Cetalkonium

Identification

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Name
Cetalkonium
Accession Number
DB11583
Type
Small Molecule
Groups
Approved
Description

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

Structure
Thumb
Synonyms
  • Benzylhexadecyldimethylammonium
  • Cetalkonium cation
  • Cetalkonium ion
Product Ingredients
IngredientUNIICASInChI Key
Cetalkonium bromideUHU0390Z3J3529-04-2DLNWMWYCSOQYSQ-UHFFFAOYSA-M
Cetalkonium chloride85474O1N9D122-18-9SXPWTBGAZSPLHA-UHFFFAOYSA-M
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bionet LozengeCetalkonium chloride (5 mg) + Benzocaine (7.5 mg)LozengeOralChurch & Dwight Company, Inc.1954-12-312015-07-31Canada
Emercol LozCetalkonium chloride (2.5 mg) + Benzocaine (7.5 mg) + Cetylpyridinium chloride (2.5 mg)LozengeOralPharmavite Laboratories (1987) Inc.1984-12-312000-08-18Canada
Teejel GelCetalkonium chloride (0.01 %) + Choline salicylate (8.7 %)GelDental; TopicalPurdue Pharma1965-12-312002-07-30Canada
Categories
UNII
FHG725432Z
CAS number
10328-34-4
Weight
Average: 360.649
Monoisotopic: 360.362476905
Chemical Formula
C25H46N
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

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

Pharmacodynamics

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.10

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.

Toxicity

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

Affected organisms
  • Fungi
  • Gram negative and gram positive bacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:24001405]
  2. Ash M. and Ash I. (2004). Handbook of preservatives. Synapse information resources, Inc. [ISBN:1-890595-66-7]
  3. Stull J. and Weese J. (2015). Infection Control. Elsevier. [ISBN:978-0-323-35669-5]
  4. Seyffart G. (1992). Drug dosage in renal insufficiency (2nd ed.). Springer Science+Business Media Dordrecht.
  5. FDA history [Link]
  6. Health Canada [Link]
  7. Bonjela: treatment for mouth ulcers [Link]
  8. Current issues in Pharmacy and medical sciences [Link]
  9. Quaternary ammonium compounds [Link]
  10. Bonjela monograph [File]
External Links
PubChem Compound
31203
PubChem Substance
347827993
ChemSpider
28944
ChEBI
135523
ChEMBL
CHEMBL1624075
Wikipedia
Cetalkonium_chloride
MSDS
Download (47.2 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LozengeOral
GelDental; Topical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)54-58 ºC'MSDS'
water solubility8.5 g/LDaull P., Lallemand F. and Garrigue J. J Pharm Pharmacol. (2014)
logP2.5Daull P., Lallemand F. and Garrigue J. J Pharm Pharmacol. (2014)
Predicted Properties
PropertyValueSource
Water Solubility3.37e-06 mg/mLALOGPS
logP4.67ALOGPS
logP4.41ChemAxon
logS-8.1ALOGPS
pKa (Strongest Acidic)18.11ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity129.6 m3·mol-1ChemAxon
Polarizability49.61 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
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

Taxonomy

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
Phenylmethylamine / Benzylamine / Aralkylamine / Tetraalkylammonium salt / Quaternary ammonium salt / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organic salt / Organonitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on April 27, 2016 14:08 / Updated on July 13, 2019 00:57