Bortezomib (CED0001407)

Record Information
Version1.0
Creation Date2016-05-22 04:30:11 UTC
Update Date2026-08-20 03:54:07 UTC
Accession NumberCHEM017627
Identification
Common NameBortezomib
ClassSmall Molecule
Description
Bortezomib (C19H25BN4O4) is a compound with an average molecular weight of 384.24 g/mol. Bortezomib belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. Biologically, it functions as a proteasome inhibitor (PMC10351539, PMC11698957, PMC9323819, PMC9687107). Its recorded protein targets include Proteasome subunit beta type-1 (PSMB1), Proteasome subunit beta type-5 (PSMB5), and Serine protease 1 (PRSS1). The compound is found in healthcare, pharmaceuticals & veterinary products as an antineoplastic agent, as well as in household cleaning & consumer products (pipe accessories, non electric simulated smoking devices) and electrical & electronic equipment (electric hearing aids, radio transmission systems, antennas). Recorded exposure routes include intravenous, parenteral, subcutaneous, intratendinous, and intracavernous. Bortezomib is used as a treatment for cancer (PMC10351539), melanoma (PMC7226512), lymphoma (PMC7532106, PMC9323819), multiple myeloma (PMC3983165, PMC5030385, PMC5053712, PMC6223128, PMC7115922, PMC9387011), renal failure (PMC7109734), and acute renal failure (PMC3227886). It has therapeutic effects on atherosclerosis (PMC12947462) and multiple myeloma (PMC4352933, PMC5916964, PMC6223128, PMC9387011). Associated health effects include nausea, vomiting, fatigue, rash, and itching (PMC10351539), as well as neutropenia and diarrhea (PMC7873303). Other reported effects include thrombosis, hypertension (PMC12946163), congestive heart failure (PMC12946163, PMC5679835), and neuropathic pain (PMC4559079). It is linked to neuropathy (PMC6223128, PMC9387011) and an increase in neuropathy (PMC4382664, PMC7214419, PMC7873303). Additionally, it is associated with thrombocytopenia (PMC10039009, PMC10351539, PMC11795829, PMC7873303) and an increase in thrombocytopenia (PMC4753325).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
N-[(1R)-1-(DIHYDROXYBORYL)-3-methylbutyl]-N-(pyrazin-2-ylcarbonyl)-L-phenylalaninamideChEBI
PS 341ChEBI
PS-341ChEBI
VelcadeChEBI
341, PSHMDB
LDP 341HMDB
LDP-341HMDB
Chemical FormulaC19H25BN4O4
Average Molecular Mass384.237 g/mol
Monoisotopic Mass384.197 g/mol
CAS Registry Number179324-69-7
IUPAC Name[(1R)-3-methyl-1-[(2S)-3-phenyl-2-(pyrazin-2-ylformamido)propanamido]butyl]boronic acid
Traditional Namebortezomib
SMILESCC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CN=CC=N1)B(O)O
InChI IdentifierInChI=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 KeyGXJABQQUPOEUTA-RDJZCZTQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Amphetamine or derivatives
  • Pyrazine carboxylic acid or derivatives
  • Pyrazinecarboxamide
  • 2-heteroaryl carboxamide
  • Monocyclic benzene moiety
  • Fatty amide
  • Pyrazine
  • Benzenoid
  • Fatty acyl
  • Heteroaromatic compound
  • Boronic acid derivative
  • Boronic acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Organic metalloid salt
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organoboron compound
  • Organopnictogen compound
  • Alkylborane
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Monoalkylborane
  • Organic salt
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.053 g/LALOGPS
logP0.89ALOGPS
logP1.53ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.04ChemAxon
pKa (Strongest Basic)-0.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.44 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity99.37 m³·mol⁻¹ChemAxon
Polarizability40.48 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-002e-9242000000-9fa602d07e0566dc1738Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0035900000-122163b342b985220f63Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-1397000000-e168634cfe7e1453d742Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0035900000-122163b342b985220f63Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-1397000000-e168634cfe7e1453d742Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0040-0945000000-717d35ff034d0823a60bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-040r-2920000000-7cf2f714cdc618ca8e8cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a59-9500000000-a64c45db287441805ffcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-4369000000-54da8c6f6ac19bc3a537Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a7i-7696000000-a8904f81583ba4b00fd9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00b9-9830000000-fb072cbf98c79ced110dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0019000000-738c7318d1c90ad3d40eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002r-2497000000-05ce46c969a07d400170Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-2910000000-b1c62abf177f3ec176c5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-0009000000-f57a7486c4cab88316bfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9012000000-f47b8deb96b3fec82f1dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-8c4defe85755665f03f3Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2777.0Log mg/kg[1600:4900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
hypertensionassociated_withNot AvailablePMC12946163
canceris_treatment_forNot AvailablePMC10351539
renal failureis_treatment_forNot AvailablePMC7109734
fatigueassociated_withNot AvailablePMC10351539
multiple myelomais_treatment_forNot AvailablePMC3983165 , PMC5030385 , PMC5053712 , PMC6223128 , PMC7115922 , PMC7115922 , PMC9387011
multiple myelomahas_therapeutic_effect_onNot AvailablePMC4352933 , PMC5916964 , PMC6223128 , PMC9387011
