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Details

Stereochemistry ACHIRAL
Molecular Formula C22H30Cl2N10.2ClH
Molecular Weight 578.368
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORHEXIDINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=WJLVQTJZDCGNJN-UHFFFAOYSA-N
InChI=1S/C22H30Cl2N10.2ClH/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);2*1H

HIDE SMILES / InChI

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

1976
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
The activity of candidate virucidal agents, low pH and genital secretions against HIV-1 in vitro.
1995 Jul-Aug
Developing a dynamic pharmacophore model for HIV-1 integrase.
2000 Jun 1
Chemoenzymatic synthesis and antimicrobial and haemolytic activities of amphiphilic bis(phenylacetylarginine) derivatives.
2006 Oct
Chlorhexidine-induced apoptosis or necrosis in L929 fibroblasts: A role for endoplasmic reticulum stress.
2009 Jan 15
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 HYDROCHLORIDE
GREEN BOOK   MART.   USAN   USP   WHO-DD  
USAN  
Official Name English
NSC-756679
Code English
CHLORHEXIDINE DIHYDROCHLORIDE [INCI]
Common Name English
CHLORHEXIDINE HYDROCHLORIDE [USAN]
Common Name English
CHLORHEXIDINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
AY-5312
Code English
CHLORHEXIDINE DIHYDROCHLORIDE [MI]
Common Name English
1,1'-HEXAMETHYLENEBIS(5-(P-CHLOROPHENYL)BIGUANIDE)DIHYDROCHLORIDE
Common Name English
2,4,11,13-TETRAAZATETRADECANEDIIMIDAMIDE, N,N''-BIS(4-CHLOROPHENYL)-3,12-DIIMINO-, DIHYDROCHLORIDE
Common Name English
CHLORHEXIDINE DIHYDROCHLORIDE
EP   INCI   MI   WHO-IP  
INCI  
Official Name English
CHLORHEXIDINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
CHLORHEXIDINE HYDROCHLORIDE [MART.]
Common Name English
CHLORHEXIDINE DIHYDROCHLORIDE [WHO-IP]
Common Name English
CHLORHEXIDINE HYDROCHLORIDE [GREEN BOOK]
Common Name English
CHLORHEXIDINE HCL
Common Name English
Chlorhexidine hydrochloride [WHO-DD]
Common Name English
CHLORHEXIDINE DIHYDROCHLORIDE [EP MONOGRAPH]
Common Name English
CHLORHEXIDINE HYDROCHLORIDE [JAN]
Common Name English
DANTROCHE HIBITANE
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C28394
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
EPA PESTICIDE CODE 481700
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL790
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY
MERCK INDEX
m3362
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY Merck Index
NSC
756679
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY
CAS
3697-42-5
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY
PUBCHEM
62517
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY
RXCUI
2361
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY RxNorm
DAILYMED
E64XL9U38K
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY
FDA UNII
E64XL9U38K
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY
DRUG BANK
DBSALT001610
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
223-026-6
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY
SMS_ID
100000092569
Created by admin on Fri Dec 15 14:59:20 GMT 2023 , Edited by admin on Fri Dec 15 14:59:20 GMT 2023
PRIMARY
NCI_THESAURUS
C65314
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID7047144
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY
EVMPD
SUB01216MIG
Created by admin on Fri Dec 15 14:59:19 GMT 2023 , Edited by admin on Fri Dec 15 14:59:19 GMT 2023
PRIMARY