CETALKONIUM CHLORIDE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H46N.Cl
Molecular Weight	396.092
Optical Activity	NONE
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1

InChI

InChIKey=SXPWTBGAZSPLHA-UHFFFAOYSA-M

InChI=1S/C25H46N.ClH/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;1H/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula	C25H46N
Molecular Weight	360.6394
Charge	1
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002066/WC500186592.pdf | http://www.medicines.org.uk/emc/PIL.23429.latest.pdf

Cetalkonium chloride is a cationic quaternary ammonium surfactant, which is used for the treatment of mouth ulcers and sores (Bonjela trade name). It is also serves as an excipient for the purpose of long-term stabilization of ciclosporin ocular formulation, used in patients with dry eye syndrom (Ikervis trade name). The antibacterial properties of cetalkonium can be explained by its detergent character. Once applied, cetalkonium blocks the survival of biofilm forming bacterias.

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Mouth ulcers 8 Sources: http://www.medicines.org.uk/emc/PIL.23429.latest.pdf	Curative	Approved 8583	BONJELA Approved Use For the relief of pain, discomfort and inflammation caused by common mouth ulcers, cold sores, denture and sore spots, as well as mouth ulcers, and sore spots due to orthodontic devices. To help to fight minor mouth infection and aid healing of sore spots and ulcers due to dentures and orthodontic devices.
Dry eye syndrome 21 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002066/WC500186592.pdf	Inactive ingredient	Approved 8583	IKERVIS Approved Use Treatment of severe keratitis in adult patients with dry eye disease, which has not improved despite treatment with tear substitutes. Launch Date 2015
Cold sores 11 Sources: http://www.medicines.org.uk/emc/PIL.23429.latest.pdf	Primary	Approved 8583	BONJELA Approved Use For the relief of pain, discomfort and inflammation caused by common mouth ulcers, cold sores, denture and sore spots, as well as mouth ulcers, and sore spots due to orthodontic devices. To help to fight minor mouth infection and aid healing of sore spots and ulcers due to dentures and orthodontic devices.

Doses

Dose	Population	Adverse events
0.1 % 1 times / day single, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: single Dose: 0.1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16426305/	healthy, 28 to 55 years Health Status: healthy Age Group: 28 to 55 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16426305/	Other AEs: Contact dermatitis... Other AEs: Contact dermatitis (37.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/16426305/

AEs

AE	Significance	Dose	Population
Contact dermatitis	37.5%	0.1 % 1 times / day single, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: single Dose: 0.1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16426305/	healthy, 28 to 55 years Health Status: healthy Age Group: 28 to 55 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16426305/

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0034Z3
A2B Chem	AB45615
AA Blocks	AA0034FN
ABI Chem	AC1L1L4P
Acros Organics	40207
ACT Chemical	ACT11069
AK Scientific	4385AB
AK Scientific	6729AF
AK Scientific	V0576
Alfa Chemistry	32377
Alfa Chemistry	ACM122189
Alfa Chemistry	ACM85851689
Alfa Chemistry	ACM85851690
Alfa Chemistry	ACM85851736
Ambeed	A545178
Angene	AGN-PC-0JKLSU
AstaTech	F16465
Bide Pharmatech	BD116269
BioSynth	W-109454
BLD Pharm	BD105520
BlocksMatrix Scientific	97507
BOC Sciences	122-18-9
BOC Sciences	30251-10-6
BOC Sciences	595073
BOC Sciences	94159-23-6
Bosche Scientific	C1384
Catsyn	SC10040
Chem-Impex International	30370
Chem Scene	CS-0013522
Chemieliva Pharmaceutical Co., Ltd	PBCM1056090
Combi-Blocks	QC-0477
Compound Cloud	31202
Compound Cloud	31203
Debye Scientific	DB-025306
eMolecules	109860826
eMolecules	109860828
eMolecules	2724313
eMolecules	36092035
eMolecules	717857
eNovation Chemicals	Y1080510	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1080510
Fluorochem	235640
Hairui	HR115437
Hangzhou Yuhao Chemical Technology	XJ0453
Innovapharm	BBV-00089346
KeyOrganics	AS-10446
KeyOrganics	AS-17528
Lab Network	LN00193357
Lab Seeker	SC-19018
mcule	MCULE-6808128344	https://mcule.com/MCULE-6808128344/
MedChem Express	HY-B1597
MolPort	MolPort-003-926-293
MolPort	MolPort-005-932-340
MuseChem	M061137
MuseChem	R013406
Nanjing Pope Bio-tech	NSTH-D09787
NCI Plated 2007	263517
NCI Plated 2007	310008
NCI Plated 2007	32942
NCI Plated 2007	4844
NCI Plated 2007	55878
Norris Pharm	NSTH-D09787
Norris Pharm	NSZB-A261728
NovoSeek	31203
Oakwood	235640
Selleck Chemicals	S6015
Sigma Aldrich	13400
Sigma Aldrich	13400\|SIAL
Sigma Aldrich	B4136
Sigma Aldrich	V900317
Sigma Aldrich	V900317\|VETEC
Sinfoo Biotech	S020835	http://www.sinfoobiotech.com/product/1024233
StruChem	SC-19018
Tetrahedron	TS69116
Tetrahedron	TS80280
Tetrahedron	TS82183
THE BioTek	bt-436611	https://www.thebiotek.com/product/others/bt-436611
TimTec	SBB060434
TimTec	ST51039868
TimTec	ST51046611
TimTec	ST51255480
Toronto Research Chemicals	C280500
Toronto Research Chemicals	C280502
W&J PharmaChem	50A280097
Wonderchem	WD04XYG
Wonderchem	WD04XYH
ZINC	ZINC000014233334	http://zinc15.docking.org/substances/ZINC000014233334

