Identification
- Summary
Cetylpyridinium is a compound used to reduce plaque and gingivitis, as well as whiten teeth.
- Brand Names
- Cepacol Antibacterial Mouthwash, Crest Mouthwash, Orajel Bleeding Gum Rinse, Orasep Reformulated Dec 2013
- Generic Name
- Cetylpyridinium
- DrugBank Accession Number
- DB11073
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cetylpyridinium (DB11073)
- Weight
- Average: 304.541
Monoisotopic: 304.299876648 - Chemical Formula
- C21H38N
- Synonyms
- 1-hexadecylpyridinium
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.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Gingivitis ••• ••• •••••• •••••••• Used in combination to treat Oral infection Combination Product in combination with: Lidocaine (DB00281) •••••••••••• ••••••• Used in combination to treat Oral pain Combination Product in combination with: Lidocaine (DB00281) ••• ••• •••••• Used in combination for symptomatic treatment of Orofacial pain Combination Product in combination with: Benzocaine (DB01086) •••••••••••• •••••• Used in combination for symptomatic treatment of Orofacial pain Combination Product in combination with: Choline salicylate (DB14006) ••• ••• ••• - Associated Therapies
- Contraindications & Blackbox Warnings
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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.
- 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.
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cetylpyridinium bromide O77BKZ14DE 140-72-7 DVBJBNKEBPCGSY-UHFFFAOYSA-M Cetylpyridinium chloride D9OM4SK49P 6004-24-6 NFCRBQADEGXVDL-UHFFFAOYSA-M - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ACT Advanced Care Plaque Guard Antigingivitis Antiplaque Clean Mint Mouthwash 0.7 mg/1mL Oral Chattem, Inc. 2015-02-02 2021-09-22 US 
ACT Advanced Care Plaque Guard Antigingivitis Antiplaque Frosted Mint Mouthwash 0.7 mg/1mL Oral Chattem, Inc. 2015-02-02 2021-01-22 US Advanced Guard Rinse 1 mg/100mL Oral H-E-B 2013-06-25 Not applicable US Alcohol Free Mouthwash 0.7 mg/1mL Oral H-E-B 2009-04-16 Not applicable US Alcohol Free Antiseptic Rinse 0.07 mg/100L Oral Demoulas Super Markets Inc 2012-04-16 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image (badiful) Antibacterial Wipes Cetylpyridinium chloride (5 mg/100mL) + Benzalkonium chloride (13 mg/100mL) + Chlorphenesin (2 mg/100mL) + Propylene glycol (2 mg/100mL) Swab Topical ZHANGZHOU KANGBEI HYGIENIC PRODUCTS CO., LTD. 2020-05-31 Not applicable US Above Mouthwash Antiseptic Cetylpyridinium chloride (0.075 mg/500g) + Menthol (0.3 mg/500g) + Methyl salicylate (0.25 mg/500g) Mouthwash Buccal; Dental Baston Industria de Aerossóis Ltda 2023-07-24 Not applicable US Actisep Cetylpyridinium chloride (0.1 g/100mL) + Benzocaine (2 g/100mL) + Menthol (0.5 g/100mL) Spray Topical Actipharma, Inc 2015-12-28 Not applicable US Actisep Cetylpyridinium chloride (0.1 g/100mL) + Benzocaine (2 g/100mL) + Menthol (0.5 g/100mL) Solution Topical Actipharma, Inc 2015-12-28 Not applicable US Alcohol Wet Tissue Cetylpyridinium chloride (0.05 g/100g) + Benzalkonium chloride (0.1 g/100g) + Chlorphenesin (0.05 g/100g) + Didecyldimethylammonium chloride (0.1 g/100g) + Ethanol (75 g/100g) Swab Topical SHANDONG PROVINCE RUNHE SANITARY MATERIALS CO.,LTD. 2020-04-13 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image (badiful) Antibacterial Wipes Cetylpyridinium chloride (5 mg/100mL) + Benzalkonium chloride (13 mg/100mL) + Chlorphenesin (2 mg/100mL) + Propylene glycol (2 mg/100mL) Swab Topical ZHANGZHOU KANGBEI HYGIENIC PRODUCTS CO., LTD. 2020-05-31 Not applicable US Breath mellow Azalea Peach Cetylpyridinium chloride (0.0085 g/17mL) Spray Topical Curescript 2021-02-01 Not applicable US Breath mellow Water Lily Cetylpyridinium chloride (0.0085 g/17mL) Spray Topical Curescript 2021-02-01 Not applicable US Cool Sense Stick Gargle Cetylpyridinium chloride (0.05 g/100mL) Liquid Dental DOCSMEDI OralBiome Co., Ltd. 2023-02-01 Not applicable US Denti Whoo Bubble Concentrated Gargle Cetylpyridinium chloride (2.296 g/100mL) Liquid Dental SUN LIFE SCIENCE CO LTD 2022-04-06 Not applicable US
