CHLORHEXIDINE HYDROCHLORIDE

First approved in 1959

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

Structure Search

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

Molecular Formula	ClH
Molecular Weight	36.461
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
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 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gingivitis 44 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019028s022lbl.pdf	Curative		Approved 8429	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

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
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
148287.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26271869	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26271869	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

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 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf Page: nda/2005/21669s000_MedR.pdf - p.83	Other AEs: Redness... Other AEs: Redness (grade 2) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21669s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019028s022lbl.pdf	healthy, child n = 1 Health Status: healthy Age Group: child Population Size: 1 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 n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 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
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
eMolecules	491622	https://www.emolecules.com/cgi-bin/more?vid=491622

PubMed

Title	Date	PubMed
Effects of chlorhexidine diacetate on Candida albicans, C. glabrata and Saccharomyces cerevisiae.	1992 Apr	1517175
[Anaphylactic shock with ventricular fibrillation induced by chlorhexidine].	1992 Mar	1560587
Clinical and pathological changes in the knee after accidental chlorhexidine irrigation during arthroscopy. Case reports and review of the literature.	1998 May	9619932
Severe anaphylaxis after a chlorhexidine bath.	1999 May	10321611
Probing depth changes following 2 years of periodontal maintenance therapy including adjunctive controlled release of chlorhexidine.	2003 Apr	12747445
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	16512751
[Ultrastructure study of pathogen of acanthamoeba keratitis].	2008 Nov	19176099
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003
Food components with anticaries activity.	2012 Apr	22030309

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 `Fri Dec 15 14:59:19 UTC 2023` Edited by `admin` on `Fri Dec 15 14:59:19 UTC 2023`
Record UNII	E64XL9U38K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHLORHEXIDINE HYDROCHLORIDE

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

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 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

EPA PESTICIDE CODE

481700

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

Code System Code Type Description

ChEMBL

CHEMBL790

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

MERCK INDEX

m3362

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

Merck Index

NSC

756679

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

CAS

3697-42-5

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

PUBCHEM

62517

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

RXCUI

2361

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

RxNorm

DAILYMED

E64XL9U38K

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

FDA UNII

E64XL9U38K

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

DRUG BANK

DBSALT001610

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

ECHA (EC/EINECS)

223-026-6

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

SMS_ID

100000092569

Created by admin on Fri Dec 15 14:59:20 UTC 2023 , Edited by admin on Fri Dec 15 14:59:20 UTC 2023

PRIMARY

NCI_THESAURUS

C65314

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

EPA CompTox

DTXSID7047144

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

EVMPD

SUB01216MIG

Created by admin on Fri Dec 15 14:59:19 UTC 2023 , Edited by admin on Fri Dec 15 14:59:19 UTC 2023

PRIMARY

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Amount:


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N<SUP>1</SUP>-(6-((N-(N-(4-CHLOROPHENYL)CARBAMIMIDOYL)CARBAMIMIDOYL)AMINO)HEXYL)-N<SUP>3</SUP>-PHENYLIMIDODICARBONIMIDIC DIAMIDE

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Amount:


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IMPURITY -> PARENT

Interaction Type:

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Qualification:

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Amount:


					284W3RP733

N-(N-(6-((N-(N-(4-CHLOROPHENYL)CARBAMIMIDOYL)CARBAMIMIDOYL)AMINO)HEXYL)CARBAMIMIDOYL)UREA

IMPURITY -> PARENT

Amount:

Related Record Type Details


					R4KO0DY52L

CHLORHEXIDINE

ACTIVE MOIETY

Comments:

Description: A white or almost white, crystalline powder; odourless. Solubility: Sparingly soluble in water; soluble in 450 parts of ethanol (~750 g/l) TS. Category: Disinfectant. Storage: Chlorhexidine dihydrochloride should be kept in a well-closed container, protected from light.

Details

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

Funbound

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

F_unbound