Succinylsulfathiazole

Chemical compound

A07AB04 (WHO)

Identifiers

IUPAC name

4-oxo-4-({4-[(1,3-thiazol-2-ylamino)sulfonyl]phenyl}amino)butanoic acid

CAS Number

116-43-8

PubChem CID

5315

UNII

RSS8647O4S

KEGG

D07060^Y

ChEMBL

ChEMBL1484857

CompTox Dashboard (EPA)

DTXSID7045281

ECHA InfoCard100.003.765

Chemical and physical dataFormulaC₁₃H₁₃N₃O₅S₂Molar mass355.38 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

OC(=O)CCC(=O)Nc1ccc(cc1)S(=O)(=O)Nc2nccs2

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Succinylsulfathiazole (also known as sulfasuxidine) is a sulfonamide.^[1]^[2] It is also spelled as succinylsulphathiazole. It is a white or yellow-white crystalline powder. It dissolves in aqueous solutions of alkali hydroxides and carbonates but is very slightly soluble in water.

It is classified as ultra long-acting drug. About 95% of the drug remains in the intestine and only 5% is hydrolyzed, slowly, to sulfathiazole and is absorbed.

The drug is used for its antibacterial activity in the GIT. The dose is 10g - 20g daily in divided doses.

The Succinyl group is attached to form a prodrug for the controlled release of the drug sulfathiazole.

References

^ Poth EJ, Knotts FL (February 1942). "Clinical use of Succinylsulfathiazole". Archives of Surgery. 44 (2): 208. doi:10.1001/archsurg.1942.01210200024002. ISSN 0004-0010.
^ Dixon CF, Benson RE (October 1944). "Closure of Colonic Stoma: Improved Results With Combined Succinylsulfathiazole and Sulfathiazole Therapy". Annals of Surgery. 120 (4): 562–571. doi:10.1097/00000658-194410000-00012. PMC 1618178. PMID 17858511.