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Cetylpyridinium Chloride

PubChem CID
31239
Structure
Cetylpyridinium Chloride_small.png
Cetylpyridinium Chloride_3D_Structure.png
Molecular Formula
Synonyms
  • cetylpyridinium chloride
  • 123-03-5
  • 1-hexadecylpyridin-1-ium chloride
  • hexadecylpyridinium chloride
  • 1-Hexadecylpyridinium chloride
Molecular Weight
340.0 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
Cetylpyridinium chloride is a pyridinium salt that has N-hexadecylpyridinium as the cation and chloride as the anion. It has antiseptic properties and is used in solutions or lozenges for the treatment of minor infections of the mouth and throat. It has a role as an antiseptic drug and a surfactant. It is a chloride salt and an organic chloride salt. It contains a cetylpyridinium.
Cetylpyridinium Chloride is the chloride salt form of cetylpyridinium, a quaternary ammonium with broad-spectrum antimicrobial activity. Upon topical administration, cetylpyridinium chloride is positively charged and reacts with the negatively charged microbial cell surfaces, thereby destroying the integrity of the cell membrane. This causes leakage of intracellular components leading to microbial cell death.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Cetylpyridinium Chloride.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-hexadecylpyridin-1-ium;chloride
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C21H38N.ClH/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;1H/q+1;/p-1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

YMKDRGPMQRFJGP-UHFFFAOYSA-M
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1.[Cl-]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C21H38N.Cl
C21H38ClN
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

123-03-5
6004-24-6

2.3.2 Deprecated CAS

136499-13-3, 2266591-56-2, 27841-61-8, 50958-35-5, 951742-58-8
136499-13-3, 2266591-56-2, 2745197-72-0, 27841-61-8, 50958-35-5, 951742-58-8
136499-13-3, 27841-61-8, 951742-58-8

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 NCI Thesaurus Code

2.3.9 NSC Number

2.3.10 RXCUI

2.3.11 Wikidata

2.3.12 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • cerigel
  • tserigel

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
340.0 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
15
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
339.2692779 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
339.2692779 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
3.9 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
23
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
208
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Other Solid
White solid; [HSDB]

3.2.2 Color / Form

White powder
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V5 4747

3.2.3 Melting Point

80 °C
Lide, DR (ed.). CRC Handbook of Chemistry and Physics. 81st Edition. CRC Press LLC, Boca Raton: FL 2000, p. 3-301

3.2.4 Solubility

Very soluble in water, chloroform
Lide, DR (ed.). CRC Handbook of Chemistry and Physics. 81st Edition. CRC Press LLC, Boca Raton: FL 2000, p. 3-301

3.2.5 LogP

log Kow= 1.71
Moschner KF, Cece A; pp. 318-31 in Environ Toxicol Risk Assess, 3rd. ASTM STP 1218. Hughes JS et al, eds. Philadelphia, PA: ASTM (1995)

3.2.6 Decomposition

When heated to decomposition it emits very toxic fumes of /nitrogen oxides and hydrogen chloride/.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 691

3.2.7 Refractive Index

INDEX OF REFRACTION (@ 20 °C): MONOCLINIC 1.509; TRICLINIC 1.566; ORTHORHOMBIC 1.613
Association of Official Analytical Chemists. Official Methods of Analysis. 10th ed. and supplements. Washington, DC: Association of Official Analytical Chemists, 1965. New editions through 13th ed. plus supplements, 1982., p. 12/1028 52.023

3.2.8 Collision Cross Section

197.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

3.2.9 Other Experimental Properties

White powder; mp: 77-83 °C; freely sol in water, alcohol, chloroform; very slightly sol in benzene, ether; ph (1% aq soln): 6.0 to 7.0; surface tension (25 °C): 43 dyn/cm (0.1% aq soln), 41 dyn/cm (1.0% aq soln), 38 dyn/cm (10% aq soln) /Cetylpyridinium chloride monohydrate/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 336

3.3 Chemical Classes

Nitrogen Compounds -> Quaternary Amines

3.3.1 Cosmetics

Emulsifying; Deodorant; Hair conditioning; Antistatic; Antimicrobial; Surfactant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra
NMR: 9798 (Sadtler Research Laboratories Spectral Collection)

4.1.1 13C NMR Spectra

Source of Sample
Lachat Chemicals, Inc., Chicago Heights, Illinois
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 UV Spectra

UV: 7089 (Sadtler Research Laboratories Spectral Collection)
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V5 4747

4.2.1 UV-VIS Spectra

Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3 IR Spectra

IR Spectra
IR: 16568 (Sadtler Research Laboratories Prism Collection)

4.3.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Greenwood Chemical Company
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Technique
KBr (1/400), water subtracted
Source of Sample
Henkel, Duesseldorf
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.3.2 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
National Biochemicals Corporation
Catalog Number
9625
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4 Raman Spectra

1 of 2
Instrument Name
Bio-Rad FTS 175C with Raman accessory
Technique
FT-Raman
Source of Sample
Greenwood Chemical Company
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Company Llc.
Catalog Number
<a href=https://www.sigmaaldrich.com/US/en/product/sigma/C9002>C9002</a>
Lot Number
110F-0508
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Other Spectra

