Sulfathiazole
Sulfathiazole tautomerism.svg
Imino (top) and amino (bottom) tautomers
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 4-amino-N-(1,3-thiazol-2-yl)benzenesulfonamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.701 Edit this at Wikidata
Chemical and physical data
FormulaC9H9N3O2S2
Molar mass255.31 g·mol−1
3D model (JSmol)
Melting point202 to 202.5 °C (395.6 to 396.5 °F)
  • O=S(=O)(Nc1nccs1)c2ccc(N)cc2
  • InChI=1S/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12) checkY
  • Key:JNMRHUJNCSQMMB-UHFFFAOYSA-N checkY
  (verify)

Sulfathiazole is an organosulfur compound used as a short-acting sulfa drug.[1] Formerly, it was a common oral and topical antimicrobial, until less toxic alternatives were discovered.[2]

Sulfathiazole exists in various forms (polymorphs). The imine tautomer is dominant, at least in the solid state. In this tautomer, the proton resides on the ring nitrogen.[3]

Cultural references

References

  1. ^ Mertschenk B, Beck F, Bauer W (2002). "Thiourea and Thiourea Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a26_803. ISBN 3527306730.
  2. ^ Rouf A, Tanyeli C (June 2015). "Bioactive thiazole and benzothiazole derivatives". European Journal of Medicinal Chemistry. 97: 911–27. doi:10.1016/j.ejmech.2014.10.058. PMID 25455640.
  3. ^ Kruger GT, Gafner G (February 1971). "The crystal structure of sulphathiazole II". Acta Crystallographica Section B. 27 (2): 326–33. doi:10.1107/S0567740871002176.
  4. ^ Chapman FS (1949). The Jungle is Neutral. WW norton. p. 108.