Categories
- ATC Codes
- D08AJ03 — Cetylpyridinium
- D08AJ — Quaternary ammonium compounds
- D08A — ANTISEPTICS AND DISINFECTANTS
- D08 — ANTISEPTICS AND DISINFECTANTS
- D — DERMATOLOGICALS
- B05CA — Antiinfectives
- B05C — IRRIGATING SOLUTIONS
- B05 — BLOOD SUBSTITUTES AND PERFUSION SOLUTIONS
- B — BLOOD AND BLOOD FORMING ORGANS
- Drug Categories
- Anti-Infective Agents
- Anti-Infective Agents, Local
- Antiseptics and Disinfectants
- Blood and Blood Forming Organs
- Blood Substitutes and Perfusion Solutions
- Compounds used in a research, industrial, or household setting
- Dermatologicals
- Detergents
- Household Products
- Irrigating Solutions
- Medicated Dressings
- Medicated Dressings With Antiinfectives
- Miscellaneous Anti-infectives
- Mouthwashes and Gargles
- Pyridines
- Pyridinium Compounds
- Quaternary Ammonium Compounds
- Surface-Active Agents
- Throat Preparations
- Chemical TaxonomyProvided by Classyfire
- 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
- Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Organic cation / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Pyridinium
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyridinium ion (CHEBI:32914)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- CUB7JI0JV3
- CAS number
- 7773-52-6
- 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
References
- General References
- Pitten FA, Kramer A: Efficacy of cetylpyridinium chloride used as oropharyngeal antiseptic. Arzneimittelforschung. 2001;51(7):588-95. [Article]
- 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. [Article]
- The Role of Cetylpyridinium Chloride Mouthwash In The Treatment of Periodontitis. [Link]
- Electronic Medicines Compendium: Cetylpyridinium chloride formulations [Link]
- Electronic Medicines Compendium: Covonia Cold & Flu Formula Monograph [Link]
- IPCS INCHEM: Quaternary ammonium profile [Link]
- Pubchem: Cetylpyridinium Chloride Profile [Link]
- Electronic Medicines Compendium: Lemsip Cough for Mucus Cough & Catarrh 100mg/2.5mg/5ml Oral Solution Monograph [Link]
- Electronic Medicines Database: Calgel Teething Gel Monograph [Link]
- DailyMed: Advanced Guard (cetylpyridinium chloride) oral rinse [Link]
- Lloyd's Farmacia: Neo Formitrol (cetylpyridinium chloride) buccal tablets [Link]
- External Links
- PubChem Compound
- 2683
- PubChem Substance
- 347827886
- ChemSpider
- 2582
- BindingDB
- 80992
- 2286
- ChEBI
- 32914
- ChEMBL
- CHEMBL305906
- ZINC
- ZINC000006845963
- Wikipedia
- Cetylpyridinium_chloride
- MSDS
- Download (48.2 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Coronavirus Disease 2019 (COVID‑19) / Infections, Coronavirus / Mouthwashes / Polymerase Chain Reaction / Saliva / Viral Load 1 4 Completed Prevention Dental Decay 1 4 Completed Prevention Generalized Aggressive Periodontitis 1 4 Completed Prevention Gingivitis / Periodontal Disease / Plaque, Dental 1 4 Completed Treatment Gingivitis 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Mouthwash Buccal; Dental Mouthwash Oral 0.7 mg/1mL Spray Topical Rinse Oral 0.07 mg/100L Tablet, chewable Oral Solution Buccal; Oral 500 mg Tablet Oral 600 MG Rinse Oral 0.07 kg/100L Rinse Oral 0.7 mg/1mL Mouthwash Oral 0.07 kg/100L Mouthwash Buccal 0.05 % Mouthwash Buccal 0.5 mg/1mL Solution Oral 0.1 % Mouthwash Buccal 0.7 mg/1mL Solution Buccal; Oral Liquid Dental Spray Oral 0.1 g/100mL Liquid Oral 