Cetylpyridinium

Identification

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Name
Cetylpyridinium
Accession Number
DB11073  (DB05748)
Type
Small Molecule
Groups
Approved
Description

Cetylpyridinium is a quaternary ammonium with broad-spectrum antiseptic properties. Its salt form, cetylpyridinium chloride, is typically found as an active ingredient in mouthwashes, toothpastes, lozenges, throat sprays, breath sprays, and nasal sprays. In these products, it generally mediates an antiseptic activity and protective action against dental plaque and reducing gingivitis.

Structure
Thumb
Synonyms
  • 1-hexadecylpyridinium
Product Ingredients
IngredientUNIICASInChI Key
Cetylpyridinium bromideO77BKZ14DE140-72-7DVBJBNKEBPCGSY-UHFFFAOYSA-M
Cetylpyridinium chlorideD9OM4SK49P6004-24-6NFCRBQADEGXVDL-UHFFFAOYSA-M
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ACT Advanced Care Plaque Guard Antigingivitis Antiplaque Clean MintMouthwash0.7 mg/1mLOralChattem, Inc.2015-02-02Not applicableUs
ACT Advanced Care Plaque Guard Antigingivitis Antiplaque Frosted MintMouthwash0.7 mg/1mLOralChattem, Inc.2015-02-02Not applicableUs
Advanced GuardRinse1 mg/100mLOralH-E-B2013-06-25Not applicableUs
Alcohol FreeMouthwash0.7 mg/1mLOralH.E.B.2009-04-16Not applicableUs
Alcohol Free AntisepticMouthwash0.7 mg/1mLOralKroger2009-05-15Not applicableUs
Alcohol Free AntisepticRinse0.07 mL/100LOralDemoulas Supermarkets, Inc.2012-04-16Not applicableUs
Alcohol Free Antiseptic OralRinse0.07 mL/100LOralTopco Associates1990-02-15Not applicableUs
Antiplaque solutionMouthwash0.5 mg/1mLBuccalSage Products LLC2009-01-09Not applicableUs
AntisepticRinse0.7 mg/1mLOralYour Military Exchanges2010-06-28Not applicableUs
AntisepticRinse0.7 mg/1mLOralValue Merchandisers2007-07-31Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ActisepCetylpyridinium chloride (0.1 g/100mL) + Benzocaine (2 g/100mL) + Levomenthol (0.5 g/100mL)SprayTopicalActipharma, Inc2015-12-28Not applicableUs
ActisepCetylpyridinium chloride (0.1 g/100mL) + Benzocaine (2 g/100mL) + Levomenthol (0.5 g/100mL)SolutionTopicalActipharma, Inc2015-12-28Not applicableUs
Antibiotic LozengesCetylpyridinium chloride (1.3 mg) + Benzocaine (5.0 mg) + Polymyxin B sulfate (1500 unit) + Tyrothricin (1.5 mg)LozengeOralNutribon (1986) Inc.1994-12-312003-07-25Canada
Balminil LozCetylpyridinium chloride (2.5 mg) + Benzocaine (5 mg)LozengeOralRougier Pharma Division Of Ratiopharm Inc1961-12-312000-09-07Canada
Beyond Antiseptic MouthwashCetylpyridinium chloride (.1 mg/1mL) + Sodium fluoride (.05 mg/1mL)LiquidDentalBeyond Technology Corp.2007-10-05Not applicableUs
BreathRx with ZytexCetylpyridinium chloride (0.75 mg/1mL) + Cetylpyridinium chloride (0.85 mg/1mL) + Sodium fluoride (2.43 mg/1g)KitDental; OralDiscus Dental, Llc2014-09-18Not applicableUs
BreathRx with ZytexCetylpyridinium chloride (0.75 mg/1mL) + Cetylpyridinium chloride (0.85 mg/1mL) + Sodium fluoride (2.43 mg/1g)KitDental; OralDiscus Dental, Llc2014-09-18Not applicableUs
BreathRx with ZytexCetylpyridinium chloride (0.75 mg/1mL) + Sodium fluoride (2.43 mg/1g)KitDental; OralDiscus Dental, Llc2017-04-19Not applicableUs
Cepacol Citrus Extra Strength LozengesCetylpyridinium chloride (1.4 mg) + Benzocaine (10 mg)LozengeOralCombe Incorporated1995-12-312009-07-09Canada
Cepacol Extra Strength LozengeCetylpyridinium chloride (2 mg) + Benzocaine (10 mg)LozengeOralCombe Incorporated2001-08-102009-07-09Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
E-zen GargleCetylpyridinium chloride (0.005 g/100mL)LiquidDentalJn Pharm2014-02-08Not applicableUs
Exoden PowderCetylpyridinium chloride (0.084 g/70g) + Domiphen bromide (0.3 1/70g)PowderTopicalLifeon Corp.2016-04-07Not applicableUs
Categories
UNII
CUB7JI0JV3
CAS number
7773-52-6
Weight
Average: 304.541
Monoisotopic: 304.299876648
Chemical Formula
C21H38N
InChI Key
NEUSVAOJNUQRTM-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-hexadecylpyridin-1-ium
SMILES
CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1

