Sulfaguanidine

Sulfaguanidine is a sulfonamide.

Sulfaguanidine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • 4-Amino-N-[amino(imino)methyl]benzenesulfonamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.000.314
Chemical and physical data
FormulaC7H10N4O2S
Molar mass214.24 g·mol−1
3D model (JSmol)
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
  (verify)

Sulfaguanidine is a guanidine derivative of sulfanilamide used in veterinary medicine. Sulfaguanidine is poorly absorbed from the gut but is well suited 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
  1. 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.
  2. 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.
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