PubMed

Title	Date	PubMed
Detection of cationic surfactants in oral rinses and a disinfectant formulation using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001	11344536
Exciplex-type behavior and partition of 3-substituted indole derivatives in reverse micelles made with benzylhexadecyldimethylammonium chloride, water and benzene.	2001 Feb	11272737
Occupational allergic contact dermatitis from alkylammonium amidobenzoate.	2001 May-Jun	11358732
The trouble with teething--misdiagnosis and misuse of a topical medicament.	2002 May	12028314
Sulfentrazone adsorbed on micelle-montmorillonite complexes for slow release in soil.	2003 May 21	12744675
Investigation of the effects of wall adsorption of the visualization agent on baseline noise characteristics for indirect UV detection in capillary electrophoresis.	2003 Sep	12973808
Influence of enhancers on the absorption and on the pharmacokinetics of cefodizime using in-vitro and in-vivo models.	2004 Apr	15099444
Static and dynamic light-scattering studies on micellar solutions of alkyldimethylbenzylammonium chlorides.	2004 Aug 15	15271569
The synaptic vesicle proteome: a comparative study in membrane protein identification.	2004 Oct	15378707
Immunoisolation of two synaptic vesicle pools from synaptosomes: a proteomics analysis.	2005 Dec	16269012
Resonance Rayleigh scattering study of interaction of heparin with some cationic surfactants and their analytical application.	2005 Mar	15683790
Enrichment of integral membrane proteins from small amounts of brain tissue.	2006 Aug	16835696
Mass spectrometrical identification of brain proteins including highly insoluble and transmembrane proteins.	2006 Aug	16616972
Equilibrium studies for the adsorption of acid dye onto modified hectorite.	2006 Aug 25	16513258
Analysis of the synaptic vesicle proteome using three gel-based protein separation techniques.	2006 Dec	17080482
Condensed film formation of binary mixtures of cetyltrimethylammonium bromide and cetyldimethylbenzylammonium chloride in a wide potential region at the mercury/electrolyte interface.	2006 Dec 1	16989847
A new multiphasic buffer system for benzyldimethyl-n-hexadecylammonium chloride polyacrylamide gel electrophoresis of proteins providing efficient stacking.	2006 Feb	16331586
Influence of absorption enhancers on the pharmacokinetic properties of non-oral beta-lactam-cefpirom using the rabbit (Chinchilla) in vivo model.	2006 Feb 17	16377108
Water remediation by micelle-clay system: case study for tetracycline and sulfonamide antibiotics.	2006 Jul	16762389
Release characteristics of anionic drug compounds from liquid crystalline gels. Part II. The effects of ion pairing and buffering on the passive delivery of anionic drugs across non-rate-limiting membranes.	2006 Mar 27	16426777
Resonance Rayleigh scattering method for the determination of cationic surfactants with chromium(VI)-iodide system.	2006 May	16770060
Dechlorination of beta-methylallyl chloride by electrogenerated [Co(I)(bipyridine)3]+: an electrochemical study in the presence of cationic surfactants.	2006 May 15	16376922
Synaptic vesicle proteins under conditions of rest and activation: analysis by 2-D difference gel electrophoresis.	2006 Sep	16944461
Visual determination of nitrite and nitrate in waters by color band formation method.	2006 Sep	16481027
Comparative study of the photophysical behavior of fisetin in homogeneous media and in anionic and cationic reverse micelles media.	2007 May-Jun	17115801
Evaluation of two proteomics technologies used to screen the membrane proteomes of wild-type Corynebacterium glutamicum and an L-lysine-producing strain.	2007 Oct	17221235
Two-dimensional separation of membrane proteins by 16-BAC-SDS-PAGE.	2009	19153699
16-BAC/SDS-PAGE analysis of membrane proteins of yeast mitochondria purified by free flow electrophoresis.	2009	19153686
Comparison of the ocular tolerability of a latanoprost cationic emulsion versus conventional formulations of prostaglandins: an in vivo toxicity assay.	2009 Aug 25	19710954
Characterization of multifunctional reverse micelles' interfaces using hemicyanines as molecular probes. II: Effect of the surfactant.	2009 May 14	19378960
Modulation of excited-state proton-transfer reactions of 7-hydroxy-4-methylcoumarin in ionic and nonionic reverse micelles.	2009 May 14	19374362
On the formation of new reverse micelles: a comparative study of benzene/surfactants/ionic liquids systems using UV-visible absorption spectroscopy and dynamic light scattering.	2009 Sep 15	19678620
Sorption of quaternary ammonium compounds to municipal sludge.	2010 Apr	20045549
Highlights on the capacities of "Gel-based" proteomics.	2010 Apr 28	20426826
Cationic reverse micelles create water with super hydrogen-bond-donor capacity for enzymatic catalysis: hydrolysis of 2-naphthyl acetate by alpha-chymotrypsin.	2010 Aug 2	20572177
Adsorptive removal of cationic surfactants from aqueous solutions onto high-area activated carbon cloth monitored by in situ UV spectroscopy.	2010 Feb 15	19815343
[Optimization of benzalkonium chloride concentration in 0.0015% tafluprost ophthalmic solution from the points of ocular surface safety and preservative efficacy].	2010 Jun	20519865
Ammonium detection by formation of colored zebra-bands in a detecting tube.	2010 Jun 15	20441924
Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride.	2013 Aug	23792315

