BO2

N-[(1R)-1-(DIHYDROXYBORYL)-3-METHYLBUTYL]-N-(PYRAZIN-2-YLCARBONYL)-L-PHENYLALANINAMIDE



Chemical Component Summary

NameN-[(1R)-1-(DIHYDROXYBORYL)-3-METHYLBUTYL]-N-(PYRAZIN-2-YLCARBONYL)-L-PHENYLALANINAMIDE
SynonymsBORTEZOMIB
Identifiers[(1R)-3-methyl-1-[[(2S)-3-phenyl-2-(pyrazin-2-ylcarbonylamino)propanoyl]amino]butyl]boronic acid
FormulaC19 H25 B N4 O4
Molecular Weight384.24
TypeNON-POLYMER
Isomeric SMILESB([C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)NC(=O)c2cnccn2)(O)O
InChIInChI=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
InChIKeyGXJABQQUPOEUTA-RDJZCZTQSA-N

Chemical Details

Formal Charge0
Atom Count53
Chiral Atom Count2
Bond Count54
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB00188 
NameBortezomib
Groups
  • approved
  • investigational
DescriptionBortezomib is a dipeptide boronic acid derivative and proteasome inhibitor used to treat multiple myeloma and mantle cell lymphoma.[A204083] The 26S proteasome is a protein complex that degrades ubiquitinated proteins in the ubiquitin-proteasome pathway: reversible inhibition of the 26S proteasome, leading to cell cycle arrest and apoptosis of cancer cells, is thought to be the main mechanism of action of bortezomib.[L14180] However, multiple mechanisms may be involved in the anticancer activity of bortezomib.[A204083] Bortezomib was first synthesized in 1995.[A204083] In May 2003, bortezomib became the first anticancer proteasome inhibitor that was approved by the FDA under the trade name VELCADE.[A204146] Phase I, II, III, and IV clinical trials are undergoing to investigate the therapeutic efficacy of bortezomib in leukemia, myasthenia gravis, systemic lupus erythematosus, rheumatoid arthritis, and solid tumours.[A214307]
Synonyms
  • N-[(1R)-1-(DIHYDROXYBORYL)-3-methylbutyl]-N-(pyrazin-2-ylcarbonyl)-L-phenylalaninamide
  • Bortezomib
  • [(1R)-3-methyl-1-({(2S)-3-phenyl-2-[(pyrazin-2-ylcarbonyl)amino]propanoyl}amino)butyl]boronic acid
Brand Names
  • Bortezomib Hospira
  • Bortezomib Fresenius Kabi
  • Velcade
  • Bortezomib Sun
  • Bortezomib
IndicationBortezomib is indicated for the treatment of adult patients with multiple myeloma or mantle cell lymphoma.[L14177]
Categories
  • Acids
  • Acids, Noncarboxylic
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • Boron Compounds
ATC-CodeL01XX32
CAS number179324-69-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Proteasome subunit beta type-5MALASVLERPLPVNQRGFFGLGGRADLLDLGPGSLSDGLSLAAPGWGVPE...unknowninhibitor
Proteasome subunit beta type-1MLSSTAMYSAPGRDLGMEPHRAAGPLQLRFSPYVFNGGTILAIAGEDFAI...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknownsubstrate,inhibitor
Cytochrome P450 2D6MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem387447
ChEBICHEBI:52717
ChEMBLCHEMBL325041
PharosCHEMBL325041