CETYLPYRIDINIUM

First approved in 1941

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H38N
Molecular Weight	304.5331
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1

InChI

InChIKey=NEUSVAOJNUQRTM-UHFFFAOYSA-N

InChI=1S/C21H38N/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/q+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
Efficacy of cetylpyridinium chloride used as oropharyngeal antiseptic.	2001	11505791
Detection of cationic surfactants in oral rinses and a disinfectant formulation using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001	11344536
Surface mucus in the non-glandular region of the equine stomach.	2001 Apr	11356094
Evaluation of shale and organoclays as sorbent additives for low-permeability soil containment barriers.	2001 Apr 1	11348096
The kinetics and thermodynamics of surfactants in solvent sublation.	2001 Aug	11583089
Acid polysaccharides in the skeletal matrix and calicoblastic epithelium of the stony coral Mycetophyllia reesi.	2001 Aug	11521954
Testing a degradable topical varnish of cetylpyridinium chloride in an experimental dental biofilm model.	2001 Aug	11481295
Spectrophotometric determination of cetylpyridinium chloride in pharmaceutical products.	2001 Aug	11451652
Retardation capacity of organophilic bentonite for anionic fission products.	2001 Feb	11288581
The effect of toothpaste on the propensity of chlorhexidine and cetyl pyridinium chloride to produce staining in vitro: a possible predictor of inactivation.	2001 Jan	11142666
A multifactorial investigation of the ability of oral health care products (OHCPs) to alleviate oral malodour.	2001 Jul	11422584
The eicosanoid, 15-(S)-HETE, stimulates secretion of mucin-like glycoprotein by the corneal epithelium.	2001 Jul	11413409
YKL-40 (cartilage gp-39) induces proliferative events in cultured chondrocytes and synoviocytes and increases glycosaminoglycan synthesis in chondrocytes.	2001 Jul 27	11467840
An investigation of the adsorption of organic dyes onto organo-montmorillonite.	2001 Mar	11346281
Incidence of Mycobacterium paratuberculosis in raw sheep and goats' milk in England, Wales and Northern Ireland.	2001 Mar 20	11230934
Cytotoxicity of potential ocular permeation enhancers evaluated on rabbit and human corneal epithelial cell lines.	2001 May 31	11397552
Occupational allergic contact dermatitis from alkylammonium amidobenzoate.	2001 May-Jun	11358732
A novel pharmacological probe links the amiloride-insensitive NaCl, KCl, and NH(4)Cl chorda tympani taste responses.	2001 Nov	11698552
Passive immunization with milk produced from an immunized cow prevents oral recolonization by Streptococcus mutans.	2001 Nov	11687453
Gene expression by human articular chondrocytes cultured in alginate beads.	2001 Oct	11561005
Effect of antimicrobial mouthrinses on the in vitro adhesion of Candida albicans to human buccal epithelial cells.	2001 Sep	11642562
Effect of different mouthrinses on morning breath.	2001 Sep	11577950
Comparative evaluation of four decontamination protocols for the isolation of Mycobacterium avium subsp. paratuberculosis from milk.	2001 Sep	11555198
Evaluation of the bactericidal activity of povidone-iodine and commercially available gargle preparations.	2002	12011519
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
Solubility, chemical and photochemical stability of curcumin in surfactant solutions. Studies of curcumin and curcuminoids, XXVIII.	2002 Dec	12561244
[The simultaneous determination of iron(III) and aluminium(III) in quartz sand by first derivative spectrophotometry].	2002 Feb	12940044
The effect of four mouthrinses on oral malodor.	2002 Jun	12789968
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
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
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
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
Isolation of intact aortic valve scaffolds for heart-valve bioprostheses: extracellular matrix structure, prevention from calcification, and cell repopulation features.	2003 Dec 15	14624521
An in vitro evaluation of the availability of cetylpyridinium chloride and chlorhexidine in some commercially available mouthrinse products.	2003 Feb 22	12627199
Inactivation kinetics of mushroom tyrosinase by cetylpyridinium chloride.	2003 Jul	14690251
Purification of sulfated fucoglucuronomannan lyase from bacterial strain of Fucobacter marina and study of appropriate conditions for its enzyme digestion.	2003 Jul-Aug	14719166
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
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
Modification of ion chromatographic separations by ionic and nonionic surfactants.	2003 May 16	12830873
The effect of antimicrobial pre-treatments on the performance of resin composite restorations.	2003 Nov-Dec	14653285
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.

Name

Type

Language

CETYLPYRIDINIUM

Systematic Name

English

CETYLPYRIDINIUM ION

Common Name

English

Cetylpyridinium [WHO-DD]

Common Name

English

CETYLPYRIDINUM

Common Name

English

1-HEXADECYLPYRIDINIUM

Systematic Name

English

PYRIDINIUM, 1-HEXADECYL

Common Name

English

CETYLPYRIDINIUM CATION

Common Name

English

CETYLPYRIDINIUM [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28394