Chlorhexidine

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 known by the salt forms
chlorhexidine gluconate, chlorhexidine
digluconate, and chlorhexidine acetate.[4]
 Chlorhexidine

Clinical data
Pronunciation klɔː(r)ˈhɛksɪdiːn
Trade names Betasept, ChloraPrep,
Chlorostat, others
Other names CHX, CHG, 1,6-bis(4-
chloro-
phenylbiguanido)hexane
AHFS/Drugs.com Monograph (https://w
ww.drugs.com/mono
graph/chlorhexidine-g
 luconate-topical.htm
l)
License data US DailyMed: Chlorhexidine
(https://dailymed.nlm.nih.g
ov/dailymed/search.cfm?l
abeltype=all&query=Chlorh
exidine)
Pregnancy AU: A
category
Routes of Topical
administration
ATC code A01AB03 (WHO (http
s://www.whocc.no/at
c_ddd_index/?code=A
01AB03) ) B05CA02
(WHO (https://www.w
hocc.no/atc_ddd_inde
x/?code=B05CA02) ),
D08AC02 (WHO (http
s://www.whocc.no/at
c_ddd_index/?code=D
08AC02) ), D09AA12
(WHO (https://www.w
hocc.no/atc_ddd_inde
x/?code=D09AA12) )
(dressing), R02AA05
(WHO (https://www.w
hocc.no/atc_ddd_inde
x/?code=R02AA05) ),
S01AX09 (WHO (http
s://www.whocc.no/at
c_ddd_index/?code=S
01AX09) ), S02AA09
(WHO (https://www.w
 hocc.no/atc_ddd_inde
x/?code=S02AA09) ),
S03AA04 (WHO (http
s://www.whocc.no/at
c_ddd_index/?code=S
03AA04) )

Legal status
Legal status AU: S5, S6, S7
US: OTC / Rx-only

Identifiers

IUPAC name
N,N′′′′1,6-Hexanediylbis[N′-(4-chlorophenyl)(imid
odicarbonimidic diamide)]
CAS Number 55-56-1 (https://com
monchemistry.cas.or
 g/detail?cas_rn=55-56
-1)  

PubChem CID 9552079 (https://pub

chem.ncbi.nlm.nih.go
v/compound/955207
9)
DrugBank DB00878 (https://ww
w.drugbank.ca/drugs/
DB00878)  

ChemSpider 2612 (https://www.ch

emspider.com/Chemi
cal-Structure.2612.ht
ml)  

UNII R4KO0DY52L (https://

precision.fda.gov/unii
 search/srs/unii/R4KO
0DY52L)
KEGG D07668 (https://www.
kegg.jp/entry/D0766
8)  

ChEBI CHEBI:3614 (https://w

ww.ebi.ac.uk/chebi/s
earchId.do?chebiId=C
HEBI:3614)  

ChEMBL ChEMBL790 (https://

www.ebi.ac.uk/chemb
ldb/index.php/compo
und/inspect/ChEMBL
790)  

CompTox Dashboard DTXSID2033314 (http

(EPA)
s://comptox.epa.gov/
 dashboard/chemical/
details/DTXSID20333
14)
ECHA InfoCard 100.000.217 (https://
echa.europa.eu/subst
ance-information/-/su
bstanceinfo/100.000.
217)

Chemical and physical data

Formula C22H30Cl2N10
Molar mass 505.45 g·mol−1
3D model (JSmol) Interactive image (htt
ps://chemapps.stolaf.
edu/jmol/jmol.php?m
odel=Clc1ccc%28N
C%28%3DN%29NC%2
 8%3DN%29NCCCCCC
NC%28%3DN%29NC%
28%3DN%29Nc2ccc%
28Cl%29cc2%29cc1)
Melting point 134 to 136 °C (273 to
277 °F)
Solubility in water 0.8

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)8-1
2-18/h5-12H,1-4,13-14H2,(H5,25,27,29,31,
33)(H5,26,28,30,32,34) 
Key:GHXZTYHSJHQHIJ-UHFFFAOYSA-N 
   (verify) (https://en.wikipedia.org/w/index.ph
p?title=Special:ComparePages&rev1=464187
733&page2=Chlorhexidine)

Side effects may include skin irritation,

tooth discoloration, and allergic
reactions,[3] although the risk appears to
be the same as other topical
antiseptics.[5][6] It may cause eye problems
if direct contact occurs.[4] Use in
pregnancy appears to be safe.[7]
Chlorhexidine may come mixed in
alcohol,[8][9][10] 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.[11] Chlorhexidine is available
over the counter in the United States.[4] It
is on the World Health Organization's List
of Essential Medicines.[12][13] In 2020, it
was the 273rd most commonly prescribed
medication in the United States, with more
than 1 million prescriptions.[14][15]

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).[16] 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."[17]

In endodontics, chlorhexidine has been

used for root canal irrigation and as an
intracanal dressing[18][19] but has been
replaced by the use of sodium
hypochlorite bleach in much of the
developed world.

Antiseptic

CHG is active against Gram-positive and

Gram-negative organisms, facultative
anaerobes, aerobes, and yeasts.[20] 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.[21]

There is strong evidence that

chlorhexidine is more effective than
povidone-iodine for clean surgery.[22][23]
Evidence shows that it is an effective
antiseptic for upper limb surgery.[5]

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.
Dental use

Perichlor brand 0.12% chlorhexidine gluconate solution

Use of a CHG-based mouthwash in

combination with normal tooth care can
help reduce the build-up of plaque and
improve mild gingivitis.[25] There is not
enough evidence to determine the effect in
moderate to severe gingivitis.[25] 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.[25] Extrinsic tooth
staining occurs when chlorhexidine rinse
has been used for 4 weeks or longer.[25]

Mouthwashes containing chlorhexidine

which stain teeth less than the classic
solution have been developed, many of
which contain chelated zinc.[26][27][28]

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".[29]

Topical

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.[20] Chlorhexidine eye drops have
been used as a treatment for eyes
affected by Acanthamoeba keratitis.[30]
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%.[31]

Side effects
CHG is ototoxic; if put into an ear canal
which has a ruptured eardrum, it can lead
to deafness.[32]
CHG 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.[21] 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.[33]
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.[34]

When ingested, CHG is poorly absorbed in

the gastrointestinal tract and can cause
stomach irritation or nausea.[35][36] 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.[36][37]
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.[20]
Chemistry
It is a cationic polybiguanide
(bisbiguanide).[38]

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.[39]

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

Two routes for chlorhexidine synthesis:[40] U.S. Patent 2,684,924 (https://patents.google.com/patent/US2684924) (1954
to I.C.I.). The compounds designated (...)2 are substituted hexanes.
Society and culture

Brands

Chlorhexidine topical is sold as Betasept,

Biopatch, Calgon Vesta, ChloraPrep One-
Step, Dyna-Hex, Hibiclens, Hibistat
Towelette, Scrub Care Exidine, Spectrum-4
among others.[41]

Chlorhexidine gluconate mouthwash is

sold as Dentohexin, Paroex, Peridex,
PerioChip, Corsodyl and Periogard, among
others.[42]
Veterinary medicine
In animals, chlorhexidine is used for
topical disinfection of wounds,[43] and to
manage skin infections.[44] Chlorhexidine-
based disinfectant products are used in
the dairy farming industry.[45]

Post-surgical respiratory problems have

been associated with the use of
chlorhexidine products in cats.[46]

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