U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H30Cl2N10
Molecular Weight 505.4473
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORHEXIDINE

SMILES

C(CCCNC(=N)NC(=N)Nc1ccc(cc1)Cl)CCNC(=N)NC(=N)Nc2ccc(cc2)Cl

InChI

InChIKey=GHXZTYHSJHQHIJ-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description
Curator's Comment:: http://www.wikidoc.org/index.php/Chlorhexidine_gluconate

Chlorhexidine is a broad-spectrum biocide effective against Gram-positive bacteria, Gram-negative bacteria and fungi. It is used primarily as its salts (e.g., the dihydrochloride, diacetate, and digluconate). Chlorhexidine inactivates microorganisms with a broader spectrum than other antimicrobials (e.g. antibiotics) and has a quicker kill rate than other antimicrobials (e.g. povidone-iodine). It has both bacteriostatic (inhibits bacterial growth) and bactericidal (kills bacteria) mechanisms of action, depending on its concentration. Chlorhexidine kills by disrupting the cell membrane. The most common side effects associated with chlorhexidine gluconate oral rinses are: 1) an increase in staining of teeth and other oral surfaces; 2) an increase in calculus formation; and 3) an alteration in taste perception; 4) toothache; 5) upper respiratory tract infection; and 6) headache.

Originator

Curator's Comment:: 1950s — Chlorhexidine is discovered by the Imperial Chemical Industries, Limited (Manchester, UK) while researching the synthesis of anti-malarial agents

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: bacterial cell wall
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
HIBICLENS

Approved Use

Use for the preparation of the patient's skin prior to surgery. Helps to reduce bacteria that potentially can cause skin infection.

Launch Date

211766400000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2007 μg/mL
2.5 mg single, dental
dose: 2.5 mg
route of administration: Dental
experiment type: SINGLE
co-administered:
CHLORHEXIDINE inflammatory exudate
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.206 μg/g
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORHEXIDINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
187083.4 μg × h/mL
2.5 mg single, dental
dose: 2.5 mg
route of administration: Dental
experiment type: SINGLE
co-administered:
CHLORHEXIDINE inflammatory exudate
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
148287.6 ng × h/mL
0.2 % single, dental
dose: 0.2 %
route of administration: Dental
experiment type: SINGLE
co-administered:
CHLORHEXIDINE saliva
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
180892.9 ng × h/mL
0.2 % 1 times / day multiple, dental
dose: 0.2 %
route of administration: Dental
experiment type: MULTIPLE
co-administered:
CHLORHEXIDINE saliva
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
17%
CHLORHEXIDINE serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
73%
CHLORHEXIDINE saliva
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 % 1 times / day single, topical
Recommended
Dose: 2 %, 1 times / day
Route: topical
Route: single
Dose: 2 %, 1 times / day
Sources:
healthy, 18-64 years
Health Status: healthy
Age Group: 18-64 years
Sex: M+F
Sources:
Other AEs: Redness...
3 % 1 times / day multiple, topical
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources:
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: M+F
Sources:
Disc. AE: Papule, Erythema...
AEs leading to
discontinuation/dose reduction:
Papule
Erythema (grade 2)
Edema (grade 1)
Sources:
3 % 1 times / day multiple, topical
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources:
healthy, 22-60 years
Health Status: healthy
Age Group: 22-60 years
Sex: M+F
Sources:
Disc. AE: Burning sensation, Petechial rash...
AEs leading to
discontinuation/dose reduction:
Burning sensation (grade 1)
Petechial rash (grade 1)
Scab
Sources:
1.5 oz 1 times / day single, oral
Studied dose
Dose: 1.5 oz, 1 times / day
Route: oral
Route: single
Dose: 1.5 oz, 1 times / day
Sources:
healthy, child
Other AEs: Distress epigastric, Nausea...
Other AEs:
Distress epigastric
Nausea
Alcohol intoxication
Sources:
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Other AEs: Toothache, Upper respiratory tract infection...
Other AEs:
Toothache (50.7%)
Upper respiratory tract infection (28.4%)
Headache (27.1%)
Sinusitis (13.8%)
Influenza-like symptoms (7.6%)
Back pain (6.7%)
Tooth disorder (6.2%)
Bronchitis (6.2%)
Abscess (5.8%)
Pain (4.9%)
Allergy (4%)
Myalgia (4%)
Gum hyperplasia (3.6%)
Pharyngitis (3.6%)
Arthralgia (3.1%)
Dysmenorrhea (3.1%)
Dyspepsia (3.1%)
Rhinitis (2.7%)
Coughing (2.7%)
Arthrosis (2.7%)
Hypertension (2.2%)
Stomatitis ulcerative (2.2%)
Tendinitis (2.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Redness grade 2
2 % 1 times / day single, topical
Recommended
Dose: 2 %, 1 times / day
Route: topical
Route: single
Dose: 2 %, 1 times / day
Sources:
healthy, 18-64 years
Health Status: healthy
Age Group: 18-64 years
Sex: M+F
Sources:
Papule Disc. AE
3 % 1 times / day multiple, topical
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources:
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: M+F
Sources:
Edema grade 1
Disc. AE
3 % 1 times / day multiple, topical
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources:
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: M+F
Sources:
Erythema grade 2
Disc. AE
3 % 1 times / day multiple, topical
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources:
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: M+F
Sources:
Scab Disc. AE
3 % 1 times / day multiple, topical
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources:
healthy, 22-60 years
Health Status: healthy
Age Group: 22-60 years
Sex: M+F
Sources:
Burning sensation grade 1
Disc. AE
3 % 1 times / day multiple, topical
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources:
healthy, 22-60 years
Health Status: healthy
Age Group: 22-60 years
Sex: M+F
Sources:
Petechial rash grade 1
Disc. AE
3 % 1 times / day multiple, topical
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources:
healthy, 22-60 years
Health Status: healthy
Age Group: 22-60 years
Sex: M+F
Sources:
Alcohol intoxication
1.5 oz 1 times / day single, oral
Studied dose
Dose: 1.5 oz, 1 times / day
Route: oral
Route: single
Dose: 1.5 oz, 1 times / day
Sources:
healthy, child
Distress epigastric
1.5 oz 1 times / day single, oral
Studied dose
Dose: 1.5 oz, 1 times / day
Route: oral
Route: single
Dose: 1.5 oz, 1 times / day
Sources:
healthy, child
Nausea
1.5 oz 1 times / day single, oral
Studied dose
Dose: 1.5 oz, 1 times / day
Route: oral
Route: single
Dose: 1.5 oz, 1 times / day
Sources:
healthy, child
Sinusitis 13.8%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Hypertension 2.2%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Stomatitis ulcerative 2.2%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Tendinitis 2.2%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Arthrosis 2.7%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Coughing 2.7%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Rhinitis 2.7%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Headache 27.1%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Upper respiratory tract infection 28.4%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Arthralgia 3.1%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Dysmenorrhea 3.1%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Dyspepsia 3.1%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Gum hyperplasia 3.6%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Pharyngitis 3.6%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Allergy 4%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Myalgia 4%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Pain 4.9%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Abscess 5.8%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Toothache 50.7%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Bronchitis 6.2%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Tooth disorder 6.2%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Back pain 6.7%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
Influenza-like symptoms 7.6%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
PubMed

