Acedapsone

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Acedapsone
Skeletal formula of acedapsone
Space-filling model of the acedapsone molecule
Systematic (IUPAC) name
N-[4-(4-acetamidophenyl)sulfonylphenyl]acetamide
Clinical data
Trade names Rodilone
Hansolar
Identifiers
CAS Number 77-46-3 N
ATC code none
PubChem CID: 6477
ChemSpider 6232 YesY
UNII 0GZ72U84TN YesY
KEGG D02751 YesY
ChEMBL CHEMBL154166 YesY
Chemical data
Formula C16H16N2O4S
Molecular mass 332.374 g/mol
  • 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) YesY
  • Key:AMTPYFGPPVFBBI-UHFFFAOYSA-N YesY
Physical data
Melting point 290 °C (554 °F)
 NYesY (what is this?)  (verify)

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

Acedapsone, or 1399 F, is a diacetyl compound, derived from dapsone. 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.

References

  1. (French) E. Fourneau, J. et Th. Tréfouël, F. Nitti, D. Bovet, « Chimiothérapie de l'infection pneumococcique par la di-(p-acétylaminophényl)-sulfone (1399 F) », C. r. Acad. sci., vol. 205, 1937, pp. 299-300.
  2. (French) Marcel Delépine, Ernest Fourneau (1872-1949) : Sa vie et son œuvre, extrait du Bulletin de la Société chimique de France, Masson et Cie, 1950, pp. 64-67.
  3. Lua error in package.lua at line 80: module 'strict' not found.

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