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 1.01
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2003), EMA (2004))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
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®
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 [4]. Bortezomib is the first-in-class proteasome inhibitor to be approved for clinical use.
Proteasome activity is reviewed in [3].
Database Links
CAS Registry No. 179324-69-7
ChEBI CHEBI:52717
ChEMBL Ligand CHEMBL325041
DrugBank Ligand DB00188
GtoPdb PubChem SID 178103007
PubChem CID 387447
RCSB PDB Ligand BO2
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Wikipedia Bortezomib