Gefitinib , CAS No.184475-35-2

CAS: 184475-35-2 Cat. No.: G1371968-GMP Molecular Weight: 446.9 EC Number: 643-034-7

Storage

Room temperature

Shipped In

Normal

Overview

Gefitinib (ZD1839) (GMP) is Gefitinib produced by using GMP guidelines. GMP small molecules work appropriately as an auxiliary reagent for cell therapy manufacture. Gefitinib is a potent, selective and orally active EGFR tyrosine kinase inhibitor.

Specifications

Storage

Room temperature

Shipped In

Normal

Product Properties

• ALogP: 4.1

Names and Identifiers

• Canonical Smiles: COC1=C(C=C2C(=C1)N=CN=C2NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4
• IUPAC Name: N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
• InChIKey: XGALLCVXEZPNRQ-UHFFFAOYSA-N
• INCHI: 1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)
• Isomeric SMILES: COC1=C(C=C2C(=C1)N=CN=C2NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4
• Molecular Weight: 446.9
• Reaxy-Rn: 8949523
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8949523&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazanaphthalenes
      • Subclass Benzodiazines
        • Level5 Quinazolines
          • Level6 Quinazolinamines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazanaphthalenes
• Subclass: Benzodiazines
• Intermediate Tree Nodes: Quinazolines
• Direct Parent: Quinazolinamines
• Alternative Parents: Aniline and substituted anilines Anisoles Alkyl aryl ethers Aminopyrimidines and derivatives Chlorobenzenes Fluorobenzenes Aryl chlorides Aryl fluorides Morpholines Imidolactams Heteroaromatic compounds Trialkylamines Dialkyl ethers Azacyclic compounds Oxacyclic compounds Secondary amines Hydrocarbon derivatives Organochlorides Organofluorides Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Quinazolinamine - Anisole - Aniline or substituted anilines - Alkyl aryl ether - Aminopyrimidine - Chlorobenzene - Fluorobenzene - Halobenzene - Aryl chloride - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - Morpholine - Oxazinane - Pyrimidine - Benzenoid - Imidolactam - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Secondary amine - Azacycle - Dialkyl ether - Ether - Oxacycle - Organonitrogen compound - Hydrocarbon derivative - Organooxygen compound - Organic nitrogen compound - Amine - Organic oxygen compound - Organofluoride - Organochloride - Organopnictogen compound - Organohalogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.
• External Descriptors: quinazolines - morpholines

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Specific Rotation[α]: 1.62
• Boil Point(°C): 586.8 °C
• Melt Point(°C): 194.0 to 198.0 °C

References

1. Xinyi Lv, Yuehan Song, Tianhua Liu, Dingdan Zhang, Xinpeng Ye, Qingqing Wang, Rongrong Li, Jiayi Chen, Shujing Zhang, Xue Yu, Chunying Hou.  (2025)  Ginsenoside Rg3 Adjunctively Increases the Efficacy of Gefitinib Against NSCLC by Regulating EGFR Copy Number.  Pharmaceuticals,  18  (7): (1077).  [PMID:40732366] [10.3390/ph18071077]

2. Jiali Wang, Xianhai He, Zhirong Jia, Aiwen Yan, Kang Xiao, Shuo Liu, Mengjun Hou, Yaling Long, Xuansheng Ding.  (2023)  Shenqi Fuzheng injection restores the sensitivity to gefitinib in non-small cell lung cancer by inhibiting the IL-22/STAT3/AKT pathway.  PHARMACEUTICAL BIOLOGY,      [PMID:38100532] [10.1080/13880209.2023.2292266]

3. Yong Huang, Yi Lin, Bowen Li, Fu Zhang, Chenyue Zhan, Xin Xie, Zhuo Yao, Chongzhi Wu, Yuan Ping, Jianliang Shen.  (2023)  Combination therapy to overcome ferroptosis resistance by biomimetic self-assembly nano-prodrug.  Asian Journal of Pharmaceutical Sciences,      [PMID:37915761] [10.1016/j.ajps.2023.100844]

