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セレコキシブ

セレコキシブ 化学構造式
169590-42-5
CAS番号.
169590-42-5
化学名:
セレコキシブ
别名:
セレコキシブ;4-[5-(4-メチルフェニル)-3-(トリフルオロメチル)-1H-ピラゾール-1-イル]ベンゼンスルホンアミド;5-(4-メチルフェニル)-1-(4-スルファモイルフェニル)-3-(トリフルオロメチル)ピラゾール;セレコキシブ (JAN)
英語化学名:
Celecoxib
英語别名:
YM 177;ecoxib;CS-453;Celebra;Celecox;CS-1846;SC 58635;celexibn;CELEBREX;Celecoxi
CBNumber:
CB7444681
化学式:
C17H14F3N3O2S
分子量:
381.37
MOL File:
169590-42-5.mol

セレコキシブ 物理性質

融点 :
157-159°C
沸点 :
529.0±60.0 °C(Predicted)
比重(密度) :
1.43±0.1 g/cm3(Predicted)
貯蔵温度 :
2-8°C
溶解性:
DMSO: >20mg/mL
酸解離定数(Pka):
9.68±0.10(Predicted)
外見 :
powder
色:
white to off-white
水溶解度 :
7mg/L(25 ºC)
Merck :
14,1956
CAS データベース:
169590-42-5(CAS DataBase Reference)
EPAの化学物質情報:
Benzenesulfonamide, 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]- (169590-42-5)

安全性情報

主な危険性  Xn
Rフレーズ  20/21/22-52-61-60
Sフレーズ  22-24/25-28-37/39
RIDADR  UN 3077 9 / PGIII
WGK Germany  3
RTECS 番号 DB2944937
国連危険物分類  IRRITANT
HSコード  29350090
有毒物質データの 169590-42-5(Hazardous Substances Data)

セレコキシブ 価格 もっと(27)

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) W01CAY10008672
Celecoxib
169590-42-5 50mg ¥8100 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01CAY10008672
Celecoxib
169590-42-5 100mg ¥15400 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01MAS047884
4-[5-(4-Methylphenyl)-3-(trifluoromethyl)-pyrazol-1-yl]benzenesulfonamide
169590-42-5 100g ¥233300 2021-03-23 購入
東京化成工業 C2816 セレコキシブ >98.0%(HPLC)(T)
Celecoxib >98.0%(HPLC)(T)
169590-42-5 200mg ¥5300 2021-03-23 購入
東京化成工業 C2816 セレコキシブ >98.0%(HPLC)(T)
Celecoxib >98.0%(HPLC)(T)
169590-42-5 1g ¥18400 2021-03-23 購入

セレコキシブ 化学特性,用途語,生産方法

外観

白色~ほとんど白色粉末~結晶

用途

選択的なシクロオキシゲナーゼ -2(COX-2)阻害剤です。

用途

セレコキシブ(Celecoxib, 日本における製品名:セレコックス)は、非ステロイド性消炎?鎮痛薬(Non-steroidal anti-inflammatory Drugs:NSAIDs)であり、100mgと200mgの錠剤がある。セレコキシブは、COX-2を選択的に阻害することを目的にドラッグデザインされ、日本でCOX-2選択的阻害剤としてカテゴライズされている唯一の薬剤である。 本においてセレコキシブは、2007年に関節リウマチ、変形性関節症、2009年に腰痛症、肩関節周囲炎、頸肩腕症候群、腱?腱鞘炎の適応を取得した。また、2011年には急性疼痛として、手術後、外傷後、抜歯後の消炎?鎮痛の適応が承認された。日本以外の国では、強直性脊椎炎や月経困難症などの適応ももっている。セレコキシブは鎮痛効果を発揮しつつ、従来のNSAIDsで見られるような消化管への副作用を最小限に抑えることを目的としてドラッグデザインされたCOX-2選択的阻害薬である。 セレコキシブの日本国内における関節リウマチ、変形性関節症、腰痛症の第III相試験結果、および肩関節周囲炎、頸肩腕症候群、腱?腱鞘炎の国内一般臨床試験において、消炎?鎮痛効果で改善効果が認められた

用途

シクロオキシゲナーゼ2 (COX-2)選択的阻害剤です。抗炎症・鎮痛 作用を示します。

効能

鎮痛薬, 抗炎症薬, シクロオキシゲナーゼ2阻害薬

商品名

セレコックス (アステラス製薬)

