Acediasulfone

Chemical compound

none

Identifiers

IUPAC name

2-([4-(4-aminophenyl)sulfonylphenyl]amino)acetic acid

CAS Number

80-03-5

PubChem CID

66451

DrugBank

DB08926^Y

ChemSpider

59823^Y

UNII

30YP2YHH8W

KEGG

D07061

ChEMBL

ChEMBL48396^Y

CompTox Dashboard (EPA)

DTXSID00229991

ECHA InfoCard100.001.131

Chemical and physical dataFormulaC₁₄H₁₄N₂O₄SMolar mass306.34 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)NCC(=O)O

InChI

InChI=1S/C14H14N2O4S/c15-10-1-5-12(6-2-10)21(19,20)13-7-3-11(4-8-13)16-9-14(17)18/h1-8,16H,9,15H2,(H,17,18)^Y
Key:FKKUMFTYSTZUJG-UHFFFAOYSA-N^Y

(verify)

Acediasulfone (INN) is an antimicrobial drug, which also has antimalarial activity. It is a long-acting prodrug of dapsone, which is used for treating leprosy.

Synthesis

Dapsone is somewhat inconvenient to administer to patients because of its rather low water solubility.

In the search for more easily administered drugs, dapsone (1) was reacted with bromoacetic acid to give acediasulfone (2) which can be administered as a water-soluble salt.

References

^ Jackson EL (February 1948). "Certain N-alkyl, N-carboxyalkyl and N-hydroxyalkyl derivatives of 4,4'-diaminodiphenyl sulfone". Journal of the American Chemical Society. 70 (2): 680–4. doi:10.1021/ja01182a074. PMID 18907772.