Sulfathiazole

Sulfathiazole
	Imino (top) and amino (bottom) tautomers
Clinical data
AHFS/Drugs.com	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 ;
PubChem CID	5340;
DrugBank	DB06147 ;
ChemSpider	5148 ;
UNII	Y7FKS2XWQH;
KEGG	D01047 ;
ChEBI	CHEBI:9337 ;
ChEMBL	CHEMBL437 ;
ECHA InfoCard	100.000.701
Chemical and physical data
Formula	C9H9N3O2S2
Molar mass	255.319 g/mol
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 ;
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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, at least in the solid state. In this tautomer, the proton resides on the ring nitrogen.^[3]

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 John Irving's novel "The World According To Garp" in chapter 1 where Garp's mother witnesses it being dispensed to World War II soldiers.

F.Spencer Chapman D.S.O. in his account of WW2, "The Jungle is Neutral", refers on p.108 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 the arduous conditions during the guerilla actions undertaken by the Malayan Communist Party against the Japanese occupying forces.At this period there was no support or communication from Allied forces.^[4]

References

↑ Bernd Mertschenk, Ferdinand Beck, Wolfgang Bauer (2002). "Thiourea and Thiourea Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a26_803.
↑ Rouf, Abdul; Tanyeli, Cihangir (2015). "Bioactive thiazole and benzothiazole derivatives". European Journal of Medicinal Chemistry. 97: 911–927. doi:10.1016/j.ejmech.2014.10.058.
↑ G. J. Kruger and G. Gafner "The crystal structure of sulphathiazole II" Acta Crystallogr. (1971). B27, 326-333.doi:10.1107/S0567740871002176
↑ F. Spencer Chapman D.S.O. book "The Jungle is Neutral"

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[Ullmann-1] Bernd Mertschenk, Ferdinand Beck, Wolfgang Bauer (2002). "Thiourea and Thiourea Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a26_803.

[2] Rouf, Abdul; Tanyeli, Cihangir (2015). "Bioactive thiazole and benzothiazole derivatives". European Journal of Medicinal Chemistry. 97: 911–927. doi:10.1016/j.ejmech.2014.10.058.

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

[4] F. Spencer Chapman D.S.O. book "The Jungle is Neutral"