AXIAL ANGLE: 2V= 88 °C ALC; OPTIC SIGN NEG, EXTINCTION INCLINED
Association of Official Analytical Chemists. Official Methods of Analysis. 10th ed. and supplements. Washington, DC: Association of Official Analytical Chemists, 1965. New editions through 13th ed. plus supplements, 1982., p. 12/1028 52.023

6 Chemical Vendors

7 Drug and Medication Information

7.1 FDA National Drug Code Directory

7.2 Drug Labels

Drug and label
Active ingredient and drug

7.3 Clinical Trials

7.3.1 ClinicalTrials.gov

7.3.2 EU Clinical Trials Register

7.3.3 NIPH Clinical Trials Search of Japan

7.4 Therapeutic Uses

Anti-infective Agents, Local
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
A LOCAL ANTI-INFECTIVE WHICH POSSESSES SURFACE-ACTIVE AS WELL AS ANTISEPTIC PROPERTIES AGAINST SENSITIVE NONSPORULATING BACTERIA ... USED FOR PREOPERATIVE PREPN OF SKIN FOR PROPHYLACTIC ANTISEPSIS OF MINOR WOUNDS & ... IRRIGATION OF OR TOPICAL APPLICATION TO MUCOUS MEMBRANES. ... ALSO INCORPORATED INTO MOUTHWASHES.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1090
A CATIONIC SURFACE-AGENT ... BACTERICIDAL OR BACTERIOSTATIC AGAINST MANY GRAM-POSITIVE & GRAM-NEG ORGANISMS. ... ALSO ACTIVE AGAINST SOME FUNGI, INCL CANDIDA ALBICANS, & AGAINST TRICHOMONAS VAGINALIS, BUT IS NOT AN EFFECTIVE ANTI-INFECTIVE ... FOR SPORES OR MOST VIRUSES.
American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 84:4:16
DOSAGE: TOPICAL, AS A 1:100 TO 1:1000 SOLN TO INTACT SKIN; 1:1000 FOR MINOR LACERATIONS; 1:2000 TO 1:10,000 TO MUCOUS MEMBRANES; 0.33 TO 3 MG IN LOZENGES OR TROCHES; FOR INSERTION INTO RECTUM, 0.05%. DOSAGE FORMS- LOZENGES NF: 1.5 MG IN 1:1500 CONCN; SOLN NF: 1:1000.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1090
For more Therapeutic Uses (Complete) data for CETYLPYRIDINIUM CHLORIDE (16 total), please visit the HSDB record page.

7.5 Drug Warnings

QUATERNARY AMMONIUM ANTISEPTICS ... APPLIED TO SKIN ... FORM FILM UNDER WHICH BACTERIA MAY REMAIN VIABLE EVEN THOUGH OUTER SURFACE OF FILM IS BACTERICIDAL. SINCE CETYLPYRIDINIUM CHLORIDE IS INACTIVATED BY SOAPS, SOAP USED IN PRE-OPERATIVE TREATMENT OF SKIN MUST BE THOROUGHLY REMOVED ... BEFORE APPLICATION OF ANTISEPTIC.
American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 84:4:16
GRAM NEGATIVE ORGANISMS, INCL STRAINS OF PSEUDOMONAS AERUGINOSA, ARE MORE RESISTANT /THAN GRAM POS/ & REQUIRE LONGER EXPOSURE /TO QUATERNARY AMMONIUM CMPD/. /QUATERNARY AMMONIUM CMPD/
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 890
ABSORBED AND INACTIVATED BY COTTON FABRICS, CELLULOSE SPONGES, CERTAIN PLASTICS (PARTICULARLY POLYVINYL CHLORIDE) OR OTHER POROUS MATERIALS. FOR THIS REASON, THESE AGENTS SHOULD NOT BE USED FOR COLD STERILIZATION OF CATHETERS, FLEXIBLE ENDOSCOPES OR OTHER INSTRUMENTS. /QUATERNARY AMMONIUM CMPD/
American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 1439
CAN CAUSE OCCASIONAL ALLERGIC RESPONSES WITH CHRONIC USE, AS WITH CERTAIN DEODORANT PREPN & DIAPER WASHES. /CATIONIC SURFACTANTS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1002
/DUE TO ADSORPTION TENDENCY/ ... REPEATED USE OF SAME SOLN FOR DISINFECTION OF POROUS MATERIALS CAN REDUCE THE CONCN OF THE AGENT BELOW THE BACTERICIDAL LIMIT. /CATIONIC SURFACTANTS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1002

8 Agrochemical Information

8.1 Agrochemical Category

Microbiocide

9 Pharmacology and Biochemistry

9.1 Absorption, Distribution and Excretion

ORAL RETENTION OF CETYLPYRIDINIUM CHLORIDE GIVEN AS 1 MIN MOUTH RINSE OF 10 ML OF 2.2 MMOL SOLN WAS 65% OF ADMIN DOSE.
BONESVOLL P, GJERMO P; ARCH ORAL BIOL 23 (4) 289-94 (1978)

