Misplaced Pages

Benzethonium chloride: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively
Page 1
Page 2
← Previous editContent deleted Content addedVisualWikitext
Revision as of 19:18, 11 December 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}}, {{drugbox}} (no changed fields - added verified revid - updated 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals← Previous edit Latest revision as of 19:34, 20 October 2024 edit undo2601:642:c303:f370:4df:e9a5:420a:1f96 (talk) Reclassified to Clostridioides in 2016. CE 
(106 intermediate revisions by 65 users not shown)
Line 1: Line 1:
{{Expert-subject|pharmacology|date=November 2008}}

{{Chembox {{Chembox
| Verifiedfields = changed
| verifiedrevid = 401818542
| Watchedfields = changed
| ImageFile = Benzethonium-chloride-2D-skeletal.png
| verifiedrevid = 401820198
| ImageName = Wireframe model of Benzethonium chloride
| ImageFile = Benzethonium-chloride-2D-skeletal.png
| PIN = ''N''-benzyl-''N'',''N''-dimethyl-2-{2-[4-(2,4,4-<br />
| ImageFile_Ref = {{chemboximage|correct|??}}
trimethylpentan-2-yl)phenoxy]ethoxy}<br />
| ImageSize = 280
ethanaminium chloride
| ImageAlt = Kekulé, skeletal formula of benzethonium chloride
| SystematicName = Benzyldimethyl(2-{2-[4-(2,4,4-trimethylpentan-<br />
| ImageFile1 = Benzethonium-chloride-3D-spacefill.png
2-yl)phenoxy]ethoxy}ethyl)azanium chloride
| ImageSize1 = 250
| Section1 = {{Chembox Identifiers
| ImageAlt1 = Space-filling model of the component ions benzethonium chloride
| InChI1 = 1/C27H42NO2.ClH/c1-26(2,3)22-27(4,5)24-13-15-25(16-14-24)30-20-19-29-18-17-28(6,7)21-23-11-9-8-10-12-23;/h8-16H,17-22H2,1-7H3;1H/q+1;/p-1
| PIN = ''N''-Benzyl-''N'',''N''-dimethyl-2-<nowiki/>{2-ethoxy}ethan-1-aminium chloride
| InChIKey1 = UREZNYTWGJKWBI-REWHXWOFAF
| SystematicName = Benzyldimethyl(2-<nowiki/>{2-ethoxy}ethyl)azanium chloride
| SMILES1 = .O(c1ccc(cc1)C(C)(C)CC(C)(C)C)CCOCC(Cc2ccccc2)(C)C
|Section1={{Chembox Identifiers
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| CASNo = 121-54-0
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 8478
| ChemSpiderID = 8165
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = PH41D05744
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 204-479-9
| UNNumber = 2923
| KEGG = D01140
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = Benzethonium
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 31264
| ChEMBL = 221753
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| RTECS = BO7175000

