Sulfathiazole

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Sulfathiazole
Sulfathiazole tautomerism.svg
Imino (top) and amino (bottom) tautomers
Systematic (IUPAC) name
4-amino-N-(1,3-thiazol-2-yl)benzenesulfonamide
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
CAS Number 72-14-0 YesY
ATC code D06BA02 (WHO) J01EB07 (WHO) QJ01EQ07 (WHO)
PubChem CID 5340
DrugBank DB06147 YesY
ChemSpider 5148 YesY
UNII Y7FKS2XWQH YesY
KEGG D01047 YesY
ChEBI CHEBI:9337 YesY
ChEMBL CHEMBL437 YesY
Chemical data
Formula C9H9N3O2S2
Molar mass 255.319 g/mol
Physical data
Melting point 202 to 202.5 °C (395.6 to 396.5 °F)
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Sulfathiazole is an organosulfur compound used as a short-acting sulfa drug. It is an organic compound. Formerly, it was a common oral and topical antimicrobial, until less toxic alternatives were discovered. It is still occasionally used, sometimes in combination with sulfabenzamide and sulfacetamide, and in aquariums.

It 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.[1]

Cultural references[edit]

Sulfathiazole is mentioned in chapter 104 of Kurt Vonnegut's novel Cat's Cradle and New Dictionary, and several of his short stories. Thomas Heggen's 1946 novel Mister Roberts mentions the use of sulfathiazole to treat gonorrhea, and Sonya Dorman's short story When I was Miss Dow in 1966. Also the 1988 movie Dead Heat mentions the chemical as a drug used with reanimation of dead bodies. In Otto Preminger's 1960 movie Exodus, American nurse Kitty Fremont tells Dr. Odenheimer that sulfathiazole is the treatment for impetigo. Dr. Odenheimer tells her that sulfathiazole is not available on the ship; soaking of the lesions and exposure to sunlight "is also a cure."

Sulfathiazole is mentioned in "The World According To Garp" in chapter 1 where Garps mother witnesses it being dispensed to WWII soldiers.

References[edit]

  1. ^ G. J. Kruger and G. Gafner "The crystal structure of sulphathiazole II" Acta Crystallogr. (1971). B27, 326-333.doi:10.1107/S0567740871002176