Acedapsone

Title: Acedapsone
CAS Registry Number: 77-46-3
CAS Name: N,N¢-(Sulfonyldi-4,1-phenylene)bisacetamide
Additional Names: 4¢,4¢¢¢-sulfonylbis[acetanilide]; bis(4-acetamidophenyl)sulfone; 4,4¢-diacetyldiaminodiphenyl sulfone; 4,4¢-diacetylaminodiphenyl sulfone; N,N¢-diacetyl-4,4¢-diaminodiphenyl sulfone; DADDS; diacetyldapsone; sulfadiamine
Manufacturers' Codes: 1399F; CI-556
Trademarks: Hansolar (Parke-Davis)
Molecular Formula: C16H16N2O4S
Molecular Weight: 332.37
Percent Composition: C 57.82%, H 4.85%, N 8.43%, O 19.25%, S 9.65%
Literature References: Prepn: Fromm, Wittmann, Ber. 41, 2270 (1908); Raiziss et al., J. Am. Chem. Soc. 61, 2763 (1939); Elslager et al., J. Med. Chem. 12, 357 (1969). Properties: Elslager, Worth, Nature 206, 630 (1965). Clinical trial in leprosy: C. R. Boughton et al., Med. J. Aust. 1, 1258 (1971); P. N. Neelan et al., Indian J. Lepr. 58, 251 (1986).
Properties: Crystalline solid, mp 289-292°. uv max (methanol): 256, 284 nm (e 25500, 36200). Soly in water: 0.003 mg/ml; in 40% benzyl benzoate-60% castor oil: 0.026 mg/ml.
Melting point: mp 289-292°
Absorption maximum: uv max (methanol): 256, 284 nm (e 25500, 36200)
Therap-Cat: Antibacterial (leprostatic).
Keywords: Antibacterial (Synthetic); Sulfones; Antimalarial; Antibacterial (Leprostatic).
Status: This monograph has been retired and is no longer subject to revision or update.
Acediasulfone Acefylline Aceglatone Aceglutamide Acemannan

Acedapsone
Acedapsone.png
Systematic (IUPAC) name
N-[4-(4-acetamidophenyl)sulfonylphenyl]acetamide
Clinical data
Trade names Rodilone
Hansolar
Legal status  ?
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 
Mol. mass 332.374 g/mol
Physical data
Melt. point 290 °C (554 °F)
 N (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.