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アセタゾラミド

アセタゾラミド 化学構造式
59-66-5
CAS番号.
59-66-5
化学名:
アセタゾラミド
别名:
アセタゾラミド;ジアモックス;アセトアゾールアミド;グラウパックス;ジアカルブ;ドンモックス;アセタゾールアミド;ダイアモックス;ベタモックス;アセタゾーラミド;ジウラミド;ジルラン;N-(2-スルファモイル-1,3,4-チアジアゾール-5-イル)アセトアミド;ジウタゾール;2-(アセチルアミノ)-1,3,4-チアジアゾール-5-スルホンアミド;N-(5-スルファモイル-1,3,4-チアジアゾール-2-イル)アセトアミド;アセタモックス;5-(アセチルアミノ)-1,3,4-チアジアゾール-2-スルホンアミド;シダメックス;ネフラミド
英語化学名:
Acetazolamide
英語别名:
6063;Didoc;Diamox;Donmox;Edemox;Glupax;DIACARB;Cidamex;Diakarb;Diluran
CBNumber:
CB0430959
化学式:
C4H6N4O3S2
分子量:
222.25
MOL File:
59-66-5.mol

アセタゾラミド 物理性質

融点 :
258-259 °C
比重(密度) :
1.610 (estimate)
屈折率 :
1.6270 (estimate)
貯蔵温度 :
2-8°C
溶解性:
Soluble in NH4OH (50 mg/mL), DMSO, Methanol and slightly soluble in Ethanol.
酸解離定数(Pka):
7.2(at 25℃)
外見 :
solid
水溶解度 :
<0.1 g/100 mL at 22 ºC
極大吸収波長 (λmax):
265nm(H2O)(lit.)
Merck :
14,53
BRN :
212994
InChIKey:
BZKPWHYZMXOIDC-UHFFFAOYSA-N
CAS データベース:
59-66-5(CAS DataBase Reference)
NISTの化学物質情報:
2-Acetylamino-1,3,4-thiadiazole-5-sulfonamide(59-66-5)
EPAの化学物質情報:
Acetazolamide (59-66-5)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xi
Rフレーズ  36/38-36/37/38
Sフレーズ  26-36
RIDADR  2811
WGK Germany  2
RTECS 番号 AC8225000
TSCA  Yes
国連危険物分類  6.1
容器等級  III
HSコード  29350090
有毒物質データの 59-66-5(Hazardous Substances Data)
毒性 LD50 oral in mouse: 4300mg/kg
絵表示(GHS)
注意喚起語 Warning
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H303 飲み込むと有害のおそれ 急性毒性、経口 5 P312
H315 皮膚刺激 皮膚腐食性/刺激性 2 警告 P264, P280, P302+P352, P321,P332+P313, P362
H319 強い眼刺激 眼に対する重篤な損傷性/眼刺激 性 2A 警告 P264, P280, P305+P351+P338,P337+P313P
H360 生殖能または胎児への悪影響のおそれ 生殖毒性 1A, 1B 危険
注意書き
P201 使用前に取扱説明書を入手すること。
P202 全ての安全注意を読み理解するまで取り扱わないこ と。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。
P308+P313 暴露または暴露の懸念がある場合:医師の診断/手当てを 受けること。
P405 施錠して保管すること。

アセタゾラミド 価格 もっと(21)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01AFAL07562 アセタゾラミド, 99%
Acetazolamide, 99%
59-66-5 5g ¥5080 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01AFAL07562 アセタゾラミド, 99%
Acetazolamide, 99%
59-66-5 25g ¥14430 2021-03-23 購入
東京化成工業 A2598 アセタゾラミド >98.0%(HPLC)(T)
Acetazolamide >98.0%(HPLC)(T)
59-66-5 25g ¥9600 2021-03-23 購入
東京化成工業 A2598 アセタゾラミド >98.0%(HPLC)(T)
Acetazolamide >98.0%(HPLC)(T)
59-66-5 100g ¥25800 2021-03-23 購入
Sigma-Aldrich Japan 97582 アセタゾールアミド analytical standard
Acetazolamide analytical standard
59-66-5 100mg ¥11900 2021-03-23 購入

アセタゾラミド MSDS


2-Acetamido-5-sulfamoyl-1,3,4-thiadiazole

アセタゾラミド 化学特性,用途語,生産方法

解説

N-[(5-aminosufamoyl)-1,3,4-thiadiazol-2-yl]acetamide.C4H6N4O3S2(222.25).5-アミノ-1,3,4-チアジアゾール-2-チオールをアセチル化後,塩素ガス,ついでアンモニアを作用させてスルホンアミドとして合成する."白色の結晶性粉末.分解点255 ℃.pKa 7.2.エタノール,水,エーテルに難溶,アルカリに可溶.炭酸脱水酵素阻害剤,利尿薬,妊娠中毒症,および緑内障治療薬として使用される.LD50 3~6 g/kg(マウス,静注).[CAS 59-66-5]
森北出版「化学辞典(第2版)

用途

炭酸脱水酵素阻害剤です。炭 酸脱水酵素阻害作用を示します。

用途

炭酸脱水酵素阻害剤です。炭 酸脱水酵素阻害作用を示します。

用途

医薬(炭酸脱水素酵素抑制剤)

効能

抗緑内障薬, 炭酸脱水酵素阻害薬

商品名

ダイアモックス (三和化学研究所)

説明

Acetazolamide is a weak diuretic with limited use in edema associated with cardiac insufficiency, glaucoma, minor epileptic attacks, and altitude sickness.

