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.

sulfonamide antibiotic ARO:3000282

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

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.

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` BindingDB target chain 1	—	Mycobacterium tuberculosis CAS/NITR204 `NCBITaxon:1310114`	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

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` BindingDB target chain 1	—	Cryptococcus neoformans `NCBITaxon:5207`	UNREVIEWED

PMID:19450983 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Resistance mechanisms

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

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 (YAML).

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