Chemical Component Summary

Name4-amino-N-(1,3-thiazol-2-yl)benzenesulfonamide
SynonymsSulfathiazole
Identifiers4-azanyl-N-(1,3-thiazol-2-yl)benzenesulfonamide
FormulaC9 H9 N3 O2 S2
Molecular Weight255.317
TypeNON-POLYMER
Isomeric SMILESc1cc(ccc1N)S(=O)(=O)Nc2nccs2
InChIInChI=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)
InChIKeyJNMRHUJNCSQMMB-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count25
Chiral Atom Count0
Bond Count26
Aromatic Bond Count11

Drug Info: DrugBank

DrugBank IDDB06147 
NameSulfathiazole
Groups
  • vet_approved
  • approved
  • withdrawn
DescriptionSulfathiazole is a short-acting sulfa drug. It used to be a common oral and topical antimicrobial until less toxic alternatives were discovered. It is still occasionally used, sometimes in combination with sulfabenzamide and sulfacetamide. Except for those formulated for vaginal use, the FDA withdrew its approval for the use of all drug products containing sulfathiazole.[L43942]
Synonyms
  • N1-2-Thiazolylsulfanilamide
  • Sulphathiazole
  • 2-Sulfonamidothiazole
  • Sulfathiazol
  • N(1)-2-Thiazolylsulfanilamide
Brand Names
  • Triple Sulfa
  • Gyne-Sulf
IndicationSulfathiazole is effective against a wide range of gram positive and gram negative pathogenic microorganisms. Although no longer used in humans, it is used in cattle.
Categories
  • Amides
  • Amines
  • Aniline Compounds
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
ATC-Code
  • G01AE10
  • J01EB07
  • D06BA02
CAS number72-14-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Dihydropteroate synthetaseIPEYKHNVLNNTIRCLYNKYVSRMKEQYNINIKENNKRIYVLKDRISYLK...unknowninhibitor
Cytochrome P450 19A1MVLEMLNPIHYNITSIVPEAMPAATMPVLLLTGLFLLVWNYEGTSSIPGP...unknowninducer
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 5340
ChEMBL CHEMBL437
ChEBI CHEBI:9337
CCDC/CSD LOFMAW01, FIFWOJ, LOFMAW, KUFWIT