PubMed

TitleDatePubMed
Nephrotoxic and hepatotoxic effects of triclosan and chlorhexidine in rats.
1977 Oct
[Disturbances of taste from oral disinfectants (author's transl)].
1978 Oct
Spermicides: anti-HIV activity and cytotoxicity in vitro.
1993 Feb
The activity of candidate virucidal agents, low pH and genital secretions against HIV-1 in vitro.
1995 Jul-Aug
The effectiveness and side effects of 0.1% and 0.2% chlorhexidine mouthrinses: a clinical study.
1998 Jul
Clinical and pathological changes in the knee after accidental chlorhexidine irrigation during arthroscopy. Case reports and review of the literature.
1998 May
6-month use of 0.2% delmopinol hydrochloride in comparison with 0.2% chlorhexidine digluconate and placebo. (I). Effect on plaque formation and gingivitis.
1998 Sep
Severe anaphylaxis after a chlorhexidine bath.
1999 May
Developing a dynamic pharmacophore model for HIV-1 integrase.
2000 Jun 1
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].
2004 May
Short-term side effects of 0.2% alcohol-free chlorhexidine mouthrinse used as an adjunct to non-surgical periodontal treatment: a double-blind clinical study.
2006 Mar
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Sample Use Guides

Recommended use is twice daily oral rinsing for 30 seconds, morning and evening after tooth brushing. Usual dosage is 15 ml (1 tablespoon) of undiluted Chlorhexidine gluconate oral rinse. Prophylaxis intervals - no longer than six months.
Route of Administration: Topical
In Vitro Use Guide
Curator's Comment:: Chlorhexidine caused significant decreases in both total anaerobe and total aerobe/facultative anaerobe counts (P < 0.05), together with lesser decreases in gram-negative anaerobes.
Minimum bactericidal concentrations are different for different bacterial strains (3.9-83.3 mg/l).
Name Type Language
CHLORHEXIDINE
HSDB   INCI   INN   MART.   MI   USP-RS   VANDF   WHO-DD  
INN   INCI  
Official Name English
CHLORHEXIDINE [INCI]
Common Name English
MERFEN-INCOLORE
Brand Name English
CHLORHEXIDINE [HSDB]
Common Name English
CHLORHEXIDINE [WHO-DD]
Common Name English
CHLORHEXIDINE [VANDF]
Common Name English
CHLORHEXADINE
Common Name English
CHLORHEXIDINE [MI]
Common Name English
DENTISEPT
Brand Name English
CHLORHEXIDINE [USP-RS]
Common Name English
CHLORHEXIDINE [MART.]
Common Name English
CHLORHEXIDINE [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC D08AC02
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-ATC S02AA09
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-ATC A01AB03
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-VATC QA01AB03
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-ATC S03AA04
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-VATC QD08AC02
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-VATC QD08AC52
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
NCI_THESAURUS C28394
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
CFR 21 CFR 524.402
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-ATC R02AA05
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-VATC QR02AA05
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
CFR 21 CFR 556.120
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-VATC QS03AA04
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-VATC QD09AA12
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-VATC QS01AX09
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
NDF-RT N0000008478
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-ATC S01AX09
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-ATC D08AC52
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-ATC D09AA12
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 15.1
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-VATC QS02AA09
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-VATC QB05CA02
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
WHO-ATC B05CA02
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
EPA PESTICIDE CODE 217100
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
Code System Code Type Description
DRUG BANK
DB00878
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-238-7
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
USP_CATALOG
1111001
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M3362
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
597
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
EVMPD
SUB06181MIG
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
MESH
D002710
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
NCI_THESAURUS
C364
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
PUBCHEM
2713
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
FDA UNII
R4KO0DY52L
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
HSDB
7196
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
CAS
55-56-1
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
WIKIPEDIA
CHLORHEXIDINE
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
EPA CompTox
55-56-1
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
INN
500
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
ChEMBL
CHEMBL790
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY
RXCUI
2358
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY RxNorm
LACTMED
Chlorhexidine
Created by admin on Sat Jun 26 12:46:25 UTC 2021 , Edited by admin on Sat Jun 26 12:46:25 UTC 2021
PRIMARY