sulfadoxine

CHEBI:9329 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A sulfonamide consisting of pyrimidine having methoxy substituents at the 5- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position. In combination with the antiprotozoal pyrimethamine (CHEBI:8673) it is used as an antimalarial. — 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:39447 CHEBI:39447
ARO:3000282 ARO:3000282

Chemical structure

Computed structure properties
Molecular formula	C12H14N4O4S
Charge	0
Average mass	310.335 Da
Monoisotopic mass	310.07358 Da
Source	ChEBI
InChIKey	PJSFRIWCGOHTNF-UHFFFAOYSA-N

SMILES

COc1ncnc(NS(=O)(=O)c2ccc(N)cc2)c1OC

InChI

InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)

Also called

sulfadoxina (INN)— chebi
sulfadoxinum (INN)— chebi
4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide (EXACT_SYNONYM)— chebi
4-Sulfanilamido-5,6-dimethoxypyrimidine (EXACT_SYNONYM)— chebi
Sulfadoxine (EXACT_SYNONYM)— chebi
Sulforthomidine (EXACT_SYNONYM)— chebi
Sulphadoxine (EXACT_SYNONYM)— chebi
Sulphormethoxine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000327
cas:2447-57-6
drugbank:DB01299
drugcentral:2503
kegg.compound:C07630
kegg.drug:D00580
lincs.smallmolecule:LSM-5657
reaxys:625453
vsdb:1784
wikipedia.en:Sulfadoxine
chembl:CHEMBL1539
pubchem.compound:17134

Activity roles

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

CHEBI:36047 CHEBI:36047
CHEBI:38068 CHEBI:38068

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:3000327`	sulfadoxine	`antibioticmech:aro-f0cbe86f0c`	2026-08-30
CHEBI	`CHEBI:9329`	sulfadoxine	`antibioticmech:chebi-54357c52d5`	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:3000327 (sulfadoxine); database assertion, not a primary citation.)

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:3000327 (sulfadoxine); database assertion, not a primary citation.)
Pneumocystis jerovecii dhfr with mutations associated with resistance to pyrimethamine-sulfadoxine	ARO:3009285	not organism-specific	—	ARO:3009285 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000327 (sulfadoxine); 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:3000327 (sulfadoxine); 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:3000327 (sulfadoxine); database assertion, not a primary citation.)
sul2	ARO:3000412	not organism-specific	—	ARO:3000412 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000327 (sulfadoxine); database assertion, not a primary citation.)
sul3	ARO:3000413	not organism-specific	—	ARO:3000413 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000327 (sulfadoxine); 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

Provenance

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