CETYLPYRIDINIUM BROMIDE

First approved in 1941

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H38N.Br
Molecular Weight	384.4374
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCCCCCC[n+]1ccccc1.[Br-]

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

Molecular Formula	BrH
Molecular Weight	80.9115
Charge	0
Count

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

Molecular Formula	C21H38N
Molecular Weight	304.5339
Charge	1
Count

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

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
Target ID: Bacterial membrane Sources: https://www.ncbi.nlm.nih.gov/pubmed/19138180	Interacts 318

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 8043	ANTISEPTIC (cetylpyridinium chloride) mouthwash Approved Use Help to control plaque that leads to gingivitis.
Dental plaque 12 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3bbd4a08-062f-40a3-a25b-f23490ee57f6	Curative		Approved 8043	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
Adsorption of phenol and m-chlorophenol on organobentonites and repeated thermal regeneration.	2002	12214970
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
Time-resolved fluorometric analysis of carbohydrates labeled with amino-aromatic compounds by reductive amination.	2002 Jul	12173660
Interaction of cetylpyridine bromide with nucleic acids and determination of nucleic acids at nanogram levels based on the enhancement of resonance Rayleigh light scattering.	2002 Jul	12164493
Molecular cloning and characterization of human chondrolectin, a novel type I transmembrane protein homologous to C-type lectins.	2002 Jul	12079284
The effect of four mouthrinses on oral malodor.	2002 Jun	12789968
A method to compare four mouthrinses: time to gingivitis level as the primary outcome variable.	2002 Jun	12296779
Cysteine challenge testing: a powerful tool for examining oral malodour processes and treatments in vivo.	2002 Jun	12090457
[Method for determining nitrogen-containing cationic surface-active agents using butyrylcholinesterase].	2002 Mar-Apr	12152307
Utility of MTT assay in three-dimensional cultured human skin model as an alternative for draize skin irritation test: approach using diffusion law of irritant in skin and toxicokinetics-toxicodynamics correlation.	2002 May	12069171
Visible absorption spectra of the 4f electron transitions of neodymium, praseodymium, holmium and erbium complexes with fleroxacin and their analytical application.	2002 May	12036131
Determination of chondroitin sulfate in raw materials by liquid chromatography.	2002 May-Jun	12083249
A mathematical model and mechanism of sublation of dye-surfactant ion complexes.	2002 Nov	12434249
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
The efficacy of amine fluoride/stannous fluoride in the suppression of morning breath odour.	2002 Oct	12445227
Glycosaminoglycan blotting on nitrocellulose membranes treated with cetylpyridinium chloride after agarose-gel electrophoretic separation.	2002 Sep	12373753
Evaluation of culture media for the recovery of Mycobacterium avium subsp. paratuberculosis from Cheddar cheese.	2003	12969490
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
Differences in antimicrobial activity of four commercial 0.12% chlorhexidine mouthrinse formulations: an in vitro contact test and salivary bacterial counts study.	2003 Apr	12694428
Clinical effects of a new mouthrinse containing chlorhexidine, cetylpyridinium chloride and zinc-lactate on oral halitosis. A dual-center, double-blind placebo-controlled study.	2003 Apr	12694427
Influence of lipophilic counter-ions in combination with phloretin and 6-ketocholestanol on the skin permeation of 5-aminolevulinic acid.	2003 Apr 14	12672607
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
A rapid procedure to ascertain the antimicrobial efficacy of oral care formulations.	2003 Dec	14622343
Isolation of intact aortic valve scaffolds for heart-valve bioprostheses: extracellular matrix structure, prevention from calcification, and cell repopulation features.	2003 Dec 15	14624521
Reduction of poliovirus 1, bacteriophages, Salmonella montevideo, and Escherichia coli O157:H7 on strawberries by physical and disinfectant washes.	2003 Feb	12597475
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
Comparative study on fluorescence enhancement and quenching of europium and terbium chelate anions in cationic micelles.	2003 Jan 15	12685900
Inactivation kinetics of mushroom tyrosinase by cetylpyridinium chloride.	2003 Jul	14690251
A salivary incubation test for evaluation of oral malodor: a pilot study.	2003 Jul	12931755
Purification of sulfated fucoglucuronomannan lyase from bacterial strain of Fucobacter marina and study of appropriate conditions for its enzyme digestion.	2003 Jul-Aug	14719166
Determination of cetylpyridinium chloride and tetracaine hydrochloride in buccal tablets by RP-HPLC.	2003 Jun 1	12763550
Effect of toothpaste on the plaque inhibitory properties of a cetylpyridinium chloride mouth rinse.	2003 Mar	12631184
Utility of formazans and cetylpyridinium chloride in rapid spectrophotometric determination of zinc in biological materials and pharmaceutical formulations.	2003 Mar 10	12615236
Cooling towers--a potential environmental source of slow-growing mycobacterial species.	2003 Mar-Apr	12688848
Inhibitory effects on selected oral bacteria of antibacterial agents incorporated in a glass ionomer cement.	2003 Mar-Apr	12652048
Evaluation of cetylpyridinium chloride for infection control in storage solution.	2003 May	12752926
Direct and specific recognition of glycosaminoglycans by antibodies after their separation by agarose gel electrophoresis and blotting on cetylpyridinium chloride-treated nitrocellulose membranes.	2003 May	12731019
The effects of a new mouthrinse containing chlorhexidine, cetylpyridinium chloride and zinc lactate on the microflora of oral halitosis patients: a dual-centre, double-blind placebo-controlled study.	2003 May	12716335
[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
A standardized test to assess the impact of different organic challenges on the antimicrobial activity of antiseptics.	2003 Oct	14529634
Inhibition of orally produced volatile sulfur compounds by zinc, chlorhexidine or cetylpyridinium chloride--effect of concentration.	2003 Oct	12974683
Soft antimicrobial agents: synthesis and activity of labile environmentally friendly long chain quaternary ammonium compounds.	2003 Sep 11	12954069
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.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 13:54:30 UTC 2021` Edited by `admin` on `Sat Jun 26 13:54:30 UTC 2021`
Record UNII	O77BKZ14DE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CETYLPYRIDINIUM BROMIDE

Systematic Name

English

1-HEXADECYLPYRIDINIUM BROMIDE

Systematic Name

English

PYRIDINIUM, 1-HEXADECYL-, BROMIDE

Systematic Name

English

CETYLPYRIDINIUM BROMIDE [WHO-DD]

Common Name

English

CETYLPYRIDINIUM BROMIDE [HSDB]

Common Name

English

NSC-8495

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C28394