Hexamethylenebis[5-(4-chlorophenyl)biguanide]
2,4,11,13-Tetraazatetradecanediimidamide, N,N''-bis(4-chlorophenyl)-3,12-diimino-
200-238-7 [EINECS]
2826432 [Beilstein]
55-56-1 [RN]
56-95-1 [RN]
Chlorhexidin [Czech]
chlorhexidine [French] [INN]
Chlorhexidine base
Chlorhexidinum [Latin] [INN]
clorhexidina [Spanish] [INN]
Diamide N,N''''-1,6-hexanediylbis[N'-(4-chlorophényl)(imidodicarbonimidique)] [French] [ACD/IUPAC Name]
MFCD00009673 [MDL number]
N,N''''-1,6-Hexandiylbis[N'-(4-chlorphenyl)(imidodikohlenstoffimiddiamid)] [German] [ACD/IUPAC Name]
N,N''''-1,6-Hexanediylbis[N'-(4-chlorophenyl)(imidodicarbonimidic diamide)] [ACD/IUPAC Name]
N,N''''-hexane-1,6-diylbis[N'-(4-chlorophenyl)(imidodicarbonimidic diamide)]
хлоргексидин [Russian] [INN]
كلورهيكسيدين [Arabic] [INN]
氯己定 [Chinese] [INN]
BIOSCRUB
BRIAN CARE
CIDA-STAT
EXIDINE [Wiki]
E-Z SCRUB
Hibispray
MICRODERM
Oro-Clense
PERIOCHIP
PERIOGARD [Wiki]
PHARMASEAL SCRUB CARE
PREVACARE R
Savloclens
Savlon Babycare
Sterido
STERI-STAT
Superspray
(1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylene]amino]methylene]amino]hexyl]-1-[amino-(4-chloroanilino)methylene]guanidine
(1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine
(1Z)-2-[6-[[Amino-[(Z)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine
(E)-1-[(E)-{AMINO[(4-CHLOROPHENYL)AMINO]METHYLIDENE}AMINO]-N`-{6-[(E)-{AMINO[(E)-{AMINO[(4-CHLOROPHENYL)AMINO]METHYLIDENE}AMINO]METHYLIDENE}AMINO]HEXYL}METHANIMIDAMIDE
[55-56-1] [RN]
{[(4-chlorophenyl)amino]iminomethyl}{[(6-{[({[(4-chlorophenyl)amino]iminomethy l}amino)iminomethyl]amino}hexyl)amino]iminomethyl}amine
{[(4-chlorophenyl)amino]iminomethyl}{[(6-{[({[(4-chlorophenyl)amino]iminomethyl}amino)iminomethyl]amino}hexyl)amino]iminomethyl}amine
1-(4-chlorophenyl)-3-[N-[6-[[N-[N-(4-chlorophenyl)carbamimidoyl]carbamimidoyl]amino]hexyl]carbamimidoyl]guanidine
1,1′-Hexamethylenebis[5-(4-chlorophenyl)biguanide]
1,1'-Hexamethylene bis(5-(p-chlorophenyl)biguanide)
1,1'-hexamethylenebis(5-(p-chlorophenyl)biguanide
1,1'-Hexamethylenebis(5-(p-chlorophenyl)biguanide)
1,1'-Hexamethylenebis[5-(p-chlorophenyl)biguanide]
1,6-Bis(5-(p-chlorophenyl)biguandino)hexane
1,6-bis(5-(p-chlorophenyl)biguanidino)hexane
1,6-Bis(N5-[p-chlorophenyl]-N1-biguanido)hexane
1,6-Bis(N5-p-chlorophenyl-N'-diguanido)hexane
1,6-Bis(p-chlorophenyldiguanido)hexane
1,6-Bis[N'-(p-chlorophenyl)-N5-biguanido]hexane
1,6-Di(4'-chlorophenyldiguanido)hexane
1,6-DI(N-P-CHLOROPHENYL-DIGUANIDO) HEXANE
1,6-Di(N-p-chlorophenyldiguanido)hexane
118-75-2 [RN]
1246816-96-5 [RN]
126-52-3 [RN]
2,4,11,13-tetraazatetadecanediimidamide
2,4,11,13-Tetraazatetradecanediimidamide, N1,N14-bis(4-chlorophenyl)-3,12-dii...