9.2 Mechanism of Action

MODE OF ACTION ... NOT YET FULLY UNDERSTOOD BUT HAS BEEN ASCRIBED TO ... THE DENATURING OF LIPOPROTEIN COMPLEXES, & POSSIBLY OTHER ACTIONS. /QUATERNARY AMMONIUM COMPD/
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 890
EVIDENCE HAS BEEN PRESENTED THAT THE MAJOR SITE OF ACTION ... MAY BE THE CELL MEMBRANE, WHERE THE AGENTS MAY CAUSE CHANGES IN PERMEABILITY THAT PERMIT ESCAPE OF ENZYMES, COENZYMES, & METABOLIC INTERMEDIATES. /CATIONIC SURFACTANTS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1001
EMULSIFY SEBACEOUS MATERIAL, WHICH IS THEN REMOVED TOGETHER WITH DIRT & BACTERIA. THE MILD DESQUAMATING EFFECT OF THE QUATERNARY AMMONIUM COMPOUNDS AIDS IN CLEANING. /QUATERNARY AMMONIUM COMPD/
American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 1439

10 Use and Manufacturing

10.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used as a preservative/antibacterial agent in cosmetics, pharmaceuticals, cough lozenges, mouthwashes, deodorants, and antiseptics; [HSDB] Quarternary ammonium compounds are used as algaecides/slimicides (swimming pools, industrial water reservoirs, and farm ponds), antiseptics for cleaning wounds, antistatic agents for textiles, softeners for paper products, and pigment dispersers; [IPCS-PIMs]
Industrial Processes with risk of exposure
For Cetylpyridinium chloride (USEPA/OPP Pesticide Code: 069160) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on Cetylpyridinium chloride (123-03-5). Available from, as of September 26, 2001: https://npirspublic.ceris.purdue.edu/ppis/
The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
USEPA/OPP; Status of Pesticides in Registration, Reregistration and Special Review p.230 (Spring, 1998) EPA 738-R-98-002
Pharmaceutic aid (preservative), antiseptic; disinfectant/monohydrate/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 336
Antiseptic; preservative(cosmetics, pharmaceuticals)
Ashford, R.D. Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd., 1994., p. 189
For more Uses (Complete) data for CETYLPYRIDINIUM CHLORIDE (9 total), please visit the HSDB record page.

10.1.1 Use Classification

Cosmetics -> Emulsifying; Deodorant; Hair conditioning; Antistatic; Antimicrobial; Surfactant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

10.1.2 Industry Uses

Other (specify)

10.1.3 Consumer Uses

Other (specify)

10.1.4 Household Products

Household & Commercial/Institutional Products

Information on 33 consumer products that contain Cetylpyridinium chloride in the following categories is provided:

• Personal Care

10.2 Methods of Manufacturing

ANHYD CMPD PREPD BY HEATING MIXT OF CETYL CHLORIDE & SLIGHT EXCESS OF PYRIDINE @ 140 °C FOR 6 HR. CRUDE PRODUCT IS DECOLORIZED WITH CHARCOAL & RECRYSTALLIZED FROM MIXED SOLVENT COMPOSED OF METHYL ETHYL KETONE & ALCOHOL ... THEN WASHED WITH ETHER & VACUUM DRIED @ 50-60 °C. /THEN RECRYSTALLIZED/ ... FROM WATER ... .
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1090
Pyridine + cetyl chloride (quaternization)
Ashford, R.D. Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd., 1994., p. 189

10.3 Formulations / Preparations

CEPACAINE SOLN (BENZOCAINE, COMBINATION, CETYLPYRIDINIUM CHLORIDE, DIBUCAINE).
JANECKE JB; CURR THER RES CLIN EXP 20 (JUL) 70-3 (1976)
CETYLPRIDINIUM CHLORIDE LOZENGES, 0.067% ... WITH BENZYL ALC (CEPACOL). LOZENGES, 0.067% ... WITH NEOMYCIN SULFATE 2.5 MG ... TYROTHRICIN 1 MG, METHYLPARABEN 4 MG, PROPYLPARABEN 1 MG, ETHYL AMINOBENZOATE 5 MG (CEPACOL ANTIBIOTIC TROCHES). SOLN, 0.025% ... WITH ALC 14% & PHOSPHATE BUFFERS; 150 & 420 ML BOTTLES (CEPACOL).
American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 52:28
AVAILABLE AS AQUEOUS OR ALCOHOL SOLUTIONS (EG, TINCTURE) IN CONCN OF 10% OR LESS.
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-280
GRADES: TECHNICAL; NF
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 183
Lozenges, 0.07%. Mouthwash, 0.05%.
Hussar, D.A. (ed.). Modell's Drugs in Current Use and New Drugs. 38th ed. New York, NY: Springer Publishing Co., 1992., p. 35

10.4 Consumption Patterns

PROBABLY 100% AS AN ANTI-INFECTIVE/DISINFECTANT (1975)
SRI

10.5 U.S. Production

Aggregated Product Volume
2019: 434,365 lb
(1972) PROBABLY GREATER THAN 4.54X10+5 G
SRI
(1975) PROBABLY GREATER THAN 4.54X10+5 G
SRI

