Sulfaguanidine

Chemical compound

A07AB03 (WHO)

Identifiers

IUPAC name

4-Amino-N-[amino(imino)methyl]benzenesulfonamide

CAS Number

57-67-0

PubChem CID

5324

ChemSpider

5133

UNII

15XQ8043FN

KEGG

D02437^Y

CompTox Dashboard (EPA)

DTXSID1023609

ECHA InfoCard100.000.314

Chemical and physical dataFormulaC₇H₁₀N₄O₂SMolar mass214.24 g·mol⁻¹3D model (JSmol)

Interactive image

Melting point190 to 193 °C (374 to 379 °F)

SMILES

c1cc(N)ccc1S(=O)(=O)N=C(N)N

InChI

InChI=1S/C7H10N4O2S/c8-5-1-3-6(4-2-5)14(12,13)11-7(9)10/h1-4H,8H2,(H4,9,10,11)
Key:BRBKOPJOKNSWSG-UHFFFAOYSA-N

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Sulfaguanidine is a sulfonamide.

Sulfaguanidine is a guanidine derivative of sulfanilamide used in veterinary medicine. Sulfaguanidine is poorly absorbed from the gut which makes it suitable for the treatment of bacillary dysentery and other enteric infections.^[1]

Sulphaguanidine (II) was independently prepared by Marshall, Bratton, White, and Litchfield and Roblin, Williams, Winnek, and English in 1940, and introduced for the treatment of bacillary dysentery on the basis of its poor absorption from the gut. Its orally administered route of administration is now well established.^[2]

References

^ Smyth CJ, Finkelstein MB, Gould SE, Koppa TM, Leeder FS (April 1943). "Acute Bacillary Dysentery (Flexner): Treatment with Sulfaguanidine and Succinylsulfathiazole". Journal of the American Medical Association. 121 (17): 1325–30. doi:10.1001/jama.1943.02840170009003.
^ Rose FL, Spinks A (June 1947). "The absorption of some sulphaguanidine derivatives in mice". British Journal of Pharmacology and Chemotherapy. 2 (2): 65–78. doi:10.1111/j.1476-5381.1947.tb00322.x. PMC 1509772. PMID 19108113.