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アロプリノール

アロプリノール 化学構造式
315-30-0
CAS番号.
315-30-0
化学名:
アロプリノール
别名:
アロプリノール;ギクテックス;アロリン;アロチーム;ケトブン;ブロキサント;アロシトール;ザイロリック;ウリプリム;アンジーフ;ススペンドール;ジロプール;アルリット;ユーリック;ウロリット;ジロプリム;タカナルミン;1-[4-オキソ-4-(4-フルオロフェニル)ブチル]-4-(4-クロロフェニル)ピリジニウム;マサトン;ゴタックス
英語化学名:
Allopurinol
英語别名:
HPP;ALO;Remid;Urbol;4-HPP;Pural;AL-100;aloral;Anzief;Apurin
CBNumber:
CB1181254
化学式:
C5H4N4O
分子量:
136.11
MOL File:
315-30-0.mol

アロプリノール 物理性質

融点 :
>300 °C (lit.)
沸点 :
250.36°C (rough estimate)
比重(密度) :
1.4295 (rough estimate)
屈折率 :
1.8500 (estimate)
貯蔵温度 :
15-25°C
溶解性:
1 M NaOH: soluble50mg/mL, clear to very slightly hazy, colorless to faintly yellow
外見 :
Powder
酸解離定数(Pka):
10.2(at 25℃)
色:
White or almost white
水溶解度 :
0.35 g/L (25 ºC)
Merck :
14,279
InChIKey:
OFCNXPDARWKPPY-UHFFFAOYSA-N
CAS データベース:
315-30-0(CAS DataBase Reference)
NISTの化学物質情報:
Allopurinol(315-30-0)
EPAの化学物質情報:
Allopurinol (315-30-0)
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  T,Xi,Xn
Rフレーズ  25-43-36/37/38-20/21/22
Sフレーズ  28-36/37-45-36/37/39-26-24-36
RIDADR  UN 2811 6.1/PG 3
WGK Germany  2
RTECS 番号 UR0785000
TSCA  Yes
国連危険物分類  6.1
容器等級  III
HSコード  29335990
有毒物質データの 315-30-0(Hazardous Substances Data)
毒性 LD50 oral in mouse: 78mg/kg
絵表示(GHS)
注意喚起語 Danger
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
H301 飲み込むと有毒 急性毒性、経口 3 危険 P264, P270, P301+P310, P321, P330,P405, P501
H317 アレルギー性皮膚反応を起こすおそれ 感作性、皮膚 1 警告 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
注意書き
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。
P270 この製品を使用する時に、飲食または喫煙をしないこ と。
P272 汚染された作業衣は作業場から出さないこと。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P301+P310 飲み込んだ場合:直ちに医師に連絡すること。
P321 特別な処置が必要である(このラベルの... を見よ)。

アロプリノール 価格 もっと(33)

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) W01TRCA547300
Allopurinol
315-30-0 100mg ¥12500 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01TRCA547300
Allopurinol
315-30-0 5g ¥17500 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01CHDASB-00001569 アロプリノール
Allopurinol
315-30-0 100mg ¥18300 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01CHDASB-00001570 アロプリノール
Allopurinol
315-30-0 1g ¥15000 2020-09-21 購入
東京化成工業 A0907 アロプリノール >98.0%(T)
Allopurinol >98.0%(T)
315-30-0 25g ¥4300 2021-03-23 購入

アロプリノール MSDS


1H-Pyrazolo[3,4-d]pyrimidin-4-ol

アロプリノール 化学特性,用途語,生産方法

外観

白色~わずかにうすい黄色, 結晶性粉末~粉末

溶解性

水に極めて溶けにくく、エタノール(95)にほとんど溶けない。

解説

高尿酸血症、痛風、尿路結石の治療薬で、化学的にはヒポキサンチンの立体異性体である。低濃度では競合的に、高濃度では非競合的にキサンチンオキシダーゼを阻害する。その結果、血中および尿中の尿酸値が著明に低下する。1日0.2~0.3グラム内服する。劇薬で、極量は1回0.2グラム、1日0.6グラム。[幸保文治][参照項目] | 異性体
小学館 日本大百科全書(ニッポニカ) )

用途

薬理研究用。

用途

キサンチンオキシダーゼを阻 害し、尿酸生成抑制作用を示します。

用途

体内での尿酸の産生を抑制し、高尿酸血症を改善することにより痛風発作の発生を予防する。

用途

アロプリノール(Allopurinol)は痛風?高尿酸血症治療薬。ヒポキサンチンの構造異性体で、キサンチンオキシダーゼの阻害活性を有する。体内での尿酸の産生を抑制し、高尿酸血症を改善することにより痛風発作の発生を予防する。

