4-amino-N-sodio-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide

• ChemBase ID: 102904
• Molecular Formular: C9H8N3NaO2S2
• Molecular Mass: 277.29849
• Monoisotopic Mass: 276.99556279
• SMILES: Nc1ccc(cc1)S(=O)(=O)N([Na])c1nccs1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)N(c1nccs1)[Na]
• InChI: InChI=1S/C9H8N3O2S2.Na/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9;/h1-6H,10H2;/q-1;+1
• InChIKey: GWIJGCIVKLITQK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-sodio-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide
• IUPAC Traditional name: 4-amino-N-sodio-N-(1,3-thiazol-2-yl)benzenesulfonamide
• Synonyms: Sulfathiazole sodium salt; 4-Amino-N-(2-thiazolyl)benzenesulfonamide sodium salt; SODIUM SULFATHIAZOLE; Sulfathiazole sodium salt; 磺胺噻唑 钠盐

Database IDs

• CAS Number: 144-74-1
• EC Number: 205-638-5
• MDL Number: MFCD00072133
• Beilstein Number: 3802297
• PubChem SID: 24899426; 162090344
• PubChem CID: 12285822

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.08956091
• LogD (pH = 7.4): -0.08940203
• Log P: -0.0894
• Molar Refractivity: 61.4723 cm^3
• Polarizability: 25.857618 Å^3
• Polar Surface Area: 76.29 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: WP2450000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99%; ≥99.0% (TLC)
• Impurities: ≤10% water
• Empirical Formula (Hill Notation): C9H8N3NaO2S2

DETAILS

MP Biomedicals - 02105207

Crystalline

Sigma Aldrich - S0127

Application
Sulfathiazole is a short-acting sulfa drug. It was a common oral and topical antibiotic until less toxic alternatives were discovered. It is no longer used in humans1. Sulfathiazole is added to the diet of laboratory animals to inhibit folate formation by gut bacteria. This ensures that the animal’s only source of available folate is from their diet2.
Biochem/physiol Actions
Sulfathiazole is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfathiazole is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid1. It is active against Gram positive bacteria, Gram negative bacteria and Chlamydia. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.