| Beilstein = 3898548
| SMILES = .CC(C)(C)CC(C)(C)c1ccc(OCCOCC(C)(C)Cc2ccccc2)cc1
| SMILES1 = .CC(C)(C)CC(C)(C)C1=CC=C(OCCOCC(C)(C)CC2=CC=CC=C2)C=C1
| StdInChI = 1S/C27H42NO2.ClH/c1-26(2,3)22-27(4,5)24-13-15-25(16-14-24)30-20-19-29-18-17-28(6,7)21-23-11-9-8-10-12-23;/h8-16H,17-22H2,1-7H3;1H/q+1;/p-1 | StdInChI = 1S/C27H42NO2.ClH/c1-26(2,3)22-27(4,5)24-13-15-25(16-14-24)30-20-19-29-18-17-28(6,7)21-23-11-9-8-10-12-23;/h8-16H,17-22H2,1-7H3;1H/q+1;/p-1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C27H42NO2.ClH/c1-26(2,3)22-27(4,5)24-13-15-25(16-14-24)30-20-19-29-18-17-28(6,7)21-23-11-9-8-10-12-23;/h8-16H,17-22H2,1-7H3;1H/q+1;/p-1
| StdInChIKey = UREZNYTWGJKWBI-UHFFFAOYSA-M | StdInChIKey = UREZNYTWGJKWBI-UHFFFAOYSA-M
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| CASNo = 121-54-0
| InChIKey = UREZNYTWGJKWBI-REWHXWOFAF
| CASNo_Ref = {{cascite|correct|CAS}}
}}
| PubChem = 8478
|Section2={{Chembox Properties
| PubChem_Ref = {{Pubchemcite}}
| C=27 | N=1 | H=42 | O=2 | Cl=1
| PubChem1 = 21644026
| MeltingPtC = 163
| PubChem1_Comment = (monohydrate)
| Solubility = 40 g dm<sup>−3</sup> (at 20&nbsp;°C)
| PubChem1_Ref = {{Pubchemcite}}
}}
| ChemSpiderID = 8165
|Section6={{Chembox Pharmacology
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ATCCode_prefix = D08
| ChemSpiderID1 = 15634421
| ATCCode_suffix = AJ08
| ChemSpiderID1_Comment = (monohydrate)
| ChemspiderID1_Ref = {{Chemspidercite}} | ATC_Supplemental = {{ATC|R02|AA09}}
| AdminRoutes = topical
| UNII = PH41D05744
| Legal_US = OTC
| UNII_Ref = {{fdacite|correct|FDA}}
}}
| EINECS = 204-479-9
|Section7={{Chembox Hazards
| KEGG = D01140
| GHSPictograms = {{GHS corrosion}} {{GHS skull and crossbones}} {{GHS environment}}
| MeSHName = Benzethonium
| ChEBI = 468083 | GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|314|400}}
| RTECS = BO7175000
| PPhrases = {{P-phrases|273|280|305+351+338|310}}
| ATCCode_prefix = D08
}}
| ATCCode_suffix = AJ08
| ATC_Supplemental = R02AA09
| SMILES = .CC(C)(C)CC(C)(C)C1=CC=C(O<br />
CCOCC(C)(C)CC2=CC=CC =C2)C<br />
=C1
| InChI = 1/C27H42NO2.ClH/c1-26(2,3)22-27(4,5)<br />
24-13-15-25(16-14-24)30-20-19-29-18-17-<br />
28(6,7)21-23-11-9-8-10-12-23;/h8-16H,<br />
17-22H2,1-7H3;1H/q+1;/p-1
| InChIKey = UREZNYTWGJKWBI-UHFFFAOYSA-M
| Beilstein = 3898548}}
| Section2 = {{Chembox Properties
| C = 27
| H = 42
| Cl = 1
| N = 1
| O = 2
| ExactMass = 447.290407300 g mol<sup>-1</sup>}}
| Section3 = {{Chembox Pharmacology
| AdminRoutes = topical
| Legal_US = OTC}}
}} }}


'''Benzethonium chloride''' is a synthetic ]. This compound is an odorless white solid; soluble in water. '''Benzethonium chloride''', also known as '''hyamine''' is a synthetic ]. This compound is an odorless white solid, soluble in water. It has ], ], and anti-infective properties and it is used as a topical ] in ] antiseptics. It is also found in ] and ] such as ], ], anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride is also used in the food industry as a hard surface ].<ref>{{CPID|id=634}}</ref>
It has ], ], and anti-infective properties, and it is used as a topical antimicrobial agent in first aid antiseptics. It is also found in ] and ] such as mouthwashes (disguised as ]; see below), anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride is also used in the food industry as a hard surface disinfectant.<ref>{{HPD|634}}</ref>


==Uses==
The FDA's tentative final monograph (21CFR333) for first aid antiseptics specifies that benzethonium chloride's safe and effective concentrations are 0.1 - 0.2% for these products. Aqueous solutions of benzethonium chloride are not absorbed through the skin. It is '''un'''approved in the USA and Europe as a food additive ingredient. In Switzerland it is classified as a class-2 poison.


===Antimicrobial===
In addition to its highly effective antimicrobial activity, benzethonium chloride contains a positively charged nitrogen atom covalently bonded to four carbon atoms. This positive charge attracts it to the skin and hair. This contributes to a soft, powdery afterfeel on the skin and hair, as well as long-lasting persistent activity against microorganisms.
Benzethonium chloride exhibits a broad spectrum of microbiocidal activity against bacteria, fungi, mold, and viruses. Independent testing shows that benzethonium chloride is highly effective against such pathogens as ], '']'', '']'', '']'', ], ], ] (HSV), ] (HIV), ] (RSV), and ].{{Citation needed|date=July 2014}}


The US ] (FDA) specifies that the safe and effective concentrations for benzethonium chloride are 0.1-0.2% in first aid products.<ref> {{webarchive |url=https://web.archive.org/web/20140522070818/http://www.havlon.com/documents/Handbook_of_topical_microbials.pdf |date=May 22, 2014 }}</ref> Aqueous solutions of benzethonium chloride are not absorbed through the skin. It is not approved in the US and Europe for use as a ]. Being a ], it is more toxic than negatively charged surfactants.<ref></ref> However, in a two-year study on rats, there was no evidence of carcinogenic activity.<ref>{{Cite journal
Benzethonium chloride exhibits a broad spectrum of microbiocidal activity against bacteria, fungi, mold and viruses. Independent testing shows that benzethonium chloride is highly effective against such pathogens as: Methicillin-Resistant ''Staphylococcus aureus'' (]), VISA, Salmonella, '']'', ''Clostridium difficile'' ('']''), ], ], ], ], ], and ].
| pmid = 12595925
| year = 1995
| last1 = National Toxicology
| first1 = Program
| title = NTP Toxicology and Carcinogenesis Studies of Benzethonium Chloride (CAS No. 121-54-0) in F344/N Rats and B6C3F1 Mice (Dermal Studies)
| journal = National Toxicology Program Technical Report Series
| volume = 438
| pages = 1–220
}}</ref>


