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Revision as of 20:02, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475180606 of page Acriflavinium_chloride for the Chem/Drugbox validation project (updated: 'UNII', 'ChEMBL', 'ChEBI', 'StdInChI', 'StdInChIKey', '...  Latest revision as of 20:27, 16 July 2024 edit ActivelyDisinterested (talk | contribs)Extended confirmed users50,386 edits Research: The paper was retracted 
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{{more medical citations needed|date=December 2016}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457803314
| verifiedrevid = 477241203
| UNII_Ref = {{fdacite|changed|FDA}}
| ImageFile = Acriflavine.png
| UNII = <!-- blanked - oldvalue: 1S73VW819C -->
| ImageName = Wireframe of acriflavine
| ImageFile = Acriflavine.png
| ImageFile2 = Acriflavinium chloride substance photo.jpg
| ImageName = Wireframe of acriflavine
| ImageCaption2 = Sample of pure acriflavine
| IUPACName = 3,6-Diamino-10-methylacridin-10-ium chloride
| ImageAlt2 = Pure acriflavinium chloride: A brown powder
| Section1 = {{Chembox Identifiers
| PIN = 3,6-Diamino-10-methylacridin-10-ium chloride
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| OtherNames = Acriflavinium chloride (])
| ChEMBL = <!-- blanked - oldvalue: 354349 -->
|Section1={{Chembox Identifiers
| StdInChI1 = 1/C14H13N3.C13H11N3.ClH/c1-17-13-7-11(15)4-2-9(13)6-10-3-5-12(16)8-14(10)17;14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10;/h2-8H,1H3,(H3,15,16);1-7H,14-15H2;1H
| UNII_Ref = {{fdacite|correct|FDA}}
| StdInChIKey1 = PEJLNXHANOHNSU-UHFFFAOYAC
| UNII = 1T3A50395T
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = 1S73VW819C
| UNII1_Comment = (])
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 354349
| SMILES1 = .n1c3c(cc2c1cc(N)cc2)ccc(c3)N.Nc3cc2(c1cc(N)ccc1cc2cc3)C | SMILES1 = .n1c3c(cc2c1cc(N)cc2)ccc(c3)N.Nc3cc2(c1cc(N)ccc1cc2cc3)C
| InChI = 1S/C14H13N3.C13H11N3.ClH/c1-17-13-7-11(15)4-2-9(13)6-10-3-5-12(16)8-14(10)17;14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10;/h2-8H,1H3,(H3,15,16);1-7H,14-15H2;1H | InChI = 1S/C14H13N3.C13H11N3.ClH/c1-17-13-7-11(15)4-2-9(13)6-10-3-5-12(16)8-14(10)17;14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10;/h2-8H,1H3,(H3,15,16);1-7H,14-15H2;1H
| InChIKey = PEJLNXHANOHNSU-UHFFFAOYSA-N | InChIKey = PEJLNXHANOHNSU-UHFFFAOYSA-N
| InChI1 = 1S/C14H13N3.C13H11N3.ClH/c1-17-13-7-11(15)4-2-9(13)6-10-3-5-12(16)8-14(10)17;14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10;/h2-8H,1H3,(H3,15,16);1-7H,14-15H2;1H
| InChIKey1 = PEJLNXHANOHNSU-UHFFFAOYSA-N | InChIKey1 = PEJLNXHANOHNSU-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 86-40-8 --> | CASNo = 65589-70-0
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 10597-46-3
| CASNo1 = 10597-46-3
| CASNo1_Comment = (hydrochloride)
| CASNo1_Comment = (])
| PubChem = 443101
| PubChem = 443101
| PubChem_Ref = {{Pubchemcite}}
| PubChem1 = 15558347 | PubChem1 = 15558347
| PubChem1_Comment = (hydrochloride) | PubChem1_Comment = (HCl)
| ChemSpiderID = 391386
| PubChem1_Ref = {{Pubchemcite}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 391386
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1 = 21018 | ChemSpiderID1 = 21018
| ChemSpiderID1_Comment = (hydrochloride) | ChemSpiderID1_Comment = (HCl)
| EINECS = 201-668-8
| ChemSpiderID1_Ref = {{Chemspidercite}}
| ChEBI_Ref = {{ebicite|changed|EBI}}
| EINECS = 201-668-8
| ChEBI = 383703
| ChEBI_Ref = {{ebicite|changed|EBI}}
| SMILES = .C1=C2C=C(N)C=CC2=CC2=C1C=C(N)C=C2
| ChEBI = <!-- blanked - oldvalue: 383703 -->
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| ATCCode_prefix = R02
| StdInChI = 1S/C14H13N3.ClH/c1-17-13-7-11(15)4-2-9(13)6-10-3-5-12(16)8-14(10)17;/h2-8H,1H3,(H3,15,16);1H
| ATCCode_suffix = AA13
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| ATC_Supplemental = QG01AC90
| StdInChIKey = KKAJSJJFBSOMGS-UHFFFAOYSA-N}}
| SMILES = .C1=C2C=C(N)C=CC2=CC2=C1C=C(N)C=C2
|Section2={{Chembox Properties
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| C=14 | H=14 | Cl=1 | N=3}}
| StdInChI = 1S/C14H13N3.C13H11N3.ClH/c1-17-13-7-11(15)4-2-9(13)6-10-3-5-12(16)8-14(10)17;14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10;/h2-8H,1H3,(H3,15,16);1-7H,14-15H2;1H
|Section6={{Chembox Pharmacology
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| ATCCode_prefix = R02
| StdInChIKey = PEJLNXHANOHNSU-UHFFFAOYSA-N
| ATCCode_suffix = AA13
| ATC_Supplemental = {{ATCvet|G01|AC90}}
}} }}
| Section2 = {{Chembox Properties
| C = 14
| H = 14
| Cl = 1
| N = 3}}
}} }}

