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エトリコキシブ

エトリコキシブ 化学構造式
202409-33-4
CAS番号.
202409-33-4
化学名:
エトリコキシブ
别名:
エトリコキシブ
英語化学名:
Etoricoxib
英語别名:
Algix;Etocox;Etoxib;MK 663;Tauxib;Arcoxia;Etobrix;Kingcox;MK 0663;Nucoxia
CBNumber:
CB0223494
化学式:
C18H15ClN2O2S
分子量:
358.84
MOL File:
202409-33-4.mol

エトリコキシブ 物理性質

融点 :
134-135°C
沸点 :
510.0±50.0 °C(Predicted)
比重(密度) :
1.298±0.06 g/cm3(Predicted)
貯蔵温度 :
Inert atmosphere,2-8°C
酸解離定数(Pka):
4.5(at 25℃)
外見 :
neat
BRN :
8073797
InChIKey:
MNJVRJDLRVPLFE-UHFFFAOYSA-N
CAS データベース:
202409-33-4(CAS DataBase Reference)
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
Rフレーズ  22-24
Sフレーズ  36/37-45
RIDADR  UN 2811 6.1 / PGII
WGK Germany  3
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
H302 飲み込むと有害 急性毒性、経口 4 警告 P264, P270, P301+P312, P330, P501
H310 皮膚に接触すると生命に危険 急性毒性、経皮 1, 2 危険 P262, P264, P270, P280, P302+P350,P310, P322, P361, P363, P405, P501
注意書き
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P302+P350 皮膚に付着した場合:多量の水と石鹸で優しく洗うこと。
P310 ただちに医師に連絡すること。

エトリコキシブ 価格 もっと(4)

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) W01MAS099471
5-Chloro-6'-methyl-3-(4-(methylsulfonyl)-phenyl)-2,3'-bipyridine
202409-33-4 250mg ¥102200 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01MAS099471
5-Chloro-6'-methyl-3-(4-(methylsulfonyl)-phenyl)-2,3'-bipyridine
202409-33-4 1g ¥230000 2021-03-23 購入
Sigma-Aldrich Japan 32097 VETRANAL?, analytical standard
Etoricoxib VETRANAL?, analytical standard
202409-33-4 25mg ¥17000 2021-03-23 購入
林純薬工業株式会社 R106310M ---
Etoricoxib ---
202409-33-4 10mg ¥5900 2021-03-22 購入

エトリコキシブ 化学特性,用途語,生産方法

効能

鎮痛薬, 抗炎症薬, シクロオキシゲナーゼ2阻害薬

説明

Etoricoxib is a COX-2 inhibitor developed as a follow-up of rofecoxib for the treatment of osteoarthritis, rheumatoid arthritis, dysmenorrhoea, gout, ankylosing spondylitis and pain. Several processes describe the preparation of etoricoxib in 4 or 5 steps from 6- methylnicotinate. The key step is the novel pyridine construction using annulation of a ketosutfone with a vinamidinium synthon. In human whole blood, in vitro, the IC50 value obtained for inhibition of COX-2 is 1 .I μM as compared to 116 μM obtained for inhibition of COX-1. Thus, etoricoxib is the most selective COX-2 inhibitor to date, with a COX-IKOX- 2 ratio of IC50 values of 106 for etoricoxib as compared to 35, 30, 7.6 for rofecoxib, valdecoxib and celecoxib, respectively. Its in vivo potency is generally comparable to that of rofecoxib in animal models against inflammation (carrageenan-induced paw edema), pyrexia (LPS-induced pyresis), pain (carrageenan-induced hyperalgesia) and arthritis (adjuvant-induced arthritis). Etoricoxib is well tolerated with dose-proportional pharmacokinetics. It has no effect on bleeding time or platelet ag regation. The gastrointestinal tolerability of etoricoxib is excellent as demonstrated by [51Cr] models of excretion in rats and squirrel monkeys. Moreover, etoricoxib, unlike naproxen is not associated with significant inhibition of gastric mucosal PGE2 synthesis compared to placebo. Etoricoxib is highly absorbed, has a tmax of 1.5 h and a half-life time of approximately 15-22h. Five metabolites, weak inhibitors of COX-1 and COX-2 have been identified after renal excretion. Finally, although multiple CYP enzymes are involved in the metabolism of etoricoxib (CYP3A4 being the major contributor), etoricoxib is not a potent CYP3A4 inhibitor or inducer. In patients undergoing molar extraction, etoricoxib showed similar efficacy to naproxen sodium with a longer duration of analgesia than acetaminophen/codeine (approximately >24 h, 22 h and 5.2 h, respectively) and a better total pain relief score over 8 h. Similar efficacy of etoricoxib and naproxen was also seen in patients suffering of osteoarthritis. In the treatment of rheumatoid arthritis and ankylosing spondylitis, etoricoxib demonstrated significantly superior efficacy compared to naproxen and placebo. Etoricoxib did not affect the pharmacokinetics of prednisolone (i.v. or p.0.) and its co-administration with antacids showed insignificant effects on the maximal concentration and its absorption. .

化学的特性

Off-White Powder

Originator

Merck & Co (USA)

使用

A specific inhibitor of COX-2 .

