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649735-46-6,MFCD13194684
Catalog No.:AA00ECA7

649735-46-6 | Brivanib

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Purity
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1mg
96%
in stock  
$15.00   $11.00
- +
2mg
96%
in stock  
$23.00   $16.00
- +
5mg
96%
in stock  
$36.00   $25.00
- +
10mg
96%
in stock  
$53.00   $37.00
- +
100mg
97%
in stock  
$363.00   $254.00
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250mg
97%
in stock  
$604.00   $423.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00ECA7
Chemical Name:
Brivanib
CAS Number:
649735-46-6
Molecular Formula:
C19H19FN4O3
Molecular Weight:
370.3776
MDL Number:
MFCD13194684
SMILES:
C[C@H](COc1cn2c(c1C)c(ncn2)Oc1ccc2c(c1F)cc([nH]2)C)O
Properties
Computed Properties
 
Complexity:
515  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
5  
XLogP3:
3  

Downstream Synthesis Route

[1]JournalofMedicinalChemistry,2008,vol.51,p.1976-1980

[2]JournalofMedicinalChemistry,2006,vol.49,p.2143-2146

C16H12FN4O2(1-)*Na(1+) 
  15448-47-2    649735-46-6 

[1]Patent:US2007/249610,2007,A1.Locationinpatent:Page/Pagecolumn5;8-9

[1]OrganicProcessResearchandDevelopment,2015,vol.19,p.900-907

[2]Patent:US2007/249610,2007,A1.Locationinpatent:Page/Pagecolumn5;9-11

[3]JournalofMedicinalChemistry,2008,vol.51,p.1976-1980

[1]JournalofMedicinalChemistry,2006,vol.49,p.2143-2146

[1]JournalofMedicinalChemistry,2006,vol.49,p.2143-2146

Literature

Title: Identification of potent Yes1 kinase inhibitors using a library screening approach.

Journal: Bioorganic & medicinal chemistry letters 20130801

Title: Lack of effect of brivanib on the pharmacokinetics of midazolam, a CYP3A4 substrate, administered intravenously and orally in healthy participants.

Journal: Journal of clinical pharmacology 20120601

Title: Phase II, open-label study of brivanib as second-line therapy in patients with advanced hepatocellular carcinoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120401

Title: Second-line therapies in hepatocellular carcinoma: emergence of resistance to sorafenib.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120401

Title: Reversible and pH-dependent weak drug-excipient binding does not affect oral bioavailability of high dose drugs.

Journal: The Journal of pharmacy and pharmacology 20120401

Title: Identification of the oxidative and conjugative enzymes involved in the biotransformation of brivanib.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20120101

Title: Lack of food effect on single-dose pharmacokinetics of brivanib, and safety and efficacy following multiple doses in subjects with advanced or metastatic solid tumors.

Journal: Cancer chemotherapy and pharmacology 20111201

Title: Comprehensive analysis of kinase inhibitor selectivity.

Journal: Nature biotechnology 20111030

Title: Malignant peripheral nerve sheath tumour presenting as a pneumothorax.

Journal: The British journal of radiology 20111001

Title: Brivanib, a dual FGF/VEGF inhibitor, is active both first and second line against mouse pancreatic neuroendocrine tumors developing adaptive/evasive resistance to VEGF inhibition.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20110815

Title: Overcoming antiangiogenic resistance.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20110815

Title: Phase I dose-escalation study to determine the safety, pharmacokinetics and pharmacodynamics of brivanib alaninate in combination with full-dose cetuximab in patients with advanced gastrointestinal malignancies who have failed prior therapy.

Journal: British journal of cancer 20110628

Title: A phase I study to determine the safety, pharmacokinetics and pharmacodynamics of a dual VEGFR and FGFR inhibitor, brivanib, in patients with advanced or metastatic solid tumors.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20110601

Title: Metabolism and disposition of [14C]brivanib alaninate after oral administration to rats, monkeys, and humans.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20110501

Title: Phase II, open-label study of brivanib as first-line therapy in patients with advanced hepatocellular carcinoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20110401

Title: Brivanib alaninate for cancer.

