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インドメタシン

インドメタシン 化学構造式
53-86-1
CAS番号.
53-86-1
化学名:
インドメタシン
别名:
インドメタシン;ラクティオン;インドメ;マタジン;インメシン;テンポラル;セラスター;インサイド;コリフメシン;2-メチル-1-(4-クロロベンゾイル)-5-メトキシ-1H-インドール-3-酢酸;アスモID;インダシン;メゾリン;1-(4-クロロベンゾイル)-2-メチル-5-メトキシ-1H-インドール-3-酢酸;インデラポロン;ミカメタン;インドシド;[1-(4-クロロベンゾイル)-2-メチル-5-メトキシ-1H-インドール-3-イル]酢酸;ハップスターID;インテナシン
英語化学名:
Indometacin
英語别名:
Amuno;Vonum;Catlep;Tannex;Inacid;Lausit;INDOCIN;Bonidin;Mobilan;53-86-1
CBNumber:
CB1750267
化学式:
C19H16ClNO4
分子量:
357.79
MOL File:
53-86-1.mol

インドメタシン 物理性質

融点 :
158-162 °C
沸点 :
499.4±45.0 °C(Predicted)
比重(密度) :
1.2135 (rough estimate)
屈折率 :
1.6800 (estimate)
貯蔵温度 :
Store at RT
溶解性:
ethanol: 50 mg/mL, clear, yellow-green
酸解離定数(Pka):
4.5(at 25℃)
外見 :
White to off-white powder
水溶解度 :
Soluble in acetone (40 mg/mL - clear, yellow solution), ethanol (20 mg/mL), ether, castor oil; Soluble in chloroform (50 mg/mL - clear, yellow, extremely viscous solution); decomposed by strong alkali but stable in neutral or slightly acidic media; insoluble in water.
Sensitive :
Light Sensitive
Merck :
14,4968
BRN :
497341
安定性::
Stable. Incompatible with strong oxidizing agents.
InChIKey:
CGIGDMFJXJATDK-UHFFFAOYSA-N
CAS データベース:
53-86-1(CAS DataBase Reference)
NISTの化学物質情報:
Indomethacin(53-86-1)
EPAの化学物質情報:
Indomethacin (53-86-1)
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,T
Rフレーズ  28-36/37/38-39/23/24/25-23/24/25
Sフレーズ  28-36/37-45-36-26
RIDADR  UN 2811 6.1/PG 1
WGK Germany  3
RTECS 番号 NL3500000
8-10
TSCA  Yes
国連危険物分類  6.1
容器等級  I
HSコード  29339900
有毒物質データの 53-86-1(Hazardous Substances Data)
毒性 LD50 i.p. in rats: 13 mg/kg (Klaassen)
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
H300 飲み込むと生命に危険 急性毒性、経口 1, 2 危険 P264, P270, P301+P310, P321, P330,P405, P501
H341 遺伝性疾患のおそれの疑い 生殖細胞変異原性 2 警告 P201,P202, P281, P308+P313, P405,P501
注意書き
P201 使用前に取扱説明書を入手すること。
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。
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。
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。

インドメタシン 価格 もっと(37)

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) W01CHDASB-00009100 インドメタシン
Indomethacin
53-86-1 1g ¥3600 2020-09-21 購入
富士フイルム和光純薬株式会社(wako) W01CHDASB-00009100 インドメタシン
Indomethacin
53-86-1 250mg ¥19000 2018-12-26 購入
東京化成工業 I0655 インドメタシン >98.0%(HPLC)(T)
Indomethacin >98.0%(HPLC)(T)
53-86-1 25g ¥4900 2021-03-23 購入
東京化成工業 I0655 インドメタシン >98.0%(HPLC)(T)
Indomethacin >98.0%(HPLC)(T)
53-86-1 100g ¥13900 2021-03-23 購入
関東化学株式会社(KANTO) 49836-11 インドメタシン標準品
Indomethacine standard
53-86-1 250mg ¥14000 2021-03-23 購入

