sulfathiazole

Also known as 4-Amino-N-2-thiazolylbenzenesulfonamide, N1-2-Thiazolylsulfanilamide, Sulfathiazolum, 2-(P-Aminobenzenesulphonamido)thiazole, Sulphathiazole, 2-(Sulfanilylamino)thiazole, Sulfathiazol, 2-Sulfanilamidothiazole

Sulfathiazole is an organosulfur compound used as a short-acting sulfa drug. Formerly, it was a common oral and topical antimicrobial, until less toxic alternatives were discovered.

In the Vinony graph

Within Vinony's link graph, sulfathiazole is referenced by 174 other articles, and connects out to sulfamethazine, antibiotic and dermatology.

It is catalogued under topics including 2-Thiazolyl compounds, 4-Aminophenyl compounds and Drugs with no legal status.

Its subject is documented across 14 Wikipedia language editions.

Key facts

Drug.verifiedrevid: 470473528
Drug.IUPAC_name: 4-amino-N-(1,3-thiazol-2-yl)benzenesulfonamide
Drug.image: Sulfathiazole tautomerism.svg
Drug.image_class: skin-invert-image
Drug.caption: Imino (top) and amino (bottom) tautomers
Drug.CAS_number: 72-14-0
Drug.ATC_prefix: D06
Drug.ATC_suffix: BA02
Drug.PubChem: 5340
Drug.DrugBank: DB06147
Drug.ChemSpiderID: 5148
Drug.UNII: Y7FKS2XWQH
Drug.KEGG: D01047
Drug.ChEBI: 9337
Drug.ChEMBL: 437
Drug.C: 9
Drug.H: 9
Drug.N: 3

via Wikipedia infobox

Chemical data

Formula: C9H9N3O2S2
Molecular weight: 255.3 g/mol
IUPAC name: 4-amino-N-(1,3-thiazol-2-yl)benzenesulfonamide
SMILES: C1=CC(=CC=C1N)S(=O)(=O)NC2=NC=CS2
InChIKey: JNMRHUJNCSQMMB-UHFFFAOYSA-N
XLogP: 0.1
Polar surface area: 122 Å²
H-bond donors: 2
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Withdrawn

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1945
Admin. routes: topical
Indications: bacterial disease

via ChEMBL · EBI

Research

1,370 papers

[Sulfathiazole-Suppopharm].Zeitschrift fur arztliche Fortbildung · 1962
Investigation of the riddle of sulfathiazole polymorphism.International journal of pharmaceutics · 2011
[Fixed sulfathiazole rash].Boletin. Sociedad Cubana de Dermatologia y Sifilografia · 1947
Polymorphism of sulfathiazole.Journal of pharmaceutical sciences · 1989
Derivatives of sulfathiazole.The Journal of organic chemistry · 1946

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 255.014
Has use: medication

Show 6 more facts

melting point: 202
chemical formula: C₉H₉N₃O₂S₂
medical condition treated: vaginitis
canonical SMILES: C1=CC(=CC=C1N)S(=O)(=O)NC2=NC=CS2
World Health Organisation international non-proprietary name: sulfathiazole
Commons category: Sulfathiazole

Sources (3)

via Wikidata · CC0

~2 min read

Encyclopedic overview

2 sections

Contents

Cultural references
References

Sulfathiazole is an organosulfur compound used as a short-acting sulfa drug. Formerly, it was a common oral and topical antimicrobial, until less toxic alternatives were discovered.

Sulfathiazole exists in various forms (polymorphs). The imine tautomer is dominant in solid samples.

Excerpted from Wikipedia’s “sulfathiazole” article, available under the CC BY-SA 4.0 licence.