Journal: Expert opinion on investigational drugs 20110401

Title: Future treatment option for hepatocellular carcinoma: a focus on brivanib.

Journal: Digestive diseases (Basel, Switzerland) 20110101

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

Journal: Chemistry & biology 20101124

Title: Metabolism, excretion, and pharmacokinetics of oral brivanib in patients with advanced or metastatic solid tumors.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20101101

Title: Brivanib, a novel dual VEGF-R2/bFGF-R inhibitor.

Journal: Anticancer research 20101101

Title: Amplification of fibroblast growth factor receptor-1 in breast cancer and the effects of brivanib alaninate.

Journal: Breast cancer research and treatment 20101001

Title: Experimental treatment of oestrogen receptor (ER) positive breast cancer with tamoxifen and brivanib alaninate, a VEGFR-2/FGFR-1 kinase inhibitor: a potential clinical application of angiogenesis inhibitors.

Journal: European journal of cancer (Oxford, England : 1990) 20100601

Title: The antiangiogenic activity in xenograft models of brivanib, a dual inhibitor of vascular endothelial growth factor receptor-2 and fibroblast growth factor receptor-1 kinases.

Journal: Molecular cancer therapeutics 20100201

Title: Preclinical pharmacokinetics and in vitro metabolism of brivanib (BMS-540215), a potent VEGFR2 inhibitor and its alanine ester prodrug brivanib alaninate.

Journal: Cancer chemotherapy and pharmacology 20091201

Title: Direct and indirect separations of five isomers of Brivanib Alaninate using chiral high-performance liquid chromatography.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20081101

Title: Brivanib alaninate, a dual inhibitor of vascular endothelial growth factor receptor and fibroblast growth factor receptor tyrosine kinases, induces growth inhibition in mouse models of human hepatocellular carcinoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20081001

Title: Discovery and preclinical studies of 5-isopropyl-6-(5-methyl-1,3,4-oxadiazol-2-yl)-N-(2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (BMS-645737), an in vivo active potent VEGFR-2 inhibitor.

Journal: Bioorganic & medicinal chemistry letters 20080501

Title: Discovery of brivanib alaninate ((S)-((R)-1-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)propan-2-yl)2-aminopropanoate), a novel prodrug of dual vascular endothelial growth factor receptor-2 and fibroblast growth factor receptor-1 kinase inhibitor (BMS-540215).

Journal: Journal of medicinal chemistry 20080327

Title: By looking back we can see the way forward: enhancing the gains achieved with antihormone therapy.

Journal: Breast cancer research : BCR 20080101

Title: Discovery and validation of biomarkers that respond to treatment with brivanib alaninate, a small-molecule VEGFR-2/FGFR-1 antagonist.

Journal: Cancer research 20070715

Title: Discovery and preclinical studies of (R)-1-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-5- methylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)propan- 2-ol (BMS-540215), an in vivo active potent VEGFR-2 inhibitor.

Journal: Journal of medicinal chemistry 20060406

Title: Bhide RS, et al. Discovery and preclinical studies of (R)-1-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-5- methylpyrrolo,1-f,2,4triazin-6-yloxy)propan- 2-ol (BMS-540215), an in vivo active potent VEGFR-2 inhibitor. J Med Chem, 2006, 49 (7), 2143-2146.

Title: Huynh H, et al. Brivanib alaninate, a dual inhibitor of vascular endothelial growth factor receptor and fibroblast growth factor receptor tyrosine kinases, induces growth inhibition in mouse models of human hepatocellular carcinoma. Clin Cancer Res, 2008,

Title: Nakamura I, et al. Correction: Brivanib Attenuates Hepatic Fibrosis In Vivo and Stellate Cell Activation In Vitro by Inhibition of FGF, VEGF and PDGF Signaling. PLoS One. 2015 Nov 3;10(11):e0142355.

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