:Cetylpyridinium chloride

OTC (over the counter) products containing cetylpyridinium chloride include oral wash, oral rinse, and ingestable products, such as lozenges[http://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=CETYLPYRIDINIUM+CHLORIDE&x=20&y=6 at least 125 OTC oral healthcare products containing CPC (as of September 2012)] and over-the-counter cough syrup.For example, [http://www.conceptpharmacy.co.uk/kilkof-cough-mixture-150ml Kilcof Cough Mixture]

The United States' federal Food and Drug Administration's monograph on oral antiseptic drug products reviewed the data regarding CPC and made this conclusion:{{quote|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).[https://web.archive.org/web/20090710142056/http://www.fda.gov/downloads/Drugs/DevelopmentApprovalProcess/DevelopmentResources/Over-the-CounterOTCDrugs/StatusofOTCRulemakings/ucm096101.pdf FDA monograph on oral antiseptic drug products], p. 6094}}

The National Library of Medicine Toxicology Data Network (TOXNET) reviewed the range of toxicity of CPC and stated "Significant toxicity is rare after exposure to low concentration products that are typically available in the home."[http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+38 National Library of Medicine Toxicology Data Network]

The fatal dose in humans ingesting cationic detergents has been estimated to be 1 to 3 g. Therefore, a person using a typical oral ingestible product that provides 0.25 mg CPC per dose would need to take 4,000 doses at one time to reach the estimated fatal dose range.

A review 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. In combination with chlorhexidine and zinc lactate, CPC has been found to be effective in treating halitosis.{{Cite journal | last1 = Winkel | first1 = E. G. | last2 = Roldán | first2 = S. | last3 = Van Winkelhoff | first3 = A. J. | last4 = Herrera | first4 = D. | last5 = Sanz | first5 = M. | title = Clinical effects of a new mouthrinse containing chlorhexidine, cetylpyridinium chloride and zinc-lactate on oral halitosis. A dual-center, double-blind placebo-controlled study | doi = 10.1034/j.1600-051X.2003.00342.x | journal = Journal of Clinical Periodontology | volume = 30 | issue = 4 | pages = 300–306 | year = 2003 | pmid = 12694427}}

CPC mouthwashes inactivate viruses, including the virus that causes COVID-19, by breaking their lipid envelope.{{cite journal | pmid=36808889 | year=2023 | last1=d'Amico | first1=F. | last2=Moro | first2=M. | last3=Saracino | first3=M. | last4=Marmiere | first4=M. | last5=Cilona | first5=M. B. | last6=Lloyd-Jones | first6=G. | last7=Zangrillo | first7=A. | title=Efficacy of Cetylpyridinium Chloride mouthwash against SARS-CoV-2: A systematic review of randomized controlled trials | journal=Molecular Oral Microbiology | volume=38 | issue=3 | pages=171–180 | doi=10.1111/omi.12408 | s2cid=257068281 | doi-access=free }}

Cetylpyridinium chloride is known to cause tooth staining in approximately 3 percent of users.{{cite news |first= Lisa Biank |last=Fasig |date=2007-04-09 |publisher=Cincinnati Business Courier |url=http://www.bizjournals.com/cincinnati/stories/2007/04/09/story3.html?market=cincinnati&year=2007&month=04&day=09&slug=story3.html&module=default&controller=stories&action=render |title=P&G hopes rinse effect won't wash away sales |quote=The company's Crest Pro-Health Rinse, launched with much promise in April 2005, is discoloring the teeth of about 3 percent of its users, the company said, because it is doing its job.}} The Crest brand has noted that this staining is actually an indication that the product is working as intended, as the stains are a result of bacteria dying on the teeth.{{cite web |publisher=Crest |access-date=2016-06-06 |title=Does Crest Pro-Health Rinse stain teeth brown? |url=http://news.crest.com/faq-item/health-rinse/does-crest-pro-health-rinse-stain-teeth-brown |archive-url=https://web.archive.org/web/20160306020259/http://news.crest.com/faq-item/health-rinse/does-crest-pro-health-rinse-stain-teeth-brown |archive-date=2016-03-06 |quote=Tooth discoloration could actually be one indication, in some people, that the product is working: after the rinse kills germs in your mouth, the dead germs can collect on the tooth surface and create the appearance of a brown stain.}} Crest stated that because of the low incidence of staining, there was no need to label Pro-Health mouthwash as a potential tooth stainer.{{cite news|last=Sewell |first=Dan |date=2008-05-07 |title=P&G's Pro-Health rinse draws complaints |url=http://abc11.com/archive/6129499/ |archive-url=https://web.archive.org/web/20160630111606/http://abc11.com/archive/6129499/ |archive-date=30 June 2016 |agency=Associated Press |quote=Brinker said P&G doesn't see a need for a warning label because the number of those affected is very small. |url-status=dead |df=mdy }} However, after numerous complaints{{cite news |title=Crest rinse fights off customer complaints |newspaper=USA Today |date=2008-05-07 |url=http://usatoday30.usatoday.com/news/health/2008-05-07-crest-rinse_N.htm |quote=But NBC's Today show reported Wednesday that the complaints have led to a consumer lawsuit alleging fraud and to further study by the Food and Drug Administration, which approved the product.}} and a federal class-action lawsuit, which was later dismissed,{{cite web |url=http://www.drbicuspid.com/index.aspx?sec=ser&sub=def&pag=dis&ItemID=305224 |title=Mouthwash staining lawsuit dismissed |date=2010-07-26 |publisher=DrBicuspid.com |archive-url=https://web.archive.org/web/20160623153103/http://www.drbicuspid.com/index.aspx?sec=ser&sub=def&pag=dis&ItemID=305224 |archive-date=23 June 2016 |quote=A U.S. District Court judge has dismissed a proposed class-action lawsuit filed against Procter and Gamble charging that the company's Crest Pro-Health mouthwash causes staining and browning of teeth |url-status=dead |df=mdy-all }} the mouthwash now contains a label warning consumers of its potential to stain teeth.

