Home Other Building Blocks 850140-72-6
850140-72-6,MFCD12407405
Catalog No.:AA0050MC

850140-72-6 | Afatinib

Pack Size
Purity
Availability
Price(USD)
Quantity
  
5mg
≥95%
in stock  
$38.00   $26.00
- +
25mg
98%
in stock  
$45.00   $32.00
- +
50mg
>97.0%(HPLC)(N)
in stock  
$68.00   $48.00
- +
250mg
≥ 99% (Chiral purity)
in stock  
$86.00   $60.00
- +
1g
≥ 99% (Chiral purity)
in stock  
$200.00   $140.00
- +
5g
99%
in stock  
$380.00   $266.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0050MC
Chemical Name:
Afatinib
CAS Number:
850140-72-6
Molecular Formula:
C24H25ClFN5O3
Molecular Weight:
485.9384
MDL Number:
MFCD12407405
SMILES:
CN(C/C=C/C(=O)Nc1cc2c(ncnc2cc1O[C@@H]1COCC1)Nc1ccc(c(c1)Cl)F)C
NSC Number:
750691
Properties
Properties
 
BP:
676.917°C at 760 mmHg  
Form:
Solid  
MP:
100 - 102°C  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
702  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
8  
XLogP3:
3.6  

Downstream Synthesis Route
850140-72-6    110-16-7   
2-butenamide,N-(4-((3-chloro-4-fluorophenyl)amino)-7-((3S)-tetrahydro-3-furanyloxy)-6-quinazolinyl)-4-(dimethylamino)-,(2E)-,(2Z)-2-butenedioate 

[1]Patent:WO2013/52157,2013,A1.Locationinpatent:Page/Pagecolumn13;14

[2]Patent:US2005/85495,2005,A1.Locationinpatent:Page/Pagecolumn6-7

[3]Patent:CN108358900,2018,A.Locationinpatent:Paragraph0045-0050

[4]Patent:CN106243092,2016,A.Locationinpatent:Paragraph0026;0049-0052;0061-0064;0073-0076;0085-0088

[5]Patent:WO2012/121764,2012,A1.Locationinpatent:Page/Pagecolumn52-53

[6]Patent:WO2016/51380,2016,A1.Locationinpatent:Page/Pagecolumn5;6

[7]Patent:WO2017/33107,2017,A1.Locationinpatent:Page/Pagecolumn27;28;29;30;31

[8]Patent:WO2017/93789,2017,A1.Locationinpatent:Page/Pagecolumn19

[9]Patent:US2018/30038,2018,A1.Locationinpatent:Paragraph0212;0213-0218;0221-0228;0231;0232;0234-0243

[10]Patent:US2018/297989,2018,A1.Locationinpatent:Paragraph0210;0215;0216;0250;0281;0282;0282;0283

[1]Patent:WO2007/85638,2007,A1.Locationinpatent:Page/Pagecolumn23

[1]Patent:WO2012/121764,2012,A1.Locationinpatent:Page/Pagecolumn49-50

[2]Patent:US2005/85495,2005,A1.Locationinpatent:Page/Pagecolumn6

[3]Patent:WO2016/166720,2016,A2.Locationinpatent:Page/Pagecolumn16

850140-72-6    97-67-6   
afatinibdi-L-malate 

[1]Patent:WO2012/121764,2012,A1.Locationinpatent:Page/Pagecolumn57-58

Literature

Title: YM155 as an inhibitor of cancer stemness simultaneously inhibits autophosphorylation of epidermal growth factor receptor and G9a-mediated stemness in lung cancer cells.

Journal: PloS one 20170101

Title: Discovery of (R,E)-N-(7-Chloro-1-(1-[4-(dimethylamino)but-2-enoyl]azepan-3-yl)-1H-benzo[d]imidazol-2-yl)-2-methylisonicotinamide (EGF816), a Novel, Potent, and WT Sparing Covalent Inhibitor of Oncogenic (L858R, ex19del) and Resistant (T790M) EGFR Mutants for the Treatment of EGFR Mutant Non-Small-Cell Lung Cancers.

Journal: Journal of medicinal chemistry 20160728

Title: EGF816 Exerts Anticancer Effects in Non-Small Cell Lung Cancer by Irreversibly and Selectively Targeting Primary and Acquired Activating Mutations in the EGF Receptor.

