4-amino-N-(6-methoxypyridazin-3-yl)benzene-1-sulfonamide

• ChemBase ID: 104656
• Molecular Formular: C11H12N4O3S
• Molecular Mass: 280.30298
• Monoisotopic Mass: 280.06301126
• SMILES: COc1ccc(NS(=O)(=O)c2ccc(N)cc2)nn1
• Canonical SMILES: COc1ccc(nn1)NS(=O)(=O)c1ccc(cc1)N
• InChI: InChI=1S/C11H12N4O3S/c1-18-11-7-6-10(13-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)
• InChIKey: VLYWMPOKSSWJAL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(6-methoxypyridazin-3-yl)benzene-1-sulfonamide
• IUPAC Traditional name: longin; 4-amino-N-(6-methoxypyridazin-3-yl)benzene-1-sulfonamide
• Synonyms: N1-(6-Methoxypyridazin-3-yl)sulfanilamide; Sulfamethoxypyridazine; SULFAMETHOXYPYRIDAZINE; 4-Amino-N-(6-methoxy-3-pyridazinyl)-benzenesulfonamide; 3-Methoxy-6-sulfanilamidopyridazine; 6-Sulfanilamido-3-methoxypyridazine; Sultirene; N1-(6-Methoxy-3-pyridazinyl)sulfanilamide; Paramid; Paramid Supra; Sulphamethoxypyridazine; Kynex; Midicel; Lederkyn; Exazol; Sulfalex; 4-氨基-N-(6-甲氧基-3-哒嗪基)苯磺酰胺; 磺胺甲氧哒嗪

Database IDs

• CAS Number: 80-35-3
• EC Number: 201-272-5
• MDL Number: MFCD00057372
• Beilstein Number: 277076
• PubChem SID: 162093090
• PubChem CID: 5330

CALCULATED PROPERTIES

• Acid pKa: 6.8447905
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.4486758
• LogD (pH = 7.4): -0.047052328
• Log P: 0.46578658
• Molar Refractivity: 72.3872 cm^3
• Polarizability: 27.145336 Å^3
• Polar Surface Area: 107.2 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 182-183°C

Safety Information

• Storage Condition: 2-8°C
• RTECS: WP0400000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 37/38-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others
• Mechanism of Action: Dihydrofolate reductase inhibitor; Folate antagonist

Product Information

• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Application(s): Antiseptic; Long-acting sulfonamide used for treatment of systemic infections.; Low acute toxicity
• Empirical Formula (Hill Notation): C11H12N4O3S

DETAILS

MP Biomedicals - 02156712

Crystalline

Sigma Aldrich - 46858

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

Toronto Research Chemicals - S699140

Antibacterial.

REFERENCES

• Tolika, E. et al.: Curr. Pharm. Analysis 6, 198 (2010)
• U.S. Pat., 1958, 2 833 761; CA, 52, 20216, (deriv)
• Horie, T. et al., Chem. Pharm. Bull., 1962, 10, 580, (synth)
• Bhni, E. et al., Chemotherapia, 1969, 14, 195, (pharmacol)
• Edwards, D., J. Pharm. Pharmacol., 1971, 23, 956, (ir)
• Turzcan, J. et al., J. Pharm. Sci., 1972, 61, 434, (pmr)
• Kracmar, J. et al., Pharmazie, 1975, 30, 447, (uv)
• Grechishkin, V.S. et al., J. Mol. Struct., 1982, 83, 345, (nqr, nmr)
• Bult, A., Pharm. Weekbl., Sci. Ed., 1983, 5, 77, (cmr)
• Basak, A.K. et al., Acta Cryst. C, 1987, 43, 735, (cryst struct)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1932; 2752
• Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 2, 876, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 210
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AKO500