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649735-63-7,MFCD22577162
Catalog No.:AA00ECA8

649735-63-7 | Brivanib alaninate

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
98%
in stock  
$33.00   $23.00
- +
2mg
98%
in stock  
$48.00   $34.00
- +
5mg
98%
in stock  
$81.00   $57.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00ECA8
Chemical Name:
Brivanib alaninate
CAS Number:
649735-63-7
Molecular Formula:
C22H24FN5O4
Molecular Weight:
441.4555
MDL Number:
MFCD22577162
SMILES:
C[C@@H](OC(=O)[C@@H](N)C)COc1cn2c(c1C)c(ncn2)Oc1ccc2c(c1F)cc([nH]2)C
Properties
Computed Properties
 
Complexity:
660  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
32  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
8  
XLogP3:
3.1  

Downstream Synthesis Route

[1]Cai,Zhen-Wei;Zhang,Yongzheng;Borzilleri,RobertM.;Qian,Ligang;Barbosa,Stephanie;Wei,Donna;Zheng,Xiaoping;Wu,Lawrence;Fan,Junying;Shi,Zhongping;Wautlet,BarriS.;Mortillo,Steve;JeyaseelanSr.,Robert;Kukral,DanielW.;Kamath,Amrita;Marathe,Punit;D'Arienzo,Celia;Derbin,George;Barrish,JoelC.;Robl,JeffreyA.;Hunt,JohnT.;Lombardo,LouisJ.;Fargnoli,Joseph;Bhide,RajeevS.[JournalofMedicinalChemistry,2008,vol.51,#6,p.1976-1980]

[2]CurrentPatentAssignee:BRISTOL-MYERSSQUIBBCO-US2007/249610,2007,A1Locationinpatent:Page/Pagecolumn5;9-10

[3]Lobben,PaulC.;Barlow,Evan;Bergum,JamesS.;Braem,Alan;Chang,Shih-Ying;Gibson,Frank;Kopp,Nathaniel;Lai,Chiajen;Laporte,ThomasL.;Leahy,DavidK.;Müslehiddinolu,Jale;Quiroz,Fernando;Skliar,Dimitri;Spangler,Lori;Srivastava,Sushil;Wasser,Daniel;Wasylyk,John;Wethman,Robert;Xu,Zhongmin[OrganicProcessResearchandDevelopment,2015,vol.19,#8,p.900-907]

[4]CurrentPatentAssignee:BRISTOL-MYERSSQUIBBCO-US2007/249610,2007,A1Locationinpatent:Page/Pagecolumn5;11-12

[5]Locationinpatent:schemeortableTran,ScottB.;Lago,MichaelW.;Tian,Yuan;Gong,SharonX.;Batra,Indu;Allentoff,AlbanJ.;Maxwell,BradD.;Bonacorsi,SamuelJ.;Ogan,Marc;Rinehart,J.Kent;Balasubramanian,Balu[Journaloflabelledcompoundsandradiopharmaceuticals,2011,vol.54,#6,p.324-331]

C22H23FN4O2 
  649735-63-7 

[1]Lobben,PaulC.;Barlow,Evan;Bergum,JamesS.;Braem,Alan;Chang,Shih-Ying;Gibson,Frank;Kopp,Nathaniel;Lai,Chiajen;Laporte,ThomasL.;Leahy,DavidK.;Müslehiddinolu,Jale;Quiroz,Fernando;Skliar,Dimitri;Spangler,Lori;Srivastava,Sushil;Wasser,Daniel;Wasylyk,John;Wethman,Robert;Xu,Zhongmin[OrganicProcessResearchandDevelopment,2015,vol.19,#8,p.900-907]

C17H14FN4O(1-)*Na(1+) 
  649735-63-7 

[1]Lobben,PaulC.;Barlow,Evan;Bergum,JamesS.;Braem,Alan;Chang,Shih-Ying;Gibson,Frank;Kopp,Nathaniel;Lai,Chiajen;Laporte,ThomasL.;Leahy,DavidK.;Müslehiddinolu,Jale;Quiroz,Fernando;Skliar,Dimitri;Spangler,Lori;Srivastava,Sushil;Wasser,Daniel;Wasylyk,John;Wethman,Robert;Xu,Zhongmin[OrganicProcessResearchandDevelopment,2015,vol.19,#8,p.900-907]

Literature

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: 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: 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 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: 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: 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.

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, 14(19), 6146-6153.

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