10.6 U.S. Imports

(1974) 1.0X10+6 G (PRINCPL CUSTMS DISTS)
SRI

10.7 General Manufacturing Information

Industry Processing Sectors
Other (requires additional information)
EPA TSCA Commercial Activity Status
Pyridinium, 1-hexadecyl-, chloride (1:1): ACTIVE
/CETYLPYRIDINIUM CHLORIDE IS/ MONOHYDRATE OF QUATERNARY SALT OF PYRIDINE & CETYL CHLORIDE.
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 254
BACTERIAL SPORES RESIST EVEN PROLONGED CONTACT. AQ SOLN OF THESE CMPD ARE NOT TUBERCULOCIDAL. /QUATERNARY AMMONIUM CMPD/
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 890
SURFACTANTS ... ARE BLENDED INTO SOME DRUG PRODUCTS TO IMPROVE DISINTEGRATION OF TABLETS OR SPREAD & CONTACT OF MEDICATIONS ... WITH BODY SURFACES. ... PRECAUTIONS ... BECAUSE SOME ... CAN INACTIVATE OTHER DRUG PRODUCT INGREDIENTS. ... TWEEN 80 BINDS ... CETYLPYRIDINIUM CHLORIDE.
Martin, E. W. (ed.). Hazards of Medication. 2nd ed. Philadelphia: J.B. Lippincott Co., l978., p. 67
PHARMACEUTICAL INSULIN PREPN FOR RECTAL ADMIN COMPRISE INSULIN, A BASE, & AS ABSORPTION ACCELERATOR, SOMETIMES A CATIONIC SURFACTANT.
KAWADA ET AL; GER OFFEN PATENT NO 2641819 4/7/77 (YAMANOUCHI PHARMACEUTICAL CO, LTD)
For more General Manufacturing Information (Complete) data for CETYLPYRIDINIUM CHLORIDE (6 total), please visit the HSDB record page.

11 Identification

11.1 Analytic Laboratory Methods

TLC DETERMINATION OF CETYLPYRIDINIUM CHLORIDE IN ADHESIVE TAPE "CYTOPLAST."
TARAGANSKA ET AL; PROBL FARM 4 61-6 (1976)
MICRO DETERMINATION OF QUATERNARY AMMONIUM CMPD BY ATOMIC ABSORPTION.
ALARY ET AL; ANN PHARM FR 34 (9-10): 345-53 (1976)
SURFACTANT QUATERNARY AMMONIUM SALTS ALONE OR IN PHARMACEUTICAL PREPN DETERMINED BY POTENTIOMETRIC TITRATION.
PINZAUTI S, LA PORTA E; ANALYST (LONDON) 102 (1221): 938-42 (1977)
TLC DETERMINATION OF CETYLPYRIDINIUM IN A MOUTHWASH.
PINZAUTI ET AL; J PHARM BELG 31 (5): 485-90 (1976)
Domiphen bromide and cetylpyridinium chloride were determined in cosmetics by HPLC on Partisil 10 SCX (10 um) with 0.05M sodium formate in a mixture of methanol-water (80:20) as the mobile phase and UV detection at 274 nm. The determination was carried out with or without an internal standard. The recovery was close to 100%, and the detection limits for domiphen bromide and cetylpyridinium chloride were 50 and 250 ng, respectively. No interference from other ingredients was observed.
Wyhowski de Bukanski B; Int J Cosmet Sci 9 (4): 193-8 (1987)

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 GHS Classification

1 of 3
View All
Note
Pictograms displayed are for 80.2% (146 of 182) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 19.8% (36 of 182) of reports.
Pictogram(s)
Corrosive
Acute Toxic
Irritant
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H301 (34.6%): Toxic if swallowed [Danger Acute toxicity, oral]

H302 (44.5%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (80.2%): Causes skin irritation [Warning Skin corrosion/irritation]

H318 (72%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H330 (79.7%): Fatal if inhaled [Danger Acute toxicity, inhalation]

H335 (78%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H400 (79.1%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (14.3%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P332+P317, P362+P364, P391, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 182 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 36 of 182 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 24 notifications provided by 146 of 182 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

12.1.2 Hazard Classes and Categories

Acute Tox. 3 (34.6%)

Acute Tox. 4 (44.5%)

Skin Irrit. 2 (80.2%)

Eye Dam. 1 (72%)

Acute Tox. 2 (79.7%)

STOT SE 3 (78%)

Aquatic Acute 1 (79.1%)

Aquatic Chronic 1 (14.3%)

Acute toxicity (Oral) - Category 3

Acute toxicity (Inhalation: Dusts and mists) - Category 2

Serious eye damage/eye irritation - Category 2

Specific target organ toxicity - Single exposure - Category 3 (Respiratory tract irritation)

12.1.3 Hazards Summary

Irritating to the skin and eyes; [HSDB] Allergic contact dermatitis is infrequently documented for quaternary ammonium compounds; [Marks, p. 266] Quaternary ammonium compounds have curare-like properties when concentrated solutions are ingested; Affected patients may have methemoglobinemia and hemolysis and die within 1-3 hours; Elevated liver function tests were reported; Concentrated solutions can cause burns; No data on carcinogenicity or teratogenicity; [IPCS-PIMs] See Benzalkonium chloride.
Marks - Marks JG, DeLeo VA. Contact and Occupational Dermatology, 2nd Ed. St. Louis: Mosby, 1997., p. 266

