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

Details

Stereochemistry ACHIRAL
Molecular Formula C22H30Cl2N10.2C2H4O2
Molecular Weight 625.551
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORHEXIDINE ACETATE

SMILES

CC(O)=O.CC(O)=O.ClC1=CC=C(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC2=CC=C(Cl)C=C2)C=C1

InChI

InChIKey=WDRFFJWBUDTUCA-UHFFFAOYSA-N
InChI=1S/C22H30Cl2N10.2C2H4O2/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;2*1-2(3)4/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34);2*1H3,(H,3,4)

HIDE SMILES / InChI

Molecular Formula C2H4O2
Molecular Weight 60.052
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H30Cl2N10
Molecular Weight 505.447
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019028s022lbl.pdf http://www.drugbank.ca/drugs/DB00878 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
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

2.11766395E11
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: Page: nda/2005/21669s000_MedR.pdf - p.83
healthy, 18-64 years
n = 36
Health Status: healthy
Age Group: 18-64 years
Sex: M+F
Population Size: 36
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
Other AEs: Redness...
Other AEs:
Redness (grade 2)
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
3 % 1 times / day multiple, topical (mean)
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
healthy, 18-79 years
n = 204
Health Status: healthy
Age Group: 18-79 years
Sex: M+F
Population Size: 204
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
Disc. AE: Papule, Erythema...
AEs leading to
discontinuation/dose reduction:
Papule
Erythema (grade 2)
Edema (grade 1)
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
3 % 1 times / day multiple, topical (mean)
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
healthy, 22-60 years
n = 23
Health Status: healthy
Age Group: 22-60 years
Sex: M+F
Population Size: 23
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
Disc. AE: Burning sensation, Petechial rash...
AEs leading to
discontinuation/dose reduction:
Burning sensation (grade 1)
Petechial rash (grade 1)
Scab
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
1.5 oz 1 times / day single, oral (mean)
Studied dose
Dose: 1.5 oz, 1 times / day
Route: oral
Route: single
Dose: 1.5 oz, 1 times / day
Sources:
healthy, child
n = 1
Health Status: healthy
Age Group: child
Population Size: 1
Sources:
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
n = 225
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: Page: nda/2005/21669s000_MedR.pdf - p.83
healthy, 18-64 years
n = 36
Health Status: healthy
Age Group: 18-64 years
Sex: M+F
Population Size: 36
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
Papule Disc. AE
3 % 1 times / day multiple, topical (mean)
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
healthy, 18-79 years
n = 204
Health Status: healthy
Age Group: 18-79 years
Sex: M+F
Population Size: 204
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
Edema grade 1
Disc. AE
3 % 1 times / day multiple, topical (mean)
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
healthy, 18-79 years
n = 204
Health Status: healthy
Age Group: 18-79 years
Sex: M+F
Population Size: 204
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
Erythema grade 2
Disc. AE
3 % 1 times / day multiple, topical (mean)
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
healthy, 18-79 years
n = 204
Health Status: healthy
Age Group: 18-79 years
Sex: M+F
Population Size: 204
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
Scab Disc. AE
3 % 1 times / day multiple, topical (mean)
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
healthy, 22-60 years
n = 23
Health Status: healthy
Age Group: 22-60 years
Sex: M+F
Population Size: 23
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
Burning sensation grade 1
Disc. AE
3 % 1 times / day multiple, topical (mean)
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
healthy, 22-60 years
n = 23
Health Status: healthy
Age Group: 22-60 years
Sex: M+F
Population Size: 23
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
Petechial rash grade 1
Disc. AE
3 % 1 times / day multiple, topical (mean)
Recommended
Dose: 3 %, 1 times / day
Route: topical
Route: multiple
Dose: 3 %, 1 times / day
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
healthy, 22-60 years
n = 23
Health Status: healthy
Age Group: 22-60 years
Sex: M+F
Population Size: 23
Sources: Page: nda/2005/21669s000_MedR.pdf - p.83
Alcohol intoxication
1.5 oz 1 times / day single, oral (mean)
Studied dose
Dose: 1.5 oz, 1 times / day
Route: oral
Route: single
Dose: 1.5 oz, 1 times / day
Sources:
healthy, child
n = 1
Health Status: healthy
Age Group: child
Population Size: 1
Sources:
Distress epigastric
1.5 oz 1 times / day single, oral (mean)
Studied dose
Dose: 1.5 oz, 1 times / day
Route: oral
Route: single
Dose: 1.5 oz, 1 times / day
Sources:
healthy, child
n = 1
Health Status: healthy
Age Group: child
Population Size: 1
Sources:
Nausea
1.5 oz 1 times / day single, oral (mean)
Studied dose
Dose: 1.5 oz, 1 times / day
Route: oral
Route: single
Dose: 1.5 oz, 1 times / day
Sources:
healthy, child
n = 1
Health Status: healthy
Age Group: child
Population Size: 1
Sources:
Sinusitis 13.8%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Hypertension 2.2%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Stomatitis ulcerative 2.2%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Tendinitis 2.2%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Arthrosis 2.7%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Coughing 2.7%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Rhinitis 2.7%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Headache 27.1%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Upper respiratory tract infection 28.4%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Arthralgia 3.1%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Dysmenorrhea 3.1%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Dyspepsia 3.1%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Gum hyperplasia 3.6%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Pharyngitis 3.6%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Allergy 4%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Myalgia 4%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Pain 4.9%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Abscess 5.8%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Toothache 50.7%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Bronchitis 6.2%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Tooth disorder 6.2%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Back pain 6.7%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
Influenza-like symptoms 7.6%
2.5 mg 3 times / month multiple, subgingival
Recommended
unhealthy, mean age 47 years
n = 225
PubMed

