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Acediasulfone

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Revision as of 20:01, 9 January 2023 by Ozzie10aaaa (talk | contribs) (Cleaned up using AutoEd)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Chemical compound Pharmaceutical compound
Acediasulfone
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 2-(amino)acetic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.131 Edit this at Wikidata
Chemical and physical data
FormulaC14H14N2O4S
Molar mass306.34 g·mol
3D model (JSmol)
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)
  • Key:FKKUMFTYSTZUJG-UHFFFAOYSA-N
  (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.

Acediasulfone synthesis: 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

  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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