SULFACHLOROPYRIDAZINE

SULFACHLOROPYRIDAZINE Basic information
Description Brand Name(s) in US Reference
Product Name:SULFACHLOROPYRIDAZINE
Synonyms:N’-(6-Chloro-3-pyridazinyl)sulfanilamide;Soxilyn;VetisullideNefrosul;AKOS B014357;Nefrosul (TN);Prinz;Sulfachlorpyridazine (USP);Vetisulid (Veterinary)
CAS:80-32-0
MF:C10H9ClN4O2S
MW:284.72
EINECS:201-269-9
Product Categories:pharmaceutical;Inhibitors;VETISULID;Amines;Aromatics;Sulfur & Selenium Compounds
Mol File:80-32-0.mol
SULFACHLOROPYRIDAZINE Structure
SULFACHLOROPYRIDAZINE Chemical Properties
Melting point 186-187℃
Boiling point 559.7±60.0 °C(Predicted)
density 1.588
refractive index 1.6300 (estimate)
storage temp. Keep in dark place,Inert atmosphere,2-8°C
solubility 0.5 M NaOH: soluble50mg/mL
pkapKa 6.10 (Uncertain)
form powder
color off-white to light yellow
BRN 261558
EPA Substance Registry SystemBenzenesulfonamide, 4-amino-N-(6-chloro-3-pyridazinyl)- (80-32-0)
Safety Information
Hazard Codes Xi
Risk Statements 43
Safety Statements 36/37
WGK Germany 3
HazardClass IRRITANT
HS Code 2935909550
MSDS Information
ProviderLanguage
SigmaAldrich English
SULFACHLOROPYRIDAZINE Usage And Synthesis
DescriptionIt is a sulfonamide antibiotic that is usually used as antibacterial anti-inflammatory drug, which has been applied in the treatment of acute urinary tract infections in childhood. Specifically, due to its antibiotic activity, this chemical has been selected as an ingredient to prepare antibacterial composition.1 Moreover, this substance can be introduced in the drinking water to fabricate aqueous liquid formulations for combating bacterial and protozoal in animals.2 In addition, this compound can act as an eco-friendly inhibitor for corrosion of mild steel in H2SO4 solution.3 Besides, sulfachloropyridazine associated to tripelennamine hydrocholoride has been demonstrated to function as an anti-stress agent in poultry after vaccinations.4
Brand Name(s) in USVetisulid
Reference
  1. Stolar, M. E., Synergistic antibacterial composition US Patent 4470978 1984.
  2. Gerhard Lukas; Atasoy, K., Aqueous liquid formulations for control of bacterial and protozoal diseases US Patent 4423043 1983.
  3. Omar A. Hazazi; Ahmed Fawzy; Awad, M. I., Sulfachloropyridazine as an Eco-Friendly Inhibitor for Corrosion of Mild Steel in H2SO4 Solution Chemical Science Review and Letters 2015, 4, 67-79.
  4. M. Nakano; M.N. Narimatsu; Portugal, M. A. S. C., Use of sulfachloropyridazine associated to tripelennamine hydrochloride as anti-stress agent in poultry after vaccinations. Biologico 1977.
OriginatorSonilyn,Mallinckrodt Inc.,US,1962
UsesSulfachloropyridazine is an antibacterial compound.This compound is a contaminant of emerging concern (CECs).
DefinitionChEBI: A sulfonamide antimicrobial used for urinary tract infections and in veterinary medicine.
Manufacturing Process1.9 parts of 3,6-dichloropyridazine, 3.4 parts of sulfanilamide, 2.7 parts of potassium carbonate and 1 part of sodium chloride were ground together. The solid mixture was heated with stirring and as the dichloropyridazine and sulfanilamide melted, the mixture became a slurry. When the bath temperature had reached 140°C a sudden evolution of carbon dioxide occurred which lasted about 5 minutes, after which the mixture set in fine granules. When no more carbon dioxide was evolved, heating was stopped and the reaction mixture was heated with sufficient water to dissolve it and the solution allowed to cool. Unreacted sulfanilamide was collected by filtration. Excess dichloropyridazine was removed from the filtrate by extraction with a water immiscible organic solvent such as ether.
The basic solution was chilled and poured into one-half volume of 1:3 acetic acid. Sufficient hydrochloric acid was added to bring the mixture to pH 4. The crude 3-sulfanilamido-6-chloropyridazine which precipitated was purified by solution in 6 parts of 1:100 ammonium hydroxide, charcoal treatment and precipitation by pouring of the filtrate into dilute acetic acid.
Brand nameNefrosul (3M Pharmaceuticals); Sonilyn,(Carter-Wallace); Vetisulid [Veterinary] (Fort Dodge Animal Health).
Therapeutic FunctionAntibacterial
SULFACHLOROPYRIDAZINE Preparation Products And Raw materials
Raw materialsMaleic anhydride-->Sulfanilamide-->3,6-Dichloropyridazine-->Maleic hydrazide
Preparation ProductsN1-(6-ethoxypyridazin-3-yl)sulphanilamide
Sulfamethoxypyridazine Sulfluramid Sulfaquinoxaline Penicillin G sodium salt Pyridazin-3-amine 3-Aminopyridazine hydrochloride 2-Methylsulfonyl-4,6-dimethoxypyrimidine 6-Chloropyridazin-3-amine SULPHADIMIDINE SODIUM SULFAMETHAZINE Pyridazine Sulfachloropyridazine sodium SULFACHLOROPYRIDAZINE 3-CHLOROPYRIDAZINE Sulfamethazine SULFACHLORPYRIDAZINE SODIUM SULFADIMIDINE-D4 SULFACHLOROPYRIDAZINE BASE

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