Cetylpyridinium chloride
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Cetylpyridinium chloride
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CAS No:
123-03-5
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Formula:
C21H38N.Cl
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Chemical Name:
Cetylpyridinium chloride
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Synonyms:
Pyridinium,1-hexadecyl-,chloride (1:1);1-Hexadecylpyridinium chloride;Pyridinium,1-hexadecyl-,chloride;Cepacol chloride;Cetamium;N-Cetylpyridinium chloride;Cetylpyridinium chloride;n-Hexadecylpyridinium chloride;Hexadecylpyridinium chloride;Pyrisept;Ammonyx CPC;Ceprim;Aktivex;Biosept;1-Cetylpyridinium chloride;Quaternario CPC;Acetoquat CPC;Intexsan CPC;Ceepryn chloride;Pristacin;1-Palmitylpyridinium chloride;Cetafilm;CPC;Merocet;Merothol;Ipanol;1-n-Hexadecanepyridinium chloride;Newkalgen B 651P;Pionin B 651P;CPC (onium compound);Dobendan;Cepacol;Medilave;Cecure;Halset;NB 401;NB 002;TsPKh;NB 003;Septolete;N-Cetylpyridium chloride;Ronacare CPC;C 9002;27841-61-8;50958-35-5;136499-13-3;951742-58-8;2266591-56-2
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CAS No:
Description
Cetylpyridinium chloride (CPC) is a white powder or crystals with a characteristic odor. It is slightly soapy to the touch.Cetylpyridinium chloride is a quaternary ammonium compound and is the active chemical in some human mouthwashes on the market. It has antiseptic properties and is used in solutions or lozenges for the treatment of minor infections of the mouth and throat.
DryPowder
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 Basic Attributes
339.99
339.269287
204-593-9
6BR7T22E2S
756673|14864
DTXSID6041761
White powder
2933399090
Characteristics
3.9
log Kow= 1.71
White Crystalline Powder
0.83 g/cm3
80 °C
496.25°C (rough estimate)
1.6000 (estimate)
Freely soluble in water; very soluble in chloroform; very slightly soluble in ether; insoluble in acetone, acetic acid, and ethanol.
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Oral-rat LD50: 200 mg/kg; Oral-Mouse LD50: 108 mg/kg
Thermal decomposition releases toxic nitrogen oxides and chloride fumes
197.5 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
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/
Safety Information
III
6.1(b)
2811
UU4900000
The warehouse is low-temperature, ventilated and dry
Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
P260, P261, P264, P270, P271, P280, P284, P301+P310, P304+P340, P305+P351+P338, P310, P312, P320, P321, P330, P337+P313, P403+P233, P405, P501
H301
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.
|Danger|H301 (83.94%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P284, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 173 companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P280, P284, P301+P310, P304+P340, P305+P351+P338, P310, P312, P320, P321, P330, P337+P313, P403+P233, P405, and P501
Mild skin irritation|A skin & eye irritant.
Toxicity
highly toxic
AVOID ALCOHOL, WHICH HAS BEEN SHOWN TO INCREASE THE ORAL TOXICITY OF ... CETYL PYRIDINIUM CHLORIDE ... .|CURARE ANTAGONISTS SUCH AS NEOSTIGMINE AND EDROPHONIUM (TENSILON) ... MAY ENHANCE THE PARALYSIS ... . /BENZALKONIUM CHLORIDE/|... ANTAGONIZED BY ANIONIC SURFACTANTS, INCL SOAPS ... .|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.
LD50 Rat oral 200 mg/kg|LD50 Rat ip 6 mg/kg|LD50 Rat sc 250 mg/kg|LD50 Rat iv 30 mg/kg|For more Non-Human Toxicity Values (Complete) data for CETYLPYRIDINIUM CHLORIDE (8 total), please visit the HSDB record page.
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).
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).|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).|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)
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).
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).
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).
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)
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).
Drug Information
Anti-infective Agents, Local|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.|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.|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.|For more Therapeutic Uses (Complete) data for CETYLPYRIDINIUM CHLORIDE (16 total), please visit the HSDB record page.
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.|GRAM NEGATIVE ORGANISMS, INCL STRAINS OF PSEUDOMONAS AERUGINOSA, ARE MORE RESISTANT /THAN GRAM POS/ & REQUIRE LONGER EXPOSURE /TO QUATERNARY AMMONIUM CMPD/. /QUATERNARY AMMONIUM CMPD/|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/|CAN CAUSE OCCASIONAL ALLERGIC RESPONSES WITH CHRONIC USE, AS WITH CERTAIN DEODORANT PREPN & DIAPER WASHES. /CATIONIC SURFACTANTS/|/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/
ORAL RETENTION OF CETYLPYRIDINIUM CHLORIDE GIVEN AS 1 MIN MOUTH RINSE OF 10 ML OF 2.2 MMOL SOLN WAS 65% OF ADMIN DOSE.