It is available under trade names '''Salanine''', '''BZT''', '''Diapp''', '''Quatrachlor''', '''Polymine D''', '''Phemithyn''', '''Antiseptol''', '''Disilyn''', '''Phermerol''', and others.<ref>{{Cite web |url=http://www.sciencelab.com/msds.php?msdsId=9923044 |title=Sciencelab.com, Benzethonium chloride MSDS |access-date=2013-06-15 |archive-date=2018-12-06 |archive-url=https://web.archive.org/web/20181206194748/http://www.sciencelab.com/msds.php?msdsId=9923044 |url-status=dead }}</ref> It is also found in several ] preparations<ref>{{Cite journal | doi = 10.1021/jf010222w| title = Identification of Benzethonium Chloride in Commercial Grapefruit Seed Extracts| journal = Journal of Agricultural and Food Chemistry| volume = 49| issue = 7| pages = 3316–20| year = 2001| last1 = Takeoka | first1 = G. | last2 = Dao | first2 = L. | last3 = Wong | first3 = R. Y. | last4 = Lundin | first4 = R. | last5 = Mahoney | first5 = N. | pmid=11453769}}</ref> and can be used as a ], as in the anaesthetics ketamine<ref>{{Cite journal | doi = 10.1038/sj.bjp.0704315| pmid = 11606328| title = Ketamine and its preservative, benzethonium chloride, both inhibit human recombinant α7 and α4β2 neuronal nicotinic acetylcholine receptors in ''Xenopusoocytes''| journal = British Journal of Pharmacology| volume = 134| issue = 4| pages = 871–9| year = 2001| last1 = Coates | first1 = K. M. | last2 = Flood | first2 = P. | pmc=1573008}}</ref> and alfaxalone.<ref>{{Cite web|url=https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=2a8e4d17-3ff3-4aa3-a990-7cb012a3123a&type=display|title = Alfaxan Multidose}}</ref>
It is available under trade names '''salanine''', '''BZT''', '''diapp''', '''quatrachlor''', '''polymine d''', '''phemithyn''', '''antiseptol''', '''disilyn''', '''phermerol''', and others.<ref></ref> It is also the principal component of various chemically denatured ]s, which are controversially marketed as "natural" health supplements / ingredients.

===Other uses===
In addition to its highly effective antimicrobial activity, benzethonium chloride contains a positively charged nitrogen atom covalently bonded to four carbon atoms. This positive charge attracts it to the skin and hair. This contributes to a soft, powdery after-feel on the skin and hair, as well as long-lasting persistent activity against micro-organisms. Also, this positively charged hydrophilic part of the molecule makes it a ].<ref></ref>

Benzethonium chloride is also used to ] the quantity of ] in a mixture of sodium dodecyl sulfate, ] and ], using ]-sulphan blue as an indicator.<ref name="euro pharmacopoeia">{{cite book | url=http://lib.njutcm.edu.cn/yaodian/ep/EP501E/16_monographs/19_monographs_q-z/sodium_laurilsulfate/0098e.pdf | title=European Pharmacopoeia 5.0 Monographs | publisher=European Pharmacopoeia Commission | pages=2440 }}{{Dead link|date=October 2019 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>

It precipitates as turbidity with anionic polymers in aqueous solution, allowing it to be used to estimate the amount of such polymers present in a sample. This test is used in commercial and industrial water treatment, where polyacrylates, polymaleates, and sulfonated polymers are commonly employed as dispersants.{{cn|date=September 2023}}

===Methylbenzethonium chloride===
A related compound ({{CAS|25155-18-4}}) is used to treat '']'' infections.

==Regulation==
Some data has suggested that long-term exposure to antibacterial ingredients could contribute to bacterial resistance or hormonal effects. Furthermore, there is little evidence that the use of such ingredients in consumer soaps is actually more effective than plain soap and water. In September 2016, the Food and Drug Administration issued a ban on nineteen consumer antiseptic wash ingredients. A ruling on benzethonium chloride, along with two other similar ingredients, was deferred for a year to allow for more data collection.<ref>{{cite web|title=FDA issues final rule on safety and effectiveness of antibacterial soaps|url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm517478.htm|website=Food & Drug Administration|publisher=U.S. Food and Drug Administration|access-date=February 7, 2017}}</ref>


==References== ==References==
{{Reflist}} {{Reflist|2}}


{{Antiseptics and disinfectants}} {{Antiseptics and disinfectants}}
Line 85: Line 107:
] ]
] ]
]

]
]
]
]
]