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CHEBI:8464 - prontosil

ChEBI IDCHEBI:8464
ChEBI Nameprontosil
Stars
DefinitionA 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.
Last Modified22 February 2017
DownloadsMolfile
FormulaC12H13N5O2S
Net Charge0
Average Mass291.336
Monoisotopic Mass291.07900
SMILESNc1ccc(/N=N/c2ccc(S(N)(=O)=O)cc2)c(N)c1
InChIInChI=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+
InChIKeyABBQGOCHXSPKHJ-WUKNDPDISA-N
Wikipedia
Roles Classification
Biological Roles:
antibacterial drug  A drug used to treat or prevent bacterial infections.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
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  Source
ProntosilKEGG COMPOUND
Prontosil rubrumKEGG COMPOUND
SulfamidochrysoidineKEGG COMPOUND
p-((2,4-Diaminophenyl)azo)benzenesulphonamideChemIDplus
RubiazolChemIDplus
Manual XrefsDatabases
C07573KEGG COMPOUND
D08542KEGG DRUG
ProntosilWikipedia
DE607537Patent
US2085037Patent
3561DrugCentral
Registry NumbersSources
Reaxys:757127Reaxys
CAS:103-12-8KEGG COMPOUND
CAS:103-12-8ChemIDplus
Citations