CHEBI:8464 - prontosil

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ChEBI Name prontosil
ChEBI ID CHEBI:8464
Definition A diphenyldiazene compound having two amino substituents at the 2- and 4-positions and an aminosulphonyl substituent at the 4'-position. It was the first antibacterial drug, (introduced 1935) and the first of the sulfonamide antibiotics.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C12H13N5O2S
Net Charge 0
Average Mass 291.32900
Monoisotopic Mass 291.079
InChI InChI=1S/C12H13N5O2S/c13-8-1-6-12(11(14)7-8)17-16-9-2-4-10(5-3-9)20(15,18)19/h1-7H,13-14H2,(H2,15,18,19)/b17-16+
InChIKey ABBQGOCHXSPKHJ-WUKNDPDISA-N
SMILES Nc1ccc(c(N)c1)\N=N\c1ccc(cc1)S(N)(=O)=O
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antibacterial drug
A drug used to treat or prevent bacterial infections.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
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ChEBI Ontology
Outgoing prontosil (CHEBI:8464) has functional parent sulfanilamide (CHEBI:45373)
prontosil (CHEBI:8464) has role antibacterial drug (CHEBI:36047)
prontosil (CHEBI:8464) has role antimicrobial agent (CHEBI:33281)
prontosil (CHEBI:8464) is a azobenzenes (CHEBI:22682)
prontosil (CHEBI:8464) is a sulfonamide (CHEBI:35358)
IUPAC Name
4-[(2,4-diaminophenyl)diazenyl]benzenesulfonamide
Synonyms Sources
p-((2,4-Diaminophenyl)azo)benzenesulphonamide ChemIDplus
Prontosil KEGG COMPOUND
Prontosil rubrum KEGG COMPOUND
Rubiazol ChemIDplus
Sulfamidochrysoidine KEGG COMPOUND
Manual Xrefs Databases
3561 DrugCentral
C07573 KEGG COMPOUND
D08542 KEGG DRUG
DE607537 Patent
Prontosil Wikipedia
US2085037 Patent
View more database links
Registry Numbers Types Sources
103-12-8 CAS Registry Number KEGG COMPOUND
103-12-8 CAS Registry Number ChemIDplus
757127 Reaxys Registry Number Reaxys
757127 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
19283418 PubMed citation Europe PMC
20781405 PubMed citation Europe PMC
2080660 PubMed citation Europe PMC
Last Modified
22 February 2017