Chemistry:Acediasulfone

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Short description: Chemical compound
Acediasulfone
Acediasulfone Structure.svg
Clinical data
ATC code
  • none
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC14H14N2O4S
Molar mass306.34 g·mol−1
3D model (JSmol)
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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.

Acediasulfone synthesis:[1] CH patent 254803 and CH patent 278482 (1949, 1952, to Cilag Ltd.); Rawlins, U.S. Patent 2,589,211 (1952 to Parke-Davis).

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

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