Chemical Properties
White solid
Application
Sulfamethoxypyridazine may be used as a reference standard for the determination of sulfamethoxypyridazine in pharmaceutical formulations by liquid chromatography method.
Definition
ChEBI: A sulfonamide consisting of pyridazine having a methoxy substituent at the 6-position and a 4-aminobenzenesulfonamido group at the 3-position.
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.
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.