Pharmacology

Indication

Typically employed as the cetylpyridinium chloride salt, this compound is commonly used as an active ingredient in various over-the-counter mouthwashes, toothpastes, lozenges, and mouth sprays where it is generally indicated for antiseptic actions, gingivitis and plaque prevention, as well as action or prevention against some other oropharyngeal bacterial infections 1,3,4.

Pharmacodynamics

Cetylpyridinium chloride is considered a cationic disinfectant with properties and uses similar to other such cationic surfactants 5. In particular, cetylpyridinium chloride has demonstrated a rapid bactericidal and fungicide effect on gram-positive pathogens and yeasts, respectively 1. Cetylpyridinium chloride is subsequently utilized in a variety of preparations for the local treatment of minor infections 5. Despite the variety of formulations in which cetylpyridinium chloride may appear as an active ingredient, it is generally accepted that it only elicits a local effect 5 owing to the compound's relatively poor absorption by route of exposure 6.

Mechanism of action

When incorporated into mouthwashes, toothpastes, lozenges, or mouth sprays, cetylpyridinium chloride is expected to elicit a mechanism of action that decreases new dental plaque growth, decreases or removes existing dental plaque, diminishes the growth of pathogenic bacteria, and inhibits the production of virulence factors 3. Cetylpyridinium chloride is a quaternary ammonium compound that demonstrates a broad spectrum anti-bacterial activity 3. It possesses a cationic surface active agent surfactant which can absorb readily to oral surfaces 3. The molecules of this agent have both hydrophilic and hydrophobic groups 3. In action, the positively charged hydrophilic region of cetylpyridinium chloride molecules enables the compound to interact with microbial cell surfaces and even integrate into the bacterial cytoplasmic membrane 3. Consequently, there is a resultant disruption of bacterial membrane integrity causing a leakage of bacterial cytoplasmic components, interference with cellular metabolism, inhibition of cell growth, and ultimately - cell death 3. Moreover, cetylpyridinium chloride can also inhibit the synthesis of insoluble glucan by streptococcal glucosyltransferase, adsorb to pellicle-covered enamel, and inhibit co-adhesion of bacteria, and bind streptococcus mutans biofilms 3. This ability of cetylpyridinium chloride to be able to adsorb to pellicle covered enamel imparts substantivity to the compound molecules - that is retention in the mouth and continued antimicrobial activity for a period of time after rinsing 3. Taking these mechanisms into consideration, cetylpyridinium chloride may be considered an active ingredient that is effective in the treatment and prevention of bacterial or fungal disorders of the oropharyngeal cavity 1.

Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

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Absorption

Most available formulations consisting of cetylpyridinium chloride as an active ingredient are either mouthwashes, tootpastes, lozenges, or mouth sprays. The oral retention of cetylpyridinium chloride given as 1 min mouth rinse of 10 mL of 2.2 MMOL solution was recorded as 65% of the administered dose 7.

