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

• ChemBase ID: 4415
• Molecular Formular: C9H9N3O2S2
• Molecular Mass: 255.31666
• Monoisotopic Mass: 255.01361854
• SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1nccs1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1nccs1
• 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)
• InChIKey: JNMRHUJNCSQMMB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide
• IUPAC Traditional name: 4-amino-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide; sulfathiazole; thiazamide
• Brand Name: Neo-Strepsan
• Synonyms: Sulfathiazole; 4-Amino-N-2-thiazolyl-benzenesulfonamide; N₁-(2-Thiazolyl)sulfanilamide; N(1)-(2-Thiazolyl)sulfanilamide; Sultrin; 4-Amino-N-2-thiazolylbenzenesulfonamide; N1-2-Thiazolylsulfanilamide; 2-(p-Aminobenzenesulfonamido)thiazole; 2-Sulfathiazole-d4; Azoquimiol; Azoseptale; Chemosept; Ciba 3714; Cibazol; Duatok; Dulana; Eleudron; Enterobiocine; Sulfathiazol; Sulfocerol; Thiozamide; 4-Amino-N-(thiazol-2-yl)benzenesulfonamide; Sulphathiazole; Sodium sulfathiazole; Sulfathiazole; 4-Amino-N-(2-thiazolyl)benzenesulfonamide; N1-(2-Thiazolyl)sulfanilamide; 4-氨基-N-(2-噻唑基)苯磺酰胺; N1-(2-噻唑基)磺胺; 磺胺噻唑

Database IDs

• CAS Number: 72-14-0
• EC Number: 200-771-5
• MDL Number: MFCD00005319
• Beilstein Number: 226178
• Merck Index: 148943
• PubChem SID: 24870550; 24846323; 24899859; 160967847
• PubChem CID: 5340
• CHEBI ID: 9337
• ATC CODE: D06BA02; QJ01EQ07; J01EB07
• CHEMBL: 437
• Chemspider ID: 5148
• DrugBank ID: DB06147
• KEGG ID: D01047
• Unique Ingredient Identifier: Y7FKS2XWQH
• Wikipedia Title: Sulfathiazole

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.9284616
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.96082556
• LogD (pH = 7.4): 0.50352055
• Log P: 0.9750279
• Molar Refractivity: 62.2723 cm^3
• Polarizability: 24.194004 Å^3
• Polar Surface Area: 85.08 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.88
• LOG S: -2.44
• Solubility (Water): 9.21e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.373 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO Methanol
• Apperance: WHite Solid
• Melting Point: 196-198°C; 200- 202°C; 200-202 °C(lit.); 200-203°C; 201-204 °C
• Hydrophobicity(logP): 0.05 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: WP2360000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: Others
• Gene Information: rat ... Ednra(24326)
• Mechanism of Action: Dihydrofolate reductase inhibitor; Dihydrofolate synthesis inhibitor; Folate-antagonist

Product Information

• Purity: ≥98.0%; ≥98.0% (N); 98%; 99%
• Grade: purum; VETRANAL™, analytical standard
• Salt Data: Free Base
• Suitability: suitable for 1694 per US EPA
• Application(s): Sulfonamide; Used in treatment of severe staphylococcal infections, but use restricted due to its systemic toxicity.
• Empirical Formula (Hill Notation): C9H9N3O2S2

DETAILS

MP Biomedicals - 02102992

Free Acid
Crystalline

DrugBank - DB06147

• Drug Groups: approved
• Description: Sulfathiazole is a short-acting sulfa drug. It used to be a common oral and topical antimicrobial until less toxic alternatives were discovered. It is still occasionally used, sometimes in combination with sulfabenzamide and sulfacetamide.
• Indication: Sulfathiazole is effective against a wide range of gram positive and gram negative pathogenic microorganisms. Although no longer used in humans, it is used in cattle.
• Toxicity: Acute oral toxicity (LD50): 4500 mg/kg [Mouse].
• Biotransformation: Metabolism of sulfonamide drugs in animals includes conjugation at the N4-position (acetyl, sulfate, glucuronic acid, and glucose), conjugation at the N1-position (sulfate and glucuronic acid), removal of the p-amino group (formation of the desamino metabolite), ring hydroxylation, and conjugation of the ring hydroxylation products. Dietary nitrite enhances the production of the desamino metabolite of sulfathiazole. The intermediate leading to the desamino metabolite of sulfamethazine is weakly mutagenic in the Ames test (Nelson et al., 1987; Paulson et al., 1987).
• External Links: Wikipedia

Sigma Aldrich - 46902

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - S9876

Biochem/physiol Actions
通过抑制二氢叶酸合成酶阻断二氢叶酸合成的磺胺类抗生素。 作用方式：在原核生物中抑制叶酸合成。 抗菌谱：革兰氏阳性菌、革兰氏阴性菌、衣原体 抗性机理：二氢叶酸合成酶或叶酸合成替代路径的改变。
包装
100, 250 g in poly bottle

Toronto Research Chemicals - S699093

Antibacterial.

REFERENCES

• Kapoor, V.K., et al.: Anal. Profiles Drug Subs. Excip., 22, 389 (1993)
• Fosbinder, R.J., J.A.C.S., 1939, 61, 2032, (synth)
• Capitan, F. et al., Inf. Quim. Anal., 1970, 24, 100, (use)
• Bass, A.D. et al., Drill's Pharmacol. Med., 4th edn., McGraw-Hill, New York, 1971, 1657, (pharmacol)
• Kracmar, J. et al., Pharmazie, 1975, 30, 447, (uv)
• Forlani, L., Gazz. Chim. Ital., 1981, 111, 159, (pmr, tautom)
• Haley, T.J., Dangerous Prop. Ind. Mater. Rep., 1983, 3, 9, (rev, pharmacol, tox)
• Bult, A., Pharm. Weekbl., Sci. Ed., 1983, 5, 77, (cmr, tautom)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1148
• Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 2, 876, (rev)
• Kapoor, V.K., Anal. Profiles Drug Subst., 1993, 22, 389, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 210
• Hughes, D.S. et al., Acta Cryst. C, 1999, 55, 1831-1833, (cryst struct)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TEX250; TEX500