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Acediasulfone

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Chemical compound
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Pharmaceutical compound
Acediasulfone
Clinical data
ATC code
  • none
Identifiers
  • 2-([4-(4-aminophenyl)sulfonylphenyl]amino)acetic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.001.131 Edit this at Wikidata
Chemical and physical data
Formula C14H14N2O4S
Molar mass 306.34 g·mol−1
3D model (JSmol)
  • C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)NCC(=O)O
  • 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) checkY
  • Key:FKKUMFTYSTZUJG-UHFFFAOYSA-N checkY
  (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

[edit ]

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

Acediasulfone synthesis:[1] CH 254803   and CH 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

[edit ]
  1. ^ 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.


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