Chemistry:Acediasulfone

Short description: Chemical compound

Acediasulfone

Clinical data
ATC code	none
Identifiers
IUPAC name 2-([4-(4-aminophenyl)sulfonylphenyl]amino)acetic acid
CAS Number	80-03-5
PubChem CID	66451
DrugBank	DB08926 Y
ChemSpider	59823 Y
UNII	30YP2YHH8W
KEGG	D07061
ChEMBL	ChEMBL48396 Y
Chemical and physical data
Formula	C14H14N2O4S
Molar mass	306.34 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)NCC(=O)O
InChI InChI=1S/C14H14N2O4S/c15-10-1-5-12(6-2-10)21(19,20)13-7-3-11(4-8-13)16-9-14(17)18/h1-8,16H,9,15H2,(H,17,18) Y Key:FKKUMFTYSTZUJG-UHFFFAOYSA-N Y
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Acediasulfone (INN) is an antimicrobial drug, which also has antimalarial activity. It is a long-acting prodrug of dapsone, which is used for treating leprosy.

Synthesis

Dapsone is somewhat inconvenient to administer to patients because of its rather low water solubility.

Acediasulfone synthesis: CH patent 254803 and CH patent 278482 (1949, 1952, to Cilag Ltd.); Rawlins, U.S. Patent 2,589,211 (1952 to Parke-Davis).

In the search for more easily administered drugs, dapsone (1) was reacted with bromoacetic acid to give acediasulfone (2) which can be administered as a water-soluble salt.