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 ;
CompTox Dashboard (EPA)	DTXSID1021295 ;
ECHA InfoCard	100.000.936
Chemical and physical data
Formula	C16H16N2O4S
Molar mass	332.374 g/mol g·mol−1
3D model (JSmol)	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 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.

Synthesis

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

Acedapsone is conveniently prepared by acetylation of dapsone.

References

(in 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.
(in 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.
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.
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.
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.
Fromm, E.; Wittmann, J. (1908). "Derivate desp-Nitrothiophenols". Berichte der Deutschen Chemischen Gesellschaft. 41 (2): 2264. doi:10.1002/cber.190804102131.

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[1] (in 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] (in 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.

[pmid12862255-3] 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.