Patents

Sample Use Guides

In Vivo Use Guide

Massage one centimetre of the topical formulation (Bonjela) onto the affected area (mouth ulcers and sores) and leave at least 30 min in case of denture sores. In dry eye disease, the recommended dose is one drop of the ocular formulation (Ikervis) once daily to be applied to the affected eye(s) at bedtime.

Route of Administration: Other

In Vitro Use Guide

Corneal human cells were treated with 0.005% cetalkonium chloride cationic oil-inwater nanoemulsion for 30 min. The emulsion was able to increase the pace of healing, as measured by the reduction of the size of the scraped area.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:32:14 GMT 2025` Edited by `admin` on `Wed Apr 02 08:32:14 GMT 2025`
Record UNII	85474O1N9D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CETALKONIUM CHLORIDE

Official Name

English

cetalkonium chloride [INN]

Preferred Name

English

ZETTYN

Brand Name

English

CDBAC

Common Name

English

CETALKONIUM CHLORIDE [VANDF]

Common Name

English

CETYL ZEPHIRAN

Common Name

English

ACQUAT CDAC

Brand Name

English

BENZENEMETHANAMINIUM, N-HEXADECYL, N,N-DIMETHYL-, CHLORIDE

Common Name

English

BANICOL

Brand Name

English

N-HEXADECYL-N,N-DIMETHYLBENZENEMETHANAMINIUM CHLORIDE

Systematic Name

English

CETALKONIUM CHLORIDE [USAN]

Common Name

English

Benzylhexadecyldimethylammonium chloride

Systematic Name

English

AMMONIUM, BENZYLHEXADECYLDIMETHYL-, CHLORIDE

Systematic Name

English

Cetalkonium chloride [WHO-DD]

Common Name

English

CETALKONIUM CHLORIDE [MART.]

Common Name

English

CETALKONIUM CHLORIDE [MI]

Common Name

English

CETYLBENZYLDIMETHYLAMMONIUM CHLORIDE

Systematic Name

English

NSC-32942

Code

English

Classification Tree Code System Code

EPA PESTICIDE CODE

69108