Sulfathiazole

Sulfathiazole
	Imino (top) and amino (bottom) tautomers
Clinical data
AHFS/Drugs	International Drug Names
ATC code	D06BA02(WHO)J01EB07(WHO)QJ01EQ07(WHO);
Identifiers
	IUPAC name 4-amino-N-(1,3-thiazol-2-yl)benzenesulfonamide;
CAS Number	72-14-0;
PubChemCID	5340;
DrugBank	DB06147;
ChemSpider	5148;
UNII	Y7FKS2XWQH;
KEGG	D01047;
ChEBI	CHEBI:9337;
ChEMBL	ChEMBL437;
CompTox Dashboard(EPA)	DTXSID8026068;
ECHA InfoCard	100.000.701
Chemical and physical data
Formula	C9H9N3O2S2
Molar mass	255.31g·mol−1
3D model (JSmol)	Interactive image;
Melting point	202 to 202.5 °C (395.6 to 396.5 °F)
	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); Key:JNMRHUJNCSQMMB-UHFFFAOYSA-N;
	(verify)

Sulfathiazoleis anorganosulfur compoundused as a short-actingsulfa drug.^[1]Formerly, it was a common oral and topicalantimicrobial,until less toxic alternatives were discovered.^[2]

Sulfathiazole exists in various forms (polymorphs). The iminetautomeris dominant in solid samples.^[3]

Cultural references

In the 1955 short story,Captive AudiencebyPhilip K. Dick,Flannery recommends the use of sulfathiazole in lieu of the unavailablePenicillinfor a ten-year-old boy's suppurating arm wound he received from "toxic crystalline poisoning".
1960 Otto Preminger's movieExodus,American nurse Kitty Fremont tells Dr. Odenheimer that sulfathiazole is the treatment forimpetigo.Dr. Odenheimer tells her that sulfathiazole is not available on the ship; soaking of the lesions and exposure to sunlight "is also a cure."
1963: Sulfathiazole is mentioned inKurt Vonnegut's novelCat's Cradleand New Dictionary, and several of his short stories.
1964:Thomas Heggen's novelMister Robertsmentions the use of sulfathiazole to treatgonorrhea.
1978:John Irving's novelThe World According to Garpin chapter 1 where Garp's mother witnesses it being dispensed toWorld War IIsoldiers.
1988: The movie Dead Heat mentions the chemical as a drug used with reanimation of dead bodies.
2003:F. Spencer ChapmanD.S.O. in his WWII memoir,The Jungle is Neutral,refers to his personal use of sulphathiazole (M.&B.) in the jungles of Malaya during May 1942. He credits the use of the drug with preventing fever and pneumonia becoming fatal in arduous conditions during the guerilla actions undertaken by the Malayan Communist Party against the Japanese occupying forces.^[4]

^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.
^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.
^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.
^Chapman FS (1949).The Jungle is Neutral.WW norton. p. 108.

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