説明

Celecoxib is a nonsteroidal antiinflammatory drug (NSAID) first launched as Celebrex in the US for the treatment of symptoms in patients with rheumatoid arthritis (RA) and osteoarthritis (OA). Celecoxib belongs to a new class of 1, 5-diarylpyrazoles and can be synthesized by heat-promoted heterocyclization of a trifiuoro-l,3-dione with appropriate arylhydrazine. Celecoxib is a highly selective inhibitor of COX-2, the inducible form of cyclooxygenase expressed during inflammatory processes; it does not block the constitutive form COX-1, thus suppressing the gastric and intestinal toxicity of most non-selective NSAIDs. The potency ratio COX1/COX2 on purified human enzymes was about 400. In several in vivo models of acute and chronic inflammation, Celecoxib demonstrated potent antiinflammatory activity without affecting gastric or urinary prostaglandin PGE2. In several clinical studies performed with patients suffering from osteoarthritis or rheumatoid arthritis, Celecoxib was shown to be well tolerated and to relieve pain and inflammation more efficiently compared with other standard NSAIDs; the gastrointestinal safety profile was significantly better than that of other NSAIDs. Interestingly, Celecoxib was approved for another indication in patients with familial adenomatous polyposis (FAP). A six-month clinical trial demonstrated a 28% reduction in the number of colorectal polyps with Celecoxib, compared to a 5% reduction with placebo.

化学的特性

White to Pale Yellow Solid

Originator

Searle (US)

使用

expectorant, gastric stimulant, insecticide

使用

For relief and management of osteoarthritis (OA), rheumatoid arthritis (RA), juvenile rheumatoid arthritis (JRA), ankylosing spondylitis, acute pain, primary dysmenorrhea and oral adjunct to usual care for patients with familial adenomatous polyposis

使用

A selective cyclooxygenase-2 (COX-2) inhibitor. Anti-inflammatory. Used in treatment of familial adenomatous polyposis

適応症

Celecoxib is indicated for the treatment of osteoarthritis and rheumatoid arthritis. Its use is contraindicated in individuals with hypersensitivity to sulfonamides or other NSAIDs. It should be used with caution in persons with hepatic disease. Interactions occur with other drugs that induce CYP2C9 (e.g. rifampin rifampin) or compete for metabolism by this enzyme (e.g. fluconazole, leflunomide). The most common adverse reactions to celecoxib are mild to moderate GI effects such as dyspepsia, diarrhea, and abdominal pain. Serious GI and renal effects have occurred rarely.

Manufacturing Process

4-(5-(4-Methylphenyl)-3-trifluoromethyl-N-pyrazol-1-yl)benzenesulfonamide To a solution of ethyl trifluoroacetate (1.90 ml, 16.0 mmol) in 7 ml of methyl tert-butyl ether was added 25% NaOMe (3.62 ml, 16.8 mmol). Next 4- chloroaceteophenone (2.08 ml, 16.0 mmol) in 2 ml of methyl tert-butyl ether was added. The mixture was stirred at room temperature overnight. To above solution was added 100 ml of 90% EtOH, followed by 4 N HCl (4.0 ml, 16 mmol) and 4-sulphonamidophenylhydrazine hydrochloride (3.58 g, 16 mmol). The mixture was heated to reflux for 3 hours. The mixture was concentrated. When 30 ml of water was added, a solid formed. The solid was filtered and washed with 20 ml of 60% EtOH to give 4.50 g of white solid. The filtrate was evaporated and taken up in ethyl acetate (100 ml), washed with saturated NaHCO3, and brine, dried over MgSO4, and concentrated. Heptane was added at boiling point of the mixture. After cooling down to 0°C, 1.01 g more product was obtained. The combined yield of the 4-(5-(4-methylphenyl)-3- trifluoromethyl-N-pyrazol-1-yl)benzenesulfonamide (Celecoxib) was 86%.

brand name

Celebrex (Searle).

Therapeutic Function

Antiinflammatory

一般的な説明

Celecoxib (Celebrex) was the first selective COX-2 inhibitordrug introduced into the market in 1998 for use in thetreatment of RA, OA, acute pain, and menstrual pain. Thereal benefit is that it has caused fewer GI complicationswhen compared with other conventional NSAIDs. It hasalso been approved for reducing the number of adenomatouscolorectal polyps in familial adenomatous polyposis (FAP).Celecoxib is well absorbed and undergoes rapid oxidativemetabolism via CYP2C9 to give its inactive metabolites. Thus, a potential drug interaction exists betweencelecoxib and warfarin because the active isomer ofwarfarin is primarily degraded by CYP2C9.

生物活性

Selective cyclooxygenase-2 (COX-2) inhibitor (IC 50 values are 15 and 0.04 μ M for COX-1 and COX-2 respectively). Anti-inflammatory with shorter plasma half-life in vivo than SC 58121 (5-(4-Fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole ). Displays chemopreventive activity in in vivo tumor models.

