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ゲフィチニブ

ゲフィチニブ 化学構造式
184475-35-2
CAS番号.
184475-35-2
化学名:
ゲフィチニブ
别名:
ゲフィチニブ;イレッサ;ゲフィチニブ (JAN)
英語化学名:
Gefitinib
英語别名:
IRESSA;CS-524;ZD 1839;efitinib;GEFITINIB;Ji Fei Ji;Gefinitib;Getfitnib;Gifitinib;AKOS 91371
CBNumber:
CB8120056
化学式:
C22H24ClFN4O3
分子量:
446.9
MOL File:
184475-35-2.mol

ゲフィチニブ 物理性質

融点 :
119-1200C
沸点 :
586.8±50.0 °C(Predicted)
比重(密度) :
1.322±0.06 g/cm3(Predicted)
貯蔵温度 :
room temp
酸解離定数(Pka):
7.00±0.10(Predicted)
外見 :
powder
色:
white to beige
CAS データベース:
184475-35-2(CAS DataBase Reference)

安全性情報

Sフレーズ  24/25
HSコード  29349990

ゲフィチニブ 価格 もっと(9)

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) W01TOC3000 イレッサ
Iressa
184475-35-2 10mg ¥47000 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01TOC3000 イレッサ
Iressa
184475-35-2 50mg ¥201000 2021-03-23 購入
東京化成工業 G0546 ゲフィチニブ >98.0%(HPLC)(T)
Gefitinib >98.0%(HPLC)(T)
184475-35-2 1g ¥7000 2021-03-23 購入
東京化成工業 G0546 ゲフィチニブ >98.0%(HPLC)(T)
Gefitinib >98.0%(HPLC)(T)
184475-35-2 5g ¥24000 2021-03-23 購入
Sigma-Aldrich Japan SML1657 ≥98% (HPLC)
Gefitinib ≥98% (HPLC)
184475-35-2 50mg ¥75100 2021-03-23 購入

ゲフィチニブ 化学特性,用途語,生産方法

外観

白色~わずかにうすい褐色、結晶性粉末~粉末

溶解性

ジメチルスルホキシド溶状:試験適合ジメチルスルホキシドに溶け、アセトン、エタノール及び水に難溶である。

用途

EGFR チロシンキナーゼ阻害 剤です。特に変異型 EGFR に対してより低濃 度で阻害活性を示します。

効能

抗悪性腫瘍薬, 受容体チロシンキナーゼ阻害薬

商品名

イレッサ (アストラゼネカ); ゲフィチニブ (ダイト); ゲフィチニブ (日医工); ゲフィチニブ (日本ジェネリック); ゲフィチニブ (日本化薬); ゲフィチニブ (沢井製薬); ゲフィチニブ (高田製薬)

説明

Gefitinib was introduced in Japan as a daily oral monotherapy for the treatment of inoperable or recurrent non-small cell lung cancers (NSCLC). This anilinoquinazoline derivative can be synthesized in 6 steps starting from 6,7-dimethoxyquinazolin-4(3H)-one by successive monodemethylationlacetylation of the 6-hydroxy-group followed by chlorination and reaction with 3-chloro-4-fluoroaniline, finally deacetylation and alkylation with 3-(4-morpholinyl)propylbromide complete the synthesis. Gefitinib reversibly inhibits the activity of the epidermal growth factor receptor tyrosine kinase (EGRF TK). This inhibits autophosphorylation of EGRF and blocks the cascade of intracellular events which have been implicated in the proliferation, survival and metastasis of cancer cells. Gefitinib diplays good selectivity for the EGRF TK relative to other growth factors in human umbilical endothelial cells. It is similarly selective relative to other kinases, for example cerB2. Data from two large phase II studies in patients with pretreated NSCLC have shown that gefitinib induces a response rate approaching 20% in patients receiving the agent as a second line therapy and approximately 10% in those pretreated with more lines of chemotherapy. Gefitinib has good bioavailability and is metabolized in the liver via the cytochrome P450 3A4 enzyme system with a mean elimination half life of 28 h. Gefitinib has been generally well tolerated in cancer patients with predominant side effects being acne-like skin-rash, diarrhea, nausea, vomiting and mild to moderate myelosuppression. .

化学的特性

Light-Yellow Crystalline Powder

Originator

Astra Zeneca (UK)

使用

Gefitinib (Iressa, ZD-1839) is an EGFR inhibitor for Tyr1173, Tyr992, Tyr1173 and Tyr992 in the NR6wtEGFR and NR6W cells with IC50 of 37 nM, 37nM, 26 nM and 57 nM, respectively.

使用

Gefitinib is an antineoplastic.

適応症

Iressa (ZD1839) is an orally active tyrosine kinase inhibitor selective for the epidermal growth factor (EGF) receptor tyrosine kinase. Iressa is undergoing clinical trials in the treatment of various solid tumors, including head and neck cancer, breast cancer and non-small cell lung cancer. Its antitumor activity is derived from the fact that the EGF receptor and EGF signaling are frequently overactivated in sensitive tumors. The major side effects include diarrhea and skin rash. Bone marrow toxicity has not been a dose-limiting problem.

