sulfanilamide
CHEBI:45373
·resolve ·ANTIBACTERIAL
·EXACT
SEEDED
A sulfonamide in which the sulfamoyl functional group is attached to aniline at the 4-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.
Chemical structure
Computed structure properties
| Molecular formula | C6H8N2O2S |
|---|
| Charge | 0 |
|---|
| Average mass | 172.209 Da |
|---|
| Monoisotopic mass | 172.03065 Da |
|---|
| Source | ChEBI |
|---|
| InChIKey | FDDDEECHVMSUSB-UHFFFAOYSA-N |
|---|
SMILES
Nc1ccc(S(N)(=O)=O)cc1
InChI
InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
Also called
- 4-aminobenzenesulfonamide (EXACT_SYNONYM)— chebi
- 4-aminobenzene sulfonic acid amide (EXACT_SYNONYM)— chebi
- 4-azanylbenzenesulfonamide (EXACT_SYNONYM)— chebi
- Prontosil album (EXACT_SYNONYM)— chebi
- SA (EXACT_SYNONYM)— chebi
- SULFANILAMIDE (EXACT_SYNONYM)— chebi
- Streptocide (EXACT_SYNONYM)— chebi
- Sulfamine (EXACT_SYNONYM)— chebi
- Sulfanilamide (EXACT_SYNONYM)— chebi
- p-aminobenzenesulfamide (EXACT_SYNONYM)— chebi
- p-aminobenzenesulfonamide (EXACT_SYNONYM)— chebi
- para-aminobenzenesulfonamide (EXACT_SYNONYM)— chebi
- sulfamine (EXACT_SYNONYM)— chebi
- sulphanilamide (EXACT_SYNONYM)— chebi
Cross-references
Equivalent identifiers for this same structure in other resources.
Activity roles
Every antimicrobial role a source asserts for this compound — the
unreduced evidence behind its antimicrobial_class.
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:3007468 |
sulfanilamide |
antibioticmech:aro-dba3a37e97 |
2026-08-30 |
| CHEBI |
CHEBI:45373 |
sulfanilamide |
antibioticmech:chebi-fac7578230 |
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.
Carbonic anhydrase PROTEIN MEASURED_TARGET_ASSOCIATION
BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).
Mycobacterium tuberculosis CAS/NITR204 NCBITaxon:1310114
Quantitative measurements
| Type | Reported value | Assay | BindingDB IDs | Reference |
|---|
| KI |
7110 nM |
CA Inhibition Assay
An Applied Photophysics stopped-flow instrument has been used for assaying the CA-catalyzed CO2 hydration activity. Phenol red has been used as indicator, working at the absorbance maximum of 557 nm. The inhibition constants were obtained by nonlinear least-squares methods. The IC50 was obtained by using curve-fitting algorithm, and Ki values were calculated by using the Cheng-Prusoff equation. The catalytic activity of these enzymes was calculated from Lineweaver-Burk plots, and represent the mean from at least three different determinations. |
RSID 53329
assay 3201_1
monomer 10857 |
PMID:19338333 |
Organism-specific examples
| Protein | Gene | Organism | Entry |
|---|
Carbonic anhydrase UniProtKB:R4ML78 |
— |
Mycobacterium tuberculosis CAS/NITR204 |
UNREVIEWED |
- PMID:19338333 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
Carbonic anhydrase PROTEIN MEASURED_TARGET_ASSOCIATION
BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).
Cryptococcus neoformans NCBITaxon:5207
Quantitative measurements
| Type | Reported value | Assay | BindingDB IDs | Reference |
|---|
| KI |
765 nM |
CA Inhibition Assay
An Applied Photophysics stopped-flow instrument has been used for assaying the CA-catalyzed CO2 hydration activity. Phenol red has been used as indicator, working at the absorbance maximum of 557 nm. The inhibition constants were obtained by nonlinear least-squares methods. The IC50 was obtained by using curve-fitting algorithm, and Ki values were calculated by using the Cheng-Prusoff equation. The catalytic activity of these enzymes was calculated from Lineweaver-Burk plots, and represent the mean from at least three different determinations. |
RSID 60910
assay 3445_1
monomer 10857 |
PMID:19450983 |
Organism-specific examples
| Protein | Gene | Organism | Entry |
|---|
Carbonic anhydrase UniProtKB:Q3I4V7 |
— |
Cryptococcus neoformans |
UNREVIEWED |
- PMID:19450983 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
Siderophore-binding protein PROTEIN MEASURED_TARGET_ASSOCIATION
BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).
Mycobacterium tuberculosis NCBITaxon:1773
Quantitative measurements
| Type | Reported value | Assay | BindingDB IDs | Reference |
|---|
| KI |
7.11e+3 nM |
CA Inhibition Assay
An Applied Photophysics stopped-flow instrument has been used for assaying the CA-catalyzed CO2 hydration activity [Khalifah et al., J. Biol. Chem., 246:2561-2573]. Phenol red (at a concentration of 0.2 mM)has been used as indicator, working at the absorbance maximum of 557 nm with 10-20 mM Hepes (pH 7.5, for α-CAs) or TRIS (pH 8.3 for β-CAs) as buffers, and20 mM Na2SO4 (for α-CAs) or 20 mM NaCl for β-CAs (for maintaining constant the ionic strength), following the initial rates of the CA-catalyzed CO2 hydration reaction for a period of 10-100 s. The CO2 concentrations ranged from 1.7 to 17 mM for the determination of the kinetic parameters and inhibition constants. For each inhibitor, at least six traces of the initial 5-10% of the reaction have been used for determining the initial velocity. The uncatalyzed rates were determined in the same manner and subtracted from the total observed rates. Stock solutions of inhibitor (10 mM) were prepared in distilled deionized water and dilutions up to 0.01 nM were done thereafter with distilled-deionized water. Inhibitor andenzyme solutions were preincubated together for 15 min at room temperature prior to assay in order to allow for the formation of the E-I complex. The inhibition constants were obtained by non-linear least-squares methods using PRISM 3, whereas the kinetic parameters for the uninhibited enzymes from Lineweaver-Burk plots,as reported earlier. |
RSID 417609
assay 8291_1
monomer 10857 |
PMID:22299588 |
Organism-specific examples
| Protein | Gene | Organism | Entry |
|---|
Siderophore-binding protein UniProtKB:A0A045J7I4 |
— |
Mycobacterium tuberculosis |
UNREVIEWED |
- PMID:22299588 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
Mechanism summary
- Clinical status
- APPROVED
Curation history
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SEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
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RESEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
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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.