Identification
- Summary
Cetalkonium is an antiseptic used as a preservative or to treat certain topical infections.
- Generic Name
- Cetalkonium
- DrugBank Accession Number
- DB11583
- Background
Cetalkonium is a C16 alkyl benzalkonium chloride derivative with an amphipathic property which allows it to be used in different types of formulations.1 It is a quaternary ammonium salt that acts as an antiseptic against a variety of bacteria and fungi.7 Cetalkonium is approved by the FDA for its use in over-the-counter products as a skin protectant.5 By Health Canada, it is also approved for its use in over-the-counter products.6
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cetalkonium (DB11583)
- Weight
- Average: 360.649
Monoisotopic: 360.362476905 - Chemical Formula
- C25H46N
- Synonyms
- Benzylhexadecyldimethylammonium
- Cetalkonium cation
- Cetalkonium ion
Pharmacology
- Indication
Cetalkonium is used as a surfactant, germicide, fungicide, mildew preventive agents in silicone-based water repellents, emulsifier, disinfectant, topical anti-infective, and antiseptic antimicrobial for pharmaceuticals. For its chemical properties and its antiseptical characteristics, cetalkonium can be used in a wide variety of products as part of the formulations and it is also determined to be an active antiseptic ingredient in over-the-counter preparations.2
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Pain Combination Product in combination with: Choline salicylate (DB14006) ••• ••• - Contraindications & Blackbox Warnings
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Cetalkonium is an antimicrobial agent and it has shown to be effective against both gram-positive, gram-negative bacteria and fungi. From this property, it has been shown to present a better activity against the gram-negative organisms.11
- Mechanism of action
The activity of cetalkonium is based on the creation of a positive charge which permits a bio-adhesive property to negative surfaces.8 This property allows cetalkonium to disrupt the cell membrane, inactivate enzymes and denature proteins. This type of mechanism allows this type of agents to present a broad spectrum.3
- Absorption
Cetalkonium is used mainly topically and it is not absorbed.4 When administered orally and parenterally, cetalkonium absorption may happen but it is very insignificant.9
- Volume of distribution
As cetalkonium is not absorbed, this pharmacokinetic property is not relevant.
- Protein binding
As cetalkonium is not absorbed, this pharmacokinetic property is not relevant.
- Metabolism
As cetalkonium is not absorbed, this pharmacokinetic property is not relevant.
- Route of elimination
As cetalkonium is not absorbed, this pharmacokinetic property is not relevant. When administered orally, most of the administered dose is excreted unchanged in the feces as it is very poorly absorbed.9
- Half-life
As cetalkonium is not absorbed, this pharmacokinetic property is not relevant.
- Clearance
As cetalkonium is not absorbed, this pharmacokinetic property is not relevant.
- Adverse Effects
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A fatal dose is reported to be in the range of 1-3 g and the LD50 observed in different preclinical studies has been from 60-400 mg/kg depending on the animal species and route of administration.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 Cetalkonium bromide UHU0390Z3J 3529-04-2 DLNWMWYCSOQYSQ-UHFFFAOYSA-M Cetalkonium chloride 85474O1N9D 122-18-9 SXPWTBGAZSPLHA-UHFFFAOYSA-M - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image AVERA GEL Cetalkonium chloride (0.01 %w/w) + Choline salicylate (8.71 %w/w) Gel APEX PHARMACY MARKETING SDN. BHD. 2020-09-08 Not applicable Malaysia 
