mafenide
CHEBI:6633
·resolve ·ANTIBACTERIAL
·EXACT
SEEDED
Mafenide is a sulfonamide used topically for treating burns. — PMID:4948236
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 | C7H10N2O2S |
|---|
| Charge | 0 |
|---|
| Average mass | 186.236 Da |
|---|
| Monoisotopic mass | 186.0463 Da |
|---|
| Source | ChEBI |
|---|
| InChIKey | TYMRLRRVMHJFTF-UHFFFAOYSA-N |
|---|
SMILES
NCc1ccc(S(N)(=O)=O)cc1
InChI
InChI=1S/C7H10N2O2S/c8-5-6-1-3-7(4-2-6)12(9,10)11/h1-4H,5,8H2,(H2,9,10,11)
Also called
- ambamide (EXACT_SYNONYM)— aro
- maphenide (EXACT_SYNONYM)— aro
- sulfamylon (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:3000684 |
mafenide |
antibioticmech:aro-8f5b2c80c0 |
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:3000684 (mafenide); database assertion, not a primary citation.)
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 |
7330 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 53332
assay 3201_1
monomer 10860 |
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 |
18490 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 60913
assay 3445_1
monomer 10860 |
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.)
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:3000684 (mafenide); database assertion, not a primary citation.)
|
| sul2 |
ARO:3000412 |
not organism-specific |
— |
- ARO:3000412 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000684 (mafenide); database assertion, not a primary citation.)
|
| sul3 |
ARO:3000413 |
not organism-specific |
— |
- ARO:3000413 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000684 (mafenide); 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:3000684 (mafenide); 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:3000684 (mafenide); 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
Provenance
Seeded by scripts/seed_from_sources.py from the committed
inventories in data/raw/.
View the record.