AntibioticMech

sulfadiazine

CHEBI:9328 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position. — ChEBI

Classification

sulfonamide antibioticARO:3000282

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:35358 CHEBI:35358
• CHEBI:39447 CHEBI:39447
• CHEBI:48975 CHEBI:48975
• CHEBI:87228 CHEBI:87228
• ARO:3000282 ARO:3000282

Chemical structure

Computed structure properties

Molecular formula	C10H10N4O2S
Charge	0
Average mass	250.283 Da
Monoisotopic mass	250.05245 Da
Source	ChEBI
InChIKey	SEEPANYCNGTZFQ-UHFFFAOYSA-N

SMILES

Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1

InChI

InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)

Also called

• sulfadiazina (INN)— chebi
• sulfadiazinum (INN)— chebi
• 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide (EXACT_SYNONYM)— chebi
• 2-sulfanilamidopyrimidine (EXACT_SYNONYM)— chebi
• 2-sulfanilylaminopyrimidine (EXACT_SYNONYM)— chebi
• 4-amino-N-2-pyrimidinylbenzenesulfonamide (EXACT_SYNONYM)— chebi
• N1-2-pyrimidinylsulfanilamide (EXACT_SYNONYM)— chebi
• N1-2-pyrimidylsulfanilamide (EXACT_SYNONYM)— chebi
• Sulfadiazine (EXACT_SYNONYM)— chebi
• sulfadiazin (EXACT_SYNONYM)— chebi
• sulfapyrimidine (EXACT_SYNONYM)— chebi
• sulphadiazine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3000324
• cas:68-35-9
• drugbank:DB00359
• drugcentral:2500
• gmelin:219136
• hmdb:HMDB0014503
• kegg.compound:C07658
• kegg.drug:D00587
• lincs.smallmolecule:LSM-5457
• patent:GB557055
• patent:US2407966
• patent:US2410793
• reaxys:235192
• vsdb:1740
• wikipedia.en:Sulfadiazine
• chembl:CHEMBL439
• pubchem.compound:5215

Activity roles

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

• CHEBI:33281 CHEBI:33281
• CHEBI:35818 CHEBI:35818
• CHEBI:35820 CHEBI:35820

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:3000324	sulfadiazine	antibioticmech:aro-ed0c0a5de0	2026-08-30
CHEBI	CHEBI:9328	sulfadiazine	antibioticmech:chebi-7bdd9ca88f	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:3000324 (sulfadiazine); 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:3000324 (sulfadiazine); database assertion, not a primary citation.)
sul2	ARO:3000412	not organism-specific	—	ARO:3000412 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000324 (sulfadiazine); database assertion, not a primary citation.)
sul3	ARO:3000413	not organism-specific	—	ARO:3000413 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000324 (sulfadiazine); 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:3000324 (sulfadiazine); 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:3000324 (sulfadiazine); 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.