Sulfathiazole

Sulfathiazole

File: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 Y
ATC code	D06BA02 (WHO) J01EB07 QJ01EQ07 (WHO)
PubChem	CID: 5340
DrugBank	DB06147 Y
ChemSpider	5148 Y
UNII	Y7FKS2XWQH Y
KEGG	D01047 Y
ChEBI	CHEBI:9337 Y
ChEMBL	CHEMBL437 Y
Chemical data
Formula	C9H9N3O2S2
Molecular mass	255.319 g/mol
SMILES O=S(=O)(Nc1nccs1)c2ccc(N)cc2
InChI 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) Y Key:JNMRHUJNCSQMMB-UHFFFAOYSA-N Y
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.

Cultural references

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.