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
Testing a degradable topical varnish of cetylpyridinium chloride in an experimental dental biofilm model.	2001 Aug	11481295
[Effect of antiseptic treatment of alveolar surgical wounds on bacterial growth on cotton suture threads].	2001 Jan-Mar	11705315
Evaluation of the bactericidal activity of povidone-iodine and commercially available gargle preparations.	2002	12011519
Survival of Listeria monocytogenes in commercial food-processing equipment cleaning solutions and subsequent sensitivity to sanitizers and heat.	2002	11849330
Development and validation of a photometric titration method for the quantitation of sodium chondroitin sulfate (bovine) in Cosequin DS chewable tablet.	2002 Apr 15	11929666
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
Molecular alignment of denatured states of staphylococcal nuclease with strained polyacrylamide gels and surfactant liquid crystalline phases.	2002 Mar 5	11863448
Buccoadhesive erodible disk for treatment of oro-dental infections: design and characterisation.	2002 May 15	11996813
Examination of murine tear film.	2003 Aug	12882802
A rapid procedure to ascertain the antimicrobial efficacy of oral care formulations.	2003 Dec	14622343
Inactivation kinetics of mushroom tyrosinase by cetylpyridinium chloride.	2003 Jul	14690251
Spectrophotometric method for the determination of manganese with phenylfluorone in the presence of Triton X-100 and cetylpyridinium chloride in pharmacological preparations and vegetable fertilizers.	2003 Jul	12861432
Modification of ion chromatographic separations by ionic and nonionic surfactants.	2003 May 16	12830873
A standardized test to assess the impact of different organic challenges on the antimicrobial activity of antiseptics.	2003 Oct	14529634
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