Sulfamidochrysoidin

Structural formula
General
Surname	Sulfamidochrysoidin
other names	4 - [(2,4-diaminophenyl) diazenyl] benzenesulfonamide ( IUPAC ) Prontosil Rubiazole
Molecular formula	C 12 H 13 N 5 O 2 S C 12 H 13 N 5 O 2 S HCl (hydrochloride)
External identifiers / databases
CAS number 103-12-8 33445-35-1 ( hydrochloride ) EC number 203-081-2 ECHA InfoCard 100.002.802 PubChem 66895 ChemSpider 16736190 Wikidata Q418758
Drug information
Drug class	Sulfonamides
properties
Molar mass	291.33 g · mol -1 327.79 g · mol -1 (hydrochloride)
Physical state	firmly
Melting point	248–250 ° C (hydrochloride)
solubility	Hydrochloride: One g dissolves in 400 ml of water, significantly more in the heat. Soluble in ethanol , acetone , fats and oils.
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

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

This first chemotherapeutic agent , developed in 1932, was synthesized by Mietzsch and Klarer at Bayer in Wuppertal - Elberfeld . The special effectiveness against bacterial diseases was discovered in 1935 by the German doctor and bacteriologist Gerhard Domagk, also in 1932, but only published in 1935. Domagk received the Nobel Prize in Medicine in 1939 for discovering the antibacterial properties of Prontosil .

Sulfamidochrysoidin has an excellent antibacterial effect, mainly against streptococci , staphylococci and coli bacteria. As an azo dye (sulfachrysoidin) it causes the skin to turn yellow-red and the urine to turn dark red.

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

Sulfamidochrysoidin was the first drug from the group of sulfonamides. After the discovery of penicillin by Alexander Fleming , the sulfonamides were only used to a limited extent. During the Second World War, Prontosil was used extensively on the German side, as the penicillin was not yet available here. In the case of injuries - like penicillin on the Allied side - it was administered as a preventive measure against wound infections.

The drug is no longer on the market worldwide.

Individual evidence

1. ↑ External identifiers or database links for sulfamidochrysoidin hydrochloride : CAS number: 33445-35-1, PubChem : 71954678 , ChemSpider : 62896247 , Wikidata : Q27255091 .
2. ^ ^{A b} The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; Pp. 1530-1531, ISBN 978-0-911910-00-1 .
3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
4. ↑ Horst Kremling : About pregnancy and kidney. A review. In: Würzburger medical history reports 17, 1998, pp. 275–282; here: p. 277.
5. ^ John Lesch, The first miracle drugs, Oxford UP 2007
6. ^ Gerhard Domagk (1935): A contribution to the chemotherapy of bacterial infections. In: German Medical Weekly. Vol. 61, p. 250.
7. ^ E. Grundmann (2001): Gerhard Domagk. A pathologist conquers the bacterial infectious diseases. In: The Pathologist. Vol. 22, pp. 241-251, doi : 10.1007 / s002920100469 .
8. ^ Information from the Nobel Foundation on the awarding of the award to Gerhard Domagk in 1939 (English).
9. ↑ J. et T. Tréfouël, F. Nitti and D. Bovet, "Activité du p -aminophénylsulfamide sur l'infection streptococcique expérimentale de la souris et du lapin", CR Soc. Biol. , 120 , November 23, 1935, p. 756.
10. ↑ ABDA database (as of December 6, 2009).

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !