Tivozanib

Base Information

• Chemical Name: Tivozanib
• CAS No.: 475108-18-0
• Molecular Formula: C22H19ClN4O5
• Molecular Weight: 454.87
• UNII: 172030934T
• DSSTox Substance ID: DTXSID20963865
• Nikkaji Number: J2.121.508B
• Wikipedia: Tivozanib
• Wikidata: Q7810457
• NCI Thesaurus Code: C85444
• RXCUI: 2534233
• Pharos Ligand ID: G8GCH7A2RSAN
• Metabolomics Workbench ID: 152897
• ChEMBL ID: CHEMBL1289494
• Mol file: 475108-18-0.mol

Synonyms:AV 951;AV-951;AV951 cpd;fotivda;KRN 951;KRN-951;KRN951;tivozanib

Chemical Property of Tivozanib

Chemical Property:

• Boiling Point: 550.4±50.0 °C(Predicted)
• PKA: 11.74±0.70(Predicted)
• PSA: 107.74000
• Density: 1.421
• LogP: 5.78410
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 454.1043974
• Heavy Atom Count: 32
• Complexity: 631

Purity/Quality:

Tivozanib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=NO1)NC(=O)NC2=C(C=C(C=C2)OC3=C4C=C(C(=CC4=NC=C3)OC)OC)Cl
• Recent ClinicalTrials: Evaluating Safety and Efficacy of Tivozanib (AV-951) in Cholangiocarcinoma
• Recent EU Clinical Trials: TiNivo-2: A Phase 3, Randomized, Controlled, Multicenter, Open-label Study to Compare Tivozanib in Combination with Nivolumab to Tivozanib Monotherapy in Subjects with Renal Cell Carcinoma Who Have Progressed Following One or Two Lines of Therapy Where One Line has an Immune Checkpoint Inhibitor
• Description: Tivozanib (AV-951) is a potent and selective VEGFR inhibitor for VEGFR1/2/3 with IC50 of 30 nM/6.5 nM/15 nM, and also inhibits PDGFR and c-Kit, low activity observed against FGFR-1, Flt3, c-Met, EGFR and IGF-1R. Phase 3.
• Uses: Tivozanib also known as AV-951 is an orally bioavailable potent VEGFR-1, 2 and 3, c-Kit and PDGFR inhibitor with IC50 of 0.21, 0.16, 0.24, 1.63 and 1.72 nM, respectively. Tivozanib is known as an oral VEGF receptor tyrosine kinase inhibitor, exhibiting antitumor effects towards renal cell carcinoma.. Tivozanib suppresses angiogenesis by selectively inhibiting against v ascular endothelial growth factor. Tivozanib is known as an oral VEGF receptor tyrosine kinase inhibitor, exhibiting antitumor effects towards renal cell carcinoma.. Tivozanib suppresses angiogenesis by selectively inhibiting against vascular endothelial growth factor. Potent VEGFR inhibitor.

Technology Process of Tivozanib

There total 9 articles about Tivozanib which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.2%

5-methylisoxazol-3-ylamine (1072-67-9) + bis(trichloromethyl) carbonate (32315-10-9) + 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline (286371-44-6) → tivozanib (475108-18-0)

Guidance literature:

bis(trichloromethyl) carbonate; 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline; With pyridine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

5-methylisoxazol-3-ylamine; In dichloromethane; at 20 ℃; for 2h; Time; Inert atmosphere;

Reference yield: 87.0%

5-methylisoxazol-3-ylamine (1072-67-9) + 1,1'-carbonyldiimidazole (530-62-1) + 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline (286371-44-6) → tivozanib (475108-18-0)

Guidance literature:

In tetrahydrofuran; dichloromethane; at 40 ℃; for 3h; Temperature;

Reference yield: 86.1%

5-methylisoxazol-3-ylamine (1072-67-9) + phenyl chloroformate (1885-14-9) + 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline (286371-44-6) → tivozanib (475108-18-0)

Guidance literature:

5-methylisoxazol-3-ylamine; phenyl chloroformate; With pyridine; In N,N-dimethyl acetamide; at 0 - 20 ℃; for 2h;

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline; In ISOPROPYLAMIDE; at 80 ℃; for 5h;

upstream raw materials:

5-methylisoxazol-3-ylamine

phenyl chloroformate

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline

methyl (5-methylisoxazol-3-yl)carbamate

Downstream raw materials:

Tivozanib hydrochloride

Refernces

• 1、 -. "Synthesis process of VEGFR inhibitor tevozanib". . . Retrieved 2022/03/27.
• 2、 Zhu, Chunping,Mao, Yongjun,Wang, Han,Xu, Jingli. "A new and practical synthesis of tivozanib". . p. 1882 - 1887. Retrieved 2016/11/06.