Acedapsone

Antimicrobial drug From Wikipedia, the free encyclopedia

Acedapsone (INN) is an antimicrobial drug, which also has antimalarial activity.

Trade namesRodilone
Hansolar
ATC code
  • none
Quick facts Clinical data, Trade names ...
Acedapsone
Skeletal formula of acedapsone
Space-filling model of the acedapsone molecule
Clinical data
Trade namesRodilone
Hansolar
ATC code
  • none
Identifiers
  • N-[4-(4-acetamidophenyl)sulfonylphenyl]acetamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.936 Edit this at Wikidata
Chemical and physical data
FormulaC16H16N2O4S
Molar mass332.37 g·mol−1
3D model (JSmol)
Melting point290 °C (554 °F)
  • CC(=O)NC1=CC=C(C=C1)S(=O)(=O)C2=CC=C(C=C2)NC(=O)C
  • InChI=1S/C16H16N2O4S/c1-11(19)17-13-3-7-15(8-4-13)23(21,22)16-9-5-14(6-10-16)18-12(2)20/h3-10H,1-2H3,(H,17,19)(H,18,20) checkY
  • Key:AMTPYFGPPVFBBI-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)
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Acedapsone is the INN for diacetyldapsone. It was synthesized and developed in 1937 by Ernest Fourneau and his team in the pharmaceutical chemistry laboratory of Pasteur Institute,[1] and it was marketed as Rodilone by the Rhône-Poulenc company.[2]

It is a long-acting prodrug of dapsone. It is used for treating leprosy.[3]

It crystallises as pale yellow needles from diethyl ether, and as leaflets from dilute ethanol. It is slightly soluble in water.[citation needed]

Synthesis

Acedapsone synthesis:[4][5][6]

Acedapsone is conveniently prepared by acetylation of dapsone.

References

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