Bionet Lozenge Cetalkonium chloride (5 mg) + Benzocaine (7.5 mg) Lozenge Oral Church & Dwight Canada Corp 1954-12-31 2015-07-31 Canada 
BONJELA Cetalkonium chloride (0.01 %w/w) + Choline salicylate (8.714 %w/w) Gel RB (HEALTH) MALAYSIA SDN BHD 2020-09-08 Not applicable Malaysia BONJELA Cetalkonium chloride (10 mg/100g) + Choline salicylate (8.7 g/100g) Gel Oral บริษัท เรกคิทท์ เบนคีเซอร์ (ประเทศไทย) จำกัด 1999-09-27 Not applicable Thailand 
BONJELA GEL Cetalkonium chloride (0.01 % w/w) + Choline salicylate (8.714 % W/W) Gel Submucosal RECKITT BENCKISER (SINGAPORE) PTE LTD 1990-04-23 Not applicable Singapore 
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylmethylamines
- Direct Parent
- Phenylmethylamines
- Alternative Parents
- Benzylamines / Aralkylamines / Tetraalkylammonium salts / Organopnictogen compounds / Organic salts / Hydrocarbon derivatives / Organic cations
- Substituents
- Amine / Aralkylamine / Aromatic homomonocyclic compound / Benzylamine / Hydrocarbon derivative / Organic cation / Organic nitrogen compound / Organic salt / Organonitrogen compound / Organopnictogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Fungi
- Gram negative and gram positive bacteria
Chemical Identifiers
- UNII
- FHG725432Z
- CAS number
- 10328-34-4
- InChI Key
- QDYLMAYUEZBUFO-UHFFFAOYSA-N
- InChI
- InChI=1S/C25H46N/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-20-23-26(2,3)24-25-21-18-17-19-22-25/h17-19,21-22H,4-16,20,23-24H2,1-3H3/q+1
- IUPAC Name
- benzyl(hexadecyl)dimethylazanium
- SMILES
- CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1
References
- General References
- Daull P, Lallemand F, Garrigue JS: Benefits of cetalkonium chloride cationic oil-in-water nanoemulsions for topical ophthalmic drug delivery. J Pharm Pharmacol. 2014 Apr;66(4):531-41. [Article]
- Ash M. and Ash I. (2004). Handbook of preservatives. Synapse information resources, Inc. [ISBN:1-890595-66-7]
- Stull J. and Weese J. (2015). Infection Control. Elsevier. [ISBN:978-0-323-35669-5]
- Seyffart G. (1992). Drug dosage in renal insufficiency (2nd ed.). Springer Science+Business Media Dordrecht.
- FDA history [Link]
- Health Canada [Link]
- Netdoctor: Bonjela treatment for mouth ulcers [Link]
- Current issues in Pharmacy and medical sciences [Link]
- Quaternary ammonium compounds [Link]
- FDA Thailand Product Information: Bonjela (choline salicylate/cetalkonium chloride) oral gel [Link]
- Bonjela monograph [File]
- External Links
- PubChem Compound
- 31203
- PubChem Substance
- 347827993
- ChemSpider
- 28944
- ChEBI
- 135523
- ChEMBL
- CHEMBL1624075
- ZINC
- ZINC000014233334
- Wikipedia
- Cetalkonium_chloride
- MSDS
- Download (47.2 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Gel Gel Oral Gel Submucosal 0.01 % w/w Lozenge Oral Gel Topical Gel Dental; Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 54-58 ºC 'MSDS' water solubility 8.5 g/L Daull P., Lallemand F. and Garrigue J. J Pharm Pharmacol. (2014) logP 2.5 Daull P., Lallemand F. and Garrigue J. J Pharm Pharmacol. (2014) - Predicted Properties
Property Value Source Water Solubility 3.37e-06 mg/mL ALOGPS logP 4.67 ALOGPS logP 4.41 Chemaxon logS -8.1 ALOGPS pKa (Strongest Acidic) 18.11 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 0 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 0 Å2 Chemaxon Rotatable Bond Count 17 Chemaxon Refractivity 129.6 m3·mol-1 Chemaxon Polarizability 49.61 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No 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 splash10-0006-9883000000-0c64835bb0d824a016c0 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]- 196.70139 predictedDeepCCS 1.0 (2019) [M+H]+ 199.25172 predictedDeepCCS 1.0 (2019) [M+Na]+ 205.59464 predictedDeepCCS 1.0 (2019)
Drug created at April 27, 2016 20:08 / Updated at May 21, 2021 10:22