4. Yao Liu, Zhichao He, Heng Liang, Minzhen Han, Jinxingyi Wang, Qian Liu, Yanping Guan.  (2023)  A high-throughput UHPLC-MS/MS method for the determination of eight anti-tumor drugs in plasma.  ANALYTICAL BIOCHEMISTRY,      [PMID:37429484] [10.1016/j.ab.2023.115230]

5. Fangjun Chen, Wenda Chen, Zhenxin Wang, Yingfei Peng, Beili Wang, Baishen Pan, Wei Guo.  (2023)  Development and clinical application of a liquid chromatography-tandem mass spectrometry-based assay to quantify eight tyrosine kinase inhibitors in human plasma.  Journal of Mass Spectrometry and Advances in the Clinical Lab,      [PMID:37234251] [10.1016/j.jmsacl.2023.05.001]

6. Zhenzhen Pan, Qiufang Chen, Xiulan Zheng, Kai Wang, Yalei Duan, Kang Xiao, Zhirong Jia, Xuansheng Ding.  (2023)  JuBei Oral Liquid Induces Mitochondria-Mediated Apoptosis in NSCLC Cells.  OncoTargets and Therapy,      [PMID:32821122] [10.2147/OTT.S254464]

7. Jiabin Zhou, Yuhan Liu, Jun Chen, Nanxiang Xiong, Dongye Yi.  (2023)  Kaempferol suppresses glioma progression and synergistically enhances the antitumor activity of gefitinib by inhibiting the EGFR/SRC/STAT3 signaling pathway.  DRUG DEVELOPMENT RESEARCH,  84  (3): (582-600).  [PMID:36852868] [10.1002/ddr.22048]

8. Yin Xiaoting, Ma Suzhen, Li Mengyuan, Lu Shuaifei, Zhang Changjing, Liu Hui, Li Caiyin, Su Pan, Bai Ming, Li Yucheng.  (2023)  Study on the hepatotoxicity and potential mechanism of gefitinib based on CYP450 in mice and AML12 cells.  JOURNAL OF PHARMACY AND PHARMACOLOGY,  75  (3): (407-414).  [PMID:36656101] [10.1093/jpp/rgac091]

9. Hao Chi, Sheng Tian, Xiu Li, Yuchu Chen, Qiumin Xu, Qixiao Wang, Wenwan Shi, Michael Adu-Frimpong, Shanshan Tong.  (2023)  Construction of lipid raft-coupled agarose gels as bioaffinity chromatography materials and validation with tropomyosin-related kinase A-targeted drugs.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:36731332] [10.1016/j.chroma.2023.463803]

10. Jianbo Lin, Rujie Zheng, Liping Huang, Yuanrong Tu, Xu Li, Jianfeng Chen.  (2022)  Folic acid-mediated MSNs@Ag@Geb multifunctional nanocomposite heterogeneous platform for combined therapy of non-small cell lung cancer.  COLLOIDS AND SURFACES B-BIOINTERFACES,      [PMID:35759894] [10.1016/j.colsurfb.2022.112639]

11. Yulin Jiang, Jing Wang, Juehan Wang, Yi Zhuang, Lin Qi, Ganjun Feng, Li Zhang.  (2022)  Fabrication of novel PNIPAM@GO microspheres loaded with dual drugs featuring on-demand drug release capability.  JOURNAL OF APPLIED POLYMER SCIENCE,  139  (27): (e52444).  [PMID:] [10.1002/app.52444]

12. Pan Zhenzhen, Wang Kai, Wang Xiniao, Jia Zhirong, Yang Yuqi, Duan Yalei, Huang Lianzhan, Wu Zhuo-Xun, Zhang Jian-ye, Ding Xuansheng.  (2022)  Cholesterol promotes EGFR-TKIs resistance in NSCLC by inducing EGFR/Src/Erk/SP1 signaling-mediated ERRα re-expression.  Molecular Cancer,  21  (1): (1-17).  [PMID:35303882] [10.1186/s12943-022-01547-3]

