Acedapsone

Acedapsone

Clinical data
Trade names	Rodilone Hansolar
ATC code	none
Identifiers
IUPAC name N-[4-(4-acetamidophenyl)sulfonylphenyl]acetamide
CAS Number	77-46-3
PubChem (CID)	6477
ChemSpider	6232
UNII	0GZ72U84TN
KEGG	D02751
ChEMBL	CHEMBL154166
Chemical and physical data
Formula	C16H16N2O4S
Molar mass	332.374 g/mol
3D model (Jmol)	Interactive image
Melting point	290 °C (554 °F)
SMILES CC(=O)NC1=CC=C(C=C1)S(=O)(=O)C2=CC=C(C=C2)NC(=O)C
InChI 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) Key:AMTPYFGPPVFBBI-UHFFFAOYSA-N
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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

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

Acedapsone is conveniently prepared by acetylation of dapsone.

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. 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.