12.1.4 Skin, Eye, and Respiratory Irritations

Mild skin irritation
Sittig, M. Handbook of Toxic and Hazardous Chemicals and Carcinogens, 1985. 2nd ed. Park Ridge, NJ: Noyes Data Corporation, 1985., p. 200
A skin & eye irritant.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 691

12.2 Accidental Release Measures

12.2.1 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

12.3 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Pyridinium, 1-hexadecyl-, chloride (1:1)
California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Toxicity Undefined

Authoritative List - CECBP - Priority Chemicals

Report - if used as a fragrance or flavor ingredient

REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Pyridinium, 1-hexadecyl-, chloride: Does not have an individual approval but may be used under an appropriate group standard
New Zealand EPA Inventory of Chemical Status
1-Hexadecylpyridinium chloride: Does not have an individual approval but may be used under an appropriate group standard

12.3.1 FIFRA Requirements

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Cetylpyridinium chloride is found on List C. Case No: 3013; Pesticide type: insecticide, fungicide, rodenticide, antimicrobial; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Cetylpyridinium chloride; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
USEPA/OPP; Status of Pesticides in Registration, Reregistration and Special Review p.230 (Spring, 1998) EPA 738-R-98-002

12.4 Other Safety Information

Chemical Assessment
Evaluation - Alkyl pyridinium surfactants

13 Toxicity

13.1 Toxicological Information

13.1.1 Adverse Effects

Neurotoxin - Other CNS neurotoxin

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

Dermatotoxin - Skin burns.

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

13.1.2 Acute Effects

13.1.3 Toxicity Data

LC50 (rat) = 90 mg/m3/4h

13.1.4 Interactions

AVOID ALCOHOL, WHICH HAS BEEN SHOWN TO INCREASE THE ORAL TOXICITY OF ... CETYL PYRIDINIUM CHLORIDE ... .
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. III-65
CURARE ANTAGONISTS SUCH AS NEOSTIGMINE AND EDROPHONIUM (TENSILON) ... MAY ENHANCE THE PARALYSIS ... . /BENZALKONIUM CHLORIDE/
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-65-6
... ANTAGONIZED BY ANIONIC SURFACTANTS, INCL SOAPS ... .
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 84:4:16
ETHANOL ACTIVATED UDP-GLUCURONOSYLTRANSFERASE ACTIVITY (P-NITROPHENOL SUBSTRATE) IN RAT LIVER IN VITRO, BUT INHIBITED ACTIVITY @ HIGHER ETHANOL CONCN. ACTIVATION NOT SEEN IN MICROSOMES PRETREATED IN VITRO WITH CETYLPYRIDINIUM CHLORIDE.
MARNIEMI J; ACTA PHARMACOL TOXICOL 37 (3): 222-32 (1975)

13.1.5 Antidote and Emergency Treatment

EARLY TREATMENT FOR CORROSIVE BURNS OF ESOPHAGUS CONSISTS OF IV FLUID THERAPY, BROAD SPECTRUM ANTIBIOTICS, SEDATION, PARENTERAL HYDROCORTISONE & MORE IMPORTANTLY MAINTAINING PATENCY OF ESOPHAGUS FOLLOWED BY DILATATION. /ALKALIES/
BALASEGARAM M; BR J SURG 62 (6) 444-7 (1975)
/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 139
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 139

13.1.6 Human Toxicity Excerpts

CONCN SOLN CAN PRODUCE CORROSIVE SKIN LESIONS WITH DEEP NECROSIS & SCARRING. /BENZALKONIUM CHLORIDE/
American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 1440
... POISONING FROM ORAL INGESTION HAS OCCURRED. /CATIONIC SURFACTANTS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1002
/Investigators/ ... studied the offspring of 292 women using this medication in the first trimester and found 9 malformations. The rate was 31 congenital defects per 1000 while the mean rate was 16 per 1000. This increase was not statistically significant.
Shepard, T.H. Catalog of Teratogenic Agents. 5th ed. Baltimore, MD: The Johns Hopkins University Press, 1986., p. 112
Large quantities may cause nausea, vomiting, collapse, convulsions and coma.
Sittig, M. Handbook of Toxic and Hazardous Chemicals and Carcinogens, 1985. 2nd ed. Park Ridge, NJ: Noyes Data Corporation, 1985., p. 200

