sulfathiazole

CHEBI:9337 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A 1,3-thiazole compound having 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

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:35358
Label unavailable CHEBI:38418
Label unavailable CHEBI:48975
sulfonamide antibiotic CHEBI:87228

Chemical structure

Computed structure properties
Molecular formula	C9H9N3O2S2
Charge	0
Average mass	255.324 Da
Monoisotopic mass	255.01362 Da
Source	ChEBI
InChIKey	JNMRHUJNCSQMMB-UHFFFAOYSA-N

SMILES

Nc1ccc(S(=O)(=O)Nc2nccs2)cc1

InChI

InChI=1S/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12)

Also called

Sulfatiazol (INN)— chebi
sulfathiazol (INN)— chebi
sulfathiazolum (INN)— chebi
4-amino-N-1,3-thiazol-2-ylbenzenesulfonamide (EXACT_SYNONYM)— chebi
2-(Sulfanilylamino)thiazole (EXACT_SYNONYM)— chebi
2-(p-Aminobenzenesulfonamido)thiazole (EXACT_SYNONYM)— chebi
2-(p-Aminobenzenesulphonamido)thiazole (EXACT_SYNONYM)— chebi
2-Sulfanilamidothiazol (EXACT_SYNONYM)— chebi
2-Sulfanilamidothiazole (EXACT_SYNONYM)— chebi
2-Sulfonamidothiazole (EXACT_SYNONYM)— chebi
4-Amino-N-2-thiazolylbenzenesulfonamide (EXACT_SYNONYM)— chebi
N1-2-Thiazolylsulfanilamide (EXACT_SYNONYM)— chebi
Sulfanilamidothiazole (EXACT_SYNONYM)— chebi
Sulphathiazole (EXACT_SYNONYM)— chebi
sulfthiazole (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.

Activity roles

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

antimicrobial agent CHEBI:33281

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
CHEBI	`CHEBI:9337`	sulfathiazole	`antibioticmech:chebi-8d169bfa8d`	2026-08-30

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

2 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
FolP-associated laboratory sulfathiazole resistance Laboratory comparisons show background dependence; FolP alone did not explain the full phenotype. UniProtKB:P0AC13 is reference-only, not the tested allele.	—	Escherichia coli `NCBITaxon:562`	folP	PMID:9449266 (Results; Figure 1; Table 2; Discussion; DOI:10.1128/aac.42.1.88.) UniProtKB:P0AC13 (Reference identity only: folP, b3177, JW3144; UniProtKB 2026_03, entry 147, sequence 1. K-12 NCBITaxon:83333 is reference context, not an experimental strain assignment.) Comparative susceptibility and enzyme-inhibition assays

UNKNOWN 1

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
Bcr-associated laboratory sulfathiazole resistance Laboratory association; direct efflux was not demonstrated. UniProtKB:P28246 is reference-only. Historical sequence differences remain unresolved; sux is not assigned to the bcr synonym suxA.	—	Escherichia coli `NCBITaxon:562`	bcr	PMID:9449266 (Results, Characterization of sur; Discussion; DOI:10.1128/aac.42.1.88.) UniProtKB:P28246 (Reference identity only: bcr, b2182, JW5363; UniProtKB 2026_03, entry 179, sequence 4. K-12 NCBITaxon:83333 is reference context, not an experimental strain assignment.) Comparative susceptibility assays

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANCE_EVIDENCE 2026-10-13 · codex · LLM-assisted
Added two qualified laboratory gene-level sulfathiazole resistance associations. Kept FolP and Bcr reference proteins separate from experimental alleles and strains, retained mechanistic uncertainty for Bcr, and assigned no numerical AST or genome identifiers. Whole-record review remains open.

Provenance

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

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