化学的特性

White Solid

Originator

Diamox ,Lederle,US ,1953

使用

carbonic anhydrase inhibitor, diuretic, antiglaucoma

使用

Acetazolamide is used for epilepsy in the absence of attacks and also in conjunction with other antiepileptic drugs.

Manufacturing Process

According to REM, hydrazine hydrate is reacted with 2 mols of ammonium thiocyanate to produce 1,2-bis(thiocarbamoyl)hydrazine which by loss of ammonia and rearrangement produces 5-amino-2-mercapto-1,3,4-thiadiazole. That compound is acetyled with acetic anhydride.
Then, as described in US Patent 2,554,816, the 2-acetylamido-5-mercapto- 1,3,4-thiadiazole is converted to the sulfonyl chloride by passing chlorine gas into a cooled (5-10°C) solution in 33% acetic acid (66 parts to 4 parts of mercapto compound) used as a reaction medium. Chlorine treatment is continued for two hours. The crude product can be dried and purified by recrystallization from ethylene chloride. The pure compound is a white crystalline solid, MP 194°C, with decomposition, when heated rapidly. The crude damp sulfonyl chloride is converted to the sulfonamide by addition to a large excess of liquid ammonia. The product is purified by recrystallization from water. The pure compound is a white, crystalline solid, MP 259°C, with decomposition. The yield of sulfonamide was 85% of theory based on mercapto compound.
An alternative process is described in US Patent 2,980,679 as follows. 15 grams of finely powdered 2-acetylamino-1,3,4-thiadiazole-5-mercaptain are suspended in 200 ml of water containing 4 grams of potassium bromide. From 0.5 to 1 gram of ferric chloride are subsequently added. The mass is energetically stirred and 52 grams of liquid bromide are added by increments for about 45 minutes, while keeping the reaction temperature below 10°C, and, preferably, at 4-8°C by employing a cooling bath. Stirring is continued for a further 10 minutes, then the 2-acetylamino-1,3,4-thiadiazole-5- sulfobromide is collected on a funnel equipped with a porous diaphragm, thoroughly washed with cold water and finally subjected to amidation with liquid ammonia. The reaction mixture is allowed to stand for a certain period, then the ammonia is evaporated, after which the residue is taken up with diluted ammonia and, after decolorizing with carbon, the sulfonamide is precipitated with hydrochloric acid. The yield of crude sulfonamide obtained with this process, with respect to the starting mercapto compound is abut 84%. If the amidation is carried out with 33% aqueous ammonia, the yield is slightly lower.

brand name

Diamox (Duramed).

Therapeutic Function

Carbonic anhydrase inhibitor, Diuretic, Antiglaucoma

一般的な説明

White to yellowish-white fine crystalline powder. No odor or taste.

空気と水の反応

Insoluble in water.

反応プロフィール

A weak acid and a diazo derivative. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.

火災危険

Flash point data for Acetazolamide are not available; however, Acetazolamide is probably combustible.

作用機序

Acetazolamide is an aromatic sulfonamide used as a carbonic anhydrase inhibitor. It facilitates production of alkaline urine with an elevated biocarbonate, sodium, and potassium ion concentrations. By inhibiting carbonic anhydrase, the drug suppresses reabsorption of sodium ions in exchange for hydrogen ions, increases reflux of bicarbonate and sodium ions and reduces reflux of chloride ions. During this process, chloride ions are kept in the kidneys to cover of insufficiency of bicarbonate ions, and for keeping an ion balance. Electrolytic contents of fluid secreted by the kidneys in patients taking carbonic anhydrase inhibitors are characterized by elevated levels of sodium, potassium, and bicarbonate ions and a moderate increase in water level. Urine becomes basic, and the concentration of bicarbonate in the plasma is reduced.

臨床応用

Acetazolamide was the first of the carbonic anhydrase inhibitors to be introduced as an orally effective diuretic, with a diuretic effect that lasts approximately 8 to 12 hours. As mentioned earlier, its diuretic action is limited because of the systemic acidosis it produces. Acetazolamide reduces the rate of aqueous humor formation and is used primarily for reducing intraocular pressure in the treatment of glaucoma. The dose is 250 mg to 1 g per day.

安全性プロファイル

Poison by subcutaneous and intravenous routes. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: dyspnea. An experimental teratogen by many routes. Other experimental reproductive effects. When heated to decomposition it emits very toxic fumes of NOx, and SOx,. A carbonic anhydrase inhibitor and dmretic used to treat glaucoma.

