prontosil (CHEBI:8464)

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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

Average Mass

291.32900

Monoisotopic Mass

291.07900

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.

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

Last Modified

22 February 2017