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183321-74-6 分子结构
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N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine

ChemBase编号:412
分子式:C22H23N3O4
平均质量:393.43572
单一同位素质量:393.16885623
SMILES和InChIs

SMILES:
O(c1c(OCCOC)cc2ncnc(Nc3cc(ccc3)C#C)c2c1)CCOC
Canonical SMILES:
COCCOc1cc2c(ncnc2cc1OCCOC)Nc1cccc(c1)C#C
InChI:
InChI=1S/C22H23N3O4/c1-4-16-6-5-7-17(12-16)25-22-18-13-20(28-10-8-26-2)21(29-11-9-27-3)14-19(18)23-15-24-22/h1,5-7,12-15H,8-11H2,2-3H3,(H,23,24,25)
InChIKey:
AAKJLRGGTJKAMG-UHFFFAOYSA-N

引用这个纪录

CBID:412 http://www.chembase.cn/molecule-412.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine
IUPAC传统名
@erlotinib
商标名
Tarceva
别名
OSI-774
erlotinib
Erlotinib
CAS号
183321-74-6
PubChem SID
46508021
160963875
PubChem CID
176870

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB00530 external link
PubChem 176870 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 16.143808  质子受体
质子供体 LogD (pH = 5.5) 3.1516304 
LogD (pH = 7.4) 3.2003288  Log P 3.2009876 
摩尔折射率 107.7859 cm3 极化性 43.13458 Å3
极化表面积 74.73 Å2 可自由旋转的化学键 10 
里宾斯基五规则 true 
Log P 3.13  LOG S -4.64 
溶解度 8.91e-03 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
Very slightly soluble (hydrochloride salt - maximal solubility of approximately 0.4 mg/mL occurs at a pH of approximately 2) expand 查看数据来源
疏水性(logP)
2.7 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00530 external link
Item Information
Drug Groups approved; investigational
Description Erlotinib hydrochloride (trade name Tarceva, Genentech/OSIP, originally coded as OSI-774) is a drug used to treat non-small cell lung cancer, pancreatic cancer and several other types of cancer.

Similar to gefitinib, erlotinib specifically targets the epidermal growth factor receptor (EGFR) tyrosine kinase. It binds in a reversible fashion to the adenosine triphosphate (ATP) binding site of the receptor. Erlotinib has recently been shown to be a potent inhibitor of JAK2V617F activity. JAK2V617F is a mutant of tyrosine kinase JAK2, is found in most patients with polycythemia vera (PV) and a substantial proportion of patients with idiopathic myelofibrosis or essential thrombocythemia. The study suggests that erlotinib may be used for treatment of JAK2V617F-positive PV and other myeloproliferative disorders.
Indication For the treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of at least one prior chemotherapy regimen. Also for use, in combination with gemcitabine, as the first-line treatment of patients with locally advanced, unresectable or metastatic pancreatic cancer.
Pharmacology Erlotinib is a Human Epidermal Growth Factor Receptor Type 1/Epidermal Growth Factor Receptor (HER1/EGFR) tyrosine kinase inhibitor.
Toxicity Symptoms of overdose include diarrhea, rash, and liver transaminase elevation.
Affected Organisms
Humans and other mammals
Biotransformation In vitro assays of cytochrome P450 metabolism showed that erlotinib is metabolized primarily by CYP3A4 and to a lesser extent by CYP1A2, and the extrahepatic isoform CYP1A1.
Absorption Erlotinib is about 60% absorbed after oral administration and its bioavailability is substantially increased by food to almost 100%.
Half Life Median half-life of 36.2 hours.
Protein Binding 93% protein bound to albumin and alpha-1 acid glycoprotein (AAG)
References
Raymond E, Faivre S, Armand JP: Epidermal growth factor receptor tyrosine kinase as a target for anticancer therapy. Drugs. 2000;60 Suppl 1:15-23; discussion 41-2. [Pubmed]
Li Z, Xu M, Xing S, Ho WT, Ishii T, Li Q, Fu X, Zhao ZJ: Erlotinib effectively inhibits JAK2V617F activity and polycythemia vera cell growth. J Biol Chem. 2007 Feb 9;282(6):3428-32. Epub 2006 Dec 18. [Pubmed]
Dudek AZ, Kmak KL, Koopmeiners J, Keshtgarpour M: Skin rash and bronchoalveolar histology correlates with clinical benefit in patients treated with gefitinib as a therapy for previously treated advanced or metastatic non-small cell lung cancer. Lung Cancer. 2006 Jan;51(1):89-96. Epub 2005 Nov 14. [Pubmed]
Jones HE, Goddard L, Gee JM, Hiscox S, Rubini M, Barrow D, Knowlden JM, Williams S, Wakeling AE, Nicholson RI: Insulin-like growth factor-I receptor signalling and acquired resistance to gefitinib (ZD1839; Iressa) in human breast and prostate cancer cells. Endocr Relat Cancer. 2004 Dec;11(4):793-814. [Pubmed]
Blum G, Gazit A, Levitzki A: Substrate competitive inhibitors of IGF-1 receptor kinase. Biochemistry. 2000 Dec 26;39(51):15705-12. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Raymond E, Faivre S, Armand JP: Epidermal growth factor receptor tyrosine kinase as a target for anticancer therapy. Drugs. 2000;60 Suppl 1:15-23; discussion 41-2. Pubmed
  • Li Z, Xu M, Xing S, Ho WT, Ishii T, Li Q, Fu X, Zhao ZJ: Erlotinib effectively inhibits JAK2V617F activity and polycythemia vera cell growth. J Biol Chem. 2007 Feb 9;282(6):3428-32. Epub 2006 Dec 18. Pubmed
  • Dudek AZ, Kmak KL, Koopmeiners J, Keshtgarpour M: Skin rash and bronchoalveolar histology correlates with clinical benefit in patients treated with gefitinib as a therapy for previously treated advanced or metastatic non-small cell lung cancer. Lung Cancer. 2006 Jan;51(1):89-96. Epub 2005 Nov 14. Pubmed
  • Jones HE, Goddard L, Gee JM, Hiscox S, Rubini M, Barrow D, Knowlden JM, Williams S, Wakeling AE, Nicholson RI: Insulin-like growth factor-I receptor signalling and acquired resistance to gefitinib (ZD1839; Iressa) in human breast and prostate cancer cells. Endocr Relat Cancer. 2004 Dec;11(4):793-814. Pubmed
  • Blum G, Gazit A, Levitzki A: Substrate competitive inhibitors of IGF-1 receptor kinase. Biochemistry. 2000 Dec 26;39(51):15705-12. Pubmed
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专利

专利

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