2-[6-[[amino-[[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine
200-302-4 [EINECS]
206986-79-0 [RN]
4-12-00-01201 [Beilstein]
Betasept [Trade name]
Biguanide, 1,1'-hexamethylenebis(5-(p-chlorophenyl)-
Bis(5-(p-chlorophenyl)biguanidinio)hexane
CHLORANIL
chlorhexamed forte
Chlorhexidin
Chlorhexidin [Czech]
Chlorhexidine Dihydrochloride
ChlorhexidineÂ
chlorhexidine-d8 dihydrochloride
Chlorhexidinum
Chlorhexidinum [INN-Latin]
chlorohex
Chlorohexidine
Cloresidina
Cloresidina [DCIT]
Clorhexidina
Clorhexidina [INN-Spanish]
clorhexidine
consepsis
Corsodyl [Trade name]
DB00878
DYNA-HEX
Eludril
Exidine (Trade name)
Fimeil
Hexadol
Hexadol (Trade name)
Hexamethylenebis(5-(4-chlorophenyl)biguanide)
hexident
Hibiclens [Trade name] [Wiki]
Hibidil [Trade name]
Hibidil (Trade name)
Hibiscrub [Trade name]
Hibiscrub (Trade name)
HIBISTAT
hibitane [Trade name]
Hibitane (Trade name)
MFCD00012532 [MDL number]
MFCD29505384
Microderm (Trade name)
N-(4-CHLOROPHENYL)-1-{N`-[6-(N-{[N`-(4-CHLOROPHENYL)CARBAMIMIDAMIDO]METHANIMIDOYL}AMINO)HEXYL]CARBAMIMIDAMIDO}METHANIMIDAMIDE
N-(4-chlorophenyl)-1-3-(6-{N-[3-(4-chlorophenyl)carbamimidamidomethanimidoyl]amino}hexyl)carbamimidamidomethanimidamide
N,N'-Bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradeca- nediimidamide
N,N''-Bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide
N,N'-Bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide
N',N'''''-hexane-1,6-diylbis[N-(4-chlorophenyl)(imidodicarbonimidic diamide)]
NOLVASAN [Wiki]
Oro-Clense (Trade name)
PAROEX
Perichlor
Peridex [Trade name]
Periogard Oral Rinse
Periogard Oral Rinse (Trade name)
Pharmaseal Scrub Care (Trade name)
Prevacare R (Trade name)
promax
Rotersept [Trade name]
Rotersept (Trade name)
SORETOL
STERILON [Trade name]
Sterilon (Trade name)
Tubulicid
UNII:R4KO0DY52L
UNII-R4KO0DY52L
хлоргексидин
كلورهيكسيدين
氯己定
500 [DBID]
DU1925000 [DBID]
R4KO0DY52L [DBID]
24798_FLUKA [DBID]
282227_ALDRICH [DBID]
348031_ALDRICH [DBID]
AIDS004810 [DBID]
AIDS-004810 [DBID]
BRN 2826432 [DBID]
C06902 [DBID]
DivK1c_000761 [DBID]
HSDB 7196 [DBID]
KBio1_000761 [DBID]
KBio2_000717 [DBID]
KBio2_003285 [DBID]
KBio2_005853 [DBID]
KBio3_001197 [DBID]
KBioGR_000774 [DBID]
KBioSS_000717 [DBID]
NCGC00016246-01 [DBID]
NCGC00091025-01 [DBID]
NINDS_000761 [DBID]
Prestwick_53 [DBID]
Prestwick0_000143 [DBID]
Prestwick1_000143 [DBID]
PubChem Substance ID 329768124 [DBID]
PubChem Substance ID 329831176 [DBID]
SPBio_000210 [DBID]
SPBio_002185 [DBID]
Spectrum_000237 [DBID]
Spectrum2_000135 [DBID]
Spectrum3_000339 [DBID]
Spectrum4_000277 [DBID]