CETYLPYRIDINIUM BROMIDE

First approved in 1941

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H38N.Br
Molecular Weight	384.437
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1

InChI

InChIKey=DVBJBNKEBPCGSY-UHFFFAOYSA-M

InChI=1S/C21H38N.BrH/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-22-20-17-15-18-21-22;/h15,17-18,20-21H,2-14,16,19H2,1H3;1H/q+1;/p-1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19138180 | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3bbd4a08-062f-40a3-a25b-f23490ee57f6

Cetylpyridinium (used in a form of chloride salt) is a cationic surface-active agent and has a broad antimicrobial spectrum, with rapid killing of gram-positive pathogens and yeast in particular. It is suggested that interaction with bacteria occurs by the disruption of membrane function, leakage of cytoplasmic material, and ultimately the collapse of the intra-cellular equilibrium. The drug is used under various trade names as an oral OTC hygiene product (mouthwash, dental kits, etc.) to control the dental plaque and to prevent the subsequent gingivitis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial membrane 6 Target ID: Bacterial membrane Sources: https://www.ncbi.nlm.nih.gov/pubmed/19138180	Interacts 323

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gingivitis 44 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3bbd4a08-062f-40a3-a25b-f23490ee57f6	Preventing		Approved 8429	ANTISEPTIC (cetylpyridinium chloride) mouthwash Approved Use Help to control plaque that leads to gingivitis.
Dental plaque 13 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3bbd4a08-062f-40a3-a25b-f23490ee57f6	Curative		Approved 8429	ANTISEPTIC (cetylpyridinium chloride) mouthwash Approved Use Help to control plaque that leads to gingivitis.

C_max

Value	Dose	Co-administered	Analyte	Population
10 mg/g EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16477395/	6 μL single, topical dose: 6 μL route of administration: Topical experiment type: SINGLE co-administered:		CETYLPYRIDINIUM unknown	Mus musculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
127 mg × h/g EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16477395/	6 μL single, topical dose: 6 μL route of administration: Topical experiment type: SINGLE co-administered:		CETYLPYRIDINIUM unknown	Mus musculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:32914	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32914
ZINC	ZINC000006845963	http://zinc15.docking.org/substances/ZINC000006845963
eMolecules	1987091	https://www.emolecules.com/cgi-bin/more?vid=1987091

