Prontosil

4 - ( 2,4- diaminophenyl ) - diazenylbenzensulfonamid

• C12H13N5O2S
• C12H13N5O2S · HCl (hydrochloride)

Sulfonamides

• 291.33 g · mol -1
• 327.79 g.mol -1 (hydrochloride)

248-250 ° C ( hydrochloride)

Hydrochloride: A g dissolves in 400 ml of water in the heat significantly more. Insoluble in ethanol, acetone, fats and oils.

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Sulfamidochrysoidin (trade name Prontosil ®) is an azo dye ( Sulfachrysoidin ) and the first drug from the group of the sulfonamides.

It was first synthesized in 1934 by Mietzsch and Clear at Bayer, Wuppertal -Elberfeld. The particular effectiveness against bacterial disease was discovered in 1935 by the German physician and bacteriologist Gerhard Domagk. For the discovery of the antibacterial activity of Prontosil Domagk was awarded the 1939 Nobel Prize for Medicine.

Sulfamidochrysoidin has excellent antibacterial activity mainly against streptococci, staphylococci and coli bacteria. As azo dye ( Sulfachrysoidin ) it causes a yellow skin and a dark red Harnfärbung.

Jacques and Thérèse Tréfouël, Federico Nitti and Daniel Bovet at the Pasteur Institute in 1935 showed that Sulfamidochrysoidin is only a prodrug that is metabolized in the body to sulfanilamide (p- Aminophenylsulfonamid ).

Sulfamidochrysoidin is the first drug from the group of the sulfonamides. However, they are only used to a limited extent, since Fleming's discovery of penicillin it has replaced. Prontosil was used extensively in World War II on the German side, as it did not yet have here on penicillin. It was for injuries - such as on the Allied side penicillin - administered preventively against wound infections.

The drug is no longer in world trade.