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MedKoo Cat#: 591860 | Name: Cetrimonium bromide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cetrimonium bromide is used in the synthesis of a novel amperometric urea-sensor

Chemical Structure

Cetrimonium bromide
CAS#57-09-0 (Br)

Theoretical Analysis

MedKoo Cat#: 591860

Name: Cetrimonium bromide

CAS#: 57-09-0 (Br)

Chemical Formula: C19H42BrN

Exact Mass: 363.2501

Molecular Weight: 363.46

Elemental Analysis: C, 62.62; H, 11.62; Br, 21.92; N, 3.84

Price and Availability

Size Price Availability Quantity
5g USD 150.00 2 Weeks
25g USD 350.00 2 Weeks
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Related CAS #
6899-10-1 (free base) 57-09-0 (Br)
Synonym
Cetrimonium bromide; NSC 32927; NSC-32927; NSC32927
IUPAC/Chemical Name
1-Hexadecanaminium, N,N,N-trimethyl-, bromide (1:1)
InChi Key
LZZYPRNAOMGNLH-UHFFFAOYSA-M
InChi Code
InChI=1S/C19H42N.BrH/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(2,3)4;/h5-19H2,1-4H3;1H/q+1;/p-1
SMILES Code
CCCCCCCCCCCCCCCC[N+](C)(C)C.[Br-]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Cetrimonium bromide (CTAB) is an amine based cationic quaternary surfactant, is one of the components of the topical antiseptic Cetrimide.
In vitro activity:
The data revealed that treatment of SK-HEP-1 cells with cetrimonium bromide (CTAB) altered their mesenchymal spindle-like morphology. CTAB exerted inhibitory effects on the migration and invasion of SK-HEP-1 cells dose-dependently, and reduced protein levels of matrix metalloproteinase-2 (MMP-2), MMP-9, snail, slug, twist, vimentin, fibronectin, N-cadherin, Smad2, Smad3, Smad4, phosphoinositide-3-kinase (PI3K), p-PI3K, Akt, p-Akt, β-catenin, mammalian target of rapamycin (mTOR), p-mTOR, p-p70S6K, p-extracellular signal-regulated kinases (ERK)1/2, p-p38 mitogen-activated protein kinase (MAPK) and p-c-Jun N-terminal kinase (JNK), but increased protein levels of tissue inhibitor matrix metalloproteinase-1 (TIMP-1), TIMP-2, claudin-1 and p-GSK3β. Based on these observations, we suggest that CTAB not only inhibits the canonical transforming growth factor-β (TGF-β) signaling pathway though reducing SMADs (an acronym from the fusion of Caenorhabditis elegans Sma genes and the Drosophila Mad, Mothers against decapentaplegic proteins), but also restrains the non-canonical TGF-β signaling including MAPK pathways like ERK1/2, p38 MAPK, JNK and PI3K. Reference: Anticancer Res. 2019 Jul;39(7):3621-3631. http://ar.iiarjournals.org/cgi/pmidlookup?view=long&pmid=31262888
In vivo activity:
To evaluate the effect of CTAB on tumorigenesis in vivo, FaDu cells treated with CTAB (EC75) were injected into the left gastrocnemius muscle of SCID mice (2.5 × 105 cells/mouse); establishing a three-dimensional system that simulates the complex tumor microenvironment. Mice implanted with CTAB-treated FaDu cells did not develop tumors even after 100 days (Fig. 6A). In contrast, mice with vehicle-treated cells (implanted with 6.25 × 104 cells, representing the proportion of viable cells after treatment with EC75), developed tumors as early as 15 days, clearly demonstrating that CTAB effectively eliminated the tumor-forming potential of FaDu cells in SCID mice. The therapeutic efficacy of CTAB in treating established FaDu xenograft tumors in SCID mice also was evaluated. Once the TLDs reached an average of 7.5 mm, the mice were treated with CTAB (daily 5 mg/kg i.p. for 5 days). The dosing regimen was not optimized for absorption, distribution, metabolism, or excretion, but a delay in tumor growth (i.e., therapeutic benefit) was nonetheless observed. CTAB induced a modest reduction in tumor development compared with the vehicle-treatment arm; delaying the mean time to reach a TLD of 14 mm by ∼3.7 days (P < 0.05; Fig. 6B). When combined with local tumor RT, CTAB seemed to have a modest additive effect by extending the mean time to reach 14 mm by ∼7.2 days (P < 0.05; Fig. 6B). These data strongly suggest that improving the pharmacokinetics and bioavailability of CTAB would render this compound highly effective, because the in vivo tumor-forming capacity of FaDu cells was completely ablated when every tumor cell was exposed to the drug (Fig. 6A). Reference: Mol Pharmacol. 2009 Nov;76(5):969-83. http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=19654225