0.1 g/100mL Spray Topical 0.0085 g/17mL Mouthwash Topical 0.3394 g/473mL Kit Dental; Oral Rinse Oral .75 mg/1mL Spray Oral 0.85 mg/1mL Tablet, chewable Buccal Solution Oral Liquid Oral 0.05 g/100mL Lozenge Oral 1.4 mg Lozenge Oral 1.4 mg / loz Mouthwash Buccal Mouthwash Buccal 0.5 mg / mL Liquid; mouthwash Buccal Mouthwash Oral Solution Topical Solution Topical 2 MG/ML Tablet Oral Solution Oral 0.283 g/473mL Liquid Oral 0.75 g/1mL Solution Buccal 0.075 % w/w Mouthwash Buccal 0.075 % w/w Rinse Dental 0.75 mg/1mL Rinse Dental 15 mg/20mL Mouthwash Dental 10.5 mg/20mL Rinse Dental 15 mg/20L Mouthwash Dental 15 mg/20mL Liquid Dental 0.05 g/100mL Rinse Oral 0.5 mg/1mL Spray Topical 1.11 g/13.0mL Rinse Topical 0.014 g/20mL Rinse Oral 0.014 g/1mL Rinse Oral 0.02 g/20mL Rinse Oral 0.05 g/1mL Mouthwash Buccal 0.07 % w/w Rinse Oral 0.014 g/20mL Mouthwash Oral Kit; rinse Buccal 0.5 mg/1mL Solution Topical Liquid Dental 2.296 g/100mL Gel Dental Gel Submucosal 0.1 % w/w Lozenge Oral 3 mg Gel Oral Gel Submucosal 10 mg/g Lozenge Oral 3.0 mg Lozenge Oral 1.5 mg Cloth Topical Swab Topical Solution Topical 5 g/100g Mouthwash Oral 2.30 g/100mL Liquid Topical 0.05 g/100mL Paste Dental 0.0023 g/100mL Paste Dental 2.296 g/100mL Mouthwash Dental 1 mg/1mL Lozenge Oral 1.33 mg Liquid Dental 0.005 g/100mL Mouthwash Oral 0.07 g/1mL Ointment Topical Lozenge Oral 1.34 mg / loz Solution Oral 2.296 g Powder Topical Rinse Oral 0.07 g/100mL Lozenge Oral 1.2 MG Spray Oral Rinse Oral 0.07 g/20mL Solution Oral 0.07 g/100mL Paste Dental Tablet, soluble Oral Pastille Oral 1.5 MG Lozenge Oral Liquid Oral 0.7 mg/1mL Liquid Buccal; Topical Spray Oral 0.05 g/100mL Kit Oral Kit Oral 0.0005 mg/1mL Lozenge Buccal Mouthwash Oral 0.5 mg/1mL Rinse Oral 1 mg/100mL Tablet Buccal; Oral Spray Topical 0.05 g/100g Spray Topical 0.05 mL/100mL Liquid; mouthwash Oral .05 % Rinse Dental 0.07 g/100g Mouthwash Oral .05 % Tablet Oral 1.5 MG Tablet Oral 1 MG Cloth Extracorporeal Tablet Buccal Liquid Oral 0.5 mg/1mL Liquid Oral .001 mL/1mL Mouthwash Buccal; Topical Rinse Oral 0.07 g/1mL Mouthwash Oral .47 mL/474mL Liquid Dental 500 ug/1mL Mouthwash Dental 0.07 % w/w Rinse Oral Liquid Oral 70 mg/1mL Mouthwash Oral 70 mg/1mL Lozenge Oral 1.66 mg Mouthwash Buccal 0.75 % w/w Kit Oral .5 mg/1mL Kit Buccal; Oral .5 mg/1mL Rinse Buccal; Oral 0.5 mg/1mL Kit; mouthwash Buccal Rinse Buccal Rinse Buccal 5 [iU]/1mL Kit Buccal Kit Buccal; Oral Spray Topical .027 mL/60mL Liquid Topical Liquid Oral 1 mg/100mL Spray Oral Tablet Transmucosal Swab Buccal 0.5 mg/1mL Kit Buccal 0.5 mg/1mL Kit Oral; Topical Kit Dental 500 mg/20mL Kit; liquid Dental 500 mg/20mL Lozenge Oral Gel Oral 0.01 % w/w Kit Oral 0.5 mg/1mL Rinse Buccal 0.5 mg/1mL Rinse Oral 0.01 mg/20mL Mouthwash Buccal 0.05 % w/w Rinse Oral 0.0005 g/1g Rinse Oral 0.015 mg/20mL Rinse Oral 0.075 mg/0.1mL Kit Buccal .5 [iU]/1mL Tablet Oral Paste, dentifrice Dental Lozenge Oral 0.46 mg Lozenge Oral 0.33 mg Lozenge Oral 0.5 mg Lozenge Oral 0.35 mg Liquid Oral 0.07 g/100g Aerosol Oral; Topical Lozenge Lozenge Oral 1.5 mg Tablet Oral 0.33 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 6.53e-06 mg/mL ALOGPS logP 3.18 ALOGPS logP 3.47 Chemaxon logS -7.7 ALOGPS Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 0 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 3.88 Å2 Chemaxon Rotatable Bond Count 15 Chemaxon Refractivity 99.14 m3·mol-1 Chemaxon Polarizability 42.21 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0059-3940000000-1eee64b743c1c4eb885a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 180.02032 predictedDeepCCS 1.0 (2019) [M+H]+ 182.57063 predictedDeepCCS 1.0 (2019) [M+Na]+ 189.5891 predictedDeepCCS 1.0 (2019)
Drug created at December 03, 2015 16:51 / Updated at April 16, 2024 12:20