13. Yan Zhang, Pei Ma, Zhiguang Duan, Yannan Liu, Yu Mi, Daidi Fan.  (2022)  Ginsenoside Rh4 Suppressed Metastasis of Lung Adenocarcinoma via Inhibiting JAK2/STAT3 Signaling.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  23  (4): (2018).  [PMID:35216134] [10.3390/ijms23042018]

14. Yuqin Zhou, Weitong Hu, Xiangli Zhang, Yi Wang, Wenya Zhuang, Fengzhi Li, Qingyong Li.  (2021)  Cellular Uptake and Transport Characteristics of FL118 Derivatives in Caco-2 Cell Monolayers.  CHEMICAL & PHARMACEUTICAL BULLETIN,  69  (11): (1054-1060).  [PMID:34719586] [10.1248/cpb.c21-00467]

15. Fangyin Zhu, Liang Xu, Xudong Li, Ziying Li, Jun Wang, Haijun Chen, Xiumei Li, Yu Gao.  (2021)  Co-delivery of gefitinib and hematoporphyrin by aptamer-modified fluorinated dendrimer for hypoxia alleviation and enhanced synergistic chemo-photodynamic therapy of NSCLC.  EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES,      [PMID:34520834] [10.1016/j.ejps.2021.106004]

16. Zhao-Yang Wang, Hai-Long Wu, Yue-Yue Chang, Tong Wang, Wei Chen, Gao-Yan Tong, Ru-Qin Yu.  (2021)  Simultaneous determination of nine tyrosine kinase inhibitors in three complex biological matrices by using high-performance liquid chromatography–diode array detection combined with a second-order calibration method.  JOURNAL OF SEPARATION SCIENCE,  44  (21): (3914-3923).  [PMID:34463059] [10.1002/jssc.202100293]

17. Tianming Dai, Weifan Jiang, Min Wang, Zizheng Guo, Renke Dai.  (2021)  Influence of two-period cross-over design on the bioequivalence study of gefitinib tablets in beagle dogs.  EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES,      [PMID:34260895] [10.1016/j.ejps.2021.105933]

18. Jiang Yuhong, Zhuo Xin, Fu Xiujuan, Wu Yue, Mao Canquan.  (2021)  Targeting PAR2 Overcomes Gefitinib Resistance in Non-Small-Cell Lung Cancer Cells Through Inhibition of EGFR Transactivation.  Frontiers in Pharmacology,      [PMID:33967759] [10.3389/fphar.2021.625289]

19. Yue-Yue Chang, Hai-Long Wu, Huan Fang, Tong Wang, Yang-Zi Ouyang, Xiao-Dong Sun, Gao-Yan Tong, Yu-Jie Ding, Ru-Qin Yu.  (2020)  Comparison of three chemometric methods for processing HPLC-DAD data with time shifts: Simultaneous determination of ten molecular targeted anti-tumor drugs in different biological samples.  TALANTA,      [PMID:33379025] [10.1016/j.talanta.2020.121798]

20. Zhixiong Hu, Xin-Yue Jiao, Li Xu.  (2019)  The N,S co-doped carbon dots with excellent luminescent properties from green tea leaf residue and its sensing of gefitinib.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2019.104588]

21. Tianhua Liu, Ling Zuo, Dongqing Guo, Xinlou Chai, Jie Xu, Zhaorui Cui, Zhiyi Wang, Chunying Hou.  (2019)  Ginsenoside Rg3 regulates DNA damage in non-small cell lung cancer cells by activating VRK1/P53BP1 pathway.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:31629252] [10.1016/j.biopha.2019.109483]

