brivanib   

GtoPdb Ligand ID: 5671

Synonyms: BMS 540215 | BMS-540215
Compound class: Synthetic organic
Comment: Brivanib (BMS-540215) is a potent ATP-competitive inhibitor of VEGFR2. Its discovery is reported in [1].
The International Non-proprietary Name (INN) brivanib alaninate has PubChem CID 11154925, and this represents the prodrug used in clinical trials.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 84.67
Molecular weight 370.14
XLogP 3.99
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC(COc1cn2c(c1C)c(ncn2)Oc1ccc2c(c1F)cc([nH]2)C)O
Isomeric SMILES C[C@H](COc1cn2c(c1C)c(ncn2)Oc1ccc2c(c1F)cc([nH]2)C)O
InChI InChI=1S/C19H19FN4O3/c1-10-6-13-14(23-10)4-5-15(17(13)20)27-19-18-12(3)16(26-8-11(2)25)7-24(18)22-9-21-19/h4-7,9,11,23,25H,8H2,1-3H3/t11-/m1/s1
InChI Key WCWUXEGQKLTGDX-LLVKDONJSA-N
No information available.
Summary of Clinical Use
Brivanib progressed to Phase 3 clinical trials for liver and colorectal cancers. Click here to link to ClinicalTrials.gov's complete list of brivanib trials. Treatment with brivanib has been linked to an increased risk of developing fatal adverse events in hepatocellular carcinoma patients in a meta-analysis report [3].
Mechanism Of Action and Pharmacodynamic Effects
Like other angiokinase inhibitors, brivanib's anti-neoplastic effect is due to its suppression of the neo-angiogenesis required for tumour growth and expansion [1].