Chemical Synthesis

Acetazolamide is 5-acetamido-1,3,4-thiadiazole-2-sulfonamide (9.7.5). The synthesis of acetazolamide is based on the production of 2-amino-5-mercapto-1,3, 4-thiadiazole (9.7.2), which is synthesized by the reaction of ammonium thiocyanate and hydrazine, forming hydrazino-N,N-bis-(thiourea) (9.7.1), which cycles into thiazole (9.7.2) upon reaction with phosgene. Acylation of (9.7.2) with acetic anhydride gives 2-acetylamino-5-mercapto-1,3,4-thiadiazol (9.7.3). The obtained product is chlorinated to give 2-acetylamino-5-mercapto-1,3,4-thiadiazol-5-sulfonylchloride (9.7.4), which is transformed into acetazolamide upon reaction with ammonia (9.7.5) [24,25].

Veterinary Drugs and Treatments

Acetazolamide has been used principally in veterinary medicine for its effects on aqueous humor production in the treatment of glaucoma, metabolic alkalosis, and for its diuretic action. It may be useful as an adjunctive treatment for syringomyelia in dogs. Acetazolamide’s use in small animals is complicated by a relatively high occurrence of adverse effects.
In horses, acetazolamide is used as an adjunctive treatment for hyperkalemic periodic paralysis (HYPP).
In humans, the drug has been used as adjunctive therapy for epilepsy and for acute high-altitude sickness.

純化方法

It is recrystallised from water. [Roblin & Clapp J Am Chem Soc 72 4890 1950, Beilstein 27 III/IV 8219.]

アセタゾラミド 上流と下流の製品情報

原材料

準備製品


アセタゾラミド 生産企業

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59-66-5(アセタゾラミド)キーワード:


  • 59-66-5
  • N-(5-[AMINOSULFONYL]-1,3,4-THIADIAZOL-2-YL)ACETAMIDE
  • N-[5-(AMINOSULFONYL)-1,3,4-THIADIOZOL-2-YL]-ACETAMIDE
  • N-(5-SULFAMOYL-1,3,4-THIADIAZOL-2-YL)ACETAMIDE
  • N-(5-SULFAMOYL-1,3,4-THIADIAZOL-2-YL)ETHANAMIDE
  • DIACARB
  • LABOTEST-BB LT00012571
  • 2-ACETAMINO-1,3,4-THIADIAZOLE-5-SULFONAMIDE
  • 2-acetamido-5-sulfamoyl-1,3,4-thiadiazole
  • 2-ACETYLAMINO-1,3,4-THIADIAZOLE-5-SULFONAMIDE
  • 5-ACETAMIDO-1,3,4-THIADIAZOLE-2-SULFONAMIDE
  • ACETAZOLAMIDE
  • ACETAMIDE N-(5-(AMINO SULPHONYL)-1,3,4 THIADIAZOL-2-YL)
  • 1,3,4-Thiadiazole-2-sulfonamide, 5-acetamido-
  • 2-Acetamido-5-sulfonamido-1,3,4-thiadiazole
  • 4-Diamox
  • 4-thiadiazole-2-sulfonamide,5-acetamido-3
  • 5-Acetamide-1,3,4-thiadiazole-2-sulfonamide
  • 5-Acetamido-1,3,4-thiadiazol-2-sulfonamide
  • 6063
  • Acetamide, N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-
  • Acetamide, N-[5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl]-
  • Acetamidothiadiazolesulfonamide
  • Acetamox
  • Acetazolamid
  • Acetazoleamide
  • Acetozalamide
  • Atenezol
  • Carbonic anhydrase inhibitor
  • Carbonic anhydrase inhibitor 6063
  • Carbonic anhydrase inhibitor no. 6063
  • アセタゾラミド
  • ジアモックス
  • アセトアゾールアミド
  • グラウパックス
  • ジアカルブ
  • ドンモックス
  • アセタゾールアミド
  • ダイアモックス
  • ベタモックス
  • アセタゾーラミド
  • ジウラミド
  • ジルラン
  • N-(2-スルファモイル-1,3,4-チアジアゾール-5-イル)アセトアミド
  • ジウタゾール
  • 2-(アセチルアミノ)-1,3,4-チアジアゾール-5-スルホンアミド
  • N-(5-スルファモイル-1,3,4-チアジアゾール-2-イル)アセトアミド
  • アセタモックス
  • 5-(アセチルアミノ)-1,3,4-チアジアゾール-2-スルホンアミド
  • シダメックス
  • ネフラミド
  • デヒドラチン
  • ナトリオネックス
  • エデモックス
  • β-インドメタシン
  • N-[5-(アミノスルホニル)-1,3,4-チアジアゾール-2-イル]アセトアミド
  • 2-アセトアミド-5-スルホンアミド-1,3,4-チアジアゾール
  • 5-アセトアミド-1,3,4-チアジアゾール-2-スルホンアミド
  • 2- アセトアミド-5- スルホンアミド- 1,3,4- チアジアゾール【アセタゾラミド】
  • 2-アセトアミド-5-スルホンアミド- 1,3,4-チアジアゾール(アセタゾラミド)
  • アセタゾラミド, 99%
  • アセタゾラミド (JP17)
  • 抗痙攣薬
  • 利尿薬
  • 炭酸アンヒドラーゼ阻害剤
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