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 ;
	(verify)

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 in solid samples.^[3]

^ 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. hdl:11511/43872. 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.

[Ullmann-1] 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.

[2] 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. hdl:11511/43872. PMID 25455640.

[3] 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.

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