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	306.34 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 ;
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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 inconvient to administer to patients because of its rather low water solubility.

Acediasulfone synthesis:[1] CH 254803 and CH 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, 1 was reacted with bromoacetic acid to give acediasulfone (3) 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.

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[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.