Skip to content
(EZ)-prontosil

Structure via PubChem · Public domain (PubChem)

EntityQ418758· pop 23· linked from 182 articles

(EZ)-prontosil

Sign in to save

Also known as prontosil

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 antisept

Chemical data

Formula
C12H13N5O2S
Molecular weight
291.33 g/mol
IUPAC name
4-[(2,4-diaminophenyl)diazenyl]benzenesulfonamide
SMILES
C1=CC(=CC=C1N=NC2=C(C=C(C=C2)N)N)S(=O)(=O)N
InChIKey
ABBQGOCHXSPKHJ-UHFFFAOYSA-N
XLogP
0.9
Polar surface area
145 Ų
H-bond donors
3
H-bond acceptors
7
Formal charge
0

via PubChem

~7 min read

Encyclopedic overview

5 sections
Contents
  • Names
  • History
  • Eclipse and legacy
  • References
  • Further reading

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.

==Names== The capitalized name "Prontosil" is Bayer's trade name; the nonproprietary names include . Because the drug predates the modern system of drug nomenclature, which ensures that nonproprietary names are well known from the inception of marketing, it was generally known among the public only by its trade name, and the trade name was the origin of some of the nonproprietary names (as also happened with "aspirin").

Excerpted from Wikipedia’s “(EZ)-prontosil” article, available under the CC BY-SA 4.0 licence.

Gallery (3)