In a small percentage of population, CPC can alter or eliminate the sense of taste. The effect generally goes away a few days after discontinuing use of the product.

The {{LD50}} of cetylpyridinium chloride has been measured at 30 mg/kg in rats and 36 mg/kg in rabbits when the chemical is administered by intravenous infusion but 200 mg/kg in rats, 400 mg/kg in rabbits, and 108 mg/kg in mice when administered orally.{{cite book | author = Lewis, R.J. | title = Sax's Dangerous Properties of Industrial Materials | edition = 9th | volume = 1-3 | location = New York, NY | publisher = Van Nostrand Reinhold | year = 1996 | page = 691}}

There is in-vitro evidence that cetylpyridinium chloride interferes with mitochondrial function at levels "that may be relevant to human exposures." The research was published in Environmental Health Perspectives" volume 125 no. 8. {{cite journal | doi=10.1289/ehp1404 | title=In Vitro Evaluation of Mitochondrial Function and Estrogen Signaling in Cell Lines Exposed to the Antiseptic Cetylpyridinium Chloride | year=2017 | last1=Datta | first1=Sandipan | last2=He | first2=Guochun | last3=Tomilov | first3=Alexey | last4=Sahdeo | first4=Sunil | last5=Denison | first5=Michael S. | last6=Cortopassi | first6=Gino | journal=Environmental Health Perspectives | volume=125 | issue=8 | page=087015 | pmid=28885978 | pmc=5783672 | bibcode=2017EnvHP.125h7015D | s2cid=3647115 }}

The molecular formula of cetylpyridinium chloride is C₂₁H₃₈NCl. In its pure form it is a solid at room temperature. It has a melting point of 77 °C when anhydrous or 80–83 °C as a monohydrate . 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 ~ 0.0009–0.0011M,{{Cite web | url=https://apps.webofknowledge.com/full_record.do?locale=en_US&errorKey=&search_mode=FullRecord&excludeEventConfig=ExcludeIfFromFullRecPage&qid=1&mode=FullRecord&log_event=yes&UT=WOS%3A000229556100013&product=WOS&product=WOS&SrcApp=Kopernio&SID=C4N3wXjfljuypCQ8b9E&SID=C4N3wXjfljuypCQ8b9E&viewType=fullRecord&doc=1 | title=Effect of salt on the micelles of cetyl pyridinium chloride}} and is strongly dependent on the salt concentration of the solution.

Some products are formulated instead with the bromide salt cetylpyridinium bromide, the properties of which are virtually identical.{{citation needed|date=September 2018}}

• Food Chemicals Codex{{cite web

|last=The United States Pharmacopeial Convention

|title=Revisions to FCC, First Supplement

|url=http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport01.html

|access-date=8 July 2009

|url-status=dead

|archive-url=https://web.archive.org/web/20100705122159/http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport01.html

|archive-date=5 July 2010

|df=dmy

}}

• United States Pharmacopeia 31{{cite web| last =USP 31| title =<1121> Nomenclature| url =http://www.usp.org/pdf/EN/USPNF/1121Nomenclature.pdf| access-date =8 July 2009| url-status =dead| archive-url =https://web.archive.org/web/20090109161828/http://www.usp.org/pdf/EN/USPNF/1121Nomenclature.pdf| archive-date =9 January 2009| df =dmy-all}}
• British Pharmacopoeia 1998{{cite web| last =Therapeutic Goods Administration| author-link =Therapeutic Goods Administration| title =Chemical Substances| url =http://www.tga.gov.au/docs/pdf/aan/aanchem.pdf| access-date =8 July 2009| archive-url =https://web.archive.org/web/20090615083950/http://www.tga.gov.au//docs/pdf/aan/aanchem.pdf| archive-date =15 June 2009| url-status =dead| df =dmy-all}}

• Mouthwash
• Oral-B
• Chlorhexidine
• Triclosan

{{Reflist}}

• [https://web.archive.org/web/20020117025701/http://physchem.ox.ac.uk/MSDS/CE/cetylpyridinium_chloride.html Material Safety Data Sheet]
• [http://www.chemicalland21.com/lifescience/phar/CETYLPYRIDINIUM%20CHLORIDE.htm Chemical Information]
• {{cite journal | doi = 10.1038/sj.bdj.4809913 | title = An in vitro evaluation of the availability of cetylpyridinium chloride and chlorhexidine in some commercially available mouthrinse products | year = 2003 | last1 = Sheen | first1 = S | last2 = Addy | first2 = M | s2cid = 39352250 | journal = British Dental Journal | volume = 194 | issue = 4 | pages = 207–10; discussion 203 | pmid = 12627199| doi-access = free }}

{{Blood substitutes and perfusion solutions}}

{{Antiseptics and disinfectants}}

{{Medicated dressings}}

{{Throat preparations}}

{{DEFAULTSORT:Cetylpyridinium Chloride}}

Category:Antiseptics

Category:Preservatives

Category:Chlorides

Category:Pyridinium compounds

Category:Cationic surfactants