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Revision as of 08:53, 10 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wiki← Previous edit Latest revision as of 18:58, 7 November 2024 edit undoG3560 (talk | contribs)406 editsm capitalization 
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{{chembox {{chembox
| verifiedrevid = 444022959 | verifiedrevid = 444024073
|ImageFile=Neosalvarsan.svg | ImageFile=Neosalvarsan.svg
|ImageSize= | ImageSize=
|ImageFile2=Neosalvarsan-3D-vdW.png | ImageFile2=Neosalvarsan-3D-vdW.png
|IUPACName= | IUPACName=
|OtherNames= Sodium 3,3'-diamino-4,4'-dihydroxyarsenobenzene-N-formaldehydesulfoxylate; Neoarsphenamine;914 | OtherNames= Sodium 3,3'-diamino-4,4'-dihydroxyarsenobenzene-N-formaldehydesulfoxylate; Neoarsphenamine;914
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9586 | ChemSpiderID = 9586
| InChI = 1/C13H14As2N2O4S.Na/c16-10-5-8(1-3-12(10)18)14-15-9-2-4-13(19)11(6-9)17-7-22(20)21;/h1-6,17-19H,7,16H2,(H,20,21);/q;+1/p-1 | InChI = 1/C13H14As2N2O4S.Na/c16-10-5-8(1-3-12(10)18)14-15-9-2-4-13(19)11(6-9)17-7-22(20)21;/h1-6,17-19H,7,16H2,(H,20,21);/q;+1/p-1
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BGYSJUFVJUJSOL-UHFFFAOYSA-M | StdInChIKey = BGYSJUFVJUJSOL-UHFFFAOYSA-M
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=457-60-3 | CASNo=457-60-3
| PubChem=9980 | PubChem=9980
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O7K7R0O4BG | UNII = O7K7R0O4BG
| SMILES = .S(=O)CNc2cc(/=/c1ccc(O)c(N)c1)ccc2O | SMILES = .S(=O)CNc2cc(/=/c1ccc(O)c(N)c1)ccc2O
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>13</sub>H<sub>13</sub>As<sub>2</sub>N<sub>2</sub>NaO<sub>4</sub>S | Formula=C<sub>13</sub>H<sub>13</sub>As<sub>2</sub>N<sub>2</sub>NaO<sub>4</sub>S
| MolarMass=466.15 g/mol | MolarMass=466.15 g/mol
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''Neosalvarsan''' is a synthetic ] that is an ]. It became available in 1912 and superseded the more toxic and less water-soluble ] as an effective treatment for ]. Because both of these arsenicals carried considerable risk of side effects, they were replaced for this indication by ] in the 1940s. '''Neosalvarsan''' is a synthetic ] that is an ]. It became available in 1912 and superseded the more toxic and less water-soluble ] as an effective treatment for ]. Because both of these arsenicals carried considerable risk of side effects, they were replaced for this indication by ] in the 1940s.


Both salvarsan and neosalvarsan were developed in the laboratory of ] in ], ]. Their discoveries were the result of the first organized team effort to optimize the biological activity of a ] through systematic chemical modifications.<ref>{{cite journal |author=Strebhardt K, Ullrich A |title=Paul Ehrlich's magic bullet concept: 100 years of progress |journal=Nat. Rev. Cancer |volume= 8|issue= 6|pages= 473|year=2008 |month=May |pmid=18469827 |doi=10.1038/nrc2394 |url=}}</ref> This scheme is the basis for most modern ] research. Both salvarsan and neosalvarsan are ]s — that is, they are ] into the active drug in the body. Both Salvarsan and Neosalvarsan were developed in the laboratory of ] in ], ]. Their discoveries were the result of the first organized team effort to optimize the ] of a ] through systematic chemical modifications.<ref>{{cite journal |vauthors=Strebhardt K, Ullrich A |title=Paul Ehrlich's magic bullet concept: 100 years of progress |journal=Nat. Rev. Cancer |volume= 8|issue= 6|pages= 473–480|date=May 2008 |pmid=18469827 |doi=10.1038/nrc2394 |s2cid=30063909 }}</ref> This scheme is the basis for most modern ] research. Both Salvarsan and Neosalvarsan are ]s{{snd}}that is, they are ] into the active drug in the body.


Although, like Salvarsan, it was originally believed to contain an arsenic-arsenic double bond, this is now known to be incorrect for Salvarsan.<ref>{{Cite journal|last1=Lloyd|first1=Nicholas C.|last2=Morgan|first2=Hugh W.|last3=Nicholson|first3=Brian K.|last4=Ronimus|first4=Ron S.|date=2005|title=The Composition of Ehrlich's Salvarsan: Resolution of a Century-Old Debate|journal=Angewandte Chemie International Edition|volume=44|issue=6|pages=941–944|doi=10.1002/anie.200461471|pmid=15624113|hdl=10289/207|issn=1521-3773|url=https://researchcommons.waikato.ac.nz/bitstream/10289/207/1/content.pdf|doi-access=free}}</ref> Presumably, Neosalvarsan also exists as a mixture of differently sized rings with arsenic-arsenic single bonds.
==Structure==
The structure of salvarsan, and of this derivative, was once believed to feature an As=As bond (as shown in the figure). In 2005, salvarsan was shown to be a mixture of the ] and a ].<ref>{{cite web |url=http://www1.accsnet.ne.jp/~kentaro/yuuki/mow/0501/salvarsan.html |title=accsnet.ne.jp |accessdate=2007-08-25 |format= |work= |archiveurl = http://web.archive.org/web/20070607150922/http://www1.accsnet.ne.jp/~kentaro/yuuki/mow/0501/salvarsan.html <!-- Bot retrieved archive --> |archivedate = 2007-06-07}}</ref><ref name="pmid15624113">{{cite journal |author=Lloyd NC, Morgan HW, Nicholson BK, Ronimus RS |title=The composition of Ehrlich's salvarsan: resolution of a century-old debate |journal=Angewandte Chemie International Edition in English |volume=44 |issue=6 |pages=941–4 |year=2005 |pmid=15624113 |doi=10.1002/anie.200461471}}</ref> The revised structure features As-As single bonds, not double bonds.


==References== ==References==
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