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

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.

Label unavailable CHEBI:35358
Label unavailable CHEBI:48975
Label unavailable CHEBI:55373
sulfonamide antibiotic CHEBI:87228
sulfonamide antibiotic 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Sulfamethoxazole

Activity roles

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

antimicrobial agent CHEBI:33281
antibacterial agent 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 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

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

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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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