Chemical Properties
White or yellowish-white, crystalline powder.
Originator
Sulfathalidine, MSD, US,1946
Definition
ChEBI: Phthalylsulfathiazole is a sulfonamide incorporating 2-carboxybenzamido and 1,3-thiazol-2-yl moieties that is a broad-spectrum antibiotic indicated in the treatment of dysentery, colitis, gastroenteritis and intestinal surgery. It is a sulfonamide, a member of 1,3-thiazoles, a dicarboxylic acid monoamide and a sulfonamide antibiotic. It derives from a phthalic acid.
Preparation
It may be prepared by the interaction of sulfathiazole and phthalic anhydride in equimolar proportions.
It exerts its bacteriostatic effect in the gastro-intestinal tract. It has been found to be twice as active as sulfaguanidine in the treatment of bowel irregularities. It is often effective in watery diarrhoeas and ulcerative colitis. It is also used in the pre-operative treatment of patients undergoing surgery of the intestinal tract. It may also be recommended in the treatment of acute bascillary dysentry of the Sonne, Flexner and Shiga species.
Manufacturing Process
5 g of phthalic anhydride was added to a boiling suspension of 10 g of sulfathiazole in 100 cc of alcohol. The mixture was then refluxed for 5 minutes after the addition was complete at which time all of the solids were in solution. The solution was then cooled and diluted with an equal volume of water, The white solid precipitate which formed was filtered and recrystallized from dilute alcohol, yielding 2-N4-phthalylsulfanilamidothiazole,which decomposes above 260°C, according to US Patent 2,324,015.
Brand name
Canidis-anti-diarr;Carbidiar;Carbotalin;Colicitina;Coliclase;Crematalil;Diacolin;Direver;Disenterol;Ef-micin;Enterocalme;Entero-hermes;Entero-red;Enterosteril;Entero-toxan;Esteraplidin mag;Eugeniteed;Fitazil;Ftalil-tiazol;Ilentazol;Inrestibla strepto;Iodentero-neomicina;Logical;Massotalil;Neo-sulfazon;Novosulfina;Phtazol;Septiftalil;Syptan;Talisulfazol;Tamil;.
Therapeutic Function
Antibacterial (intestinal)
World Health Organization (WHO)
Phthalylsulfathiazole, a sulfonamide anti-infective agent, was
introduced in 1946 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. Although phthalylsulfathiazole, which is poorly absorbed from the
gastrointestinal tract, is no longer recommended in some countries, it continues to
be used in others for the treatment of local intestinal infections, including bacterial
dysentery, and for pre-operative bowel preparation.
Flammability and Explosibility
Nonflammable
Mode of action
Phthalylsulfathiazole is of low inherent toxicity. Besides, it also enjoys an additional plus point for being only slightly absorbed by the intestinal mucosa ; and, therefore, may be safely administered in comparatively large doses in the management and treatment of bacillary infections of the intestine. The drug is not absorbed orally and is mostly employed for ulcerative colitis.