22. Zhou Leilei, Weng Qi, Zheng Yixin, Zhou Yuqin, Li Qingyong, Li Fengzhi.  (2019)  Uptake and efflux of FL118 and two FL118 derivatives in 3D cell model.  CYTOTECHNOLOGY,  71  (4): (785-795).  [PMID:31309350] [10.1007/s10616-019-00322-5]

23. Weng Qi, Zhou Leilei, Xia Lihua, Zheng Yixin, Zhang Xiangli, Li Fengzhi, Li Qingyong.  (2019)  In vitro evaluation of FL118 and 9-Q20 cytotoxicity and cellular uptake in 2D and 3D different cell models.  CANCER CHEMOTHERAPY AND PHARMACOLOGY,  84  (3): (527-537).  [PMID:31030236] [10.1007/s00280-019-03846-x]

24. Yang Lehe, Lin Shichong, Kang Yanting, Xiang Youqun, Xu Lingyuan, Li Jifa, Dai Xuanxuan, Liang Guang, Huang Xiaoying, Zhao Chengguang.  (2019)  Rhein sensitizes human pancreatic cancer cells to EGFR inhibitors by inhibiting STAT3 pathway.  JOURNAL OF EXPERIMENTAL & CLINICAL CANCER RESEARCH,  38  (1): (1-13).  [PMID:30674340] [10.1186/s13046-018-1015-9]

25. Xuanxuan Dai, Junru Zhang, Guilong Guo, Yuepiao Cai, Ri Cui, Changtian Yin, Weidong Liu, Rajamanickam Vinothkumar, Tingting Zhang, Guang Liang, Xiaohua Zhang.  (2018)  A mono-carbonyl analog of curcumin induces apoptosis in drug-resistant EGFR-mutant lung cancer through the generation of oxidative stress and mitochondrial dysfunction.  Cancer Management and Research,      [PMID:30214301] [10.2147/CMAR.S159660]

26. Guan Huang, Yanli Tong, Qidi He, Jie Wang, Zuanguang Chen.  (2017)  Aucklandia lappa DC. extract enhances gefitinib efficacy in gefitinib-resistance secondary epidermal growth factor receptor mutations.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:28619365] [10.1016/j.jep.2017.06.011]

27. Yun-Yun Xi, Qing Tang, Ying Huang, Zhu Tao, Sai-Feng Xue, Qingdi Zhou, Gang Wei.  (2017)  A novel fluorescent indicator displacement assay for sensing the anticancer drug gefitinib.  SUPRAMOLECULAR CHEMISTRY,      [PMID:] [10.1080/10610278.2016.1202413]

28. Peng Mei, Huang Yanjun, Tao Ting, Peng Cai-Yun, Su Qiongli, Xu Wanjun, Darko Kwame Oteng, Tao Xiaojun, Yang Xiaoping.  (2016)  Metformin and gefitinib cooperate to inhibit bladder cancer growth via both AMPK and EGFR pathways joining at Akt and Erk.  Scientific Reports,  6  (1): (1-10).  [PMID:27334428] [10.1038/srep28611]

29. Li Chenjia, Liao Qi, Wang Rui, Zhang Xinping, Ma Mengyang, Liu Yonghong, Xiao Lei, Jiao Ying, Wang Nan.  (2024)  An OPRM1-SNAP-tag/CMC method to directly identify drug components in sewage.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,      [PMID:39613988] [10.1007/s00216-024-05672-4]

30. Zhihong Hu, Xixi Hou, Yongjing Ren, Ziyuan Wu, Dong Yan, Hong Chen, Lan Wang.  (2025)  Anti-cancer activity of synthetic gefitinib-1,2,3-triazole derivatives against Hela cells via induction of apoptosis.  Frontiers in Chemistry,      [PMID:39926646] [10.3389/fchem.2025.1456743]