PubMed

TitleDatePubMed
Further studies on effects of irrigation solutions on rat bladders.
1976 Dec
[Disturbances of taste from oral disinfectants (author's transl)].
1978 Oct
Combined effects of Zn(2+)-chlorhexidine and Zn(2+)-cetylpyridinium chloride on caries incidence in partially desalivated rats.
1991 Aug
[Anaphylactic shock with ventricular fibrillation induced by chlorhexidine].
1992 Mar
The activity of candidate virucidal agents, low pH and genital secretions against HIV-1 in vitro.
1995 Jul-Aug
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
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
Cysticidal effect on acanthamoeba and toxicity on human keratocytes by polyhexamethylene biguanide and chlorhexidine.
2007 Jul
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:00:58 UTC 2023
Edited
by admin
on Fri Dec 15 15:00:58 UTC 2023
Record UNII
5908ZUF22Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLORHEXIDINE ACETATE
GREEN BOOK   MART.   USP   USP-RS  
Common Name English
CHLORHEXIDINE DIACETATE [WHO-IP]
Common Name English
1,1'-HEXAMETHYLENEBIS(5-(4-CHLOROPHENYL)BIGUANIDE) DIACETATE
Systematic Name English
NSC-526936
Code English
CHLORHEXIDINE ACETATE [USP-RS]
Common Name English
CHLORHEXIDINE DIACETATE [EP MONOGRAPH]
Common Name English
CHLORHEXIDINI DIACETAS [WHO-IP LATIN]
Common Name English
CHLORHEXIDINE DIACETATE [INCI]
Common Name English
CHLORHEXIDINE DIACETATE
EP   INCI   MI   WHO-DD   WHO-IP  
INCI  
Official Name English
CHLORHEXIDINE ACETATE [MART.]
Common Name English
CHLORHEXIDINE ACETATE [GREEN BOOK]
Common Name English
CHLORHEXIDINE DIACETATE [MI]
Common Name English
CHLORHEXIDINE ACETATE [USP MONOGRAPH]
Common Name English
Chlorhexidine diacetate [WHO-DD]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 45502
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
Code System Code Type Description
RXCUI
2359
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
ALTERNATIVE
RXCUI
133054
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
CHEBI
81711
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
RS_ITEM_NUM
1111103
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
PUBCHEM
5967
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
EPA CompTox
DTXSID7032345
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
NSC
526936
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
MERCK INDEX
m3362
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY Merck Index
DAILYMED
5908ZUF22Y
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
SMS_ID
100000092204
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
DRUG BANK
DBSALT001123
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
FDA UNII
5908ZUF22Y
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
CAS
56-95-1
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-302-4
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
EVMPD
SUB20822
Created by admin on Fri Dec 15 15:00:58 UTC 2023 , Edited by admin on Fri Dec 15 15:00:58 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Description. A white or yellowish white, microcrystalline powder; odourless or almost odourless. Solubility. Soluble in 55 parts of water and in 15 parts of ethanol (~750 g/l) TS; very slightly soluble in glycerol R. Category. Disinfectant. Storage. Chlorhexidine diacetate should be kept in a well-closed container, protected from light.