13.1.7 Non-Human Toxicity Excerpts

IN ISOLATED OBSERVATION ... NO INHIBITION OF PLASMA CHOLINESTERASE WAS FOUND IN RATS SACRIFICED IN EXTREMIS AFTER AN IP INJECTION OF ... CETYL PYRIDINIUM CHLORIDE. A 50% INHIBITION OF RED CELL CHOLINESTERASE ... /WAS/ NOTED, BUT SUCH A DEPRESSION IS NOT EXPECTED TO PRODUCE UNTOWARD REACTIONS.
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. III-65
A CURARE-LIKE PARALYSIS OF SKELETAL MUSCLES ... ASCRIBED ... SPECIFICALLY TO CETYL PYRIDINIUM CHLORIDE ... . PARENTERAL INJECTIONS IN RATS, RABBITS AND DOGS HAVE RESULTED IN PROMPT BUT TRANSIENT LIMB PARALYSIS AND SOMETIMES FATAL PARESIS OF THE RESPIRATORY MUSCLES.
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. III-65
... TESTED ... @ CONCN OF 0.1% TO 1.0% IN WATER ... SIGNIFICANTLY IRRITATING OR INJURIOUS TO RABBIT EYE.
Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 870
CETYLPYRIDINIUM CHLORIDE FOUND ... TO BE LETHAL TO RABBITS IN ORAL DOSE 400 MG/KG (180 MG/LB). TOXIC EFFECTS INCL ACTION ON CARDIOVASCULAR SYSTEM ... .
Garner's Veterinary Toxicology. 3rd ed., rev. by E.G.C. Clarke and M.L. Clarke. Baltimore: Williams and Wilkins, 1967., p. 156
For more Non-Human Toxicity Excerpts (Complete) data for CETYLPYRIDINIUM CHLORIDE (7 total), please visit the HSDB record page.

13.1.8 Non-Human Toxicity Values

LD50 Rat oral 200 mg/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 691
LD50 Rat ip 6 mg/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 691
LD50 Rat sc 250 mg/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 691
LD50 Rat iv 30 mg/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 691
For more Non-Human Toxicity Values (Complete) data for CETYLPYRIDINIUM CHLORIDE (8 total), please visit the HSDB record page.

13.2 Ecological Information

13.2.1 EPA Ecotoxicity

Pesticide Ecotoxicity Data from EPA

13.2.2 Environmental Fate / Exposure Summary

Cetylpyridinium chloride's production and use as an antiseptic, as a preservative in cosmetics and pharmaceuticals, and as an ingredient in external deodorants and in mouthwash may result in its release to the environment through various waste streams. If released to air, cetylpyridinium chloride will exist as an ion and, thus, will be found solely in the particulate phase in the ambient atmosphere. Particulate-phase cetylpyridinium chloride will be removed from the atmosphere by wet and dry deposition. If released to soil, cetylpyridinium chloride is expected to have moderate mobility based upon an estimated Koc of 200. However, quaternary ammonium compounds are known to sorb strongly, and rapidly in well-mixed systems, to a wide variety of materials (such as sewage sludge, sediment, clay) and the mobility of cetylpyridinium chloride in soil may be considerably less than the estimated value. Volatilization from moist soil surfaces will not be an important fate process as this compound is expected to exist in the environment in the dissociated form. Cetylpyridinium chloride will not volatilize from dry soil surfaces as ions do not volatilize. Cetylpyridinium chloride is expected to biodegrade rapidly in aerobic soil and water environments based on studies for structurally-similar compounds. Dodecyl and tetradecylpyridinium chloride, were biodegraded in the Spanish official test (93 and 94%, respectively) and in the OECD Confirmatory test (91 and 92%, respectively). If released into water, cetylpyridinium chloride is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process as this compound is expected to exist in the dissociated form in the environment. An estimated BCF of 2 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis of cetylpyridinium chloride is not expected due to the lack of hydrolyzable functional groups. Occupational exposure to cetylpyridinium chloride may occur through inhalation and dermal contact with this compound at workplaces where cetylpyridinium chloride is produced or used. The general population will most likely be exposed to cetylpyridinium chloride via ingestion and dermal contact with consumer products containing cetylpyridinium chloride. (SRC)

13.2.3 Artificial Pollution Sources

Cetylpyridinium chloride's production and use as an antiseptic, as a preservative in cosmetics and pharmaceuticals(1) and as an ingredient in external deodorants(2), and in mouthwash(3) may result in its release to the environment through various waste streams(SRC).
(1) Ashford RD; Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publ. Ltd p. 189 (1994)
(2) Block SS; Kirk Othmer's Encycl Chem Technol. 4th ed. NY, NY: John Wiley & Sons 8: 259 (1993)
(3) Rieger MM; Kirk Othmer's Encycl Chem Technol. 4th ed. NY, NY: John Wiley & Sons 7: 581 (1993)

