Arsphenamines

Unconjugated hyperbilirubinemia can result from toxin-induced liver dysfunction such as that caused by chloroform, arsphenamines, carbon tetrachloride, acetaminophen, hepatitis virus, cirrhosis, and Amanita... 

Another organic compound of arsenic that is of historical significance was discovered in 1901 by P. Ehrlich. That compound is known as arsphenamine or Salvarsan, which has the structure... 

Arsphenamin was the first drug substance with thermotropic mesomorphism [19] to be used therapeutically as Salvarsan during the first half of the 19th century. This drug is effective against microorganisms and offered for the first time a therapy for venereal diseases. Today it has been replaced by antibiotics with less serious side effects. 

The molecular structure of arsphenamin is a typical representative of a thermotropic mesogen. With its symmetrical arrangement of the atoms the same holds for disodium cromoglycate, DNCG [20], which forms both thermotropic liquid crystals and lyotropic mesophases in the presence of water. Micronized DNCG powder applied to the mucosa of the nose or the bronchi absorbs water from the high relative humidity of the respiration tract and is first transformed into a lyotropic mesophase and then into a solution depending on the amount of water available. 

Freundlieh, H., Stern, R., and Zoeher, H., The eolloidal ehemistry of arsphenamine and neoars-phsnamme, Biochem. Z., 138 307-317 (1923). 

Under the intellectual leadership of Paul Ehrlich, the dye industry provided arsphenamine, the first effective agent against syphilis. Syphilis is an infectious disease spread by sexual contact. It is caused by the spirochete Treponema pallidum. Syphilis runs various courses over many years and can result in death if not treated. Penicillins are now the dmgs of choice for syphilis. Chemists discovered two other medicinal agents in the early years of the twentieth century tryparsamide for trypanosomiasis, a parasitic disease, and oxophenarsine, also for syphilis. 

The compound arsphenamine is also called compound 606 because it was the 606th arsenic compound that Paul Ehrlich (1854-1915) had synthesized for use in treating diseases. His assistant found this compound to be effective as a treatment for syphilis. Ehrlich also coined the word chemotherapy. ... 

Following the discovery of arsphenamine (Salvarsan) in Germany in 1907, it was imported into the United Kingdom until the beginning of World War 1, when the Board of Trade issued licences to certain British manufacturers... 

A virus, therapeutic serum, toxin, antitoxin, vaccine, blood, blood component or derivative, allergenic product or analogous product, or arsphenamine or its derivatives or any other trivalent organic arsenic compound applicable to the prevention, cure or treatment of disease or conditions of human beings... 

Paul Ehrlich s "magic bullet" for syphilis (arsphenamine, Salvarsan) was an arsenical. 

Spiegel L. 1931. A discoloration of the skin and mucous membranes resembling argyria, following the use of bismuth and silver arsphenamine. Archives of Dermatology and syphilology 23 266-286. 

Ehrlich s approach to developing arsphenamine involved extensive screening studies on each newly prepared compound. Information gained from earlier screens helped determine the structure of the next compound to be synthesized. This iterative method is the predominant method for modem lead optimization in medicinal chemistry. Under his method, Ehrlich s antibacterial research continued to progress and ultimately resulted in the discovery of the sulfa drugs. 

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