Sulfathiazole

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Sulfathiazole
Sulfathiazole tautomerism.svg
Imino (top) and amino (bottom) tautomers
Clinical data
AHFS/Drugs.com International 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 InfoCard 100.000.701 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C9H9N3O2S2
Molar mass 255.31 g·mol−1
3D model (JSmol)
Melting point 202 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) Yes check.svgY
  • Key:JNMRHUJNCSQMMB-UHFFFAOYSA-N Yes check.svgY
   (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 in solid samples. [3]

Cultural references

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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. Bibcode:1971AcCrB..27..326K. doi: 10.1107/S0567740871002176 .
  4. Chapman FS (1949). The Jungle is Neutral. WW norton. p. 108.