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

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

sulfone antibioticARO:3003401

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:35850
Label unavailable CHEBI:48975
sulfone antibiotic 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

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.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

leprostatic drug CHEBI:35816
antimalarial 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 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

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

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
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
RESEEDED_FROM_SOURCES 2026-09-10 · 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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