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;
ChemSpider	59823 ;
UNII	30YP2YHH8W;
ChEMBL	ChEMBL48396 ;
CompTox Dashboard (EPA)	DTXSID00229991 ;
ECHA InfoCard	100.001.131
Chemical and physical data
Formula	C14H14N2O4S
Molar mass	306.337 g/mol 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 inconvient to administer to patients because of its rather low water solubility.

In the search for more easily administered drugs, 1 was reacted with bromoacetic acid to give acediasulfone (3) which can be adminsistered as a water soluble salt.

References

^ Jackson, Ernest L. (1948). "Certain N-Alkyl, N-Carboxyalkyl and N-Hydroxyalkyl Derivatives of 4,4'-Diamino-diphenyl Sulfone". Journal of the American Chemical Society. 70 (2): 680–4. doi:10.1021/ja01182a074. PMID 18907772.

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[1] Jackson, Ernest L. (1948). "Certain N-Alkyl, N-Carboxyalkyl and N-Hydroxyalkyl Derivatives of 4,4'-Diamino-diphenyl Sulfone". Journal of the American Chemical Society. 70 (2): 680–4. doi:10.1021/ja01182a074. PMID 18907772.

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