Acediasulfone

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 ;
ChemSpider	59823 ;
UNII	30YP2YHH8W;
KEGG	D07061;
ChEMBL	ChEMBL48396 ;
CompTox Dashboard (EPA)	DTXSID00229991 ;
ECHA InfoCard	100.001.131
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) ; Key:FKKUMFTYSTZUJG-UHFFFAOYSA-N ;
	(verify)

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.

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.

References

^ Jackson EL (February 1948). "Certain N-alkyl, N-carboxyalkyl and N-hydroxyalkyl derivatives of 4,4'-diaminodiphenyl sulfone". Journal of the American Chemical Society. 70 (2): 680–4. doi:10.1021/ja01182a074. PMID 18907772.

[1] Jackson EL (February 1948). "Certain N-alkyl, N-carboxyalkyl and N-hydroxyalkyl derivatives of 4,4'-diaminodiphenyl sulfone". Journal of the American Chemical Society. 70 (2): 680–4. doi:10.1021/ja01182a074. PMID 18907772.