Phthalylsulfathiazole

Chemical properties

White or yellowish-white, crystalline powder.

Originator

Sulfathalidine, MSD, US,1946

The Uses of Phthalylsulfathiazole

Phthalylsulfathiazole is a sulfonamide antibacterial drug with similar and stronger effects than Sulfaguanidine and Succinylsulfathiazole. It is rarely absorbed orally and slowly decomposes in the intestine to release Sulfathiazole and exert intestinal antibacterial effects, and is used in the treatment of dysentery, colitis, and gastroenteritis.

Background

Phthalylsulfathiazole is a broad spectrum antibiotic which is part of the drug class, sulfonamides. It was used as an antibiotic for bowel surgery, and for infections of the colon .

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

Non flammable

Metabolism

Not Available

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.