PubMed

Title	Date	PubMed
Detection of cationic surfactants in oral rinses and a disinfectant formulation using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001	11344536
The kinetics and thermodynamics of surfactants in solvent sublation.	2001 Aug	11583089
Spectrophotometric determination of cetylpyridinium chloride in pharmaceutical products.	2001 Aug	11451652
Efficacy of cetylpyridinium chloride in immersion treatment for reducing populations of pathogenic bacteria on fresh-cut vegetables.	2001 Dec	11770641
Voltammetric behavior of L-cysteine in the presence of CPB at a silver electrode.	2001 Mar 1	11270224
Cytotoxicity of potential ocular permeation enhancers evaluated on rabbit and human corneal epithelial cell lines.	2001 May 31	11397552
PVC matrix membrane sensor for potentiometric determination of cetylpyridinium chloride.	2001 Sep	11708056
TiO2-based photocatalytic degradation of 2-chlorophenol adsorbed on hydrophobic clay.	2002 Aug 15	12214657
Solubility, chemical and photochemical stability of curcumin in surfactant solutions. Studies of curcumin and curcuminoids, XXVIII.	2002 Dec	12561244
[Prospect of the development of new bactericidal drugs against Helicobacter pylori for eradication therapy].	2002 Feb	11979883
Time-resolved fluorometric analysis of carbohydrates labeled with amino-aromatic compounds by reductive amination.	2002 Jul	12173660
Molecular cloning and characterization of human chondrolectin, a novel type I transmembrane protein homologous to C-type lectins.	2002 Jul	12079284
Cysteine challenge testing: a powerful tool for examining oral malodour processes and treatments in vivo.	2002 Jun	12090457
Liquid-liquid extraction of palladium(II) from hydrobromic acid media by hexadecylpyridinium bromide.	2002 Mar	11918190
[Method for determining nitrogen-containing cationic surface-active agents using butyrylcholinesterase].	2002 Mar-Apr	12152307
Thermodynamics and micellar properties of tetradecyltrimethylammonium bromide in formamide-water mixtures.	2002 Nov 15	12505087
Effects of various antiplaque agents on fructosyltransferase activity in solution and immobilized onto hydroxyapatite.	2002 Oct	12664468
Comparative evaluation of the MGIT and BACTEC culture systems for the recovery of Mycobacterium avium subsp. paratuberculosis from milk.	2003	12807471
[Delmopinol--an alternative to chlorhexidine?].	2003	12680413
Combined effect of zinc ions and cationic antibacterial agents on intraoral volatile sulphur compounds (VSC).	2003 Aug	12953892
Examination of murine tear film.	2003 Aug	12882802
Dissolved organic matter effects on the performance of a barrier to polycyclic aromatic hydrocarbon transport by groundwater.	2003 Feb	12504364
An in vitro evaluation of the availability of cetylpyridinium chloride and chlorhexidine in some commercially available mouthrinse products.	2003 Feb 22	12627199
A salivary incubation test for evaluation of oral malodor: a pilot study.	2003 Jul	12931755
Impact of brief exposure to balanced salts solution or cetylpyridinium chloride on the surface appearance of the rabbit corneal epithelium--a scanning electron microscopy study.	2003 Jun	12868014
Effect of toothpaste on the plaque inhibitory properties of a cetylpyridinium chloride mouth rinse.	2003 Mar	12631184
Evaluation of cetylpyridinium chloride for infection control in storage solution.	2003 May	12752926
Modification of ion chromatographic separations by ionic and nonionic surfactants.	2003 May 16	12830873
[DNA complexes, formed on aqueous phase surfaces: new planar polymeric and composite nanostructures].	2003 Nov-Dec	14714516
The effect of antimicrobial pre-treatments on the performance of resin composite restorations.	2003 Nov-Dec	14653285
Reversible and irreversible adsorption of surfactants at a hanging mercury drop electrode.	2003 Oct	14596402
Inhibition of orally produced volatile sulfur compounds by zinc, chlorhexidine or cetylpyridinium chloride--effect of concentration.	2003 Oct	12974683
Quenching of fluorescence of 1-hydroxypyrene-3,6,8-trisulfonate (HPTS) by Cu2+, Co2+, Ni2+, I-, and cetylpyridinium (CP+) ions in water/AOT/heptane microemulsion.	2004 Mar 1	14757089

Patents

Sample Use Guides

In Vivo Use Guide

Rinse for 30 seconds with 20 ml (4 teaspoonsfuls) twice a day, do not swallow.

Route of Administration: Dental

In Vitro Use Guide

The panel of 24 laboratory strains including 18 oral bacteria, five nonoral bacterialspecies and the yeast Candida albicans was incubated with twofold serial dilutions of the 0.05% cetylpyridinium chloride mouthrinse for 48-72 h at 35 celsius degrees. For the agar dilution assays of cultivable plaque bacte-ria, the drug was added at a final concentration of 1%. MIC values were 1.5-3% for Aggregatibacter actinomycetemcomitans and Capnocytophaga gingivalis, 0.375% for Actinomyces meyeri, Moraxella catarrhalis, Campylobacter rectus, 0.187-0.375 % for Porphyromonas gingivalis, etc.

Name

Type

Language

CETYLPYRIDINIUM BROMIDE

Systematic Name

English

1-HEXADECYLPYRIDINIUM BROMIDE

Systematic Name

English

PYRIDINIUM, 1-HEXADECYL-, BROMIDE

Systematic Name

English

CETYLPYRIDINIUM BROMIDE [HSDB]

Common Name

English

NSC-8495

Code

English

Cetylpyridinium bromide [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28394