Сульфацетамид

Химические свойства

white crystalline powder

Определение

ChEBI: A sulfonamide that is sulfanilamide acylated on the sulfonamide nitrogen.

Общее описание

Sulfacetamide’s plasmahalf-life is 7 hours. This compound is a white crystallinepowder, soluble in water (1:62.5 at 37°C) and in alcohol. It is very soluble in hot water, and its water solution is acidic.It has a pKa of 5.4.

Реакции воздуха и воды

Insoluble in water.

Профиль реактивности

N-((4-Aminophenyl)sulfonyl)acetamide is an amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generate mixed oxides of nitrogen (NOx)

Пожароопасность

Flash point data for N-((4-Aminophenyl)sulfonyl)acetamide are not available. N-((4-Aminophenyl)sulfonyl)acetamide is probably combustible.

Фармацевтические приложения

N-acetylsulfanilamide. It is very soluble in water and was formerly used in urinary tract infection. It is available in some countries in ophthalmic preparations and as a component (with sulfathiazole and sulfabenzamide) of a triple sulfonamide cream for the topical treatment of bacterial vaginosis.
Sulfacetamide is one of the least active sulfonamides. It is well absorbed when given orally and is excreted in the urine with a half-life of around 9 h. About 70% is excreted unchanged, the remainder being present as the acetyl metabolite. Adverse reactions are those common to the group. Stevens–Johnson syndrome has been reported several times after topical use in conjunctivitis.

Профиль безопасности

Mildly toxic by ingestion and intravenous routes. An experimental teratogen. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Методы очистки

Crystallise the amide from aqueous EtOH. [Beilstein 14 IV 2662.]