インドメタシン 化学特性,用途語,生産方法

外観

白色~うすい黄色, 結晶性粉末~粉末

溶解性

中性, 弱酸性液中では安定であるが、濃いアルカリ液中では分解がおこる。水酸化ナトリウム溶液に可溶、メタノール, エーテル, クロロホルムに難溶、水に不溶。

解説

1-(p-chloro-benzoyl)-5-methoxy-2-methylindole-3-acetic acid.C19H16ClNO4(357.79).ρ-メトキシフェニルヒドラジンとアセトアルデヒドとの反応物をρ-クロロベンゾイルクロリドでアシル化し,加水分解後,レブリン酸と加熱閉環すると得られる."白色~淡黄色の微細な結晶.融点155 ℃ と162 ℃ の2形がある.エタノール,エーテル,アセトンに可溶,水に不溶.光によって黄褐色に着色する.シクロオキシゲナーゼを阻害することによりプロスタグランジンの生合成を抑制する.pKa 4.5.効力が強く,低毒性の消炎,鎮痛薬.関節リウマチ,痛風発作など炎症性疾患に用いる.LD50 50 mg/kg(マウス,経口).[CAS 53-86-1]
森北出版「化学辞典(第2版)

用途

薬理研究用。

用途

インドール酢酸系化合物です。 シクロオキシゲナーゼ1(COX-1)を特異的 に阻害します。

用途

インドール酢酸系化合物です。シクロオキシゲナーゼⅠを特異的に阻害する作用を示します。

用途

インドメタシン(英: indometacin)とは非ステロイド性抗炎症薬の一つ。アラキドン酸カスケードにおけるシクロオキシゲナーゼ(COX)を阻害することによりプロスタグランジン類の生成を抑制することによって抗炎症作用を示す。また、抗炎症作用以外に鎮痛作用を持つ。

効能

鎮痛薬, 抗炎症薬, 解熱薬, シクロオキシゲナーゼ阻害薬

商品名

アコニップ (テイカ製薬); アコニップ (テイカ製薬); イドメシン (興和); イドメシン (興和); インサイド (久光製薬); インテナース (東光薬品工業); インテナース (東光薬品工業); インテナース (東光薬品工業); インテバン (帝國製薬); インテバン (帝國製薬); インテバン (帝國製薬); インテバン (帝國製薬); インドメタシン (ニプロ); インドメタシン (長生堂製薬); カトレップ (帝國製薬); カトレップ (帝國製薬); コリフメシン (東和製薬-和歌山); ゼムパック (救急薬品工業); ハップスター (大石膏盛堂); ラクティオン (テイカ製薬); ラクティオン (テイカ製薬)

説明

Aqueous solutions of indomethacin are not stable because of the ease of hydrolysis of the p-chlorobenzoyl group. The original synthesis of indomethacin by Shen et al. involved the formation of 2-methyl-5-methoxyindole acetic acid and subsequent acylation after protection of the carboxyl group as the t-butyl ester. It was introduced in the United States in 1965. It is still one of the most potent NSAIDs in use. It also is a more potent antipyretic than either aspirin or acetaminophen, and it possesses approximately 10 times the analgetic potency of aspirin.

化学的特性

Crystalline Solid

Originator

Indocin,MSD,US,1965

使用

Indomethacin is used in rheumatoid arthritis, nonspecific infectious polyarthritis, gouty arthritis, osteoarthritis, ankylosing spondylitis, arthrosis, back pain, neuralgia, myalgia, and other diseases accompanied by inflammation.

使用

antiinflammatory, antipyretic, analgesic

使用

Inhibits cyclooxygenase (IC50=0.1uM) selectively over liposygenases (IC50=100uM for 5-,12- and 15-LO). A clinically useful NAISD

定義

The antiinflammatory drug indomethacin.

適応症

Indomethacin (Indocin) is used in the treatment of acute gouty arthritis, rheumatoid arthritis, ankylosing spondylitis, and osteoarthritis. It is not recommended for use as a simple analgesic or antipyretic because of its potential for toxicity.While indomethacin inhibits both COX-1 and COX-2, it is moderately selective for COX- 1. It produces more CNS side effects than most of the other NSAIDs. Severe headache occurs in 25 to 50% of patients; vertigo, confusion, and psychological disturbances occur with some regularity. GI symptoms also are more frequent and severe than with most other NSAIDs. Hematopoietic side effects (e.g., leukopenia, hemolytic anemia, aplastic anemia, purpura, thrombocytopenia, and agranulocytosis) also may occur. Ocular effects (blurred vision, corneal deposits) have been observed in patients receiving indomethacin, and regular ophthalmological examinations are necessary when the drug is used for long periods. Hepatitis, jaundice, pancreatitis, and hypersensitivity reactions also have been noted.

