Sulfamethoxypyridazine

Chemical properties

White or slightly yellow crystalline powder; odorless, bitter taste; discolored when exposed to light. The product is slightly soluble in acetone, very slightly soluble in ethanol, almost insoluble in water; easily soluble in dilute hydrochloric acid or alkali hydroxide solution.

The Uses of Sulfamethoxypyridazine

Sulfamethoxypyridazine is a long-acting sulfonamide antibiotic with anti-inflammatory and antibacterial effects, mainly used for streptococcus, staphylococcus, Escherichia coli and other infections, especially for urinary tract infections.

Indications

This 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.

What are the applications of Application

Sulfamethoxypyridazine may be used as a reference standard for the determination of sulfamethoxypyridazine in pharmaceutical formulations by liquid chromatography method.

Definition

ChEBI: Sulfamethoxypyridazine is a sulfonamide consisting of pyridazine having a methoxy substituent at the 6-position and a 4-aminobenzenesulfonamido group at the 3-position. It has a role as an antiinfective agent, an EC 2.5.1.15 (dihydropteroate synthase) inhibitor and a drug allergen. It is a member of pyridazines, a sulfonamide and a sulfonamide antibiotic. It derives from a sulfanilamide.

brand name

Amidin;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.

General Description

Sulfamethoxypyridazine is a sulfonamide antibiotic mainly used to prevent infections as well as conditions such as coccidiosis, diarrhea and gastroenteritis.

Pharmaceutical Applications

3-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.

Synthesis

Sulfamethoxypyridazine, 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.