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
Molar mass 332.374 g/mol
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.

Synthesis[edit]

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

Acedapsone is conveniently prepared by acetylation of dapsone.

References[edit]

  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. ^ Shaw IN, Christian M, Jesudasan K, Kurian N, Rao GS (June 2003). "Effectiveness of multidrug therapy in multibacillary leprosy: a long-term follow-up of 34 multibacillary leprosy patients treated with multidrug regimens till skin smear negativity". Lepr Rev 74 (2): 141–7. PMID 12862255. 
  4. ^ Elslager, Edward F.; Gavrilis, Zoe B.; Phillips, Annette A.; Worth, Donald F. (1969). "Repository drugs. IV. 4',4 ' ' ' -Sulfonylbisacetanilide (acedapsone, DADDS) and related sulfanilylanilides with prolonged antimalarial and antileprotic action". Journal of Medicinal Chemistry 12 (3): 357. doi:10.1021/jm00303a003. PMID 4892242. 
  5. ^ Raiziss, G. W.; Clemence, L. W.; Severac, M.; Moetsch, J. C. (1939). "Chemistry and Chemotherapy of 4,4′-Diaminodiphenylsulfone, 4-Amino-4′-hydroxy-diphenylsulfone and Related Compounds". Journal of the American Chemical Society 61 (10): 2763. doi:10.1021/ja01265a060. 
  6. ^ Fromm, E.; Wittmann, J. (1908). "Derivate desp-Nitrothiophenols". Berichte der deutschen chemischen Gesellschaft 41 (2): 2264. doi:10.1002/cber.190804102131.