72-14-0

Chemical Properties

white to cream powder

Originator

Tiazol,C. and C.

Definition

ChEBI: A 1,3-thiazole compound having a 4-aminobenzenesulfonamido group at the 2-position.

Manufacturing Process

116 parts 4-acetamidobenzolsufonyl chloride (prepared from acetanilide and chlorosulfonic acid) was mixed with 100 parts 2-aminothiasole in 1000 parts water by cooling and stirred for some hours. The bis-amide obtained was filtered off and re-crystallized from 50% ethanol to give bis-(pacetylaminobenzolsulfo)- 2-aminothiazol with MP: 129°C.10 parts above bis-amide was heated with 10% sodium hydroxide solution for 0.5 hour on water bath. On cooling and filtration the alkaline solution was acidified with glacial acetic acid. The amide obtained was cleared by recrystallized from water to give N1-2-thiazolylsulfanilamide; MP: 202°-203°C.

Brand name

Argazol;Bucosol;Chemiovis;Coryza;Crionil;Csp 500;Csp-250;Edifeno;Femakzem;Formotablin antidiarreico;Gyne-sulf;Gyn-sulf;Neosutrin;Polvos wilfe;Pomada wilfe;Prothiazol;Septex cream no. 2;Streptacillin;Sulfa-orzon;Sulfazol;Sulfhatose;Sulfintestin;Sulfopyrol;Sulfour;Sulfzol;Sulnac;Sulphatriad;Tampovagan pss;Thiadyl;Thiuramide;Tiadyl;Trimeto;Trisulpha;Trysul;Tylasul;Ufa 902-duo;Vetoprim mi;Wintrazol.

Therapeutic Function

Antibacterial

World Health Organization (WHO)

Sulfathiazole, a sulfonamide anti-infective agent, was introduced more than 25 years ago 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. Although preparations remain available, use of the drug has been discontinued in many countries.

General Description

White crystalline powder. Is dimorphous: form I is consists of prismatic rods and form II of six-sided plates and prisms. Insoluble in water and soluble in dil aqueous acid and aqueous base.

Air & Water Reactions

May be sensitive to heat, air and light during long-term storage . Insoluble in water.

Reactivity Profile

Sulfathiazole is an amino acid.

Fire Hazard

Flash point data for Sulfathiazole are not available, but Sulfathiazole is probably combustible.

Pharmaceutical Applications

2-Sulfanilamidothiazole. A short-acting compound (half-life c. 4 h) with relatively high activity. Protein binding is c. 75%. Its use has declined because of a high incidence of side effects. It is one of the constituents of triple sulfonamide mixtures, of which local preparations are still available. Two compounds, phthalylsulfathiazole (sulfathalidine) and succinylsulfathiazole (sulfasuxidine) owe their activity to the slow liberation of sulfathiazole in the bowel. They are poorly soluble and very little is absorbed after oral administration. They were formerly used in the treatment of intestinal infections and in bowel preparation before surgery. They are available in multi-ingredient preparations in some countries.

Biochem/physiol Actions

Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.Mode of Action: Inhibits folic acid synthesis in prokaryotes.Anti-microbial Spectrum: Gram positive, Gram negative, ChlamydiaMode of Resistance: Alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.

Safety Profile

Human poison by unspecified route. Experimental poison by intraperitoneal route, Moderately toxic by intravenous, subcutaneous, and parenteral routes. Mildly toxic by ingestion. Human systemic effects by unspecified route: conjunctiva irritation, tubule changes, and allergic skin dermatitis. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data, Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Who Evaluation

Evaluation year: 1989