Acedapsone
Appearance
![]() | |
![]() | |
Clinical data | |
---|---|
Trade names | Rodilone Hansolar |
ATC code |
|
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
KEGG | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.000.936 |
Chemical and physical data | |
Formula | C16H16N2O4S |
Molar mass | 332.37 g·mol−1 |
3D model (JSmol) | |
Melting point | 290 °C (554 °F) |
| |
| |
![]() ![]() |
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.[citation needed]
Synthesis
[edit]![](http://upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Acedapsone_synthesis.svg/500px-Acedapsone_synthesis.svg.png)
Acedapsone is conveniently prepared by acetylation of dapsone.
References
[edit]- ^ Fourneau E, Tréfouël J, Nitti F, Bovet D (July 1937). "Chimiothérapie de l'infection pneumococcique par la di-(p-acétylaminophényl)-sulfone (1399 F)". Compt. Rend. Acad. Sci. (in French). 205: 299.
- ^ Fourneau JP (1987). "Ernest Fourneau, fondateur de la chimie thérapeutique française: feuillets d'album". Revue d'Histoire de la Pharmacie (in French). 75 (275): 335–55. doi:10.3406/pharm.1987.2904.
- ^ 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". Leprosy Review. 74 (2): 141–7. doi:10.47276/lr.74.2.141. PMID 12862255.
- ^ Elslager EF, Gavrilis ZB, Phillips AA, Worth DF (May 1969). "Repository drugs. IV. 4',4'''-Sulfonylbisacetanilide (Acedapsone, DADDS) and related sulfanilylanilides with prolonged antimalarial and antileprotic action". Journal of Medicinal Chemistry. 12 (3): 357–63. doi:10.1021/jm00303a003. PMID 4892242.
- ^ Raiziss GW, Clemence LW, Severac M, Moetsch JC (1939). "Chemistry and Chemotherapy of 4,4′-Diaminodiphenylsulfone, 4-Amino-4′-hydroxy-diphenylsulfone and Related Compounds". Journal of the American Chemical Society. 61 (10): 2763–2765. doi:10.1021/ja01265a060.
- ^ Fromm E, Wittmann J (1908). "Derivate desp-Nitrothiophenols". Berichte der Deutschen Chemischen Gesellschaft. 41 (2): 2264–2273. doi:10.1002/cber.190804102131.