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^Y
ChemSpider	59823^Y
UNII	30YP2YHH8W
KEGG	D07061
ChEMBL	ChEMBL48396^Y
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)^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.

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.

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This page was last edited on 15 March 2024, at 21:05

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Synthesis

References