Acedapsone

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

Acedapsone

Clinical data
Trade names	Rodilone Hansolar
ATC code	none
Identifiers
IUPAC name N-[4-(4-acetamidophenyl)sulfonylphenyl]acetamide
CAS Number	77-46-3 N
PubChem CID	6477
ChemSpider	6232 Y
UNII	0GZ72U84TN
KEGG	D02751 Y
ChEMBL	ChEMBL154166 Y
CompTox Dashboard (EPA)	DTXSID1021295
ECHA InfoCard	100.000.936
Chemical and physical data
Formula	C16H16N2O4S
Molar mass	332.37 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) Y Key:AMTPYFGPPVFBBI-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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.