diarrheaassociated_withNot AvailablePMC7873303
neutropeniaassociated_withNot AvailablePMC7873303
thrombocytopeniaassociated_withNot AvailablePMC10039009 , PMC10351539 , PMC11795829 , PMC7873303 , PMC7873303
thrombocytopeniaassociated_withincreasePMC4753325
neuropathic painassociated_withNot AvailablePMC4559079
congestive heart failureassociated_withNot AvailablePMC12946163 , PMC5679835
melanomais_treatment_forNot AvailablePMC7226512
atherosclerosishas_therapeutic_effect_onNot AvailablePMC12947462
lymphomais_treatment_forNot AvailablePMC7532106 , PMC9323819
nauseaassociated_withNot AvailablePMC10351539 , PMC10351539
vomitingassociated_withNot AvailablePMC10351539 , PMC10351539
rashassociated_withNot AvailablePMC10351539
neuropathyassociated_withNot AvailablePMC6223128 , PMC9387011
neuropathyassociated_withincreasePMC4382664 , PMC4382664 , PMC7214419 , PMC7873303
itchingassociated_withNot AvailablePMC10351539
thrombosisassociated_withNot AvailablePMC12946163
acute renal failureis_treatment_forNot AvailablePMC3227886
plasma cell leukemiais_treatment_forNot AvailablePMC6223128 , PMC9387011
plasma cell leukemiahas_therapeutic_effect_onNot AvailablePMC4044724
mantle cell lymphomais_treatment_forNot AvailablePMC12735847 , PMC4725701 , PMC4725701 , PMC5436301 , PMC7705367
POEMS syndromeis_treatment_forNot AvailablePMC6067145
lymphopeniaassociated_withNot AvailablePMC7873303
pancreatitisassociated_withNot AvailablePMC9323819
glomerulosclerosishas_therapeutic_effect_onNot AvailablePMC6355407
plasmablastic lymphomais_treatment_forNot AvailablePMC5372231
lymphoplasmacytic lymphomais_treatment_forNot AvailablePMC9323819
Exposure Sources
Source IDSourceSectorReference
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Proteasome subunit beta type-5 structureClick to view 3D structureProteasome subunit beta type-5P28074HumansPredicted (SEA)1.01204
Lon protease homolog, mitochondrial structureClick to view 3D structureLon protease homolog, mitochondrialP36776HumansPredicted (SEA)0.0778492
Proteasome subunit beta type-8 structureClick to view 3D structureProteasome subunit beta type-8P28062HumansPredicted (SEA)1.08989
Proteasome subunit beta type-1 structureClick to view 3D structureProteasome subunit beta type-1P20618HumansPredicted (SEA)0.467095
Proteasome subunit beta type-9 structureClick to view 3D structureProteasome subunit beta type-9P28065HumansPredicted (SEA)0.856341
Proteasome subunit beta type-2 structureClick to view 3D structureProteasome subunit beta type-2P49721HumansPredicted (SEA)1.86838
Proteasome subunit beta type-10 structureClick to view 3D structureProteasome subunit beta type-10P40306HumansPredicted (SEA)0.934191
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)22.5763
Histone deacetylase 2 structureClick to view 3D structureHistone deacetylase 2Q92769HumansPredicted (SEA)11.5217
Histone deacetylase 3 structureClick to view 3D structureHistone deacetylase 3O15379HumansPredicted (SEA)8.95266
Click to view 3D structureNACHT, LRR and PYD domains-containing protein 3Q8R4B8Mus musculusPredicted (SEA)0.155698
Chymase structureClick to view 3D structureChymaseP23946HumansPredicted (SEA)1.40129
Histone deacetylase 8 structureClick to view 3D structureHistone deacetylase 8Q9BY41HumansPredicted (SEA)13.5458
Neutrophil elastase structureClick to view 3D structureNeutrophil elastaseP08246HumansPredicted (SEA)7.55137
Proteasome subunit beta type-6 structureClick to view 3D structureProteasome subunit beta type-6P28072HumansPredicted (SEA)0.155698
Click to view 3D structureProteasome subunit beta type-8P28063Mus musculusPredicted (SEA)0.778492
Cathepsin G structureClick to view 3D structureCathepsin GP08311HumansPredicted (SEA)8.87481
Click to view 3D structureChymotrypsinogen AP00766Bos taurusPredicted (SEA)0.622794
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)43.5956
Click to view 3D structureCytosol aminopeptidaseP00727Bos taurusPredicted (SEA)5.29375
Click to view 3D structureChymotrypsinogen BP17538HumansPredicted (SEA)1.32344
Click to view 3D structureCalpain-2 catalytic subunitQ27971Bos taurusPredicted (SEA)20.3186
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)47.5659
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)19.7737
Neutrophil collagenase structureClick to view 3D structureNeutrophil collagenaseP22894HumansPredicted (SEA)51.8476
Concentrations
Not Available
External Links
DrugBank IDDB00188
HMDB IDHMDB0014334
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDBO2
Wikipedia LinkBortezomib
Chemspider ID343402
ChEBI ID52717
PubChem Compound ID387447
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Voorhees PM, Dees EC, O'Neil B, Orlowski RZ: The proteasome as a target for cancer therapy. Clin Cancer Res. 2003 Dec 15;9(17):6316-25.
2. Adams J, Kauffman M: Development of the proteasome inhibitor Velcade (Bortezomib). Cancer Invest. 2004;22(2):304-11.
3. Oakervee HE, Popat R, Curry N, Smith P, Morris C, Drake M, Agrawal S, Stec J, Schenkein D, Esseltine DL, Cavenagh JD: PAD combination therapy (PS-341/bortezomib, doxorubicin and dexamethasone) for previously untreated patients with multiple myeloma. Br J Haematol. 2005 Jun;129(6):755-62.
4. Bonvini P, Zorzi E, Basso G, Rosolen A: Bortezomib-mediated 26S proteasome inhibition causes cell-cycle arrest and induces apoptosis in CD-30+ anaplastic large cell lymphoma. Leukemia. 2007 Apr;21(4):838-42. Epub 2007 Feb 1.
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18484921
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18980173
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21504411
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21865767