Journal: Cancer research 20160315

Title: Treatment approaches for EGFR-inhibitor-resistant patients with non-small-cell lung cancer.

Journal: The Lancet. Oncology 20150901

Title: Targeted therapies: Afatinib--new therapy option for EGFR-mutant lung cancer.

Journal: Nature reviews. Clinical oncology 20131001

Title: Identification of novel scaffold of benzothiazepinones as non-ATP competitive glycogen synthase kinase-3β inhibitors through virtual screening.

Journal: Bioorganic & medicinal chemistry letters 20121201

Title: Target binding properties and cellular activity of afatinib (BIBW 2992), an irreversible ErbB family blocker.

Journal: The Journal of pharmacology and experimental therapeutics 20121101

Title: Activation of IL-6R/JAK1/STAT3 signaling induces de novo resistance to irreversible EGFR inhibitors in non-small cell lung cancer with T790M resistance mutation.

Journal: Molecular cancer therapeutics 20121001

Title: Second-generation irreversible epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors (TKIs): a better mousetrap? A review of the clinical evidence.

Journal: Critical reviews in oncology/hematology 20120901

Title: Monitoring reversible and irreversible EGFR inhibition with erlotinib and afatinib in a patient with EGFR-mutated non-small cell lung cancer (NSCLC) using sequential [18F]fluorothymidine (FLT-)PET.

Journal: Lung cancer (Amsterdam, Netherlands) 20120901

Title: New therapies in HER2-positive breast cancer: a major step towards a cure of the disease?

Journal: Cancer treatment reviews 20120801

Title: A phase II trial to assess efficacy and safety of afatinib in extensively pretreated patients with HER2-negative metastatic breast cancer.

Journal: Breast cancer research and treatment 20120801

Title: Irreversible protein kinase inhibitors: balancing the benefits and risks.

Journal: Journal of medicinal chemistry 20120726

Title: Structural analysis of the EGFR TK domain and potential implications for EGFR targeted therapy.

Journal: International journal of oncology 20120601

Title: A phase II study of afatinib (BIBW 2992), an irreversible ErbB family blocker, in patients with HER2-positive metastatic breast cancer progressing after trastuzumab.

Journal: Breast cancer research and treatment 20120601

Title: Afatinib for patients with lung adenocarcinoma and epidermal growth factor receptor mutations (LUX-Lung 2): a phase 2 trial.

Journal: The Lancet. Oncology 20120501

Title: Afatinib versus placebo for patients with advanced, metastatic non-small-cell lung cancer after failure of erlotinib, gefitinib, or both, and one or two lines of chemotherapy (LUX-Lung 1): a phase 2b/3 randomised trial.

Journal: The Lancet. Oncology 20120501

Title: Phase I study of continuous afatinib (BIBW 2992) in patients with advanced non-small cell lung cancer after prior chemotherapy/erlotinib/gefitinib (LUX-Lung 4).

Journal: Cancer chemotherapy and pharmacology 20120401

Title: Afatinib pharmacokinetics and metabolism after oral administration to healthy male volunteers.

Journal: Cancer chemotherapy and pharmacology 20120401

Title: Clinical activity of afatinib (BIBW 2992) in patients with lung adenocarcinoma with mutations in the kinase domain of HER2/neu.

Journal: Lung cancer (Amsterdam, Netherlands) 20120401

Title: EGFR exon 19 insertions: a new family of sensitizing EGFR mutations in lung adenocarcinoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120315

Title: The EGFR T790M mutation in acquired resistance to an irreversible second-generation EGFR inhibitor.

Journal: Molecular cancer therapeutics 20120301

Title: Targeting the epidermal growth factor receptor in non-small cell lung cancer cells: the effect of combining RNA interference with tyrosine kinase inhibitors or cetuximab.

Journal: BMC medicine 20120101

Title: Anti-tumour activity of afatinib, an irreversible ErbB family blocker, in human pancreatic tumour cells.

Journal: British journal of cancer 20111108

Title: Comprehensive analysis of kinase inhibitor selectivity.

Journal: Nature biotechnology 20111030

Title: EGFR- and VEGF(R)-targeted small molecules show synergistic activity in colorectal cancer models refractory to combinations of monoclonal antibodies.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20111015

Title: Growth response of human colorectal tumour cell lines to treatment with afatinib (BIBW2992), an irreversible erbB family blocker, and its association with expression of HER family members.