Additionally, it has been recorded that quaternary ammonium compounds like Cetylpyridinium chloride are generally poorly absorbed by the oral route 6. Furthermore, although systemic absorption from the parenteral route of administration is possible, systemic effects from percutaneous absorption through intact skin is considered rare 6.

Volume of distribution

No readily available data regarding the volume of distribution of cetylpyridinium chloride is available 6 and various products that actually contain cetylpyridinium chloride as an active ingredient suggest that no pharmacokinetic data are available for the agent 8.

Protein binding

No readily available data regarding the protein binding of cetylpyridinium chloride is available 6 and various products that actually contain cetylpyridinium chloride as an active ingredient suggest that no pharmacokinetic data are available for the agent 8.

Metabolism

No readily available data regarding the metabolism of cetylpyridinium chloride is available 6 and various products that actually contain cetylpyridinium chloride as an active ingredient suggest that no pharmacokinetic data are available for the agent 8.

Route of elimination

As the quaternary ammonium compound cetylpyridinium chloride is poorly absorbed by oral route, relatively large amounts of the compound are therefore eliminated in faeces 6.

Half life

No readily available data regarding the half-life of cetylpyridinium chloride is available 6 and various products that actually contain cetylpyridinium chloride as an active ingredient suggest that no pharmacokinetic data are available for the agent 8.

Clearance

No readily available data regarding the clearance of cetylpyridinium chloride is available 6 and various products that actually contain cetylpyridinium chloride as an active ingredient suggest that no pharmacokinetic data are available for the agent 8.

