スルファニルアミド 化学特性,用途語,生産方法
外観
白色, 結晶〜結晶性粉末
溶解性
水に難溶。エタノール, アセトンに易溶。エーテル, ベンゼンに不溶。エタノールに溶けやすく、水に溶けにくく、エーテルにほとんど溶けない。
解説
スルファニル‐アミド，スルファミンともよばれるサルファ剤の一つ．p-アセタミドベンゼンスルホニルクロリドとアンモニアを反応させたのち，脱アセチルすると得られる．結晶性粉末．融点166 ℃．アセトン，エタノールに可溶．細菌感染症の治療に用いられたが，現在は，ほかの多くの誘導体が開発されている．亜硝酸の比色定量に用いられる．水に溶けにくく、エーテル・ベンゼンに溶けず、エチルアルコール・アセトンに溶ける。
用途
容量分析(NaNO2液の標定)、有機合成原料。
用途
スルファニルアミド（SulfanilamideまたはSulphanilamide）は、スルホンアミド系抗生物質の1つである。化学的には、パラ位にスルホンアミド基を有するアニリン誘導体である。粉末のスルファニルアミドは、第二次世界大戦中に連合国側で感染予防に用いられ、それ以前と比較して劇的に死亡率を低下させた。現代では戦場では他の抗生物質に取って代わられているが、膣真菌感染症には今でも用いられる。
効能
抗菌薬, 葉酸合成阻害薬
説明
Sulfanilamide is an organic sulfur compound structurally similar to p-aminobenzoic acid (PABA) with antibacterial property. Sulfanilamide competes with PABA for the bacterial enzyme dihydropteroate synthase, thereby preventing the incorporation of PABA into dihydrofolic acid, the immediate precursor of folic acid. This leads to an inhibition of bacterial folic acid synthesis and de novo synthesis of purines and pyrimidines, ultimately resulting in cell growth arrest and cell death.
化学的特性
White granules or powder crystals, odorless. Taste slightly bitter. Slightly soluble in cold water, ethanol, methanol, ether and acetone, easily soluble in boiling water, glycerin, hydrochloric acid, potassium hydroxide and sodium hydroxide solution, insoluble in chloroform, ether, benzene and petroleum ether.
使用
Sulfanilamide is an antibacterial agent and antimicrobial agent of sulfonamide type (topical and vaginal).
製造方法
Sulfonamide is synthesized from acetanilide by chlorosulfonation, amination, hydrolysis, and neutralization:
Acetanilide is reacted with chlorosulfonic acid at 40～50℃, then cooled, slowly added to water for acid decomposition, precipitated at the same time, dried and filtered to obtain p-acetamidobenzenesulfonyl chloride, and then subjected to ammoniation, and the amination temperature is controlled at 40～ 45 ℃, and then hydrolyzed, acidified to obtain sulfonamide.
定義
ChEBI: Sulfanilamide is a sulfonamide in which the sulfamoyl functional group is attached to aniline at the 4-position. It has a role as an EC 4.2.1.1 (carbonic anhydrase) inhibitor, an antibacterial agent and a drug allergen. It is a substituted aniline, a sulfonamide antibiotic and a sulfonamide.
世界保健機関（WHO）
Sulfanilamide, a sulfonamide anti-infective agent, was introduced
in 1936 for the treatment of bacterial infections. The importance of sulfonamides
has subsequently decreased as a result of increasing 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. Sulfanilamide is still used in some countries as a
pessaries or as vaginal cream.
一般的な説明
White powder. pH of 0.5% aqueous solution: 5.8-6.1.
空気と水の反応
May be unstable if exposed for long periods air and light . Slightly water soluble.
反応プロフィール
Sulfanilamide is an amino acid. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May react with azo and diazo compounds to generate toxic gases.
火災危険
Flash point data for Sulfanilamide are not available but Sulfanilamide is probably combustible.
安全性プロファイル
Poison by intraperitoneal route. Moderately toxic by ingestion, subcutaneous, and intravenous routes. Human teratogenic effects by unspecified route: developmental abnormalities of the blood and lymphatic systems (including the spleen and bone marrow). Experimental reproductive effects. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. Implicated in aplastic anemia. When heated to decomposition it emits very toxic fumes of NOx and SOx.
スルファニルアミド 上流と下流の製品情報
原材料
準備製品