効能

痛風治療薬, 尿酸生合成抑制薬, キサンチンオキシダーゼ阻害薬

商品名

アロプリノール (ナガセ医薬品); ザイロリック (グラクソ・スミスクライン)

化学的特性

White to Off-White Solid

Originator

Zyloprim ,Burroughs-Wellcome ,US ,1966

使用

Allopurinol does not reduce serum uric acid levels by increasing renal uric acid excretion; instead it lowers plasma urate levels by inhibiting the final steps in uric acid biosynthesis.
Uric acid in humans is formed primarily by xanthine oxidase-catalyzed oxidation of hypoxanthine and xanthine to uric acid. Allopurinol (8) and its primary metabolite, alloxanthine (9) [CAS: 2465-59-0], are inhibitors of xanthine oxidase. Inhibition of the last two steps in uric acid biosynthesis by blocking xanthine oxidase reduces the plasma concentration and urinary excretion of uric acid and increases the plasma levels and renal excretion of the more soluble oxypurine precursors. Normally, in humans the urinary purine content is almost solely uric acid; treatment with allopurinol results in the urinary excretion of hypoxanthine, xanthine, and uric acid, each with its independent solubility. Lowering the uric acid concentration in plasma below its limit of solubility facilitates the dissolution of uric acid deposits. The effectiveness of allopurinol in the treatment of gout and hyperuricemia that results from hematogical disorders and antineoplastic therapy has been demonstrated.

使用

Xanthine oxidase inhibitor; decreases uric acid production. Used in treatment of hyperuricemia and chronic gout. Antiurolithic

使用

antihyperuricemia, antigout, antiurolithic

適応症

Allopurinol (Zyloprim) is the drug of choice in the treatment of chronic tophaceous gout and is especially useful in patients whose treatment is complicated by renal insufficiency.

Manufacturing Process

3-Morpholino-2-cyanoacrylamide: A stirred mixture of cyanoacetamide (63 g), triethylorthoformate (134 g), morpholine (82.5 g) and acetonitrile (37.5 ml) was heated under reflux for 4 hours. The initial reflux temperature was 117°C and the final reflux temperature was 82°C.
At the end of the reflux period the mixture was cooled to 30°C and the heavy crystalline precipitate was collected and washed with 2 x 75 ml of ethanol. The product was dried in vacuum at 30°C. Wt = 111 g. Yield = 82%, MP 173- 175°C.
3-Aminopyrazole-4-carbxamide hemisulfate: To water (253 ml) at 60°C was added 3-morpholino-2-cyanoacrylamide (63.4 g) and 85% technical hydrazine hydrate (22.7 g). The mixture was rapidly heated to 95°C and the temperature was maintained at >90°C for 20 minutes. The mixture was then cooled to 60°C and the pH carefully adjusted to 1.5 by the addition of a mixture of sulfuric acid (45.7 g) and ice. The acidified reaction was cooled to 5°C and the crystalline product collected and washed with cold water (2 x 100 ml) and acetone (2 x 50 ml). The product was dried in vacuum at 80°C. Wt =5.8 g. Yield =95%, MP 237-239°C.
4-Hydroxypyrazolo[3,4-d]pyrimidine: A suspension of 3-aminopyrazole-4- carboxamide hemisulfate (113 g) in formamide (325 g) was stirred and heated to 145°C. The reaction was held at 145°C for 5 hours. The reaction was then cooled to 30°C and the product collected and washed with formamide (2 x 50 ml), water (2 x 150 ml) and acetone (2 x 100 ml). Wt of crude product = 79 g. The crude product was recrystallized by dissolution in a solution made from sodium hydroxide (25 g) in water (1,200 ml) with treatment at 25°C with charcoal (8 g), followed by reprecipitation by the addition of concentrated hydrochloric acid to pH 5. The product was collected and washed with cold water (2 x 300 ml), acetone (2 x 200 ml) and dried in vacuum at 60°C. Wt = 70 g. Yield = 80%.

brand name

Lopurin (Abbott); Lopurin (BASF); Zyloprim (Promethus).

Therapeutic Function

Xanthine oxidase inhibitor, Gout therapy

一般的な説明

Odorless tasteless white microcrystalline powder.

空気と水の反応

Insoluble in water.

反応プロフィール

Allopurinol is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Allopurinol darkens above 572° F, and at an indefinite high temperature, Allopurinol chars and decomposes. At 221° F, maximum stability occurs at pH 3.1- 3.4. Allopurinol decomposes in acidic and basic solutions.