使用

anti-inflammatory, analgesic;cyclooxygenase inhibitor

使用

For the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout.

使用

Labeled Etoricoxib, intended for use as an internal standard for the quantification of Etoricoxib by GC- or LC-mass spectrometry.

使用

Etoricoxib is a dipyridinyl compound that demonstrates high in vitro and ex vivo selectivity for COX-2 over COX-1 in several assays, e.g., in the production of PGE2 by CHO cells expressing either COX-2 (IC50 = 79 nM) or COX-1 (IC50 > 50 μM). Oral etoricoxib is well absorbed and metabolized extensively via oxidation, with metabolites excreted largely in the urine.[Cayman Chemical]

定義

ChEBI: A member of the class of bipyridines that is 2,3'-bipyridine which is substituted at the 3, 5, and 6' positions by 4-(methylsulfonyl)phenyl, chlorine, and methyl groups, respectively.

brand name

Arcoxia

薬物動態学

Etoricoxib is rapidly absorbed, with an oral bioavailability of 80 to 100%, and reaches maximum plasma concentrations in 1 to 2 hours after dosing. Food decreases the rate of absorption but has no effect on the extent of absorption. It exhibits a long elimination half-life of approximately 22 hours, demonstrating linear plasma pharmacokinetics with no accumulation during multiple dosing.

臨床応用

Etoricoxib is a selective COX-2 inhibitor being developed for postsurgical treatment of dental pain (120 mg) and osteoarthritis. It has a methylsulfonyl group common to the other coxib inhibitors.

Chemical Synthesis

The synthesis of etoricoxib (8) was explored extensively by the Merck process research group. Key intermediate 85 was synthesized through at least three different routes. In the Horner-Wittig approach, 6-methyl methylnicotinate (79) was converted into Weinreb amide 80 in 95% yield. Amide 80 was then converted to aldehyde 81 via a DIBAL-H mediated reduction. Subsequent treatment of a solution of aldehyde 81 in isopropyl acetate with aniline and diphenyl phosphite provided N,P-acetal 82 in 87% yield. The Horner-Wittig reaction of N,P-acetal 82 with 4-methanesulfonylbenzaldehyde (83) furnished enamine 84, which was hydrolyzed to ketosulfone 85. A Grignard approach was also developed in the preparation of ketosulfone 85. Addition of Grignard reagent 86 to Weinreb amide 80 in toluene/THF provided ketosulfide 85 in 80% yield. Tungstate-catalyzed oxidation of ketosulfide 87 using hydrogen peroxide provided ketosulfone 85 in 89% yield by simple filtration. Ketosulfone 85 was prepared through Claisen condensation protocol as well. Thus, reaction of 4-methanesulfonyl phenyl acetic acid (88) with methyl nicotinate 79 under Ivanoff condition, i.e., the magnesium dianion in THF, resulted 58% yield of ketosulfone 85. Treatment of ketosulfone 85 with a three-carbon electrophile, 2-chloro-N,Ndimethylaminotrimethinium hexafluorophos-phate (89) in the presence of potassium t-butoxide at ambient temperature resulted adduct 90. Inverse quench of adduct 90 into a mixture of HOAc /TFA led to the putative intermediate 91. Ring closure of the pyridine ring occurred upon heating at reflux in the presence of an excess of aqueous ammonium hydroxide to give desired etoricoxib (8) in 97% yield in a one-pot process from 85.

代謝

Etoricoxib is metabolized involving oxidation of its 6′-methyl group primarily by CYP3A4 but is not an inhibitor of CYP3A4. Other metabolites include 1′-N-oxide and glucuronides. Etoricoxib is primarily excreted as metabolites into the urine.

エトリコキシブ 上流と下流の製品情報

原材料

準備製品


エトリコキシブ 生産企業

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202409-33-4(エトリコキシブ)キーワード:


  • 202409-33-4
  • Etoricoxib Solution, 100ppm
  • Etoricoxib (MK-663
  • Etoricoxib Tablets
  • Etoricoxib(5-chloro-6'-Methyl-3-(4-(Methylsulfonyl)phenyl)-2,3'-bipyridine
  • Cis-Anetho   
  • Etoricoxib (200 mg)
  • Etoricoxib impurity A
  • Etoricoxib, >=98%
  • 5-chloro-2-(6-methylpyridin-3-yl)-3-(4-methylsulfonylphenyl)pyridine
  • ETORICOXIB
  • 5-Chloro-6'-methyl-3-[4-(methylsulfonyl) phenyl]-2,3'-bipyridine
  • Arcoxia
  • 5-chloro-3-(4-Methanesulfonylphenyl)-2-(6-Methylpyridin-3-yl)pyridine
  • Etoricoxib-D4
  • 2,3'-Bipyridine, 5-chloro-6'-Methyl-3-[4-(Methylsulfonyl)phenyl]-
  • Algix
  • Etobrix
  • Etocox
  • Etoxib
  • Etropain
  • Kingcox
  • MK 0663
  • MK 663
  • Tauxib
  • Torcoxia
  • Etoricoxib Etoricoxib
  • Etoricoxib API
  • L-791456
  • Nucoxia
  • Etoricoxib USP/EP/BP
  • エトリコキシブ
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