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16 July 2024 edit ActivelyDisinterested (talk | contribs)Extended confirmed users50,386 edits →Research: The paper was retracted |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}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 457803314 |
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| verifiedrevid = 477241203 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| ImageFile = Acriflavine.png |
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| UNII = <!-- blanked - oldvalue: 1S73VW819C --> |
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| ImageName = Wireframe of acriflavine |
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| ImageFile = Acriflavine.png |
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| ImageFile2 = Acriflavinium chloride substance photo.jpg |
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| ImageName = Wireframe of acriflavine |
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| ImageCaption2 = Sample of pure acriflavine |
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| IUPACName = 3,6-Diamino-10-methylacridin-10-ium chloride |
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| ImageAlt2 = Pure acriflavinium chloride: A brown powder |
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| Section1 = {{Chembox Identifiers |
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| PIN = 3,6-Diamino-10-methylacridin-10-ium chloride |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| OtherNames = Acriflavinium chloride (]) |
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| ChEMBL = <!-- blanked - oldvalue: 354349 --> |
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|Section1={{Chembox Identifiers |
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| 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 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| StdInChIKey1 = PEJLNXHANOHNSU-UHFFFAOYAC |
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| UNII = 1T3A50395T |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = 1S73VW819C |
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| UNII1_Comment = (]) |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 354349 |
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| SMILES1 = .n1c3c(cc2c1cc(N)cc2)ccc(c3)N.Nc3cc2(c1cc(N)ccc1cc2cc3)C |
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| SMILES1 = .n1c3c(cc2c1cc(N)cc2)ccc(c3)N.Nc3cc2(c1cc(N)ccc1cc2cc3)C |
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| 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 |
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| 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 |
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| InChIKey = PEJLNXHANOHNSU-UHFFFAOYSA-N |
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| InChIKey = PEJLNXHANOHNSU-UHFFFAOYSA-N |
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| 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 |
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| InChIKey1 = PEJLNXHANOHNSU-UHFFFAOYSA-N |
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| InChIKey1 = PEJLNXHANOHNSU-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 86-40-8 --> |
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| CASNo = 65589-70-0 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 10597-46-3 |
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| CASNo1 = 10597-46-3 |
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| CASNo1_Comment = (hydrochloride) |
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| CASNo1_Comment = (]) |
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| PubChem = 443101 |
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| PubChem = 443101 |
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| PubChem_Ref = {{Pubchemcite}} |
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| PubChem1 = 15558347 |
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| PubChem1 = 15558347 |
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| PubChem1_Comment = (hydrochloride) |
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| PubChem1_Comment = (HCl) |
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| ChemSpiderID = 391386 |
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| PubChem1_Ref = {{Pubchemcite}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 391386 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1 = 21018 |
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| ChemSpiderID1 = 21018 |
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| ChemSpiderID1_Comment = (hydrochloride) |
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| ChemSpiderID1_Comment = (HCl) |
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| EINECS = 201-668-8 |
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| ChemSpiderID1_Ref = {{Chemspidercite}} |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| EINECS = 201-668-8 |
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| ChEBI = 383703 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| SMILES = .C1=C2C=C(N)C=CC2=CC2=C1C=C(N)C=C2 |
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| ChEBI = <!-- blanked - oldvalue: 383703 --> |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| ATCCode_prefix = R02 |
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| 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 |
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| ATCCode_suffix = AA13 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| ATC_Supplemental = QG01AC90 |
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| StdInChIKey = KKAJSJJFBSOMGS-UHFFFAOYSA-N}} |
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| SMILES = .C1=C2C=C(N)C=CC2=CC2=C1C=C(N)C=C2 |
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|Section2={{Chembox Properties |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| C=14 | H=14 | Cl=1 | N=3}} |
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| 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 |
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|Section6={{Chembox Pharmacology |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| ATCCode_prefix = R02 |
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| StdInChIKey = PEJLNXHANOHNSU-UHFFFAOYSA-N |
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| ATCCode_suffix = AA13 |
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| ATC_Supplemental = {{ATCvet|G01|AC90}} |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| C = 14 |
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| H = 14 |
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| Cl = 1 |
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| N = 3}} |
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}} |
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}} |
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'''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. |
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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. |
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==Uses== |
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===Medical use=== |
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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> |
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===Other uses=== |
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Acriflavine is used in biochemistry for fluorescently labeling high molecular weight RNA.<ref name=Sigma/> |
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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> |
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==Research== |
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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> |
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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> |
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==Legal status== |
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===Australia=== |
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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}} |
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==References== |
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{{Reflist}} |
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==External links== |
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* {{Commons category-inline}} |
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* |
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] |
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] |
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] |