prontosil

CHEBI:8464 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:22682 CHEBI:22682
CHEBI:35358 CHEBI:35358

Chemical structure

Computed structure properties
Molecular formula	C12H13N5O2S
Charge	0
Average mass	291.336 Da
Monoisotopic mass	291.079 Da
Source	ChEBI
InChIKey	ABBQGOCHXSPKHJ-WUKNDPDISA-N

SMILES

Nc1ccc(/N=N/c2ccc(S(N)(=O)=O)cc2)c(N)c1

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+

Also called

4-[(2,4-diaminophenyl)diazenyl]benzenesulfonamide (EXACT_SYNONYM)— chebi
Prontosil (EXACT_SYNONYM)— chebi
Prontosil rubrum (EXACT_SYNONYM)— chebi
Rubiazol (EXACT_SYNONYM)— chebi
Sulfamidochrysoidine (EXACT_SYNONYM)— chebi
p-((2,4-Diaminophenyl)azo)benzenesulphonamide (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:103-12-8
drugcentral:3561
kegg.compound:C07573
kegg.drug:D08542
patent:DE607537
patent:US2085037
reaxys:757127
wikipedia.en:Prontosil

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281
CHEBI:36047 CHEBI:36047

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:8464`	prontosil	`antibioticmech:chebi-2190edc2f6`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.