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 ;
CompTox Dashboard (EPA)	DTXSID8026068 ;
ECHA InfoCard	100.000.701
Chemical and physical data
Formula	C9H9N3O2S2
Molar mass	255.31 g·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 ;
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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

1960 Otto Preminger's 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."
1963: Sulfathiazole is mentioned in Kurt Vonnegut's novel Cat's Cradle and New Dictionary, and several of his short stories.
1964: Thomas Heggen's novel Mister Roberts mentions the use of sulfathiazole to treat gonorrhea.
1978: 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.
1988: The movie Dead Heat mentions the chemical as a drug used with reanimation of dead bodies.
2003: F. Spencer Chapman D.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]

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.CS1 maint: uses authors parameter (link)
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.CS1 maint: uses authors parameter (link)
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, The Jungle is Neutral p. 108

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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.CS1 maint: uses authors parameter (link)

[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.CS1 maint: uses authors parameter (link)

[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, The Jungle is Neutral p. 108