適応症

The EGFR or ErbB1 inhibitor gefitinib (Iressa(R), AstraZeneca) was originally approved by the US FDA in 2003 under accelerated regulations for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC) after progression on docetaxel- and platinum-based chemotherapy. AstraZeneca voluntarily withdrew gefitinib from the market in 2005, owing to failed verification of clinical benefit during post-approval studies. In July 2015, FDA reinstated the approval of gefitinib for a different group of patients (i.e., NSCLC patients with EGFR mutations).
Other approved kinase inhibitors targeting the ErbB family, which includes ErbB1/EGFR, ErbB2/human epidermal growth factor receptor 2 (Her2), ErbB3/ Her3, and ErbB4/Her4, are erlotinib (Tarceva(R), OSI Pharm.), lapatinib (Tykerb(R), GlaxoSmithKline), vandetanib (Caprelsa(R), AstraZeneca), afatinib (Gilotrif(R), Boehringer Ingelheim) , and osimertinib (Tagrisso(R), AstraZeneca). All approved EGFR family inhibitors share a common quinazoline scaffold with the exception of osimertinib, which has a pyrimidinylphenylamine scaffold that resembles that of imatinib and nilotinib. Gefitinib and vandetanib adopt the type I binding mode with “DFG-in” and αC-helix “in” conformation, while erlotinib and lapatinib bind to“DFG-in”with the αC-helix adopting an “out” conformation. Afatinib and osimertinib are covalent inhibitors with an electrophilic enone moiety.

brand name

Iressa (AstraZeneca).

一般的な説明

Geftinib is available as 250-mg tablets for oral administrationin the treatment of NSCLC for those patients who have failedto respond to platinum-based therapies and docetaxel and hasalso been used against squamous cell cancers of the head andneck. The agent is an inhibitor of the TK of EGF-R and possiblyother TKs as well. Gefitinib is both a substrate and inhibitorof Pgp and BCRP. The agent is absorbed slowly afterbeing administered orally with 60% bioavailability.Metabolism occurs in the liver and is mediated primarily byCYP3A4 to give eight identified metabolites resulting fromdefluorination of the phenyl ring, oxidative-O-demethylation,and multiple products arising as a result of oxidation of themorpholine ring. The O-demethylated product represents thepredominate metabolite and is 14-fold less active comparedwith the parent. The parent and metabolites are eliminated inthe feces with a terminal elimination half-life of 48 hours.The drug appears to be well tolerated with the most commonlyreported side effects being rash and diarrhea. It mayalso cause elevations in blood pressure especially in those patientswith preexisting hypertension, elevation of transaminaselevels, and mild nausea and mucositits.

生物活性

Orally active, selective inhibitor of EGFR tyrosine kinase (IC 50 = 23-79 nM). Shows minimal activity against ErbB2, KDR, c-flt, PKC, MEK and ERK-2. Blocks EGFR autophosphorylation and inhibits tumor growth in mice bearing a range of human xenografts.

Chemical Synthesis

A mixture of 4,5-dimethoxyanthranilic acid (133) and formamide was heated to generate the cyclized quinazoline 134. The quinazoline was selectively monodemethylated with methionine in refluxing methanesulfonic acid to afford 135 in 47% yield. Compound 135 was acylated to give acetate 136, which was treated with refluxing thionyl chloride to yield chloropyrimidine 137. Chloride 137 was condensed with 3-chloro-4-fluoroaniline (138) in refluxing IPA to yield anilinoquinazoline 139 in 56% yield from 136. The acetate protecting group in compound 139 was hydrolyzed with ammonium hydroxide in methanol, and the free phenol was alkylated with 3-(4- morpholinyl)propyl chloride (140) to give gefitinib (13) in 55% yield.

ゲフィチニブ 上流と下流の製品情報

原材料

準備製品


ゲフィチニブ 生産企業

Global( 532)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
AFINE CHEMICALS LIMITED
008657185134551
008657185134895 info@afinechem.com CHINA 15559 58
Hangzhou Huarong Pharm Co., Ltd.
+8613588754946 +86-571-86758373
0086-571-81131109 sales@huarongpharm.com CHINA 3149 58
Frapp's ChemicalNFTZ Co., Ltd.
+86 (576) 8169-6106
+86 (576) 8169-6105 sales@frappschem.com China 886 50
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20010 60
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 21032 58
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
010-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8882 55
Guangzhou PI PI Biotech Inc
+8618371201331
020-81716319 sales@pipitech.com;87478684@qq.com China 3245 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
product@chemlin.com.cn CHINA 3013 60

184475-35-2(ゲフィチニブ)キーワード:


  • 184475-35-2
  • N-(3-Chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine Gefitinib
  • Gefitinib, >=99%
  • N-(3-Chlor-4-fluorophenyl)-7-[methoxy-6-[(3-morpholin-4-yl)propoxyl]-quinazolin-4-yl]amine
  • GEFITINIB RELATED COMPOUND
  • Gefitinib N-(3-Chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
  • IRESSA
  • GEFITINIB
  • n-(3-chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
  • N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-4-quinazolinamine
  • ZD 1839
  • 4-Quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-
  • Ji Fei Ji
  • Gefitinib Tablets
  • 4-[(3-Chloro-4-fluorophenyl)amino]-7-methoxy-6-(3-morpholinopropoxy)quinazoline
  • AKOS 91371
  • Gefitinib(TINIBS)
  • 6-(Benzyloxy)-7-methoxyquinazolin-4(3H)-one
  • Gefinitib
  • (3-chloro-4-fluoro-phenyl)-[7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-yl]amine
  • N-(4-bromo-2-fluorophenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine
  • Gefitinib, Iressa, ZD1839
  • ZD1839; IRESSA
  • Getfitnib
  • N-(3-Chloro-4-fluorophenyl)-7-Methoxy-6-(3-Morpholinopropoxy)quinazolin-4-aMine
  • Gifitinib
  • Gefitinib (ZD1839)
  • Gefitinib WS
  • Gefitinib 184475-35-2
  • Gefitinib(AZ-1839)
  • CS-524
  • ゲフィチニブ
  • イレッサ
  • ゲフィチニブ (JAN)
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