31. Wu Yu, Shi Xiao-Jie, Dai Xin-Yi, Song Tian Shun, Li Xiang-Ling, Xie Jing Jing.  (2024)  Biogated mesoporous silica nanoagents for inhibition of cell migration and combined cancer therapy.  MICROCHIMICA ACTA,  191  (6): (1-9).  [PMID:38740583] [10.1007/s00604-024-06401-5]

32. Yuan Liang, Qing Wang, Dianwen Zhang, Yiyao Gong, Qiuyan Jiang, Cong Ma, Libo Si, Tiehua Zhang, Jie Zhang, Zheng Ma.  (2024)  Ginsenoside CK ameliorates tumor growth in lung cancer mice via inhibiting EGFR.  Journal of Functional Foods,      [PMID:] [10.1016/j.jff.2024.106446]

33. Min Li, Shuaijun Peng, Jingjing Bu, Siqi Quan, Liming Liu, Zhouli Yue, Linlin Wang, Yucheng Li.  (2025)  Glycyrrhizic acid alleviates gefitinib-induced liver injury by regulating the p53/p21 pathway and releasing cell cycle arrest.  FOOD AND CHEMICAL TOXICOLOGY,      [PMID:40122507] [10.1016/j.fct.2025.115405]

34. Yilan Huang, Siwei Wang, Xiaojun Zhang, Chen Yang, Sikai Wang, Hongxia Cheng, Aiwu Ke, Chao Gao, Kun Guo.  (2024)  Identification of Fasudil as a collaborator to promote the anti-tumor effect of lenvatinib in hepatocellular carcinoma by inhibiting GLI2-mediated hedgehog signaling pathway.  PHARMACOLOGICAL RESEARCH,      [PMID:38280440] [10.1016/j.phrs.2024.107082]

35. Gen Li, Chunxiu Cai, Ning Zhang, Zijia Wang, Mingzhe Zhang, Quan Liu, Siyu Chen, Yanfei Shang, Chengqing Zhao, Shenzhen Ren, Hailong An.  (2025)  Carrier-free procyanidin-ferric nanonetworks loading gefitinib to inhibit TMEM16A-EGFR mutual activation loop for photothermally enhanced breast cancer targeted therapy.  Materials Today Bio,      [PMID:41158712] [10.1016/j.mtbio.2025.102426]

36. Cong Xie, Tongshu Guan, Jin Huang, Jiayu Chen, Yilei Li, Ping Zheng.  (2025)  Cyp3a4-Mediated in vitro Metabolism and in vivo Disposition of Lorlatinib in Rats.  Drug Design Development and Therapy,      [PMID:41169706] [10.2147/DDDT.S565228]

37. Xinying Ni, Hong Wang, Wenwen Chen, Xiao Meng, Mengping Zhang, Hua Shao, Fang Zhang, Cuijuan Wang.  (2026)  Field-ready detection of antineoplastic drugs in workplaces using a wearable flexible surface-enhanced Raman spectroscopy platform.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2026.139447]

38. Deng Yiting, Li Jin, Wang Peng, Luo Xuelian, Xu Hongxia, Xiao Yu, Wang Zhenchuan, Lu Yifei, Chen Ying, Ge Feng.  (2026)  DNAJB6 as an immuno-oncogenic hub in liver hepatocellular carcinoma: multi-omic profiling reveals prognostic significance and therapeutic vulnerability.  JOURNAL OF MOLECULAR HISTOLOGY,  57  (1): (57).  [PMID:41559348] [10.1007/s10735-026-10717-2]

39. Jiansong Zhao, Tian Yin, Yaxin Deng, Hongbing Liu, Mingli Wei, Chenxiao Chu, Xinxin Liang, Xiaoshuang Bi, Haibing He, Jingxin Gou, Xing Tang, Yu Zhang.  (2026)  Harnessing semen-derived exosomes for noninvasive fundus drug delivery: A paradigm for exosome-based ocular fundus therapeutics.  Science Advances,  12  (13):   [PMID:] [10.1126/sciadv.adw7275]