Prontosil

Overview

Prontosil is an antibacterial drug of the sulfonamide group. It has a relatively broad effect against gram-positive cocci but not against enterobacteria. One of the earliest antimicrobial drugs, it was widely used in the mid-20th century but is little used today because better options now exist. The discovery and development of this first sulfonamide-containing drug opened a new era in medicine, because it greatly widened the success of antimicrobial chemotherapy in an era when many physicians doubted its still largely untapped potential. At the time, disinfectant cleaners and topical antiseptic wound care were widely used but there were very few antimicrobial drugs to use safely inside living bodies. Antibiotic drugs derived from microbes, which are relied on heavily today, did not yet exist. Prontosil was discovered in 1932 by a research team at the Bayer Laboratories of the IG Farben conglomerate in Germany led by Gerhard Domagk. Domagk received the 1939 Nobel Prize in Physiology or Medicine for that discovery.[1][2][3] WP

History

History

This compound was first synthesized by Bayer chemists Josef Klarer and Fritz Mietzsch as part of a research program designed to find dyes that might act as antibacterial drugs in the body. The molecule was tested and in the late autumn of 1932 was found effective against some important bacterial infections in mice by Gerhard Domagk, who subsequently received the 1939 Nobel Prize in Medicine. Prontosil was the result of five years of testing involving thousands of compounds related to azo dyes. WP

The crucial test result (in a murine model of Streptococcus pyogenes systemic infection) that preliminarily established the antibacterial efficacy of Prontosil in mice dates from late December 1931. IG Farben filed a German patent application concerning its medical utility on December 25, 1932. The synthesis of the compound had been first reported by Paul Gelmo, a chemistry student working at the University of Vienna in his 1909 thesis, although he had not realized its medical potential.[4] WP

The readily water-soluble sodium salt of sulfonamidochrysoidine, which gives a burgundy red solution and was trademarked Prontosil Solubile, was clinically investigated between 1932 and 1934, first at the nearby hospital at Wuppertal-Elberfeld headed by Philipp Klee, and then at the Düsseldorf University Hospital. The results were published in a series of articles in the February 15, 1935 issue of Germany's then preeminent medical scientific journal, Deutsche Medizinische Wochenschrift, and were initially received with some skepticism by a medical community bent on vaccination and crude immunotherapy.[5] WP⚠ Wikipedia itself has flagged this text: clarification needed.

Leonard Colebrook introduced it as a cure for puerperal fever. As impressive clinical successes with Prontosil started to be reported from all over Europe, and especially after a widely published treatment in 1936 of Franklin Delano Roosevelt, Jr. (a son of U.S. president Franklin D. Roosevelt), acceptance was quick and dozens of medicinal chemistry teams set out to improve Prontosil.[6][7][8] WP

Chemistry

Formula

C12H13N5O2S PC

CAS number

103-12-8 PC

Molar mass (g/mol)

291.33 PC

IUPAC name (computed by PubChem)

4-[(2,4-diaminophenyl)diazenyl]benzenesulfonamide PC

SMILES

C1=CC(=CC=C1N=NC2=C(C=C(C=C2)N)N)S(=O)(=O)N PC

InChIKey

ABBQGOCHXSPKHJ-UHFFFAOYSA-N PC

PubChem CID

66895

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Hager, Thomas. The Demon Under the Microscope: From Battlefield Hospitals to Nazi Labs, One Doctor's Heroic Search for the World's First Miracle Drug. 2006
2. Other Oxford Handbook of Infectious Diseases and Microbiology. 2009
3. Other Physiology or Medicine 1939 – Presentation Speech
4. Other Lesch JE. The first miracle drugs: how the sulfa drugs transformed medicine. 2007
5. Journal / agency Domagk G. Ein Beitrag zur Chemotherapie der bakteriellen Infektionen. Dtsch. Med. Wochenschr. 15 February 1935. doi:10.1055/s-0028-1129486
6. Journal / agency Dunn PM. Dr Leonard Colebrook, FRS (1883-1967) and the chemotherapeutic conquest of puerperal infection. Archives of Disease in Childhood. Fetal and Neonatal Edition. May 2008. doi:10.1136/adc.2006.104448 · PMID 18426926
7. Journal / agency Rubin RP. A brief history of great discoveries in pharmacology: in celebration of the centennial anniversary of the founding of the American Society of Pharmacology and Experimental Therapeutics. Pharmacological Reviews. December 2007. doi:10.1124/pr.107.70102 · PMID 18160700
8. Other Medicine: Prontosil. December 28, 1936

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.