AntibioticMech

sulfamethoxazole

CHEBI:9332 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position. — ChEBI

Classification

sulfonamide antibioticARO:3000282

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:35358 CHEBI:35358
• CHEBI:48975 CHEBI:48975
• CHEBI:55373 CHEBI:55373
• CHEBI:87228 CHEBI:87228
• ARO:3000282 ARO:3000282

Chemical structure

Computed structure properties

Molecular formula	C10H11N3O3S
Charge	0
Average mass	253.283 Da
Monoisotopic mass	253.05211 Da
Source	ChEBI
InChIKey	JLKIGFTWXXRPMT-UHFFFAOYSA-N

SMILES

Cc1cc(NS(=O)(=O)c2ccc(N)cc2)no1

InChI

InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)

Also called

• 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide (EXACT_SYNONYM)— chebi
• 3-(p-Aminophenylsulfonamido)-5-methylisoxazole (EXACT_SYNONYM)— chebi
• 3-Sulfanilamido-5-methylisoxazole (EXACT_SYNONYM)— chebi
• 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide (EXACT_SYNONYM)— chebi
• Gantanol (TN) (EXACT_SYNONYM)— chebi
• SMX (EXACT_SYNONYM)— chebi
• Sulfamethoxazole (EXACT_SYNONYM)— chebi
• sulphamethoxazole (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3000329
• cas:723-46-6
• drugbank:DB01015
• drugcentral:2514
• gmelin:226453
• hmdb:HMDB0015150
• kegg.compound:C07315
• kegg.drug:D00447
• lincs.smallmolecule:LSM-5422
• reaxys:226453
• wikipedia.en:Sulfamethoxazole
• chembl:CHEMBL443
• pubchem.compound:5329

Activity roles

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

• CHEBI:33281 CHEBI:33281
• CHEBI:33282 CHEBI:33282

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:3000329	sulfamethoxazole	antibioticmech:aro-2120ad1e5a	2026-08-30
CHEBI	CHEBI:9332	sulfamethoxazole	antibioticmech:chebi-8619bfe622	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:3000329 (sulfamethoxazole); 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

8 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 4

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:3000329 (sulfamethoxazole); database assertion, not a primary citation.)
sul2	ARO:3000412	not organism-specific	—	ARO:3000412 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000329 (sulfamethoxazole); database assertion, not a primary citation.)
sul3	ARO:3000413	not organism-specific	—	ARO:3000413 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000329 (sulfamethoxazole); database assertion, not a primary citation.)
sul4	ARO:3004361	not organism-specific	—	ARO:3004361 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000329 (sulfamethoxazole); database assertion, not a primary citation.)

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:3000329 (sulfamethoxazole); database assertion, not a primary citation.)
Salmonella gallinarum folP with mutation conferring resistance to sulfonamides	ARO:3007749	not organism-specific	—	ARO:3007749 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000329 (sulfamethoxazole); 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:3000329 (sulfamethoxazole); database assertion, not a primary citation.)

UNKNOWN 1

UNKNOWN

Determinant	ARO ID	Organism	Gene families	Evidence
ThfT	ARO:3007427	not organism-specific	—	ARO:3007427 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000329 (sulfamethoxazole); database assertion, not a primary citation.)

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. 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.