CHLORHEXIDINE ACETATE

First approved in 1959

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 Search

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	C22H30Cl2N10
Molecular Weight	505.447
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019028s022lbl.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
bacterial cell wall 7 Target ID: bacterial cell wall Sources: http://chlorhexidinefacts.com/mechanism-of-action.html	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gingivitis 45 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019028s022lbl.pdf	Curative		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
2007 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9869352	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019028s022lbl.pdf	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

Value	Dose	Analyte	Population
148287.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26271869	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	CHLORHEXIDINE saliva	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
180892.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26271869	20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CHLORHEXIDINE saliva	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
187083.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9869352	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
17% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4269593			CHLORHEXIDINE serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
73% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4269593/			CHLORHEXIDINE saliva	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 % 1 times / day single, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: single Dose: 2 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf	healthy, 18-64 years Health Status: healthy Age Group: 18-64 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf	Other AEs: Redness... Other AEs: Redness (grade 2) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf
3 % 1 times / day multiple, topical Recommended Dose: 3 %, 1 times / day Route: topical Route: multiple Dose: 3 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf	healthy, 18-79 years Health Status: healthy Age Group: 18-79 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf	Disc. AE: Papule, Erythema... AEs leading to discontinuation/dose reduction: Papule Erythema (grade 2) Edema (grade 1) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf
3 % 1 times / day multiple, topical Recommended Dose: 3 %, 1 times / day Route: topical Route: multiple Dose: 3 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf	healthy, 22-60 years Health Status: healthy Age Group: 22-60 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf	Disc. AE: Burning sensation, Petechial rash... AEs leading to discontinuation/dose reduction: Burning sensation (grade 1) Petechial rash (grade 1) Scab Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019028s022lbl.pdf	healthy, child Health Status: healthy Age Group: child Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019028s022lbl.pdf	Other AEs: Distress epigastric, Nausea... Other AEs: Distress epigastric Nausea Alcohol intoxication Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019028s022lbl.pdf
2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1998/20774lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20774-ltr-lab-mr.pdf https://pubmed.ncbi.nlm.nih.gov/9776027/	unhealthy, mean age 47 years Health Status: unhealthy Age Group: mean age 47 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1998/20774lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20774-ltr-lab-mr.pdf https://pubmed.ncbi.nlm.nih.gov/9776027/	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/1998/20774lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20774-ltr-lab-mr.pdf https://pubmed.ncbi.nlm.nih.gov/9776027/

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3614	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3614
ChemicalBook	CB2771984	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2771984
ChemicalBook	CB4732251	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4732251
eMolecules	491622	https://www.emolecules.com/cgi-bin/more?vid=491622
MolPort	MolPort-002-541-741	https://www.molport.com/shop/molecule-link/MolPort-002-541-741
MolPort	MolPort-006-167-649	https://www.molport.com/shop/molecule-link/MolPort-006-167-649
ZINC	ZINC000014768621	http://zinc15.docking.org/substances/ZINC000014768621

PubMed

Title	Date	PubMed
Cytotoxicity and genotoxicity of chlorhexidine on macrophages in vitro.	2014-04	22488977
Food components with anticaries activity.	2012-04	22030309
Identification and characterization of inhibitors of the aminoglycoside resistance acetyltransferase Eis from Mycobacterium tuberculosis.	2012-01-02	21898832
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011-07-14	21599003
Chlorhexidine-induced apoptosis or necrosis in L929 fibroblasts: A role for endoplasmic reticulum stress.	2009-01-15	19027770
[Ultrastructure study of pathogen of acanthamoeba keratitis].	2008-11	19176099
Adverse events associated with chlorhexidine use: results from the Department of Veterans Affairs Dental Diabetes Study.	2008-02	18245686
Cysticidal effect on acanthamoeba and toxicity on human keratocytes by polyhexamethylene biguanide and chlorhexidine.	2007-07	17592327
Chemoenzymatic synthesis and antimicrobial and haemolytic activities of amphiphilic bis(phenylacetylarginine) derivatives.	2006-10	16972292
Chlorhexidine in urethral gel: does it cause pain at flexible cystoscopy?	2006-04	16566965
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.	2006-03	16512751
Remineralisation of carious enamel lesions after application of a CHX/F-mouthrinse compared with sole CHX- and placebo-application.	2006	17153647
Chlorhexidine induces DNA damage in rat peripheral leukocytes and oral mucosal cells.	2004-10	15324357
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].	2004-05	15218738
Effects of a chlorhexidine gluconate-containing mouthwash on the vitality and antimicrobial susceptibility of in vitro oral bacterial ecosystems.	2003-08	12902270
Probing depth changes following 2 years of periodontal maintenance therapy including adjunctive controlled release of chlorhexidine.	2003-04	12747445
Developing a dynamic pharmacophore model for HIV-1 integrase.	2000-06-01	10841789
Chlorhexidine and taste. Influence of mouthwashes concentration and of rinsing time.	2000-05	11068420
Severe anaphylaxis after a chlorhexidine bath.	1999-05	10321611
6-month use of 0.2% delmopinol hydrochloride in comparison with 0.2% chlorhexidine digluconate and placebo. (I). Effect on plaque formation and gingivitis.	1998-09	9763330
The effectiveness and side effects of 0.1% and 0.2% chlorhexidine mouthrinses: a clinical study.	1998-07	9759061
Clinical and pathological changes in the knee after accidental chlorhexidine irrigation during arthroscopy. Case reports and review of the literature.	1998-05	9619932
The activity of candidate virucidal agents, low pH and genital secretions against HIV-1 in vitro.	1995-07-01	7548290
Spermicides: anti-HIV activity and cytotoxicity in vitro.	1993-02	8466700
Effects of chlorhexidine diacetate on Candida albicans, C. glabrata and Saccharomyces cerevisiae.	1992-04	1517175
[Anaphylactic shock with ventricular fibrillation induced by chlorhexidine].	1992-03	1560587
Combined effects of Zn(2+)-chlorhexidine and Zn(2+)-cetylpyridinium chloride on caries incidence in partially desalivated rats.	1991-08	1771376
Bradycardia associated with chlorhexidine spray.	1989-06	2774629
Some toxic effects of lead, other metals and antibacterial agents on the nervous system--animal experiment models.	1984	6592932
[Disturbances of taste from oral disinfectants (author's transl)].	1978-10	711516
Nephrotoxic and hepatotoxic effects of triclosan and chlorhexidine in rats.	1977-10	145039
Further studies on effects of irrigation solutions on rat bladders.	1976-12	1009330
The effect of chlorhexidine irrigation of the bladder in the rat.	1975-10	1191923

Patents

Sample Use Guides

In Vivo Use Guide

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

Minimum bactericidal concentrations are different for different bacterial strains (3.9-83.3 mg/l).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:17 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:17 GMT 2025`
Record UNII	5908ZUF22Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHLORHEXIDINE DIACETATE

Preferred Name

English

CHLORHEXIDINE ACETATE

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 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