MODE OF ACTION ... NOT YET FULLY UNDERSTOOD BUT HAS BEEN ASCRIBED TO ... THE DENATURING OF LIPOPROTEIN COMPLEXES, & POSSIBLY OTHER ACTIONS. /QUATERNARY AMMONIUM COMPD/|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/|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/
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/|/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/|/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/
CONCN SOLN CAN PRODUCE CORROSIVE SKIN LESIONS WITH DEEP NECROSIS & SCARRING. /BENZALKONIUM CHLORIDE/|... POISONING FROM ORAL INGESTION HAS OCCURRED. /CATIONIC SURFACTANTS/|/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.|Large quantities may cause nausea, vomiting, collapse, convulsions and coma.
cerigel
Cetylpyridinium chloride Use and 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 ... .|Pyridine + cetyl chloride (quaternization)
Antibacterial in cough lozenges and syrups;
emulsifier.
1-Hexadecylpyridinium chloride is a white powder that isvery soluble in water and alcohol. In this compound, thequaternary nitrogen atom is a member of an aromatic pyridinering.
The cetyl derivative is the most active of a series ofalkylpyridinium compounds. It is used as a general antisepticin concentrations of 1:100 to 1:1,000 for intact skin,1:1,000 for minor lacerations, and 1:2,000 to 1:10,000 forthe irrigation of mucous membran
active pharmaceutical intermediate
Personal care products
500,000 - 1,000,000 lb|(1972) PROBABLY GREATER THAN 4.54X10+5 G|(1975) PROBABLY GREATER THAN 4.54X10+5 G
PROBABLY 100% AS AN ANTI-INFECTIVE/DISINFECTANT (1975)
CEPACAINE SOLN (BENZOCAINE, COMBINATION, CETYLPYRIDINIUM CHLORIDE, DIBUCAINE).|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).|AVAILABLE AS AQUEOUS OR ALCOHOL SOLUTIONS (EG, TINCTURE) IN CONCN OF 10% OR LESS.|GRADES: TECHNICAL; NF|Lozenges, 0.07%. Mouthwash, 0.05%.
Food, beverage, and tobacco product manufacturing|Pyridinium, 1-hexadecyl-, chloride (1:1): ACTIVE|/CETYLPYRIDINIUM CHLORIDE IS/ MONOHYDRATE OF QUATERNARY SALT OF PYRIDINE & CETYL CHLORIDE.|BACTERIAL SPORES RESIST EVEN PROLONGED CONTACT. AQ SOLN OF THESE CMPD ARE NOT TUBERCULOCIDAL. /QUATERNARY AMMONIUM CMPD/|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.|PHARMACEUTICAL INSULIN PREPN FOR RECTAL ADMIN COMPRISE INSULIN, A BASE, & AS ABSORPTION ACCELERATOR, SOMETIMES A CATIONIC SURFACTANT.|For more General Manufacturing Information (Complete) data for CETYLPYRIDINIUM CHLORIDE (6 total), please visit the HSDB record page.
TLC DETERMINATION OF CETYLPYRIDINIUM CHLORIDE IN ADHESIVE TAPE "CYTOPLAST."|MICRO DETERMINATION OF QUATERNARY AMMONIUM CMPD BY ATOMIC ABSORPTION.|SURFACTANT QUATERNARY AMMONIUM SALTS ALONE OR IN PHARMACEUTICAL PREPN DETERMINED BY POTENTIOMETRIC TITRATION.|TLC DETERMINATION OF CETYLPYRIDINIUM IN A MOUTHWASH.|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.
Cosmetics -> Antimicrobial; Antistatic; Deodorant; Emulsifying; Hair conditioning; Surfactant
Computed Properties
Molecular Weight:340.0
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:15
Exact Mass:339.2692779
Monoisotopic Mass:339.2692779
Topological Polar Surface Area:3.9
Heavy Atom Count:23
Complexity:208
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Extract from the above information
Registered Holders
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DISHMAN CARBOGEN AMCIS LTD
Active
United States
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Minsheng Group Shaoxing Pharmaceutical Co., Ltd.
Active
China
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Henan Lixin Pharmaceutical Limited By Share Ltd
Active
China
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