sulfisoxazole

CHEBI:102484 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A sulfonamide antibacterial with an oxazole substituent. It has antibiotic activity against a wide range of gram-negative and gram-positive organisms. — 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

sulfonamide antibioticARO:3000282

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:35358 CHEBI:35358
CHEBI:55373 CHEBI:55373
CHEBI:87228 CHEBI:87228
ARO:3000282 ARO:3000282

Chemical structure

Computed structure properties
Molecular formula	C11H13N3O3S
Charge	0
Average mass	267.31 Da
Monoisotopic mass	267.06776 Da
Source	ChEBI
InChIKey	NHUHCSRWZMLRLA-UHFFFAOYSA-N

SMILES

Cc1noc(NS(=O)(=O)c2ccc(N)cc2)c1C

InChI

InChI=1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3

Also called

sulfafurazole (INN)— chebi
sulfafurazolum (INN)— chebi
4-amino-N-(3,4-dimethylisoxazol-5-yl)benzenesulfonamide (EXACT_SYNONYM)— chebi
3,4-Dimethyl-5-sulfanilamidoisoxazole (EXACT_SYNONYM)— chebi
3,4-Dimethyl-5-sulfonamidoisoxazole (EXACT_SYNONYM)— chebi
3,4-Dimethyl-5-sulphanilamidoisoxazole (EXACT_SYNONYM)— chebi
3,4-Dimethyl-5-sulphonamidoisoxazole (EXACT_SYNONYM)— chebi
3,4-Dimethylisoxazole-5-sulfanilamide (EXACT_SYNONYM)— chebi
3,4-Dimethylisoxazole-5-sulphanilamide (EXACT_SYNONYM)— chebi
4-Amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide (EXACT_SYNONYM)— chebi
4-Amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulphonamide (EXACT_SYNONYM)— chebi
5-(4-Aminophenylsulfonamido)-3,4-dimethylisoxazole (EXACT_SYNONYM)— chebi
5-(p-Aminobenzenesulfonamido)-3,4-dimethylisoxazole (EXACT_SYNONYM)— chebi
5-(p-Aminobenzenesulphonamido)-3,4-dimethylisoxazole (EXACT_SYNONYM)— chebi
5-Sulfanilamido-3,4-dimethylisoxazole (EXACT_SYNONYM)— chebi
5-Sulphanilamido-3,4-dimethyl-isoxazole (EXACT_SYNONYM)— chebi
N'-(3,4)Dimethylisoxazol-5-yl-sulphanilamide (EXACT_SYNONYM)— chebi
N1-(3,4-dimethyl-5-isoxazolyl)sulfanilamide (EXACT_SYNONYM)— chebi
N1-(3,4-dimethyl-5-isoxazolyl)sulphanilamide (EXACT_SYNONYM)— chebi
Sulfadimethylisoxazole (EXACT_SYNONYM)— chebi
Sulfafurazol (EXACT_SYNONYM)— chebi
Sulfaisoxazole (EXACT_SYNONYM)— chebi
Sulfasoxazole (EXACT_SYNONYM)— chebi
Sulfisonazole (EXACT_SYNONYM)— chebi
Sulfisoxasole (EXACT_SYNONYM)— chebi
Sulfisoxazol (EXACT_SYNONYM)— chebi
Sulfofurazole (EXACT_SYNONYM)— chebi
Sulphadimethylisoxazole (EXACT_SYNONYM)— chebi
Sulphafurazol (EXACT_SYNONYM)— chebi
Sulphafurazole (EXACT_SYNONYM)— chebi
Sulphaisoxazole (EXACT_SYNONYM)— chebi
Sulphisoxazol (EXACT_SYNONYM)— chebi
Sulphofurazole (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000330
beilstein:263871
cas:127-69-5
drugbank:DB00263
drugcentral:2529
gmelin:864477
kegg.compound:C07318
kegg.drug:D00450
lincs.smallmolecule:LSM-3120
patent:US2430094
wikipedia.en:Sulfisoxazole
chembl:CHEMBL453
pubchem.compound:5344

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
ARO	`ARO:3000330`	sulfisoxazole	`antibioticmech:aro-532eb18065`	2026-08-30
CHEBI	`CHEBI:102484`	sulfisoxazole	`antibioticmech:chebi-6e3f755bcb`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

antibiotic sensitive dihydropteroate synthase PROTEIN DIRECT_BINDING_TARGET

ARO:3000744

CARD/ARO database assertion; target organism, strain, and assay are not specified. Dihydropteroate synthase is asserted as the inhibited enzyme. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000744 (CARD/ARO asserts targeted_by_antibiotic ARO:3000330 (sulfisoxazole); database assertion, not a primary citation.)

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

6 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_TARGET_ALTERATION 3

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Escherichia coli folP with mutation conferring resistance to sulfonamides	ARO:3003386	not organism-specific	—	ARO:3003386 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000330 (sulfisoxazole); database assertion, not a primary citation.)
Neisseria gonorrhoeae folP with mutation conferring resistance to sulfonamides	ARO:3004873	not organism-specific	—	ARO:3004873 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000330 (sulfisoxazole); database assertion, not a primary citation.)
Streptococcus pyogenes folP with mutation conferring resistance to sulfonamides	ARO:3003387	not organism-specific	—	ARO:3003387 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000330 (sulfisoxazole); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_REPLACEMENT 3

ANTIBIOTIC_TARGET_REPLACEMENT
Determinant	ARO ID	Organism	Gene families	Evidence
sul1	ARO:3000410	not organism-specific	—	ARO:3000410 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000330 (sulfisoxazole); database assertion, not a primary citation.)
sul2	ARO:3000412	not organism-specific	—	ARO:3000412 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000330 (sulfisoxazole); database assertion, not a primary citation.)
sul3	ARO:3000413	not organism-specific	—	ARO:3000413 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000330 (sulfisoxazole); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, 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
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · 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.