Solvent mg/mL mM comments
Solubility
DMSO 10.0 27.44
Water 4.6 12.48
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 363.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Wu TK, Chen CH, Pan YR, Hu CW, Huang FM, Liu JY, Lee CJ. Cetrimonium Bromide Inhibits Cell Migration and Invasion of Human Hepatic SK-HEP-1 Cells Through Modulating the Canonical and Non-canonical TGF-β Signaling Pathways. Anticancer Res. 2019 Jul;39(7):3621-3631. doi: 10.21873/anticanres.13510. PMID: 31262888. 2. Ito E, Yip KW, Katz D, Fonseca SB, Hedley DW, Chow S, Xu GW, Wood TE, Bastianutto C, Schimmer AD, Kelley SO, Liu FF. Potential use of cetrimonium bromide as an apoptosis-promoting anticancer agent for head and neck cancer. Mol Pharmacol. 2009 Nov;76(5):969-83. doi: 10.1124/mol.109.055277. Epub 2009 Aug 4. PMID: 19654225.
In vivo protocol:
1. Ito E, Yip KW, Katz D, Fonseca SB, Hedley DW, Chow S, Xu GW, Wood TE, Bastianutto C, Schimmer AD, Kelley SO, Liu FF. Potential use of cetrimonium bromide as an apoptosis-promoting anticancer agent for head and neck cancer. Mol Pharmacol. 2009 Nov;76(5):969-83. doi: 10.1124/mol.109.055277. Epub 2009 Aug 4. PMID: 19654225.
1: Parsaee Z. Synthesis of novel amperometric urea-sensor using hybrid synthesized NiO-NPs/GO modified GCE in aqueous solution of cetrimonium bromide. Ultrason Sonochem. 2018 Jun;44:120-128. doi: 10.1016/j.ultsonch.2018.02.021. Epub 2018 Feb 11. PubMed PMID: 29680593. 2: Koolivand A, Clayton S, Rion H, Oloumi A, O'Brien A, Khaledi MG. Fluoroalcohol - Induced coacervates for selective enrichment and extraction of hydrophobic proteins. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Apr 15;1083:180-188. doi: 10.1016/j.jchromb.2018.03.004. Epub 2018 Mar 3. PubMed PMID: 29549741. 3: de Araújo BRS, Linares León JJ. Electrochemical treatment of cetrimonium chloride with boron-doped diamond anodes. A technical and economical approach. J Environ Manage. 2018 May 15;214:86-93. doi: 10.1016/j.jenvman.2018.02.094. Epub 2018 Mar 5. PubMed PMID: 29518599. 4: Holubnycha V, Kalinkevich O, Ivashchenko O, Pogorielov M. Antibacterial Activity of In Situ Prepared Chitosan/Silver Nanoparticles Solution Against Methicillin-Resistant Strains of Staphylococcus aureus. Nanoscale Res Lett. 2018 Mar 2;13(1):71. doi: 10.1186/s11671-018-2482-9. PubMed PMID: 29500654; PubMed Central PMCID: PMC5834410. 5: Sun H, Guo S, Nan Y, Ma R. Direct determination of surfactant effects on the uptake of gaseous parent and alkylated PAHs by crop leaf surfaces. Ecotoxicol Environ Saf. 2018 Jun 15;154:206-213. doi: 10.1016/j.ecoenv.2018.02.045. Epub 2018 Feb 22. PubMed PMID: 29476969. 6: Zhang Z, Cheng H, Chen H, Chen K, Lu X, Ouyang P, Fu J. Enhancement in the aromatic yield from the catalytic fast pyrolysis of rice straw over hexadecyl trimethyl ammonium bromide modified hierarchical HZSM-5. Bioresour Technol. 2018 May;256:241-246. doi: 10.1016/j.biortech.2018.02.036. Epub 2018 Feb 8. PubMed PMID: 29453050. 7: Chakraborty G, Chowdhury MP, Hassan PA, Tsuchiya K, Torigoe K, Saha SK. Interaction of Tyrosine Analogues with Quaternary Ammonium Head Groups at the Micelle/Water Interface and Contrasting Effect of Molecular Folding on the Hydrophobic Outcome and End-Cap Geometry. J Phys Chem B. 2018 Mar 1;122(8):2355-2367. doi: 10.1021/acs.jpcb.7b11167. Epub 2018 Feb 14. PubMed PMID: 29406731. 