Manufacturing Process

(A) 2-Methyl-5-Merhoxy-3-Indolylacetic Anhydride: Dicyclohexylcarbodiimide (10 g, 0.049 mol) is dissolved in a solution of 2-methyl-5-methoxy-3-indolylacetic acid (22 g, 0.10 mol) in 200 ml of THF, and the solution is allowed to stand at room temperature for 2 hours. The precipitated urea is removed by filtration, and the filtrate is evaporated in vacuo to a residue and flushed with Skellysolve 6. The residual oily anhydride is used without purification in the next step.
(B) t-Butyl 2-Methyl-5-Merhoxy-3-Indolylacetate: t-Butyl alcohol (25 ml) and fused zinc chloride (0.3 g) are added to the anhydride from Part A. The solution is refluxed for 16 hours and excess alcohol is removed in vacuo. The residue is dissolved in ether, washed several times with saturated bicarbonate, water, and saturated salt solution. After drying over magnesium sulfate, the solution is treated with charcoal, evaporated, and flushed several times with Skellysolve B for complete removal of alcohol. The residual oily ester (18 g, 93%) is used without purification.
(C) t-Buryl 1-p-Chlorobenzoyl-2-Methyl-5-Mefhoxy-3-Indolylacetate: A stirred solution of ester (18 g, 0.065 mol) in dry DMF (450 ml) is cooled to 4°C in an ice bath, and sodium hydride (4.9 g, 0.098 mol, 50% susp.) is added in portions. After 15 minutes, p-chlorobenzoyl chloride (15 g, 0.085 mol) is added dropwise during 10 minutes, and the mixture is stirred for 9 hours without replenishing the ice bath. The mixture is then poured into one liter of 5% acetic acid, extracted with a mixture of ether and benzene, washed thoroughly with water, bicarbonate, saturated salt, dried over magnesium sulfate, treated with charcoal, and evaporated to a residue which partly crystallizes. This is shaken with ether, filtered and the filtrate is evaporated to a residue (17 g) which solidifies after being refrigerated overnight.
The crude product is boiled with 300 ml of Skellysolve 6, cooled to room temperature, decanted from some gummy material, treated with charcoal, concentrated to 100 ml, and allowed to crystallize. The product thus obtained (10 g) is recrystallized from 50 ml of methanol and gives 4.5 g of analytically pure material, MP 103° to 104°C.
(D) 1 -p-Chlorobenzoyl-2-Methyl-5-Methoxy-3-Indolylacetic Acid: A mixture of 1 g ester and 0.1 g powdered porous plate is heated in an oil bath at 210°C with magnetic stirring under a blanket of nitrogen for about 2 hours. No intensification of color (pale yellow) occurs during this period. After cooling under nitrogen, the product is dissolved in benzene and ether, filtered, and extracted with bicarbonate. The aqueous solution is filtered with suction to remove ether, neutralized with acetic acid, and then acidified weakly with dilute hydrochloric acid. The crude product (0.4 g, 47%) is recrystallized from aqueous ethanol and dried in vacuo at 65°C: MP 151°C.

brand name

Indocin (Merck);Argan.

Therapeutic Function

Antiinflammatory

世界保健機関(WHO)

Indometacin was introduced in 1963 and it is one of the first NSAIDs. Convulsions are rarely reported in relation with the use of this group of agents. Indometacin farnesil is a pro-drug of indometacin, and the occurrence of gastro-intestinal adverse effects could be expected. See also under nonsteroidal antiinflammatory agents.

生物学の機能

Indomethacin (Indocin) is an acetic acid derivative related functionally to sulindac (Clinoril), a prodrug with a long half-life, and etodolac (Lodine).They are metabolized in the liver and excreted as metabolites in the bile and via the kidney. They are potent inhibitors of COX and thus extremely effective antiinflammatory agents.

