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

• ChemBase ID: 546
• Molecular Formular: C11H12N4O3S
• Molecular Mass: 280.30298
• Monoisotopic Mass: 280.06301126
• SMILES: S(=O)(=O)(Nc1nccnc1OC)c1ccc(N)cc1
• Canonical SMILES: COc1nccnc1NS(=O)(=O)c1ccc(cc1)N
• InChI: InChI=1S/C11H12N4O3S/c1-18-11-10(13-6-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)
• InChIKey: KXRZBTAEDBELFD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide
• IUPAC Traditional name: sulfametopyrazine; longum; 4-amino-N-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide
• Brand Name: Dalysep; Farmitalia 204/122; Kelfizin; Kelfizina; Kelfizine; Kelfizine W; Longum; Polycidal; SMP; SMP2; Solfametopirazina [Dcit]; Sulfalen; Sulfalene; Sulfalene [Usan:Inn]; Sulfaleno [INN-Spanish]; Sulfalenum [INN-Latin]; Sulfamethopyrazine; Sulfamethoxypyrazine; Sulfamethoxysuccinate; Sulfametoxypyridazin; Sulfapyrazinemethoxine; Sulfapyrazinemethoxyine; Sulfapyrazinemethoxyne
• Synonyms: Sulfametopyrazine; 4-Amino-N-(3-methoxy-2-pyrazinyl)-benzenesulfonamide; 4-amino-N-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide; F.I. 5978; Farmitalia 204/122; Kelfizin; Kelfizina; Kelfizine W; Longum; N1-(3-Methoxy-2-pyrazinyl)sulfanilamide; NSC 110433; Policydal; Polycidal; SMP2; Sulfalene; Sulfamethopyrazine; Sulfamethoxypyrazine; Sulfametopyrazine; Sulfapyrazinemethoxine; Sulfapyrazinemethoxyine; Sulfapyrazinemethoxyne; Vetkelfizina; Sulfamethoxypyrazine; 4-Amino-N-(3-methoxypyrazinyl)-benzenesulfonamide; N1-(3-Methoxypyrazinyl)-sulfanilamide; 2-Methoxy-3-sulfanilamidopyrazine; 2-Sulfanilamido-3-methoxypyrazine; 3-Methoxy-2-sulfanilamidopyrazine; 3-Methoxy-2-sulfapyrazine; 3-Methoxypyrazine Sulfanilamide; AS 18908; Dalysep; Kelfizine; Sulfalene

Database IDs

• CAS Number: 152-47-6
• MDL Number: MFCD00437754
• PubChem SID: 160964009; 46505111
• PubChem CID: 9047

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.91424
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.104915224
• LogD (pH = 7.4): -0.61960566
• Log P: 0.22788408
• Molar Refractivity: 70.367 cm^3
• Polarizability: 27.139517 Å^3
• Polar Surface Area: 107.2 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.41
• LOG S: -2.84
• Solubility (Water): 4.06e-01 g/l

PROPERTIES

Physical Property

• Solubility: 4030 mg/L; Dichloromethane; Methanol
• Apperance: Yellow Solid
• Melting Point: 168 - 170°C
• Hydrophobicity(logP): 0.7; 1.048

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Mechanism of Action: Competitive inhibitor of bacterial para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase; The inhibited reaction is necessary in these organisms for the synthesis of folic acid

Product Information

• Purity: 95%
• Application(s): Antiseptic; Long-acting sulfonamide used in treatment of respiratory and urinary-tract infections

DETAILS

DrugBank - DB00664

• Drug Groups: approved; withdrawn
• Description: Long-acting plasma-bound sulfonamide used for respiratory and urinary tract infections and also for malaria. [PubChem]
• Indication: For the treatment of urinary tract infection and chronic bronchitis.
• Pharmacology: Sulfametopyrazine 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: Gram negative, positive bacteria and plasmodium

Toronto Research Chemicals - S699230

A possible antimalarial drug.

REFERENCES

• Davidson D.E.Jr. et al; Am. J. Trop. Med. Hyg. 25, 26 (1976)
• Launchbury, A.P., Pharm. J., 1975, 214, 14, (pharmacol)
• Kracmar, J. et al., Pharmazie, 1975, 30, 447, (uv)
• Padeiskaya, E.N. et al., Khim.-Farm. Zh., 1977, 11, 141, (rev, pharmacol)
• Botta, M. et al., J. Het. Chem., 1979, 16, 193, (synth)
• Anisimova, O.S. et al., Khim.-Farm. Zh., 1980, 14, 92, (ms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 205
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MFN500