AntibioticMech

dapsone

CHEBI:4325 ·resolve ·ANTIMYCOBACTERIAL ·EXACT SEEDED

A sulfone that is diphenylsulfone in which the hydrogen atom at the 4 position of each of the phenyl groups is substituted by an amino group. It is active against a wide range of bacteria, but is mainly employed for its actions against Mycobacterium leprae, being used as part of multidrug regimens in the treatment of all forms of leprosy. — ChEBI

Classification

sulfone antibioticARO:3003401

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:35850 CHEBI:35850
• CHEBI:48975 CHEBI:48975
• ARO:3003401 ARO:3003401

Chemical structure

Computed structure properties

Molecular formula	C12H12N2O2S
Charge	0
Average mass	248.307 Da
Monoisotopic mass	248.06195 Da
Source	ChEBI
InChIKey	MQJKPEGWNLWLTK-UHFFFAOYSA-N

SMILES

Nc1ccc(S(=O)(=O)c2ccc(N)cc2)cc1

InChI

InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2

Also called

• dapsona (INN)— chebi
• dapsonum (INN)— chebi
• 4,4'-sulfonyldianiline (EXACT_SYNONYM)— chebi
• 1,1'-sulfonylbis(4-aminobenzene) (EXACT_SYNONYM)— chebi
• 4,4'-Sulfonylbisbenzenamine (EXACT_SYNONYM)— chebi
• 4,4'-dapsone (EXACT_SYNONYM)— chebi
• 4,4'-diaminodiphenyl sulfone (EXACT_SYNONYM)— chebi
• 4,4'-sulfonylbisaniline (EXACT_SYNONYM)— chebi
• 4-(4-amino-benzenesulfonyl)-phenylamine (EXACT_SYNONYM)— chebi
• 4-(4-aminophenylsulfonyl)aniline (EXACT_SYNONYM)— chebi
• 4-(4-aminophenylsulfonyl)benzenamine (EXACT_SYNONYM)— chebi
• 4-aminophenyl sulfone (EXACT_SYNONYM)— chebi
• Bis(p-aminophenyl) sulfone (EXACT_SYNONYM)— chebi
• DADPS (EXACT_SYNONYM)— chebi
• DAPSONE (EXACT_SYNONYM)— chebi
• DDS (EXACT_SYNONYM)— chebi
• DIAPHENYLSULFONE (EXACT_SYNONYM)— chebi
• Dapsone (EXACT_SYNONYM)— chebi
• Diaphenylsulfone (EXACT_SYNONYM)— chebi
• bis(4-aminophenyl)sulfone (EXACT_SYNONYM)— chebi
• p,p'-diaminodiphenyl sulfone (EXACT_SYNONYM)— chebi
• p,p-sulphonylbisbenzamine (EXACT_SYNONYM)— chebi
• p,p-sulphonylbisbenzenamine (EXACT_SYNONYM)— chebi
• p-aminophenyl sulfone (EXACT_SYNONYM)— chebi
• diaminodiphenyl sulfone (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3003412
• cas:80-08-0
• drugbank:DB00250
• drugcentral:782
• hmdb:HMDB0014395
• kegg.compound:C07666
• kegg.drug:D00592
• lincs.smallmolecule:LSM-5714
• patent:FR829926
• reaxys:788055
• wikipedia.en:Dapsone
• chembl:CHEMBL1043
• pubchem.compound:2955

Activity roles

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

• CHEBI:35816 CHEBI:35816
• CHEBI:38068 CHEBI:38068

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:3003412	dapsone	antibioticmech:aro-64d15320ca	2026-08-30
CHEBI	CHEBI:4325	dapsone	antibioticmech:chebi-e4c33d0b87	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:3003412 (dapsone); database assertion, not a primary citation.)

Mechanism summary

Clinical status

APPROVED

Resistance mechanisms

1 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_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION

Determinant	ARO ID	Organism	Gene families	Evidence
Mycobacterium leprae folP with mutation conferring resistance to dapsone	ARO:3003389	not organism-specific	—	ARO:3003389 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003412 (dapsone); database assertion, not a primary citation.)

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. 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.