薬物動態学

Celecoxib is well absorbed from the GI tract, with peak plasma concentrations generally being attained within 3 hours of administration. Peak plasma levels in geriatric patients may be increased, but dosage adjustments in elderly patients generally are not required unless the patient weighs less than 50 kg.

臨床応用

Celecoxib is currently indicated for the relief of signs and symptoms of osteoarthritis and rheumatoid arthritis and to reduce the number of adenomatous colorectal polyps in familial adenomatous polyposis as an adjunct to usual care.
Celecoxib is synthesized by condensing 4-methyl-acetophenone and ethyltrifluoroacetate with sodium methoxide and the resulting butanedione derivative cyclized with 4-hydrazinophenylsulfonamide. It was the first NSAID to be marketed as a selective COX-2 inhibitor.

代謝

Celecoxib is excreted in the urine and feces primarily as inactive metabolites, with less than 3% of an administered dose being excreted as unchanged drug. Metabolism occurs primarily in the liver by CYP2C9 and involves hydroxylation of the 4-methyl group to the primary alcohol, which is subsequently oxidized to its corresponding carboxylic acid, the major metabolite (73% of the administered dose). The carboxylic acid is conjugated, to a slight extent, with glucuronic acid to form the corresponding glucuronide. None of the isolated metabolites have been shown to exhibit pharmacological activity as inhibitors of either COX-1 or COX-2. Celecoxib also inhibits CYP2D6; thus, the potential of celecoxib to alter the pharmacokinetic profiles of other drugs inhibited by this isoenzyme exists. Celecoxib, however, does not appear to inhibit other CYP isoforms, such as CYP2C19 or CYP3A4. Other drug interactions related to the metabolic profile of celecoxib have been noted, particularly with other drugs that inhibit CYP2C.

セレコキシブ 上流と下流の製品情報

原材料

準備製品


セレコキシブ 生産企業

Global( 586)Suppliers
名前 電話番号 ファックス番号 電子メール 国籍 製品カタログ 優位度
Baoji Guokang Bio-Technology Co., Ltd.
09173909592
09173909592 cngksw@aliyun.com CHINA 9447 58
AFINE CHEMICALS LIMITED
008657185134551
008657185134895 info@afinechem.com CHINA 15559 58
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20010 60
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
010-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233
+86-21-37127788 Candy@bj-chem.com CHINA 497 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
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Shanghai Time Chemicals CO., Ltd.
+8618017249410 +86-021-57951555
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Guangzhou PI PI Biotech Inc
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Shanghai Yingrui Biopharma Co., Ltd.
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Hubei XinRunde Chemical Co., Ltd.
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169590-42-5(セレコキシブ)キーワード:


  • 169590-42-5
  • 4-[5-(4-Methylphenyl)-3-trifluoromethyl)-1H-pyrazol-yl]benzenesulfonamide Celecoxib
  • CJ-016377
  • CP-598107
  • PF-00345549
  • PHA-00846533
  • Celecoxib Solution, 100ppm
  • Celecoxib (200 mg)
  • Celocoxib, >=99%
  • Benzenesulfonamide, 4-5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl-
  • 4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
  • Celecoxib API
  • celexicob
  • Celebra
  • Celecox
  • Celocoxib
  • SC 58635
  • YM 177
  • 4-(5-(p-tolyl)-3-(trifluoroMethyl)-1H-pyrazol-1-yl)benzenesulfonaMide
  • celexibn
  • Eprosartan Mesylate and its interMediate
  • SaMMy Westbrook
  • 4-[5-(p-Tolyl)-3-(trifluoromethyl)-1-pyrazolyl]benzenesulfonamide
  • CELEBREX
  • CELECOXIB
  • 4-[[5-(4-METHYLPHENYL)-3-TRIFLUOROMETHYL]-1H-PYRAZOL-YL]BENZENESULFONAMIDE
  • 4-[5-((4-METHYLPHENYL)-3-TRIFLUORPMETHYL)-1H-PYRAZOL-YL]BENENESULFONAMIDE
  • Celecoxib, 4-[5-(4-Methylphenyl)-3-trifluoromethyl)-1H-pyrazol-yl]benzenesulfonamide
  • Celecoxib Factory
  • ecoxib
  • (184007-95-2) celecoxib
  • セレコキシブ
  • 4-[5-(4-メチルフェニル)-3-(トリフルオロメチル)-1H-ピラゾール-1-イル]ベンゼンスルホンアミド
  • 5-(4-メチルフェニル)-1-(4-スルファモイルフェニル)-3-(トリフルオロメチル)ピラゾール
  • セレコキシブ (JAN)
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