Journal: International journal of oncology 20110801

Title: Afatinib (BIBW 2992) development in non-small-cell lung cancer.

Journal: Future oncology (London, England) 20110701

Title: The search for improved systemic therapy of non-small cell lung cancer--what are today's options?

Journal: Lung cancer (Amsterdam, Netherlands) 20110601

Title: Phase II trial of weekly alternating sequential BIBF 1120 and afatinib for advanced colorectal cancer.

Journal: Anticancer research 20110601

Title: The LUX-Lung clinical trial program of afatinib for non-small-cell lung cancer.

Journal: Expert review of anticancer therapy 20110501

Title: Genotype-driven therapies for non-small cell lung cancer: focus on EGFR, KRAS and ALK gene abnormalities.

Journal: Therapeutic advances in medical oncology 20110501

Title: Cysteine mapping in conformationally distinct kinase nucleotide binding sites: application to the design of selective covalent inhibitors.

Journal: Journal of medicinal chemistry 20110310

Title: BIBW 2992 in non-small cell lung cancer.

Journal: Expert opinion on investigational drugs 20110301

Title: Irreversible EGFR inhibitor EKB-569 targets low-LET γ-radiation-triggered rel orchestration and potentiates cell death in squamous cell carcinoma.

Journal: PloS one 20110101

Title: EGFR inhibitors in non-small cell lung cancer (NSCLC): the emerging role of the dual irreversible EGFR/HER2 inhibitor BIBW 2992.

Journal: Targeted oncology 20101201

Title: New drugs in advanced non-small-cell lung cancer: searching for the correct clinical development.

Journal: Expert opinion on investigational drugs 20101201

Title: Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.

Journal: Chemistry & biology 20101124

Title: Phase I trial of the irreversible EGFR and HER2 kinase inhibitor BIBW 2992 in patients with advanced solid tumors.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20100901

Title: Fast-forwarding hit to lead: aurora and epidermal growth factor receptor kinase inhibitor lead identification.

Journal: Journal of medicinal chemistry 20100708

Title: Enhanced anticancer effect of the combination of BIBW2992 and thymidylate synthase-targeted agents in non-small cell lung cancer with the T790M mutation of epidermal growth factor receptor.

Journal: Molecular cancer therapeutics 20100601

Title: The role of irreversible EGFR inhibitors in the treatment of non-small cell lung cancer: overcoming resistance to reversible EGFR inhibitors.

Journal: Cancer investigation 20100501

Title: Chemogenomic profiling provides insights into the limited activity of irreversible EGFR Inhibitors in tumor cells expressing the T790M EGFR resistance mutation.

Journal: Cancer research 20100201

Title: Irreversible pan-ErbB tyrosine kinase inhibitors and breast cancer: current status and future directions.

Journal: Cancer treatment reviews 20091201

Title: Dual targeting of EGFR can overcome a major drug resistance mutation in mouse models of EGFR mutant lung cancer.

Journal: The Journal of clinical investigation 20091001

Title: Acquired resistance to epidermal growth factor receptor tyrosine kinase inhibitors in non-small-cell lung cancers dependent on the epidermal growth factor receptor pathway.

Journal: Clinical lung cancer 20090701

Title: Synthesis and stereochemical effects of pyrrolidinyl-acetylenic thieno[3,2-d]pyrimidines as EGFR and ErbB-2 inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20090101

Title: BIBW-2992, a dual receptor tyrosine kinase inhibitor for the treatment of solid tumors.

Journal: Current opinion in investigational drugs (London, England : 2000) 20081201

Title: Acquired resistance to epidermal growth factor receptor kinase inhibitors associated with a novel T854A mutation in a patient with EGFR-mutant lung adenocarcinoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20081115

Title: BIBW2992, an irreversible EGFR/HER2 inhibitor highly effective in preclinical lung cancer models.

Journal: Oncogene 20080807

Title: A phase I dose escalation study of BIBW 2992, an irreversible dual inhibitor of epidermal growth factor receptor 1 (EGFR) and 2 (HER2) tyrosine kinase in a 2-week on, 2-week off schedule in patients with advanced solid tumours.

Journal: British journal of cancer 20080115

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Tags:850140-72-6 Molecular Formula|850140-72-6 MDL|850140-72-6 SMILES|850140-72-6 Afatinib