Cetrimide hydroxide

• CAT Number: I024409
• CAS Number: 505-86-2
• Molecular Formula: C19H43NO
• Molecular Weight: 301.56
• Purity: 98%
• Synonyms: Cetrimide; Cetyltrimethylammonium hydroxide; Cetrimide hydroxide
• Solubility: Soluble in DMSO
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 1-Hexadecanaminium, N,N,N-trimethyl-, hydroxide
• InChI: InChI=1S/C19H42N.H2O/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(2,3)4;/h5-19H2,1-4H3;1H2/q+1;/p-1
• InChIKey: WJLUBOLDZCQZEV-UHFFFAOYSA-M
• SMILES: CCCCCCCCCCCCCCCC[N+](C)(C)C.[OH-]

Cetrimide is an antiseptic used to irrigate root canals to ensure disinfection and removal of microbial residues. Note: this product is being supplied as 10% wt in water.

Reference

1: María Ferrer-Luque C, Teresa Arias-Moliz M, Ruíz-Linares M, Elena Martínez García M, Baca P. Residual activity of cetrimide and chlorhexidine on Enterococcus faecalis-infected root canals. Int J Oral Sci. 2014 Mar;6(1):46-9. doi: 10.1038/ijos.2013.95. Epub 2013 Dec 20. PubMed PMID: 24357857; PubMed Central PMCID: PMC3967309.
2: Aydin C, Kayaalp C, Nessar G, Zengin N, Balkan M, Unal B, Ozgurtas T. Is cetrimide-chlorhexidine risky for secondary sclerosing cholangitis? Adv Clin Exp Med. 2014 May-Jun;23(3):395-8. PubMed PMID: 24979510.
3: Poggio C, Dagna A, Colombo M, Scribante A, Chiesa M. Decalcifying efficacy of different irrigating solutions: effect of cetrimide addition. Braz Oral Res. 2014;28:1-6. Epub 2014 Sep 26. PubMed PMID: 25271964.
4: Engebretsen KA, Hald M, Johansen JD, Thyssen JP. Allergic contact dermatitis caused by an antiseptic containing cetrimide. Contact Dermatitis. 2015 Jan;72(1):60-1. doi: 10.1111/cod.12303. PubMed PMID: 25524123.
5: Ruiz-Linares M, Ferrer-Luque CM, Arias-Moliz T, de Castro P, Aguado B, Baca P. Antimicrobial activity of alexidine, chlorhexidine and cetrimide against Streptococcus mutans biofilm. Ann Clin Microbiol Antimicrob. 2014 Aug 20;13:41. doi: 10.1186/s12941-014-0041-5. PubMed PMID: 25139679; PubMed Central PMCID: PMC4236523.
6: Bailón-Sánchez ME, Baca P, Ruiz-Linares M, Ferrer-Luque CM. Antibacterial and anti-biofilm activity of AH plus with chlorhexidine and cetrimide. J Endod. 2014 Jul;40(7):977-81. doi: 10.1016/j.joen.2013.11.020. Epub 2014 Jan 10. PubMed PMID: 24935547.
7: Guerreiro-Tanomaru JM, Nascimento CA, Faria-Júnior NB, Graeff MS, Watanabe E, Tanomaru-Filho M. Antibiofilm activity of irrigating solutions associated with cetrimide. Confocal laser scanning microscopy. Int Endod J. 2014 Nov;47(11):1058-63. doi: 10.1111/iej.12248. Epub 2014 Feb 13. PubMed PMID: 24433253.
8: de Almeida LH, Leonardo NG, Gomes AP, Giardino L, Souza EM, Pappen FG. Pulp tissue dissolution capacity of sodium hypochlorite combined with cetrimide and polypropylene glycol. Braz Dent J. 2013 Sep-Oct;24(5):477-81. doi: 10.1590/0103-6440201302041. PubMed PMID: 24474288.
