Sulfaguanidine

Chemical properties

white powder

Originator

Sulfaguanidine,Lederle,US,1941

The Uses of Sulfaguanidine

Sulfaguanidine is a sulfonamide based antibiotic drug with potential application in veterinary medicine.

The Uses of Sulfaguanidine

Sulfonamide antibacterial.

Definition

ChEBI: Sulfaguanidine is a sulfonamide incorporating a guanidine moiety used to block the synthesis of folic acid; mostly used in veterinary medicine It has a role as an antiinfective agent.

Manufacturing Process

10 parts of guanidine hydrochloride (0.1 mol) was dissolved in 75 parts of water and the pH adjusted to 8 to 9. The solution was warmed to 50°C to 60°C and kept at this temperature while a slurry of 25 parts (0.113 mol) of pnitrobenzenesulfonyl chloride was added slowly with mechanical stirring. The pH was kept at 8 to 9 by the addition of 40% sodium hydroxide solution. At the end of the reaction the solution was cooled and filtered from the separated solid. The p-nitrobenzene sulfonyl guanidine was recrystallized from hot water.
5 parts (0.024 mol) of p-nitrobenzene sulfonyl guanidine was dissolved in 50 parts of boiling 95% alcohol and to the solution was added 0.5 part of concentrated hydrochloric acid. The solution was heated to reflux and 6 parts of iron dust was added. The suspension was refluxed for 3 hours, made basic with potassium carbonate, and filtered hot. The alcohol was evaporated off and the p-aminobenzene sulfonyl guanidine recrystallized from boiling water with the addition of decolorizing charcoal.

brand name

Aseptil-guanidina;Coliseptale;Devaguanil;Dirkan;Emerin;Ente-rivo simplex;Granidan;Guamide;Guanicil;Guanimycin;Guanowept;Guasept;Inorgan;Intestovet;Ordenol;Orgaguanidon;Resulfon;Ruocil;Sgd;S-guanidan;S-guanidine;Shigatox;Suganyl;Sulfacarbon;Sulfentidine;Sulfogua;Tetrawest;Trisulvet.

Therapeutic Function

Antimicrobial

World Health Organization (WHO)

Sulfaguanidine, a sulfonamide anti-infective agent, was introduced in 1941 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 sulfaguanidine, 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 preoperative bowel preparation.

Pharmaceutical Applications

1-Sulfanilylguanidine. A poorly absorbed compound, less potent than succinylsulfathiazole but with similar uses. Blood concentrations of 15–40 mg/L have been found after single doses of 1–7 g. Excretion in the urine is rapid.

Safety Profile

Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. See also SULFONATES. When heated to decomposition it emits very toxic fumes of SO, and NO,.

Purification Methods

Crystallise the antibacterial from hot water (7mL/g). [Beilstein 14 III 1970, 14 IV 2668.]