bortezomib   Click here for help

GtoPdb Ligand ID: 6391

Synonyms: peptide boronate | PS-341 | Velcade®
Approved drug PDB Ligand Immunopharmacology Ligand Antimalarial Ligand
bortezomib is an approved drug (FDA (2003), EMA (2004))
Compound class: Synthetic organic
Comment: 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].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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Canonical SMILES CC(CC(B(O)O)NC(=O)C(NC(=O)c1cnccn1)Cc1ccccc1)C
Isomeric SMILES CC(C[C@@H](B(O)O)NC(=O)[C@@H](NC(=O)c1cnccn1)Cc1ccccc1)C
InChI InChI=1S/C19H25BN4O4/c1-13(2)10-17(20(27)28)24-18(25)15(11-14-6-4-3-5-7-14)23-19(26)16-12-21-8-9-22-16/h3-9,12-13,15,17,27-28H,10-11H2,1-2H3,(H,23,26)(H,24,25)/t15-,17-/m0/s1
InChI Key GXJABQQUPOEUTA-RDJZCZTQSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (2003), EMA (2004))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
[(1R)-3-methyl-1-[[(2S)-3-phenyl-2-(pyrazine-2-carbonylamino)propanoyl]amino]butyl]boronic acid
International Nonproprietary Names Click here for help
INN number INN
8331 bortezomib
Synonyms Click here for help
peptide boronate | PS-341 | Velcade®
Database Links Click here for help
CAS Registry No. 179324-69-7
ChEBI CHEBI:52717
ChEMBL Ligand CHEMBL325041
DrugBank Ligand DB00188
DrugCentral Ligand 391
GtoPdb PubChem SID 178103007
PubChem CID 387447
RCSB PDB Ligand BO2
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Wikipedia Bortezomib