13.2.4 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 200(SRC), determined from a log Kow of 1.71(2) and a regression-derived equation(3), indicates that cetylpyridinium chloride is expected to have moderate mobility in soil(SRC). However, quaternary ammonium compounds are known to sorb strongly and rapidly in well-mixed systems, to a wide variety of materials (such as sewage sludge, sediment, clay)(4) and the mobility of cetylpyridinium bromide in soil may be considerably less than estimated. Volatilization of cetylpyridinium chloride from moist soil surfaces is not expected as this compound is a salt(SRC). Cetylpyridinium chloride is also not expected to volatilize from dry soil surfaces(SRC) as ions do not volatilize. Cetylpyridinium chloride is expected to biodegrade rapidly in soil(SRC) based on sewage studies for structurally-similar compounds. Dodecyl and tetradecylpyridinium chloride, were biodegraded in the Spanish official test (93 and 94%, respectively) and in the OECD Confirmatory test (91 and 92%, respectively)(4).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Moschner KF, Cece A; pp. 318-31 in Environ Toxicol Risk Assess, 3rd. ASTM STP 1218, Hughes, JS et al, eds. Philadelphia, PA: ASTM (1995)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
(4) Boethling RS; pp. 95-135 in Cationic Surfactants. Cross J, Singer EJ, eds. NY, NY: Marcel Dekker Inc (1994)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 200(SRC), determined from a log Kow of 1.71(2) and a regression-derived equation(3), indicates that cetylpyridinium chloride is not expected to adsorb to suspended solids and sediment(SRC). However, quaternary ammonium compounds are known to sorb strongly, and rapidly in well-mixed systems, to a wide variety of materials (such as sewage sludge, sediment, clay)(7); therefore, cetylpyridinium bromide should be strongly adsorbed to suspended solids and sediment in water. This compound is expected to exist in the dissociated form in the environment and therefore volatilization from water surfaces will not be an important fate process(SRC). According to a classification scheme(5), an estimated BCF of 2(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Cetylpyridinium chloride is expected to biodegrade rapidly in water(SRC) based on sewage studies for structurally-similar compounds. Dodecyl and tetradecylpyridinium chloride, were biodegraded in the Spanish official test (93 and 94%, respectively) and in the OECD Confirmatory test (91 and 92%, respectively)(7).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Moschner KF, Cece A; pp. 318-31 in Environ Toxicol Risk Assess, 3rd. ASTM STP 1218, Hughes, JS et al, eds. Philadelphia, PA: ASTM (1995)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
(4) Franke C et al; Chemosphere 29: 1501-14 (1994)
(5) Knezovich JP et al; Bull Environ Contam Toxicol 42: 87-93 (1989)
(6) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(7) Boethling RS; pp. 95-135 in Cationic Surfactants. Cross J, Singer EJ, eds. NY, NY: Marcel Dekker Inc (1994)
ATMOSPHERIC FATE: Cetylpyridinium chloride will exist as the ion in the environment and, thus, will be present solely in the particulate phase in the atmosphere. Particulate-phase cetylpyridinium chloride may be removed from the air by wet and dry deposition. (SRC)

13.2.5 Environmental Biodegradation

ALKYLPYRIDINIUM DERIVATIVES ARE LESS BIODEGRADABLE THAN MONOALKYLTRIMETHYL & ALKYLBENZYL DIMETHYL AMMONIUM CHLORIDES. /ALKYLPYRIDINIUM DERIVATIVES/
MASUDA ET AL; STUDIES ON BIODEGRADABILITY OF SOME CATIONIC SURFACTANTS, TR. - MEZHDUNAR KONGR POVERKHN -AKT VESHCHESTVAM, 7TH, 129-138 (1978)
AEROBIC: Biodegradation data for cetylpyridinium chloride were not located although, based on data for structurally-similar compounds, this compound is expected to biodegrade rapidly in the environment(SRC). Structurally-similar compounds, dodecyl and tetradecylpyridinium chloride, were biodegraded in the Spanish official test (93 and 94%, respectively) and in the OECD Confirmatory test (91 and 92%, respectively)(1). Mean cetylpyridinium (counterion unspecified) removal of 96.0 and 77.2%, respectively, was observed at an activated sludge and a trickling filter wastewater treatment plant in England; in the Heidelsheim plant in Germany, 95% removal was reported(1). Cetylpyridinium bromide is readily biodegraded in sewage, particularly when the inoculum has been previously acclimated(2,3).
(1) Boethling RS; pp. 95-135 in Cationic Surfactants. Cross J, Singer EJ, eds. NY, NY: Marcel Dekker Inc (1994)
(2) Boethling RS, Lynch DG; in Handbook of Environmental Chemistry. Hutzinger O, ed. Heidelberg, Berlin: Springer-Verlag 3F: 146-77 (1992)
(3) Baleux B, Caumette P; Wat Res 11: 833-41 (1977)

13.2.6 Environmental Abiotic Degradation

Cetylpyridinium chloride is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(1). Pyridine has a weak absorption band that extends into the environmental UV spectrum(3), which suggests that direct photolysis is not likely to be an important fate process for cetylpyridinium chloride (SRC).
(1) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5 (1990)
(2) Lide DR, Milne GWA; Handbook of Data on Organic Compounds. Boca Raton, FL: CRC Press 5: 4747 (1994)

13.2.7 Environmental Bioconcentration

Whole body BCF values of 21, 22, and 13, were measured for clams, fathead minnows, and tadpoles, respectively, under flow-through conditions over a 7-day period, for a structurally-similar compound, cetylpyridinium bromide(1). An estimated BCF of 2 was calculated for cetylpyridinium chloride(SRC), using a log Kow of 1.71(2) and a regression-derived equation(3). According to a classification scheme(4), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Knezovich JP et al; Bull Environ Contam Toxicol 42: 87-93 (1989)
(2) Moschner KF, Cece A; pp. 318-31 in Environ Toxicol Risk Assess, 3rd. ASTM STP 1218, Hughes, JS et al, eds. Philadelphia, PA: ASTM (1995)
(3) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(4) Franke C et al; Chemosphere 29: 1501-14 (1994)

