CETYLPYRIDINIUM ACETATE

First approved in 1941

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H38N.C2H3O2
Molecular Weight	363.5771
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC([O-])=O.CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1

InChI

InChIKey=CBRUQZUHJAXNHS-UHFFFAOYSA-M

InChI=1S/C21H38N.C2H4O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-22-20-17-15-18-21-22;1-2(3)4/h15,17-18,20-21H,2-14,16,19H2,1H3;1H3,(H,3,4)/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
Efficacy of cetylpyridinium chloride used as oropharyngeal antiseptic.	2001	11505791
The kinetics and thermodynamics of surfactants in solvent sublation.	2001 Aug	11583089
Effect of different chlorhexidine formulations in mouthrinses on de novo plaque formation.	2001 Dec	11737510
Morphology of three lyotropic liquid crystalline biological NMR media studied by translational diffusion anisotropy.	2001 Dec 12	11734036
Cationic solid-lipid nanoparticles can efficiently bind and transfect plasmid DNA.	2001 Dec 13	11733101
Hyaluronate receptors mediating glioma cell migration and proliferation.	2001 Jun	11716065
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
PVC matrix membrane sensor for potentiometric determination of cetylpyridinium chloride.	2001 Sep	11708056
Effect of antimicrobial mouthrinses on the in vitro adhesion of Candida albicans to human buccal epithelial cells.	2001 Sep	11642562
Comparative evaluation of four decontamination protocols for the isolation of Mycobacterium avium subsp. paratuberculosis from milk.	2001 Sep	11555198
Adsorption of phenol and m-chlorophenol on organobentonites and repeated thermal regeneration.	2002	12214970
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
Solubility, chemical and photochemical stability of curcumin in surfactant solutions. Studies of curcumin and curcuminoids, XXVIII.	2002 Dec	12561244
Lidocaine-loaded non-ionic surfactant vesicles: characterization and in vitro permeation studies.	2002 Jan 1	11719010
Differential effects of cadmium on proteoglycan synthesis of arterial smooth muscle cells: increase in small dermatan sulfate proteoglycans, biglycan and decorin, in the extracellular matrix at low cell density.	2002 Jan 15	11750086
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
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
Molecular alignment of denatured states of staphylococcal nuclease with strained polyacrylamide gels and surfactant liquid crystalline phases.	2002 Mar 5	11863448
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
Buccoadhesive erodible disk for treatment of oro-dental infections: design and characterisation.	2002 May 15	11996813
A mathematical model and mechanism of sublation of dye-surfactant ion complexes.	2002 Nov	12434249
Glycosaminoglycan blotting on nitrocellulose membranes treated with cetylpyridinium chloride after agarose-gel electrophoretic separation.	2002 Sep	12373753
Comparative evaluation of the MGIT and BACTEC culture systems for the recovery of Mycobacterium avium subsp. paratuberculosis from milk.	2003	12807471
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
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
Ocular toxicity of some corneal penetration enhancers evaluated by electrophysiology measurements on isolated rabbit corneas.	2003 Aug	12849734
Dissolved organic matter effects on the performance of a barrier to polycyclic aromatic hydrocarbon transport by groundwater.	2003 Feb	12504364
A salivary incubation test for evaluation of oral malodor: a pilot study.	2003 Jul	12931755
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
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
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
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
[DNA complexes, formed on aqueous phase surfaces: new planar polymeric and composite nanostructures].	2003 Nov-Dec	14714516
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
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 ACETATE

Systematic Name

English

1-HEXADECYLPYRIDINIUM ACETATE

Systematic Name

English

PYRIDINIUM, 1-HEXADECYL-, ACETATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28394