火災危険

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

Biochem/physiol Actions

Inhibitor of xanthine oxidase and de novo pyrimidine biosynthesis. A classical agent in treatment of hyperuricemia and gout.

作用機序

Allopurinol, in contrast to the uricosuric drugs, reduces serum urate levels through a competitive inhibition of uric acid synthesis rather than by impairing renal urate reabsorption. This action is accomplished by inhibiting xanthine oxidase, the enzyme involved in the metabolism of hypoxanthine and xanthine to uric acid. After enzyme inhibition, the urinary and blood concentrations of uric acid are greatly reduced and there is a simultaneous increase in the excretion of the more soluble uric acid precursors, xanthine and hypoxanthine.
Allopurinol itself is metabolized by xanthine oxidase to form the active metabolite oxypurinol, which tends to accumulate after chronic administration of the parent drug.This phenomenon contributes to the therapeutic effectiveness of allopurinol in long-term use. Oxypurinol is probably responsible for the antigout effects of allopurinol. Oxypurinol itself is not administered because it is not well absorbed orally.

薬物動態学

Allopurinol was synthesized in 1956 as part of a study of purine antagonists. It is well absorbed on oral administration, with peak plasma concentrations appearing within 1 hour. Decreases of uric acid can be observed within 24 to 48 hours. Excretion of allopurinol and its metabolite occurs primarily in the urine, with approximately 20% of a dose being excreted in the feces.

臨床応用

Allopurinol is especially indicated in the treatment of chronic tophaceous gout, since patients receiving it show a pronounced decrease in their serum and urinary uric acid levels. Because it does not depend on renal mechanisms for its efficacy, allopurinol is particularly beneficial for patients who already have developed renal uric acid stones, patients with excessively high urate excretion (e.g., above 1,200 mg in 24 hours), patients with a variety of blood disorders (e.g., leukemia, polycythemia vera), patients with excessive tophus deposition, and patients who fail to respond well to the uricosuric drugs.
Allopurinol also inhibits reperfusion injury. This injury occurs when organs that either have been transplanted or have had their usual blood perfusion blocked are reperfused with blood or an appropriate buffer solution. The cause of this injury is local formation of free radicals, such as the superoxide anion, the hydroxyl free radical, or peroxynitrite. These substances are strong oxidants and are quite damaging to tissues.

副作用

Common toxicities associated with allopurinol administration include a variety of skin rashes, gastrointestinal upset, hepatotoxicity, and fever. These reactions are often sufficiently severe to dictate termination of drug therapy. It is advised that therapy not be initiated during an acute attack of gouty arthritis. As with the uricosuric drugs, therapy with allopurinol should be accompanied both by a sufficient increase in fluid intake to ensure water diuresis and by alkalinization of the urine. Prophylactic use of colchicine also helps to prevent acute attacks of gout that may be brought on during the initial period of allopurinol ingestion.

安全性プロファイル

Human poison by ingestion. Poison experimentally by intraperitoneal and subcutaneous routes. An experimental teratogen. Human systemic effects by ingestion: blood leukopenia, dermatitis, jaundice, muscle weakness, thrombocytopenia. When heated to decomposition it emits toxic fumes of NOx. An FDA proprietary drug used as a xanthine oxidase inhibitor.

Veterinary Drugs and Treatments

The principle veterinary uses for allopurinol are for the prophylactic treatment of recurrent uric acid uroliths and hyperuricosuric calcium oxalate uroliths in small animals. It has also been used in an attempt to treat gout in pet birds and reptiles.
Allopurinol has been recommended as an alternative treatment for canine Leishmaniasis. Although it appears to have clinical efficacy, it does not apparently clear the parasite in most dogs at usual dosages. Allopurinol may also be useful for American Trypanosomiasis.

代謝

Allopurinol is rapidly metabolized via oxidation and the formation of numerous ribonucleoside derivatives. The major oxidation metabolite, alloxanthine or oxypurinol, has a much longer half-life (18–30 hours versus 2–3 hours) than the parent drug and is an effective, although less potent, inhibitor of xanthine oxidase. The longer plasma half-life of alloxanthine results in an accumulation in the body during chronic administration, thus contributing significantly to the overall therapeutic effects of allopurinol.

