Cetylpyridinium chloride

Cetylpyridinium chloride
Skeletal formula of cetylpyridinium cation with a chloride anion
Space-filling models of the component ions of cetylpyridinium chloride
Names
IUPAC name
1-Hexadecylpyridinium chloride
Other names
Acetoquat CPC;
Pyrisept EXADECYL-PYRIDINIUM, CHLORIDE
Identifiers
123-03-5 YesY
6004-24-6 (monohydrate) D08AJ03 (WHO),
D09AA07 (WHO) (dressing), R02AA06 (WHO) N
3D model (Jmol) Interactive image
3578606
ChEBI CHEBI:32915 YesY
ChEMBL ChEMBL34833 YesY
ChemSpider 28979 YesY
ECHA InfoCard 100.004.177
PubChem 31239
UNII 6BR7T22E2S YesY
Properties
C21H38ClN
Molar mass 339.99 g·mol−1
Appearance solid
Melting point 77 °C (171 °F; 350 K)
Pharmacology
B05CA01 (WHO)
Hazards
Lethal dose or concentration (LD, LC):
36 mg/kg (rabbit, iv)[1]
400 mg/kg (rabbit, oral)[1]
6 mg/kg (rat, ip)[1]
30 mg/kg (rat, iv)[1]
200 mg/kg (rat, oral)[1]
250 mg/kg (rat, sc)[1]
10 mg/kg (mouse, ip)[1]
108 mg/kg (mouse, oral)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Cetylpyridinium chloride (CPC) is a cationic quaternary ammonium compound used in some types of mouthwashes, toothpastes, lozenges, throat sprays, breath sprays, and nasal sprays. It is an antiseptic that kills bacteria and other microorganisms. It has been shown to be effective in preventing dental plaque and reducing gingivitis.[2][3] It has also been used as an ingredient in certain pesticides. Cetylpyridinium chloride may cause brown stains between the teeth and on the surface of teeth.[4][5] However, these stains can be easily removed by a dental hygienist during a routine check-up.[4][5]

Synonyms

Cetylpyridinium chloride is present in commercial products such as 1-palmitylpyridinium chloride, C16-alkylpyridinium chloride, 1-hexadecylpyridinium chloride, acetoquat CPC, aktivex, ammonyx CPC, cecure, ceepryn chloride, cepacol, ceprim, cepacol chloride, cetafilm, cetamium, dobendan, halset, ipanol, medilave, mercocet, merothol, pionin B, pristacin, pyrisept, and asept.

Chemistry

Cetylpyridinium chloride has the molecular formula C21H38NCl and at its pure form is in a solid state at room temperature. It has a melting point of 77 °C when anhydrous or 80–83 °C in its monohydrate form. It is soluble in water but insoluble in acetone, acetic acid, or ethanol. It has a pyridine-like odor. It is combustible. Concentrated solutions are destructive to mucous membranes. Its critical micelle concentration (CMC) is 0.00012M,[6] and is strongly dependent on the salt concentration of the solution.

In some products, the bromide salt, cetylpyridinium bromide, is used instead. Its properties are virtually identical.

Toxicology and pharmacology

With intravenous infusion as the delivery mechanism, the LD50 of cetylpyridinium chloride has been measured at 30 mg/kg in rats and 36 mg/kg in rabbits. Conversely, with oral administration LD50 levels are higher, having been measured at 200 mg/kg in rats, 400 mg/kg in rabbits, and 108 mg/kg in mice.[7]

Use in over-the-counter drugs

OTC products containing cetylpyridinium chloride include oral wash, oral rinse, as well as ingestable products (e.g. CPC lozenges).[8] In addition, cough syrups containing CPC are also available as OTC medications.[9]

The FDA monograph on oral antiseptic drug products reviewed the data regarding CPC and concluded the following: "The agency believes that the information contained in its adverse reaction files, 30 years of safe marketing of an OTC mouthwash containing cetylpyridinium chloride (NDA 14- 598), and the safety data evaluated by the Oral Cavity Panel are sufficient to conclude that 0.025 to 0.1 percent cetylpyridinium chloride is safe as an OTC oral antiseptic when labeled for short-term use (not to exceed 7 days)."[10]

In addition, the National Library of Medicine Toxicology Data Network (TOXNET) reviewed the range of toxicity of CPC, and stated that, "Significant toxicity is rare after exposure to low concentration products that are typically available in the home."[11]

The fatal dose in humans ingesting cationic detergents has been estimated to be 1 to 3 g.[11] Therefore, a person using a typical oral ingestible product that provides 0.25 mg CPC per dose will need to take 4000 doses at one time before they would be in the estimated fatal dose range.

A review of clinical studies on cetylpyridinium chloride found that mouthwashes containing CPC "provide a small but significant additional benefit when compared with toothbrushing only or toothbrushing followed by a placebo rinse" in reducing plaque and gingivitis-inflammation.[3] In combination with chlorhexidine and zinc lactate, CPC has been found to be effective in treating halitosis.[12]

Compendial status

See also

Notes

  1. 1 2 3 4 5 6 7 8 Lewis, Richard J. (1996). Sax's Dangerous Properties of Industrial Materials (9th ed.). New York, NY: Van Nostrand Reinhold. p. 691.
  2. ↑ Asadoorian, Joanna; Williams, Karen (2008). "Cetylpyridinium chloride mouth rinse on gingivitis and plaque". Journal of Dental Hygiene. 82 (5).
  3. 1 2 Haps, S.; Slot, D. E.; Berchier, C. E.; Van Der Weijden, G. A. (2008). "The effect of cetylpyridinium chloride-containing mouth rinses as adjuncts to toothbrushing on plaque and parameters of gingival inflammation: A systematic review". International Journal of Dental Hygiene. 6 (4): 290–303. doi:10.1111/j.1601-5037.2008.00344.x. PMID 19138180.
  4. 1 2 "Tooth Discoloration: Causes and Treatments".
  5. 1 2 "Tooth Discoloration : Article by Jonathan A Ship, DMD".
  6. ↑ http://www.applichem.com/en/shop/product-detail/as/cetylpyridiniumchlorid-monohydrat-ibiochemicai/?getspecpdf=1
  7. ↑ Lewis, R.J (1996). Sax's Dangerous Properties of Industrial Materials. 1–3 (9th ed.). New York, NY: Van Nostrand Reinhold. p. 691.
  8. ↑ at least 125 OTC oral healthcare products containing CPC (as of September 2012)
  9. ↑ For example, Kilcof Cough Mixture
  10. ↑ FDA monograph on oral antiseptic drug products, page 6094
  11. 1 2 National Library of Medicine Toxicology Data Network
  12. ↑ Winkel, E. G.; Roldán, S.; Van Winkelhoff, A. J.; Herrera, D.; Sanz, M. (2003). "Clinical effects of a new mouthrinse containing chlorhexidine, cetylpyridinium chloride and zinc-lactate on oral halitosis. A dual-center, double-blind placebo-controlled study". Journal of Clinical Periodontology. 30 (4): 300–306. doi:10.1034/j.1600-051X.2003.00342.x. PMID 12694427.
  13. ↑ The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". Archived from the original on 5 July 2010. Retrieved 8 July 2009.
  14. ↑ USP 31. "<1121> Nomenclature" (PDF). Retrieved 8 July 2009.
  15. ↑ Therapeutic Goods Administration. "Chemical Substances" (PDF). Retrieved 8 July 2009.
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