一般的な説明

From the time of its introduction in 1965, indomethacin(Indocin) has been widely used as an analgesic to relieve inflammatorypain associated with RA, OA and ankylosingspondylitis, and, to a lesser extent, in gout. Although both itsanalgesic and anti-inflammatory activities are well established,its use is often limited because of frequent GI distressand potential drug interactions, especially with warfarinfurosemide, and lithium (i.e., it elevates blood levels oflithium as a result of reducing renal blood flow and thereforeincreases lithium toxicities).
Following oral administration, indomethacin is rapidlyabsorbed and is 90% protein bound at therapeutic plasmaconcentrations. The drug has a biological half-life ofabout 5 to 10 hours and a plasma clearance of 1 to 2.5 ml/kgper minute. It is metabolized to its inactive, O-desmethyl,N-deschlorobenzoyl-, and O-desmethyl, N-deschlorobenzoylindomethacinmetabolites.

一般的な説明

Crystals.

空気と水の反応

Practically insoluble in water. Decomposes in alkali.

反応プロフィール

A weak organic acid.

火災危険

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

応用例(製薬)

Indomethacin is a nonsteroidal anti-inflammatory agent used in pain and moderate to severe inflammation in rheumatic diseases and other musculoskeletal disorders. It is a COX (cyclooxygenase) inhibitor and therefore interrupts the production of prostaglandins.
A series of new silicon compounds, based on the structure of indomethacin, have been synthesised and are under investigation as novel anticancer agents. The carboxyl group of indomethacin was reacted with a series of amino-functionalised silanes. The resulting products have been shown to be significantly more lipophilic and more selective to COX-2. Furthermore, in vitro testing has shown an increased uptake of the new compounds at the tumour site. The silane-functionalised indomethacin derivatives exhibited a 15-fold increased antiproliferative effect when tested against pancreatic cancer .

応用例(製薬)

Indomethacinis a nonsteroidal anti-inflammatory agent used in pain and moderate to severe inflammation in rheumatic diseases and other musculoskeletal disorders. It is a COX (cyclooxygenase) inhibitor and therefore interrupts the production of prostaglandins.

生物活性

Cyclooxgenase (COX) inhibitor; displays selectivity for COX-1 (IC 50 values are 230 and 630 nM for human COX-1 and COX-2 respectively). Widely used anti-inflammatory agent.

臨床応用

Indomethacin is available for the short-term treatment of acute gouty arthritis, acute pain of ankylosing spondylitis, and osteoarthritis. An injectable form to be reconstituted also is available as the sodium trihydrate salt for IV use in premature infants with patent ductus arteriosus. Because of its ability to suppress uterine activity by inhibiting prostaglandin biosynthesis, indomethacin also has an unlabeled use to prevent premature labor.

副作用

All of these drugs produce analgesic effects, antipyresis, and antiinflammatory effects.Due to the high incidence of gastric irritation, headache, nausea, and other side effects, including hematological effects and coronary vasoconstriction, they are not useful as an initial treatment for pain. GI irritation and ulceration occur to a lesser extent with etodolac. Indomethacin is useful in the treatment of acute gout, osteoarthritis, ankylosing spondylitis, and acceleration of the closure of the ductus arteriosus in premature infants. The tocolytic effects of indomethacin to prevent preterm labor are the result of its effects on prostaglandin synthesis. However, the toxicity of the drug limits such application, since it increases fetal morbidity. Indomethacin is contraindicated in pregnancy, in asthmatics, and in those with gastric ulcers or other ulceration of the GI tract. Indomethacin may increase the symptoms associated with depression or other psychiatric disturbances and those associated with epilepsy and Parkinson’s disease. The drug should be used with caution in such patients.