予防処置

Since allopurinol is metabolized by the hepatic microsomaldrug-metabolizing enzymes, coadministration ofdrugs also metabolized by this system should be donewith caution. Because allopurinol inhibits the oxidationof mercaptopurine and azathioprine, their individualadministered doses must be decreased by as much as75% when they are given together with allopurinol.Allopurinol may also increase the toxicity of other cytotoxicdrugs (e.g., vidarabine). The actions of allopurinolare not antagonized by the coadministration of salicylates.

アロプリノール 上流と下流の製品情報

原材料

準備製品


アロプリノール 生産企業

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315-30-0(アロプリノール)キーワード:


  • 315-30-0
  • Hydroxypyrazolodpyrimidine
  • pyrazolo(3,4-d)pyrimidin-1-ol
  • AllopurinolBp2001
  • 4-Oxopyrazolo[3,4-d]pyrimidine
  • NSC 101655
  • ALLOPURINOL,USP
  • 1,5-DIHYDRO-4H-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE(ALLOPURINOL)
  • ALLOPURINOL(P)
  • ALLOPURINOL(RG)
  • 4-HYDROXYPYRAZOLO(3,4-D)-PYRIMIDINE (ALLOPURINOL)
  • 4-HYDROXYPYROZOLO(3,4-D)PYRIMIDINE
  • ALLOPURIONAL
  • 4H-Pyrazolo[3,4-d]pyrimidin-4-one, 1,5-dihydro- (7CI,8CI,9CI)
  • ALLOPURINOL, PHARMA
  • 4-Hydroxypyrazolo3,4-dü-pyrimidine, 98%
  • 1H-Pyrazolo(3,4-d)pyrimidin-4-ol, 4-Hydroxypyrazolo(3,4-d)pyrimidine, 4-Hydroxypyrazolo[3,4-d]pyrimidine, HPP
  • Adenock
  • Ailural
  • AL-100
  • Allopur
  • allo-puren
  • Allopurinol(I)
  • Allozym
  • Allural
  • aloral
  • Alositol
  • Aluline
  • Anoprolin
  • Anzief
  • apulonga
  • アロプリノール
  • ギクテックス
  • アロリン
  • アロチーム
  • ケトブン
  • ブロキサント
  • アロシトール
  • ザイロリック
  • ウリプリム
  • アンジーフ
  • ススペンドール
  • ジロプール
  • アルリット
  • ユーリック
  • ウロリット
  • ジロプリム
  • タカナルミン
  • 1-[4-オキソ-4-(4-フルオロフェニル)ブチル]-4-(4-クロロフェニル)ピリジニウム
  • マサトン
  • ゴタックス
  • アデノック
  • ホリガン
  • リボール
  • サスペンドール
  • エンバリン
  • プラール
  • 1H-ピラゾロ[3,4-d]ピリミジン-4-オール
  • ウロシン
  • サロベール
  • ジロリック
  • アルラール
  • ミルリット
  • プロデック
  • アリスメット
  • ミニプラノール
  • 1-[3-(4-フルオロベンゾイル)プロピル]-4-(4-クロロフェニル)ピリジニウム
  • 1,5-ジヒドロ-4H-ピラゾロ[3,4-d]ピリミジン-4-オン
  • 4-(4-クロロフェニル)-1-[4-(4-フルオロフェニル)-4-オキソブチル]ピリジニウム
  • ウリスセル
  • アイデイト
  • 1-[4-(4-フルオロフェニル)-4-オキソブチル]-4-(4-クロロフェニル)ピリジニウム
  • アチスリル
  • ズリム
  • ウリセミル
  • ノイファン
  • アロック
  • アノプロリン
  • エピドロパール
  • 4-(p-クロロフェニル)-1-[4-(p-フルオロフェニル)-4-オキソブチル]ピリジニウム
  • レミド
  • 4,5-ジヒドロ-1H-ピラゾロ[3,4-d]ピリミジン-4-オン
  • 4-[4-(4-クロロフェニル)ピリジニオ]-1-(4-フルオロフェニル)-1-ブタノン
  • アロプリノ-ル
  • 4-ヒドロキシピラゾロ[3,4-D]ピリミジン
  • 4-ヒドロキシピラゾロ〔3,4-D〕ピリミジン
  • 4‐ヒドロキシピラゾロ[3,4‐D]ピリミジン
  • アロプリノール標準品
  • アロプリノール (JP17)
  • ヌクレオシド,ヌクレオチド&関連試薬
  • 核酸塩基と類似体
  • 抗炎症薬成分
  • 生化学
  • 試験研究用抗腫瘍剤
  • 薬理研究用試薬
  • スカベンジャー
  • 代謝拮抗物質
  • 酵素阻害剤
  • 抗リウマチ薬
  • 尿酸排出促進薬
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