'''Acriflavine''' (]: '''acriflavinium chloride''') is a topical ]. It has the form of an orange or brown powder. It may be harmful in the eyes or if inhaled. It is a dye and it stains the skin and may irritate. The ] form is more irritating than the neutral form.
It is derived from ]. Commercial preparations are often mixtures with ].<ref name=Sigma>{{cite web | url = http://www.sigmaaldrich.com/catalog/product/sigma/a8126?lang=en | title = Acriflavine | publisher = ]}}</ref> It is known by a variety of commercial names.

==Uses==
===Medical use===
Acriflavine was developed in 1912 by ], a German medical researcher, and was used during the ] against ] and as a topical antiseptic.<ref name=EB></ref>

===Other uses===
Acriflavine is used in biochemistry for fluorescently labeling high molecular weight RNA.<ref name=Sigma/>

It is used as treatment for external ]s of aquarium fish.<ref>{{Cite web |url=http://freshaquarium.about.com/od/Fish_Health_Treatments/fl/Acriflavine.htm |title=Acriflavine use in aquaria |access-date=2016-01-24 |archive-date=2016-01-29 |archive-url=https://web.archive.org/web/20160129182528/http://freshaquarium.about.com/od/Fish_Health_Treatments/fl/Acriflavine.htm |url-status=dead }}</ref>

==Research==
Acriflavine might be effective in fighting common cold virus, and also aid the fight against increasingly antibiotic resistant bacteria <ref>{{cite news | url = http://www.abc.net.au/news/2016-11-28/antiseptic-used-in-wwi-could-hold-key-to-treating-superbugs/8062496 | title = Antiseptic used in WWI could hold key to treating superbugs, viral infections, Melbourne researchers say | publisher = ABC | date = November 28, 2016}}</ref><ref>{{cite news | url = http://www.sciencealert.com/this-forgotten-wwi-antiseptic-could-be-the-key-to-fighting-antibiotic-resistance | title = This forgotten WWI antiseptic could be the key to fighting antibiotic resistance | publisher = Science Alert | date = November 30, 2016}}</ref><ref>{{Cite journal | doi = 10.1093/nar/gkw878 | title = Activation of cGAS-dependent antiviral responses by DNA intercalating agents | journal = Nucleic Acids Research | year = 2016 | pmid = 27694309| pmc = 5224509| volume=45 | issue = 1 | pages=198–205| last1 = Pépin | first1 = Geneviève | last2 = Nejad | first2 = Charlotte | last3 = Thomas | first3 = Belinda J | last4 = Ferrand | first4 = Jonathan | last5 = McArthur | first5 = Kate | last6 = Bardin | first6 = Philip G | last7 = Williams | first7 = Bryan RG | last8 = Gantier | first8 = Michael P }}</ref> because it can cure (remove) plasmids containing antimicrobial resistance genes from Gram positive bacteria.<ref>{{Cite journal | doi = 10.1016/S0147-619X(03)00074-X | pmid = 14711527 | title = Plasmid curing of ''Oenococcus oeni''. | journal = Plasmid | year = 2004 | volume=51 | issue = 1 | pages=37–40| last1 = Mesas | first1 = J.M. | last2 = Rodriguez | first2 = M.C. | last3 = Alegre | first3 = M.T.}}</ref>

Since 2014, acriflavine has been undergoing testing as an antimalarial drug to treat parasites with resistance to ] and modern anti-parasitic medicines.<ref>{{Cite journal | doi = 10.1021/cb500476q| pmid = 25089658| title = Potent Antimalarial Activity of Acriflavine ''In'' Vitroand ''In'' Vivo| journal = ACS Chemical Biology| volume = 9| issue = 10| pages = 2366–73| year = 2014| last1 = Dana| first1 = Srikanta| last2 = Prusty| first2 = Dhaneswar| last3 = Dhayal| first3 = Devender| last4 = Gupta| first4 = Mohit Kumar| last5 = Dar| first5 = Ashraf| last6 = Sen| first6 = Sobhan| last7 = Mukhopadhyay| first7 = Pritam| last8 = Adak| first8 = Tridibesh| last9 = Dhar| first9 = Suman Kumar| pmc=4201339}}</ref>

==Legal status==
===Australia===
Acriflavine is a controlled substance in Australia and dependent on situation,{{clarify|date=January 2016}} is considered either a Schedule 5 (Caution) or Schedule 7 (Dangerous Poison) substance. The use, storage and preparation of the chemical is subject to strict state and territory laws.{{citation needed|date=January 2016}}

==References==
{{Reflist}}

==External links==
* {{Commons category-inline}}
*

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