Chemical Synthesis

Indomethacin, 1-(n-chlorobenzoyl)-5-methoxy-2-methylindol-3-acetic acid (3.2.51), has been synthesized by various methods. All of the proposed methods of synthesis start with 4-methoxyphenylhydrazine. According to the first method, a reaction is done to make indole from phenylhydrazone (3.2.46) by Fischer’s method, using levulinic acid methyl ester as a carbonyl component, hydrogen chloride as a catalyst, and ethanol as a solvent, to give the methyl ester of 5-methoxy-2-methyl-3-indolylacetic acid (3.2.47). This product is hydrolyzed by an alkali into 5-methoxy-2-methyl-3-indolylacetic acid (3.2.48), from which tert-butyl ester of 5-methoxy-2-methyl-3-indolylacetic acid (3.2.49) is formed by using tert-butyl alcohol and zinc chloride in the presence of dicyclohexylcarbodiimide. The resulting product undergoes acylation at the indole nitrogen atom by p-chorobenzoyl chloride in dimethylformamide, using sodium hydride as a base. The resulting tert-butyl ester of 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetic acid (3.2.50), further undergoes thermal decomposition to the desired acid, indomethacin (3.2.51) [111,112].

インドメタシン 上流と下流の製品情報

原材料

準備製品


インドメタシン 生産企業

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53-86-1(インドメタシン)キーワード:


  • 53-86-1
  • 1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-ylacetic acid
  • indomethacin crystalline
  • indomethacin methanol solution
  • indomethacin usp
  • AURORA KA-6542
  • INDOCIN
  • INDOMETACIN
  • INDOMETACINE
  • INDOMETHACINE
  • LABOTEST-BB LT00244830
  • INDOMETHACIN BP99
  • ndomethacin
  • N-(4-Chlorobenzoyl)-4-Methoxyphenyl-Hydrazine
  • 1-(P-CHLOROBENZYL)-5-METHOXY-2-METHYLINDOLE-3-ACETIC ACID
  • 1-(P-CHLOROBENZOYL)-5-METHOXY-2-METHYL-1H-INDOLE-3-ACETIC ACID
  • 1-(p-chlorobenzoyl)-2-methyl-5-methoxyindole-3-aceticacid
  • 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylaceticacid
  • 1-(p-Chlorobenzoyl)-5-methoxy-2-methylindol-3-acetic acid
  • 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-indole-3-aceticaci
  • 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-
  • 1-p-Cloro-benzoil-5-metoxi-2-metilindol-3-acido acetico
  • 1-p-cloro-benzoil-5-metoxi-2-metilindol-3-acidoacetico
  • alpha-(1-(p-Chlorobenzoyl)-2-methyl-5-methoxy-3-indolyl)acetic acid
  • alpha-(1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indolyl)aceticacid
  • Amuno
  • Artracin
  • Artrinovo
  • Artrivia
  • Bonidin
  • Catlep
  • インドメタシン
  • ラクティオン
  • インドメ
  • マタジン
  • インメシン
  • テンポラル
  • セラスター
  • インサイド
  • コリフメシン
  • 2-メチル-1-(4-クロロベンゾイル)-5-メトキシ-1H-インドール-3-酢酸
  • アスモID
  • インダシン
  • メゾリン
  • 1-(4-クロロベンゾイル)-2-メチル-5-メトキシ-1H-インドール-3-酢酸
  • インデラポロン
  • ミカメタン
  • インドシド
  • [1-(4-クロロベンゾイル)-2-メチル-5-メトキシ-1H-インドール-3-イル]酢酸
  • ハップスターID
  • インテナシン
  • サロダン
  • インナミット
  • メチンドール
  • 1-(4-クロロベンゾイル)-5-メトキシ-2-メチル-1H-インドール-3-酢酸
  • インテバンSP
  • インドメロール
  • メサジン
  • インテバン
  • ゼムパック
  • インテナース
  • ヨードメタシン
  • インメタン
  • インドシン
  • アコニップ
  • インテダール
  • カトレップ
  • イドメシン
  • プロアリシン
  • インデラニック
  • トラップオン
  • 1-(p-クロロベンゾイル)-5-メトキシ-2-メチル-1H-インドール-3-酢酸
  • インドノール
  • 1-(4-クロロベンゾイル)-5-メトキシ-2-メチル-3-インドール酢酸
  • インドメタシン標準品
  • インドメタシン (JP17)
  • 生化学
  • 阻害剤
  • 非ステロイド系消炎薬
  • 酵素阻害剤
  • 解熱鎮痛薬
  • 抗リウマチ薬
  • 循環器系作用薬
  • 眼科用薬
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