8: Liu N, Wang Y, Ge F, Liu S, Xiao H. Antagonistic effect of nano-ZnO and cetyltrimethyl ammonium chloride on the growth of Chlorella vulgaris: Dissolution and accumulation of nano-ZnO. Chemosphere. 2018 Apr;196:566-574. doi: 10.1016/j.chemosphere.2017.12.184. Epub 2017 Dec 29. PubMed PMID: 29331620. 9: Li X, Sun D, Chen Y, Wang K, He Q, Wang G. Studying compaction-decompaction of DNA molecules induced by surfactants. Biochem Biophys Res Commun. 2018 Jan 22;495(4):2559-2565. doi: 10.1016/j.bbrc.2017.12.151. Epub 2017 Dec 27. PubMed PMID: 29288663. 10: Rütering M, Schmid J, Gansbiller M, Braun A, Kleinen J, Schilling M, Sieber V. Rheological characterization of the exopolysaccharide Paenan in surfactant systems. Carbohydr Polym. 2018 Feb 1;181:719-726. doi: 10.1016/j.carbpol.2017.11.086. Epub 2017 Nov 26. PubMed PMID: 29254028. 11: Lee YS. Assembly of Lyotropic Liquid Crystals with Solid Crystal's Structural Order Translated from the Lipid Rafts in Cell Membranes. J Am Chem Soc. 2017 Nov 29;139(47):17044-17051. doi: 10.1021/jacs.7b06720. Epub 2017 Nov 15. PubMed PMID: 29111698. 12: Iñiguez-Moreno M, Gutiérrez-Lomelí M, Guerrero-Medina PJ, Avila-Novoa MG. Biofilm formation by Staphylococcus aureus and Salmonella spp. under mono and dual-species conditions and their sensitivity to cetrimonium bromide, peracetic acid and sodium hypochlorite. Braz J Microbiol. 2018 Apr - Jun;49(2):310-319. doi: 10.1016/j.bjm.2017.08.002. Epub 2017 Oct 13. PubMed PMID: 29100930; PubMed Central PMCID: PMC5913829. 13: Xu C, Jiao C, Yao R, Lin A, Jiao W. Adsorption and regeneration of expanded graphite modified by CTAB-KBr/H(3)PO(4) for marine oil pollution. Environ Pollut. 2018 Feb;233:194-200. doi: 10.1016/j.envpol.2017.10.026. Epub 2017 Nov 5. PubMed PMID: 29078123. 14: Gan L, Lu Z, Cao D, Chen Z. Effects of cetyltrimethylammonium bromide on the morphology of green synthesized Fe(3)O(4) nanoparticles used to remove phosphate. Mater Sci Eng C Mater Biol Appl. 2018 Jan 1;82:41-45. doi: 10.1016/j.msec.2017.08.073. Epub 2017 Aug 17. PubMed PMID: 29025673. 15: Cao J, Yang B, Wang Y, Wei C, Wang H, Li S. Polymer brush hexadecyltrimethylammonium bromide (CTAB) modified poly (propylene-g-styrene sulphonic acid) fiber (ZB-1): CTAB/ZB-1 as a promising strategy for improving the dissolution and physical stability of poorly water-soluble drugs. Mater Sci Eng C Mater Biol Appl. 2017 Nov 1;80:282-295. doi: 10.1016/j.msec.2017.05.139. Epub 2017 May 30. PubMed PMID: 28866166. 16: Yu G, Hatta A, Periyannan S, Lagudah E, Wulff BBH. Isolation of Wheat Genomic DNA for Gene Mapping and Cloning. Methods Mol Biol. 2017;1659:207-213. doi: 10.1007/978-1-4939-7249-4_18. PubMed PMID: 28856653. 17: Meena R, Kumar S, Kumar R, Gaharwar US, Rajamani P. PLGA-CTAB curcumin nanoparticles: Fabrication, characterization and molecular basis of anticancer activity in triple negative breast cancer cell lines (MDA-MB-231 cells). Biomed Pharmacother. 2017 Oct;94:944-954. doi: 10.1016/j.biopha.2017.07.151. Epub 2017 Aug 12. PubMed PMID: 28810532. 18: Demirçivi P, Saygılı GN. Response surface modeling of boron adsorption from aqueous solution by vermiculite using different adsorption agents: Box-Behnken experimental design. Water Sci Technol. 2017 Jul;76(3-4):515-530. doi: 10.2166/wst.2017.200. PubMed PMID: 28759435; PubMed Central PMCID: wst_2017_200. 19: Thomas P, Agrawal M, Bharathkumar CB. Use of Plant Preservative Mixture™ for establishing in vitro cultures from field plants: Experience with papaya reveals several PPM™ tolerant endophytic bacteria. Plant Cell Rep. 2017 Nov;36(11):1717-1730. doi: 10.1007/s00299-017-2185-1. Epub 2017 Jul 26. PubMed PMID: 28748257. 20: Yu T, Lin M, Wan J, Cao X. Molecular interaction mechanisms in reverse micellar extraction of microbial transglutaminase. J Chromatogr A. 2017 Aug 18;1511:25-36. doi: 10.1016/j.chroma.2017.07.006. Epub 2017 Jul 5. PubMed PMID: 28697931.