sulfasalazine
CHEBI:9334
·resolve ·ANTIBACTERIAL
·EXACT
SEEDED
Sulfasalazine is a derivative of the early sulfonamide sulfapyridine (salicylazosulfapyridine). It was developed to increase water solubility and is taken orally for ulcerative colitis. — PMID:22555
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.
Chemical structure
Computed structure properties
| Molecular formula | C18H14N4O5S |
|---|
| Charge | 0 |
|---|
| Average mass | 398.4 Da |
|---|
| Monoisotopic mass | 398.06849 Da |
|---|
| Source | ChEBI |
|---|
| InChIKey | NCEXYHBECQHGNR-QZQOTICOSA-N |
|---|
SMILES
O=C(O)c1cc(/N=N/c2ccc(S(=O)(=O)Nc3ccccn3)cc2)ccc1O
InChI
InChI=1S/C18H14N4O5S/c23-16-9-6-13(11-15(16)18(24)25)21-20-12-4-7-14(8-5-12)28(26,27)22-17-3-1-2-10-19-17/h1-11,23H,(H,19,22)(H,24,25)/b21-20+
Also called
- salicylazosulfapyridine (EXACT_SYNONYM)— aro
Cross-references
Equivalent identifiers for this same structure in other resources.
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:3000698 |
sulfasalazine |
antibioticmech:aro-5ef94be97c |
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:3000698 (sulfasalazine); database assertion, not a primary citation.)
Mechanism summary
- 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:3000698 (sulfasalazine); database assertion, not a primary citation.)
|
| sul2 |
ARO:3000412 |
not organism-specific |
— |
- ARO:3000412 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000698 (sulfasalazine); database assertion, not a primary citation.)
|
| sul3 |
ARO:3000413 |
not organism-specific |
— |
- ARO:3000413 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000698 (sulfasalazine); 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:3000698 (sulfasalazine); 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:3000698 (sulfasalazine); database assertion, not a primary citation.)
|
Curation history
-
SEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO)
-
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
Provenance
Seeded by scripts/seed_from_sources.py from the committed
inventories in data/raw/.
View the record.