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neosalvarsan
Sign in to saveAlso known as Neosalvarsán
Neosalvarsan (also known as neoarsphenamine) is a synthetic chemotherapeutic that is an organoarsenic compound. It became available in 1912 and superseded the more toxic and less water-soluble Salvarsan as an effective treatment for syphilis. Because both of these arsenicals carried considerable risk of side effects, they were replaced for this indication by penicillin in the 1940s.
Chemical data
- Formula
- C13H13As2N2NaO4S
- Molecular weight
- 466.15 g/mol
- IUPAC name
- sodium [5-(3-amino-4-hydroxyphenyl)arsanylidenearsanyl-2-hydroxyanilino]methanesulfinate
- SMILES
- C1=CC(=C(C=C1[As]=[As]C2=CC(=C(C=C2)O)NCS(=O)[O-])N)O.[Na+]
- InChIKey
- BGYSJUFVJUJSOL-UHFFFAOYSA-M
- Polar surface area
- 138 Ų
- H-bond donors
- 4
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
161 papers- Neosalvarsan.The Indian medical gazette · 1929
- Neosalvarsan.Journal of the National Medical Association · 1912
- Neosalvarsan.Buffalo medical journal · 1912
- Neo-Salvarsan.The Indian medical gazette · 1912
- [Fixed neosalvarsan exanthem].Zeitschrift fur Haut- und Geschlechtskrankheiten · 1950
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 465.892565
Show 4 more facts
- chemical formula
- C₁₃H₁₃As₂N₂NaO₄S
- Commons category
- Neosalvarsan
- canonical SMILES
- C1=CC(=C(C=C1[As]=[As]C2=CC(=C(C=C2)O)NCS(=O)[O-])N)O.[Na+]
- isomeric SMILES
- C1=CC(=C(C=C1/[As]=[As]/C2=CC=C(C(=C2)NCS(=O)[O-])O)N)O.[Na+]
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Neosalvarsan (also known as neoarsphenamine) is a synthetic chemotherapeutic that is an organoarsenic compound. It became available in 1912 and superseded the more toxic and less water-soluble Salvarsan as an effective treatment for syphilis. Because both of these arsenicals carried considerable risk of side effects, they were replaced for this indication by penicillin in the 1940s.
Both Salvarsan and Neosalvarsan were developed in the laboratory of Paul Ehrlich in Frankfurt, Germany. Their discoveries were the result of the first organized team effort to optimize the biological activity of a lead compound through systematic chemical modifications. This scheme is the basis for most modern pharmaceutical research. Both Salvarsan and Neosalvarsan are prodrugsthat is, they are metabolised into the active drug in the body.
Excerpted from Wikipedia’s “neosalvarsan” article, available under the CC BY-SA 4.0 licence.