13.2.8 Soil Adsorption / Mobility

The Koc of cetylpyridinium chloride is estimated as 200(SRC), using a measured log Kow of 1.71(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that cetylpyridinium chloride is expected to have moderate mobility in soil. However, quaternary ammonium compounds are known to sorb strongly, and rapidly in well-mixed systems, to a wide variety of materials (such as sewage sludge, sediment, clay)(4) and the mobility of cetylpyridinium chloride in soil may be considerably less than estimated(SRC).
(1) Moschner KF, Cece A; pp. 318-31 in Environ Toxicol Risk Assess, 3rd. ASTM STP 1218. Hughes, JS et al, eds. Philadelphia, PA: ASTM (1995)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
(3) Swann RL et al; Res Rev 85: 17-28 (1983)
(4) Boethling RS, Lynch DG; in Handbook of Environmental Chemistry. Hutzinger O, ed, Heidelberg, Berlin: Springer-Verlag 3F: 146-77 (1992)

13.2.9 Volatilization from Water / Soil

Cetylpyridinium chloride is expected to exist in the dissociated form in the environment and, therefore, volatilization from water surfaces or moist soil surfaces will not an important fate process. Cetylpyridinium chloride is not expected to volatilize from dry soil surfaces as it exists as an ion in the environment and ions do not volatilize. (SRC)

13.2.10 Probable Routes of Human Exposure

NIOSH (NOES Survey 1981-1983) has statistically estimated that 98,375 workers (86,013 of these are female) are potentially exposed to cetylpyridinium chloride in the US(1). Occupational exposure to cetylpyridinium chloride may occur through inhalation and dermal contact with this compound at workplaces where cetylpyridinium chloride is produced or used(SRC). The general population may be exposed to cetylpyridinium chloride predominantly via ingestion or dermal contact due to its use in consumer products, such as mouthwash, external deodorants, and cough lozenges and syrups(SRC).
(1) NIOSH; National Occupational Exposure Survey (NOES) (1983)

14 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound
Contact dermatitis, allergic [Category: Skin Disease]

15 Literature

15.1 Consolidated References

15.2 NLM Curated PubMed Citations

15.3 Springer Nature References

15.4 Thieme References

15.5 Chemical Co-Occurrences in Literature

15.6 Chemical-Gene Co-Occurrences in Literature

15.7 Chemical-Disease Co-Occurrences in Literature

16 Patents

16.1 Depositor-Supplied Patent Identifiers

16.2 WIPO PATENTSCOPE

16.3 Chemical Co-Occurrences in Patents

16.4 Chemical-Disease Co-Occurrences in Patents

16.5 Chemical-Gene Co-Occurrences in Patents

17 Biological Test Results

17.1 BioAssay Results

18 Classification

18.1 MeSH Tree

18.2 NCI Thesaurus Tree

18.3 ChEBI Ontology

18.4 ChemIDplus

18.5 ChEMBL Target Tree

18.6 UN GHS Classification

18.7 EPA CPDat Classification

18.8 NORMAN Suspect List Exchange Classification

18.9 CCSBase Classification

18.10 EPA DSSTox Classification

18.11 Consumer Product Information Database Classification

18.12 EPA TSCA and CDR Classification

18.13 EPA Substance Registry Services Tree

18.14 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
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  19. Consumer Product Information Database (CPID)
    LICENSE
    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  20. DailyMed
  21. EPA Chemical and Products Database (CPDat)
  22. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
    Cetylpyridinium chloride
    https://haz-map.com/Agents/8088
  23. EPA Pesticide Ecotoxicity Database
  24. EU Clinical Trials Register
  25. NITE-CMC
    Cetylpyridinium chloride - FY2010 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/10-mhlw-0087e.html
    Cetylpyridinium chloride - FY2022 (Revised classification)
    https://www.chem-info.nite.go.jp/chem/english/ghs/22-jniosh-2076e.html
  26. National Drug Code (NDC) Directory
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  27. NIPH Clinical Trials Search of Japan
  28. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
    cetylpyridinium chloride anhydrous
    https://rxnav.nlm.nih.gov/id/rxnorm/1311527
  29. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  30. SpectraBase
    Hexadecylpyridiniumchloride, ether soluble part; product contains unquaternized nh
    https://spectrabase.com/spectrum/6CHGkClayEB
    1-HEXADECYLPYRIDINIUM CHLORIDE
    https://spectrabase.com/spectrum/C4xOOfgtsMB
    1-hexadecylpyridinium chloride
    https://spectrabase.com/spectrum/Eri0R74BrdK
  31. Springer Nature
  32. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  33. Wikidata
  34. Wikipedia
  35. PubChem
  36. Medical Subject Headings (MeSH)
    LICENSE
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    https://www.nlm.nih.gov/copyright.html
  37. GHS Classification (UNECE)
  38. EPA Substance Registry Services
  39. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  40. PATENTSCOPE (WIPO)
CONTENTS