Arsphenamine

Arsphenamine is a drugthat was used to treat syphilisand trypanosomiasis. It was the first modern chemotherapeutic agent. Sahachiro Hatadiscovered the anti-syphiliticactivity of this compound in 1908 in the laboratory of Paul Ehrlich, during a survey of hundreds of newly-synthesized organic arsenical compounds. Ehrlich had theorized that by screening many compounds a drug could be discovered with anti-microbial activity. Ehrlich's team began their search for such a magic bulletamong chemical derivatives of the dangerously-toxic drug atoxyl. This was the first organized team effort to optimize the biological activity of a lead compound through systematic chemical modifications, the basis for nearly all modern pharmaceuticalresearch.

Arsphenamine was marketed under the trade nameSalvarsan in 1910. It was also called 606, because it was the 606th compound synthesized for testing. Salvarsan was the first organic anti-syphillitic, and a great improvement over the inorganic mercurycompounds that had been used previously. A more soluble (but slightly less effective) arsenicalcompound, Neosalvarsan, (neoarsphenamine), became available in 1912. These arsenicalcompounds came with considerable risk of side effects, and they were supplanted as treatments for syphilisin the 1940s by penicillin.

The bacteriumthat causes syphilis is a spirochete, Treponema pallidum. Arsphenamine is not toxic to spirochetes until it has been converted to an active form by the body, so the discovery of this drug could not have been made without Hata's animal testing. After leaving Erlich's laboratory, Hata continued parallel investigation of the new medicine in Japan.^{[{{fullurl:Template:FULLPAGENAME}}#endnote_Hata]}

The structure was believed to be:

Image:Arsphenamine.png

However, in 2005, researchers determined Arsphenamine's structure to be a compound of a cyclic trimer and a pentamer[1].

References

1. ^  Izumi, Yoshio; and Isozumi, Kazuo. (2001). Modern Japanese medical history and the European influence.Keio Journal of Medicine 50 (2), 91-99. PMID 11450598.
2. Nicholas C. Lloyd, Hugh W. Morgan, Prof., Brian K. Nicholson, Prof. *, Ron S. Ronimus, Dr. (2005). The Composition of Ehrlich's Salvarsan: Resolution of a Century-Old DebateAngewandte Chemie 117 (6), 963-966. PMID 15624113.
3. Yarnell, A. (2005) Salvarsan'Chemical and Engineering News' 83(25).de:Salvarsan

nl:Salvarsan pl:Salwarsan

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It uses material from the http://en.wikipedia.org/wiki/Arsphenamine Wikipedia article Arsphenamine.