bortezomib

Ligand id: 6391

Name: bortezomib

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 11
Topological polar surface area 124.44
Molecular weight 384.2
XLogP 3.24
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2003), EMA (2004))
IUPAC Name
[(1R)-3-methyl-1-[[(2S)-3-phenyl-2-(pyrazine-2-carbonylamino)propanoyl]amino]butyl]boronic acid
International Nonproprietary Names
INN number INN
8331 bortezomib
Synonyms
peptide boronate | PS-341 | Velcade®
Database Links
CAS Registry No. 179324-69-7
ChEBI CHEBI:52717
ChEMBL Ligand CHEMBL325041
DrugBank Ligand DB00188
PubChem CID 387447
RCSB PDB Ligand BO2
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Search UniChem for chemical match using the InChIKey GXJABQQUPOEUTA-RDJZCZTQSA-N
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Wikipedia Bortezomib
Comments
Bortezomib is a dipeptide (Phe-Leu), with a pyrazinoic acid protecting the N-terminus and a boronic acid replacing the C-terminal carboxylic acid. The boron atom is believed to interact with and inactivate the catalytic site on β subunits which form the active core of the proteasome, preferentially binding β5 active site [3]. Bortezomib is the first-in-class proteasome inhibitor to be approved for clinical use.
Proteasome activity is reviewed in [2].