4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide

• ChemBase ID: 458
• Molecular Formular: C9H10N4O2S2
• Molecular Mass: 270.3313
• Monoisotopic Mass: 270.02451758
• SMILES: S(=O)(=O)(Nc1sc(nn1)C)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1nnc(s1)C
• InChI: InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)
• InChIKey: VACCAVUAMIDAGB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide
• IUPAC Traditional name: sulfamethizole
• Brand Name: Sulfamethizole [Usan:Inn:Jan]; Sulfamethizolum [INN-Latin]; Sulfamethylthiadiazole; Sulfametizol [INN-Spanish]; Sulfapyelon; Sulfstat; Sulfurine; Sulphamethizole; Sulphamethyltiadiazole; Tetracid; Thidicur; Thiosulfil; Thiosulfil Forte; Ultrasul; Urocydal; Urodiaton; Urolucosil; Urosulfin; Uroz; Ayerlucil; Famet; Lucosil; Methazol; Microsul; Proklar; Renasul; Rufol; Sulfamethiazole; Salimol; Solfametizolo [Dcit]; Sulamethizole; Sulfa Gram; Sulfamethazole; Sulfamethizol
• Synonyms: Sulfamethizole; Sulfamethizol; Sulfamethizole; 4-Amino-N-[5-methyl-1,3,4-thiadiazol-2-yl]benzenesulfonamide; 4-Amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide; N1-(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanilamide; Proklar; Sulfamethizole (Proklar); 4-氨基-N-(5-甲基-1,3,4-噻二唑-2-基)苯磺酰胺; N1-(5-甲基-1,3,4-噻二唑-2-基)磺胺; 磺胺甲二唑

Database IDs

• CAS Number: 144-82-1
• EC Number: 205-641-1
• MDL Number: MFCD00053363
• Beilstein Number: 255002
• PubChem SID: 46508656; 24870514; 160963921; 24899662
• PubChem CID: 5328

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.707642
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.19116575
• LogD (pH = 7.4): -0.364739
• Log P: 0.21434596
• Molar Refractivity: 66.8358 cm^3
• Polarizability: 25.134037 Å^3
• Polar Surface Area: 97.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.53
• LOG S: -2.65
• Solubility (Water): 6.11e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1050 mg/L
• Hydrophobicity(logP): 0.9

Safety Information

• Storage Condition: 2-8°C
• RTECS: WP0875000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥99% (HPLC); 98%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Suitability: suitable for 1694 per US EPA
• Empirical Formula (Hill Notation): C9H10N4O2S2

DETAILS

MP Biomedicals - 02156710

Crystalline
Purity: 98%

DrugBank - DB00576

• Drug Groups: approved
• Description: A sulfathiazole antibacterial agent. [PubChem]
• Indication: For the treatment of urinary tract infection
• Pharmacology: Sulfamethizole is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic.
• Absorption: Rapidly absorbed.
• Half Life: 3-8 hours
• Protein Binding: 98-99%
• References: Ratanajamit C, Skriver MV, Norgaard M, Jepsen P, Schonheyder HC, Sorensen HT: Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study. J Antimicrob Chemother. 2003 Nov;52(5):837-41. Epub 2003 Sep 30. [Pubmed] ; Kerrn MB, Frimodt-Moller N, Espersen F: Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model. Antimicrob Agents Chemother. 2003 Mar;47(3):1002-9. [Pubmed] ; Watanabe H, Hastings JW: Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine. Biochim Biophys Acta. 1990 Jun 26;1017(3):229-34. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - 46842

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

REFERENCES

• Ratanajamit C, Skriver MV, Norgaard M, Jepsen P, Schonheyder HC, Sorensen HT: Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study. J Antimicrob Chemother. 2003 Nov;52(5):837-41. Epub 2003 Sep 30. Pubmed
• Kerrn MB, Frimodt-Moller N, Espersen F: Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model. Antimicrob Agents Chemother. 2003 Mar;47(3):1002-9. Pubmed
• Watanabe H, Hastings JW: Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine. Biochim Biophys Acta. 1990 Jun 26;1017(3):229-34. Pubmed