9: Zhang R, Chen M, Lu Y, Guo X, Qiao F, Wu L. Antibacterial and residual antimicrobial activities against Enterococcus faecalis biofilm: A comparison between EDTA, chlorhexidine, cetrimide, MTAD and QMix. Sci Rep. 2015 Aug 6;5:12944. doi: 10.1038/srep12944. PubMed PMID: 26245711; PubMed Central PMCID: PMC4526883.
10: Nascimento CA, Tanomaru-Filho M, Faria-Junior NB, Faria G, Guerreiro-Tanomaru JM. Antimicrobial activity of root canal irrigants associated with cetrimide against biofilm and planktonic Enterococcus faecalis. J Contemp Dent Pract. 2014 Sep 1;15(5):603-7. PubMed PMID: 25707833.
11: Ruiz-Linares M, Bailón-Sánchez ME, Baca P, Valderrama M, Ferrer-Luque CM. Physical properties of AH Plus with chlorhexidine and cetrimide. J Endod. 2013 Dec;39(12):1611-4. doi: 10.1016/j.joen.2013.08.002. Epub 2013 Sep 11. PubMed PMID: 24238458.
12: Arias-Moliz MT, Ferrer-Luque CM, González-Rodríguez MP, Valderrama MJ, Baca P. Eradication of Enterococcus faecalis biofilms by cetrimide and chlorhexidine. J Endod. 2010 Jan;36(1):87-90. doi: 10.1016/j.joen.2009.10.013. PubMed PMID: 20003941.
13: Fortuna G, Cerchione E, Di Lorenzo M. Cetrimide-induced oral mucositis: an unusual adverse drug reaction. Eur J Clin Pharmacol. 2016 Nov;72(11):1415-1416. Epub 2016 Aug 9. PubMed PMID: 27501935.
14: Tripathy S, Sasmal P, Rao PB, Mishra TS, Nayak S. Cetrimide-chlorhexidine-induced multiorgan failure in surgery of pulmonary hydatid cyst. Ann Card Anaesth. 2016 Jul-Sep;19(3):557-60. doi: 10.4103/0971-9784.185565. PubMed PMID: 27397471; PubMed Central PMCID: PMC4971995.
15: Baca P, Junco P, Arias-Moliz MT, Castillo F, Rodríguez-Archilla A, Ferrer-Luque CM. Antimicrobial substantivity over time of chlorhexidine and cetrimide. J Endod. 2012 Jul;38(7):927-30. doi: 10.1016/j.joen.2012.04.003. Epub 2012 May 15. PubMed PMID: 22703655.
16: Deepalakshmi M, Poorni S, Miglani R, Rajamani I, Ramachandran S. Evaluation of the antibacterial and physical properties of glass ionomer cements containing chlorhexidine and cetrimide: an in-vitro study. Indian J Dent Res. 2010 Oct-Dec;21(4):552-6. doi: 10.4103/0970-9290.74217. PubMed PMID: 21187624.
17: Korkmaz FM, Tüzüner T, Baygin O, Buruk CK, Durkan R, Bagis B. Antibacterial activity, surface roughness, flexural strength, and solubility of conventional luting cements containing chlorhexidine diacetate/cetrimide mixtures. J Prosthet Dent. 2013 Aug;110(2):107-15. doi: 10.1016/S0022-3913(13)60349-2. PubMed PMID: 23929372.
18: Lee JY. Pathogenesis of abnormal keratinization in ichthyosiform cetrimide dermatitis: an ultrastructural study. Am J Dermatopathol. 1997 Apr;19(2):162-7. PubMed PMID: 9129701.
19: Danchaivijitr S, Chokloikaew S, Trakoolsomboon S, Tangtrakool T. Contamination of mercurochrome and chlorhexidine-cetrimide in a teaching hospital. J Med Assoc Thai. 1995 Jul;78 Suppl 1:S40-3. PubMed PMID: 7545205.
20: Vaddi HK, Wang LZ, Ho PC, Chan YW, Chan SY. Effect of cetrimide and ascorbic acid on in vitro human skin permeation of haloperidol. Chem Pharm Bull (Tokyo). 2001 Nov;49(11):1395-400. PubMed PMID: 11724228.