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Details

Stereochemistry ACHIRAL
Molecular Formula C22H30Cl2N10.2C6H8NO3P
Molecular Weight 851.659
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORHEXIDINE PHOSPHANILATE

SMILES

NC1=CC=C(C=C1)P(O)(O)=O.NC2=CC=C(C=C2)P(O)(O)=O.ClC3=CC=C(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC4=CC=C(Cl)C=C4)C=C3

InChI

InChIKey=NSCOCGOFKMUTMW-UHFFFAOYSA-N
InChI=1S/C22H30Cl2N10.2C6H8NO3P/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*7-5-1-3-6(4-2-5)11(8,9)10/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34);2*1-4H,7H2,(H2,8,9,10)

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 effect of chlorhexidine irrigation of the bladder in the rat.
1975 Oct
Further studies on effects of irrigation solutions on rat bladders.
1976 Dec
Nephrotoxic and hepatotoxic effects of triclosan and chlorhexidine in rats.
1977 Oct
[Disturbances of taste from oral disinfectants (author's transl)].
1978 Oct
Some toxic effects of lead, other metals and antibacterial agents on the nervous system--animal experiment models.
1984
Bradycardia associated with chlorhexidine spray.
1989 Jun
Combined effects of Zn(2+)-chlorhexidine and Zn(2+)-cetylpyridinium chloride on caries incidence in partially desalivated rats.
1991 Aug
Effects of chlorhexidine diacetate on Candida albicans, C. glabrata and Saccharomyces cerevisiae.
1992 Apr
[Anaphylactic shock with ventricular fibrillation induced by chlorhexidine].
1992 Mar
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
Chlorhexidine and taste. Influence of mouthwashes concentration and of rinsing time.
2000 May
Probing depth changes following 2 years of periodontal maintenance therapy including adjunctive controlled release of chlorhexidine.
2003 Apr
Effects of a chlorhexidine gluconate-containing mouthwash on the vitality and antimicrobial susceptibility of in vitro oral bacterial ecosystems.
2003 Aug
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].
2004 May
Chlorhexidine induces DNA damage in rat peripheral leukocytes and oral mucosal cells.
2004 Oct
Remineralisation of carious enamel lesions after application of a CHX/F-mouthrinse compared with sole CHX- and placebo-application.
2006
Chlorhexidine in urethral gel: does it cause pain at flexible cystoscopy?
2006 Apr
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
Chemoenzymatic synthesis and antimicrobial and haemolytic activities of amphiphilic bis(phenylacetylarginine) derivatives.
2006 Oct
Cysticidal effect on acanthamoeba and toxicity on human keratocytes by polyhexamethylene biguanide and chlorhexidine.
2007 Jul
Adverse events associated with chlorhexidine use: results from the Department of Veterans Affairs Dental Diabetes Study.
2008 Feb
[Ultrastructure study of pathogen of acanthamoeba keratitis].
2008 Nov
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
Food components with anticaries activity.
2012 Apr
Identification and characterization of inhibitors of the aminoglycoside resistance acetyltransferase Eis from Mycobacterium tuberculosis.
2012 Jan 2
Cytotoxicity and genotoxicity of chlorhexidine on macrophages in vitro.
2014 Apr
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 PHOSPHANILATE
USAN  
USAN  
Official Name English
WP-973
Code English
BMY-30120
Code English
2,4,11,13-TETRAAZATETRADECANEDIIMIDAMIDE, N,N''-BIS(4-CHLOROPHENYL)-3,12-DIIMINO-, (4-AMINOPHENYL)PHOSPHONATE (1:2)
Common Name English
1,1'-HEXAMETHYLENEBIS(5-(P-CHLOROPHENYL)BIGUANIDE) (P-AMINOPHENYL)PHOSPHONATE (1:2)
Common Name English
CHLORHEXIDINE PHOSPHANILATE [USAN]
Common Name English
CHP
Common Name English
Code System Code Type Description
MESH
C048279
Created by admin on Fri Dec 15 18:09:32 GMT 2023 , Edited by admin on Fri Dec 15 18:09:32 GMT 2023
PRIMARY
USAN
AA-20
Created by admin on Fri Dec 15 18:09:32 GMT 2023 , Edited by admin on Fri Dec 15 18:09:32 GMT 2023
PRIMARY
CAS
77146-42-0
Created by admin on Fri Dec 15 18:09:32 GMT 2023 , Edited by admin on Fri Dec 15 18:09:32 GMT 2023
PRIMARY
PUBCHEM
9919060
Created by admin on Fri Dec 15 18:09:32 GMT 2023 , Edited by admin on Fri Dec 15 18:09:32 GMT 2023
PRIMARY
FDA UNII
I20F29W4EO
Created by admin on Fri Dec 15 18:09:32 GMT 2023 , Edited by admin on Fri Dec 15 18:09:32 GMT 2023
PRIMARY
NCI_THESAURUS
C169844
Created by admin on Fri Dec 15 18:09:32 GMT 2023 , Edited by admin on Fri Dec 15 18:09:32 GMT 2023
PRIMARY
ChEMBL
CHEMBL790
Created by admin on Fri Dec 15 18:09:32 GMT 2023 , Edited by admin on Fri Dec 15 18:09:32 GMT 2023
PRIMARY
EPA CompTox
DTXSID70998405
Created by admin on Fri Dec 15 18:09:32 GMT 2023 , Edited by admin on Fri Dec 15 18:09:32 GMT 2023
PRIMARY