Toxicity

Ingestion of cetylpyridinium chloride in large doses may cause gastric upset and central nervous system depression 9. However, such overdose symptoms are only observed in doses 70 times greater than the concentrations of cetylpyridinium chloride found in most over-the-counter cetylpyridinium chloride products 9.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Pitten FA, Kramer A: Efficacy of cetylpyridinium chloride used as oropharyngeal antiseptic. Arzneimittelforschung. 2001;51(7):588-95. [PubMed:11505791]
  2. Albert-Kiszely A, Pjetursson BE, Salvi GE, Witt J, Hamilton A, Persson GR, Lang NP: Comparison of the effects of cetylpyridinium chloride with an essential oil mouth rinse on dental plaque and gingivitis - a six-month randomized controlled clinical trial. J Clin Periodontol. 2007 Aug;34(8):658-67. [PubMed:17635245]
  3. The Role of Cetylpyridinium Chloride Mouthwash In The Treatment of Periodontitis. [Link]
  4. Electronic Medicines Compendium: Cetylpyridinium chloride formulations [Link]
  5. Electronic Medicines Compendium: Covonia Cold & Flu Formula Monograph [Link]
  6. IPCS INCHEM: Quaternary ammonium profile [Link]
  7. Pubchem: Cetylpyridinium Chloride Profile [Link]
  8. Electronic Medicines Compendium: Lemsip Cough for Mucus Cough & Catarrh 100mg/2.5mg/5ml Oral Solution Monograph [Link]
  9. Electronic Medicines Database: Calgel Teething Gel Monograph [Link]
External Links
PubChem Compound
2683
PubChem Substance
347827886
ChemSpider
2582
BindingDB
80992
ChEBI
32914
ChEMBL
CHEMBL305906
Wikipedia
Cetylpyridinium
ATC Codes
D08AJ03 — CetylpyridiniumB05CA01 — CetylpyridiniumR02AA06 — CetylpyridiniumD09AA07 — Cetylpyridinium
AHFS Codes
  • 52:04.92 — Miscellaneous Anti-infectives
  • 52:28.00 — Mouthwashes and Gargles
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Unknown StatusPreventionSarcopenia1
1Active Not RecruitingTreatmentHead and Neck Carcinoma / Oral Mucositis1
1, 2Unknown StatusTreatmentType 2 Diabetes Mellitus1
2CompletedTreatmentOnychomycosis1
2CompletedTreatmentPeriodontitis / Premature Birth of Newborn1
2WithdrawnOtherViral Upper Respiratory Tract Infection1
2, 3CompletedPreventionSepsis1
3CompletedSupportive CareHealthy Volunteers1
3CompletedTreatmentHygiene1
3CompletedTreatmentPain Teeth1
3Not Yet RecruitingTreatmentAplasia1
4CompletedPreventionNeonatal Infections1
4CompletedTreatmentDental Plaque / Gingival Inflammation1
4Enrolling by InvitationPreventionGingival Inflammation1
4Unknown StatusBasic ScienceGingival Inflammation / Oral Biofilm / Periodontitis1
Not AvailableCompletedNot AvailablePeriodontal Diseases / Type 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentDental Decay1
Not AvailableCompletedTreatmentGingival Inflammation / Pregnancy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SolutionTopical
SprayTopical
RinseOral0.07 mL/100L
MouthwashOral0.7 mg/1mL
RinseOral0.07 kg/100L
RinseOral0.7 mg/1mL
MouthwashOral0.07 kg/100L
LiquidOral; Topical0.05 %
MouthwashBuccal0.5 mg/1mL
MouthwashBuccal0.7 mg/1mL
MouthwashTopical0.3394 g/473mL
KitDental; Oral
RinseOral0.75 mg/1mL
SprayOral0.85 mg/1mL
LiquidOral0.05 g/100mL
LozengeOral1.4 mg
LozengeOral
MouthwashBuccal
MouthwashBuccal0.5 mg
Liquid; mouthwashBuccal
SolutionBuccal0.07 %
SolutionOral0.283 g/473mL
SolutionBuccal0.075 %
MouthwashBuccal0.075 %
RinseDental0.75 mg/1mL
RinseDental15 mg/20mL
MouthwashDental10.5 mg/20mL
RinseOral0.5 mg/1mL
RinseTopical0.7 mg/1mL
RinseOral0.014 g/1mL
RinseOral0.02 g/20mL
RinseOral0.014 g/20mL
MouthwashBuccal0.07 %
RinseOral0.05 g/1mL
MouthwashOral0.07 %
LiquidDental0.005 g/100mL
MouthwashOral0.07 g/1mL
OintmentTopical
LozengeOral1.34 mg
PowderTopical
RinseOral0.07 g/20mL
MouthwashOral
PasteDental
LiquidOral0.7 mg/1mL
LiquidBuccal; Topical
Kit0.0005 mg/1mL
LozengeBuccal
RinseOral1 mg/100mL
SprayTopical0.05 g/100g
SprayTopical0.05 mL/100mL
Liquid; mouthwashOral.05 %
RinseDental0.07 g/100g
MouthwashOral.05 %
LiquidOral0.5 mg/1mL
LiquidOral.001 mL/1mL
MouthwashBuccal; Topical
MouthwashOral.47 mL/474mL
LiquidDental
LiquidDental500 ug/1mL
LiquidTopical
Kit.5 mg/1mL
Kit0.5 mg/1mL
Kit5 [iU]/1mL
Kit
MouthwashBuccal0.05 %
SprayTopical.027 mL/60mL
Kit500 mg/20mL
RinseOral0.0005 g/1g
LozengeOral1.5 mg
Kit.5 [iU]/1mL
LiquidOral0.07 g/100g
AerosolOral; Topical
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.53e-06 mg/mLALOGPS
logP3.18ALOGPS
logP3.47ChemAxon
logS-7.7ALOGPS
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.88 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity99.14 m3·mol-1ChemAxon
Polarizability42.21 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyridinium derivatives. These are compounds containing a pyridinium ring, which is the cationic form of pyridine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Pyridinium derivatives
Direct Parent
Pyridinium derivatives
Alternative Parents
Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives / Organic cations
Substituents
Pyridinium / Heteroaromatic compound / Azacycle / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Organic cation / Aromatic heteromonocyclic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyridinium ion (CHEBI:32914)

Drug created on December 03, 2015 09:51 / Updated on June 24, 2019 13:09