sulfamethazine

CHEBI:102265 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-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.

CHEBI:35358 CHEBI:35358
CHEBI:39447 CHEBI:39447
CHEBI:87228 CHEBI:87228
ARO:3000282 ARO:3000282

Chemical structure

Computed structure properties
Molecular formula	C12H14N4O2S
Charge	0
Average mass	278.337 Da
Monoisotopic mass	278.08375 Da
Source	ChEBI
InChIKey	ASWVTGNCAZCNNR-UHFFFAOYSA-N

SMILES

Cc1cc(C)nc(NS(=O)(=O)c2ccc(N)cc2)n1

InChI

InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)

Also called

sulfadimidina (INN)— chebi
sulfadimidine (INN)— chebi
sulfadimidinum (INN)— chebi
4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (EXACT_SYNONYM)— chebi
(p-Aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidin (EXACT_SYNONYM)— chebi
2-(4-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine (EXACT_SYNONYM)— chebi
2-(p-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine (EXACT_SYNONYM)— chebi
2-Sulfanilamido-4,6-dimethylpyrimidine (EXACT_SYNONYM)— chebi
4,6-Dimethyl-2-sulfanilamidopyrimidine (EXACT_SYNONYM)— chebi
4-Amino-N-(2,6-dimethyl-4-pyrimidinyl)benzenesulfonamide (EXACT_SYNONYM)— chebi
4-Amino-N-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide (EXACT_SYNONYM)— chebi
6-(4'-Aminobenzol-sulfonamido)-2,4-dimethylpyrimidin (EXACT_SYNONYM)— chebi
N-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide (EXACT_SYNONYM)— chebi
N1-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide (EXACT_SYNONYM)— chebi
N1-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide (EXACT_SYNONYM)— chebi
SMZ (EXACT_SYNONYM)— chebi
Sulfadimethyldiazine (EXACT_SYNONYM)— chebi
Sulfadimethylpyrimidine (EXACT_SYNONYM)— chebi
Sulfametazina (EXACT_SYNONYM)— chebi
Sulfametazyny (EXACT_SYNONYM)— chebi
Sulfamezathine (EXACT_SYNONYM)— chebi
Sulphadimethylpyrimidine (EXACT_SYNONYM)— chebi
Sulphamethazine (EXACT_SYNONYM)— chebi
sulfamethazone (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000325
cas:57-68-1
drugbank:DB01582
drugcentral:2502
gmelin:1009759
hmdb:HMDB0015522
kegg.compound:C19530
kegg.drug:D02436
lincs.smallmolecule:LSM-5295
patent:EP1861101
patent:GB546158
patent:GB552887
patent:US2407966
patent:US3119818
patent:WO2005016386
reaxys:261304
vsdb:1829
wikipedia.en:Sulfadimidine
chembl:CHEMBL446
pubchem.compound:5327

Activity roles

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

CHEBI:33281 CHEBI:33281
CHEBI:36047 CHEBI:36047

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:3000325`	sulfadimidine	`antibioticmech:aro-ea37816ce5`	2026-08-30
CHEBI	`CHEBI:102265`	sulfamethazine	`antibioticmech:chebi-0baecafe50`	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:3000325 (sulfadimidine); 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.

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:3000325 (sulfadimidine); database assertion, not a primary citation.)
sul2	ARO:3000412	not organism-specific	—	ARO:3000412 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000325 (sulfadimidine); database assertion, not a primary citation.)
sul3	ARO:3000413	not organism-specific	—	ARO:3000413 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000325 (sulfadimidine); 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:3000325 (sulfadimidine); 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:3000325 (sulfadimidine); 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.