- /ɑːsˈfɛnəmaɪn/, /ɑːsˈfɛnəmiːn/
- In the context of "pharmaceutical drug|organic compound": A
phenolic amine derivative of arsenic that was used to treat
syphilis (under the
trade name of Salvarsan).
- 2001: The 606th compound was one that contained arsenic and was called arsphenamine. — Leslie Iversen, Drugs: A Very Short Introduction (Oxford 2001, p. 9)
Arsphenamine, also known as Salvarsan and 606, is a drug that was used to treat syphilis and trypanosomiasis. It was the first modern chemotherapeutic agent.
HistorySahachiro Hata discovered the anti-syphilitic activity 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 bullet" among 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 pharmaceutical research.
Arsphenamine was marketed under the trade name Salvarsan in 1910. It was also called 606, because it was the 606th compound synthesized for testing [In Germany it was the trend to designate compounds by their development number. Another compound known commonly in Germany by its number is Parathion, which was the 605th compound to be developed in search for insecticide. It is commonly known as E605 (E stands for Entwicklungsnummer (German for "development number")]. Salvarsan was the first organic anti-syphillitic, and a great improvement over the inorganic mercury compounds that had been used previously. A more soluble (but slightly less effective) arsenical compound, Neosalvarsan, (neoarsphenamine), became available in 1912. These arsenical compounds came with considerable risk of side effects, and they were supplanted as treatments for syphilis in the 1940s by penicillin.
The bacterium that 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.
After leaving Erlich's laboratory, Hata continued parallel investigation of the new medicine in Japan.
StructureThe structure was believed to feature an As=As bond. However, in 2005, it was shown to be a mixture of the cyclic trimer and a pentamer. The revised structure features As-As single bonds, not double bonds.
arsphenamine in German: Salvarsan
arsphenamine in Spanish: Arsfenamina
arsphenamine in Dutch: Arsfenamine
arsphenamine in Japanese: サルバルサン
arsphenamine in Polish: Salwarsan
arsphenamine in Romanian: Salvarsan