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Sulfamethoxypyridazine

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Sulfamethoxypyridazine Basic information
Sulfamethoxypyridazine Chemical Properties
  • Melting point:182-183°
  • Boiling point:564.9±60.0 °C(Predicted)
  • Density 1.3936 (rough estimate)
  • refractive index 1.6200 (estimate)
  • storage temp. 2-8°C
  • form Crystalline Powder
  • pka6.7(at 25℃)
  • color White to yellow
  • Water Solubility 579.5mg/L(25 ºC)
  • Merck 14,8919
  • BRN 277076
  • CAS DataBase Reference80-35-3(CAS DataBase Reference)
  • NIST Chemistry ReferencePyridazine, sulfamethoxy-(80-35-3)
Safety Information
  • Hazard Codes Xi
  • Risk Statements 37/38-41
  • Safety Statements 26-39
  • WGK Germany 2
  • RTECS WP0400000
  • 10
  • HS Code 29350090
  • ToxicityLD50 orally in mice: 1750 mg/kg, (Seki)
MSDS
Sulfamethoxypyridazine Usage And Synthesis
  • Chemical PropertiesWhite solid
  • UsesAntibacterial.
  • DefinitionChEBI: A sulfonamide consisting of pyridazine having a methoxy substituent at the 6-position and a 4-aminobenzenesulfonamido group at the 3-position.
  • IndicationsThis drug possesses antibacterial activity with respect to a few cocci and colon bacillus. It is a long-lasting drug. It is used for treating pneumonia, bronchitis, tonsillitis, purulent otitis and meningitis, purulent infections of the urinary tract, dysentery, and others. Synonyms of this drug are sulfapyridazine, sufalex, retasulfin, and many others.
  • brand nameAmidin;Aseptilex;Asey-sulfa;Bimalong;Biocorn;Bio-cron;Bio-pectodil;Davosin suspension;Deltavagin;Desulfon;Durasul jarabe;Elix;Ensulfa;Eusulfa;Exazole;Farinffnicol;Fercasulf;Hesse-sulfon;Ketiak;Kynex acetyl;Lentosulfa;Linder;Logisul jarabe;Longamid;Longisul;Metamit;Metazina;Metuzina;Minikel;Novosulfin;Pirasulfon;Ralenta;Rotardon;S.d.m.;Septotryl;Smop;Sulamin;Sulfa spirig;Sulfabon;Sulfadazina;Sulfadepot;Sulfadin;Sulfadurazin;Sulfaintensa;Sulfakeyn;Sulfametopyridazin;Sulfamizina;Sulfamyd;Sulfapyrazin;Sulfatar;Sulfocidan;Sulfonamid;Sulforetent;Sulfo-rit;Unisulfa dulcis;Uroplex;Velaten;Volocid;Vtg 44.
  • World Health Organization (WHO)Sulfamethoxypyridazine, a sulfonamide anti-infective agent, was introduced in 1957 for the treatment of bacterial infections. The importance of sulfonamides has subsequently decreased as a result of increasing bacterial resistance and their replacement by antibiotics which are generally more active and less toxic. The sulfonamides are known to cause serious adverse effects such as renal toxicity, sometimes fatal exfoliative dermatitis and erythema multiforma and dangerous adverse reactions affecting blood formation such as agranulocytosis and haemolytic or aplastic anaemia. Commercial manufacture of the drug has been discontinued by at least one major manufacturer but supplies can still be obtained on special request, particularly for patients with dermatitis herpetiformis in which condition it has been claimed to be beneficial.
  • Pharmaceutical Applications3-Sulfanilamido-6-methoxypyridazine. Properties are similar to those of sulfadimethoxine. A rapidly absorbed, long-acting compound (half-life 38 h) with a high degree of protein binding (96%). A 1 g oral dose achieves a peak plasma concentration of around 100 mg/L after 5 h. Its use has been largely discontinued because of frequent adverse effects, but there are reports of benefit in dermatitis herpetiformis. It has been used in combination with trimethoprim.
  • Chemical SynthesisSulfamethoxypyridazine, N1 -(6-methoxy-3-pyridazinyl)sulfanilamide (33.1.43), is synthesized by replacing the chlorine atom in 6-chloro-3-(4-aminobenzenesulfonilamido)pyridazine with a methoxy group in 33.1.42 using sodium methoxide. The initial 6-chloro-3-(4-aminobenzenesulfonylamido)-pyridazine (33.1.42) is in turn synthesized by reacting 4-aminobenzenesulfanilamide with easily accessible 3,6-dichloropyridazine.

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