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

• ChemBase ID: 57089
• Molecular Formular: C10H9ClN4O2S
• Molecular Mass: 284.72206
• Monoisotopic Mass: 284.01347423
• SMILES: c1(S(=O)(=O)Nc2ccc(nn2)Cl)ccc(cc1)N
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1ccc(nn1)Cl
• InChI: InChI=1S/C10H9ClN4O2S/c11-9-5-6-10(14-13-9)15-18(16,17)8-3-1-7(12)2-4-8/h1-6H,12H2,(H,14,15)
• InChIKey: XOXHILFPRYWFOD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(6-chloropyridazin-3-yl)benzene-1-sulfonamide
• IUPAC Traditional name: sulfachloropyridazine; 4-amino-N-(6-chloropyridazin-3-yl)benzene-1-sulfonamide
• Synonyms: 4-Amino-N-(6-chloropyridazin-3-yl)-benzenesulfonamide; 4-Amino-N-[6-chloro-3-pyridazinyl]-benzenesulfonamide; SULFACHLOROPYRIDAZINE; Sulfachloropyridazine; 4-Amino-N-(6-chloro-3-pyridazinyl)benzenesulfonamide; 4-Amino-N-(6-chloro-3-pyridazinyl)-benzenesulfonamide Sodium; 3-Chloro-6-sulfanilamidopyridazine Sodium; N1-(6-Chloro-3-pyridazinyl)sulfanilamide Monosodium Salt; Prinzone; Sodium Sulfachloropyridazine; Sodium Sulfachlorpyridazine; Sulfachloropyridazine Sodium; Sulfachlorpyridazine Sodium Salt; Vetisulid; Sulfachlorpyridazine Sodium; Vetisulide; Nefrosul; Sonilyn; Sulfachlorpyridazine; 4-氨基-N-(6-氯-3-哒嗪基)苯磺酰胺; 磺胺氯哒嗪

Database IDs

• CAS Number: 80-32-0
• EC Number: 201-269-9
• MDL Number: MFCD00057371
• Beilstein Number: 261558
• PubChem SID: 24899860; 162061852; 24870436
• PubChem CID: 6634

CALCULATED PROPERTIES

• Acid pKa: 6.59534
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.82350135
• LogD (pH = 7.4): 0.22266842
• Log P: 0.85322213
• Molar Refractivity: 71.4766 cm^3
• Polarizability: 26.594187 Å^3
• Polar Surface Area: 97.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43
• Safety Statements: 36/37
• TSCA Listed: false
• 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

Pharmacology Properties

• Mechanism of Action: Folic acid biosynthesis antagonist

Product Information

• Purity: 98%
• Grade: VETRANAL™, analytical standard
• Suitability: suitable for 1694 per US EPA
• Application(s): Antiseptic; Veterinary antibacterial agent
• Empirical Formula (Hill Notation): C10H9ClN4O2S

DETAILS

MP Biomedicals - 02156705

Purity: 98%

Sigma Aldrich - S9882

Application
Sulfachloropyridazine is a sulfonamide antibiotic that is used to study kinetics, reaction pathways and toxicity evolution1. Sulfachloropyridazine has been used to treat acute urinary tract infections in pediatric patients2.
Biochem/physiol Actions
Sulfachloropyridazine is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfachloropyridazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid3. 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. Sulfachloropyridazine is rapidly absorbed and rapidly excreted in the urine4.

Sigma Aldrich - 46778

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

Toronto Research Chemicals - S689060

Sulfachlorpyridazine is an antibacterial compound.

REFERENCES

• Wammer, K.: Environ. Toxicol. Chem. 25, 1480 (2006).
• U.S. Pat., 1957, Cyanamid, 2 790 798; CA, 51, 15610i, (synth, pharmacol)
• Horie, T. et al., Chem. Pharm. Bull., 1962, 10, 580, (synth)
• Krueger-Theimer, E. et al., Arzneim.-Forsch., 1965, 15, 1309, (pharmacol)
• Turczan, J. et al., J. Pharm. Sci., 1972, 61, 434, (nmr)
• Martindale, The Extra Pharmacopoeia, 28th/29th edn., Pharmaceutical Press, 1982, 4929
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1430
• Lewis, R.J., Food Additives Handbook, Van Nostrand Reinhold International, New York, 1989, SNH900