sulfamethizole

CHEBI:9331 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A sulfonamide consisting of a 1,3,4-thiadiazole nucleus with a methyl substituent at C-5 and a 4-aminobenzenesulfonamido group at C-2. — 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:38099 CHEBI:38099
CHEBI:87228 CHEBI:87228
ARO:3000282 ARO:3000282

Chemical structure

Computed structure properties
Molecular formula	C9H10N4O2S2
Charge	0
Average mass	270.339 Da
Monoisotopic mass	270.02452 Da
Source	ChEBI
InChIKey	VACCAVUAMIDAGB-UHFFFAOYSA-N

SMILES

Cc1nnc(NS(=O)(=O)c2ccc(N)cc2)s1

InChI

InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)

Also called

Rufol (BRAND_NAME)— chebi
sulfamethizolum (INN)— chebi
sulfametizol (INN)— chebi
sulfaméthizol (INN)— chebi
4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide (EXACT_SYNONYM)— chebi
Sulfamethizole (EXACT_SYNONYM)— chebi
sulfamethylthiadiazole (EXACT_SYNONYM)— chebi
sulphamethazole (EXACT_SYNONYM)— chebi
sulphamethiozole (EXACT_SYNONYM)— chebi
Urolucosil (EXACT_SYNONYM)— aro
sulfamethizol (EXACT_SYNONYM)— aro
sulphamethizole (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000699
cas:144-82-1
drugbank:DB00576
drugcentral:2512
kegg.compound:C08050
kegg.drug:D00870
lincs.smallmolecule:LSM-5455
patent:US2447702
reaxys:255002
wikipedia.en:Sulfamethizole
chembl:CHEMBL1191
pubchem.compound:5328

Activity roles

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

CHEBI:33281 CHEBI:33281

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:3000699`	sulfamethizole	`antibioticmech:aro-c36c766b6e`	2026-08-30
CHEBI	`CHEBI:9331`	sulfamethizole	`antibioticmech:chebi-7edf5cc5fa`	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:3000699 (sulfamethizole); database assertion, not a primary citation.)

Mechanism summary

Mode of action: FOLATE_PATHWAY_INHIBITION microbial target — Assigned from ChEBI role CHEBI:50502 (EC 2.5.1.15 (dihydropteroate synthase) inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.
Clinical status: APPROVED

Resistance mechanisms

5 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_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:3000699 (sulfamethizole); database assertion, not a primary citation.)
sul2	ARO:3000412	not organism-specific	—	ARO:3000412 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000699 (sulfamethizole); database assertion, not a primary citation.)
sul3	ARO:3000413	not organism-specific	—	ARO:3000413 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000699 (sulfamethizole); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 2

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:3000699 (sulfamethizole); 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:3000699 (sulfamethizole); 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.