Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0221)
Drug Name
Bortezomib
Synonyms
Bortezomib; Bortezomib (PS-341); Bortezomib (Velcade); LDP-341; MLN-341; PS-341; Peptide boronate; Ps 341; Velcade; 179324-69-7; 69G8BD63PP; CHEMBL325041; DPBA; N-[(1R)-1-(DIHYDROXYBORYL)-3-METHYLBUTYL]-N-(PYRAZIN-2-YLCARBONYL)-L-PHENYLALANINAMIDE; UNII-69G8BD63PP; [(1R)-3-Methyl-1-[[(2S)-1-oxo-3-phenyl-2-[(pyrazinylcarbonyl)amino]propyl]amino]butyl]boronic acid; [(1R)-3-methyl-1-[[(2S)-3-phenyl-2-(pyrazine-2-carbonylamino)propanoyl]amino]butyl]boronic acid
Indication Breast cancer [ICD11: 2C60] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 384.2 Topological Polar Surface Area 124
Heavy Atom Count 28 Rotatable Bond Count 9
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
387447
PubChem SID
518755 ; 600019 ; 10276517 ; 11433362 ; 12015194 ; 14853748 ; 17137090 ; 17397304 ; 46508736 ; 50726119 ; 53787350 ; 56311715 ; 56311812 ; 56312401 ; 56313329 ; 56314055 ; 56314414 ; 56314469 ; 56314470 ; 57402302 ; 85096715 ; 87325438 ; 91611228 ; 99432365 ; 99443946 ; 103338073 ; 103963945 ; 104603020 ; 118048485 ; 118318599 ; 121360388 ; 124756934 ; 124950705 ; 125163741 ; 134340388 ; 135696579 ; 136023422 ; 136342479 ; 136367512 ; 136920302 ; 137030372 ; 141858114 ; 143497187 ; 144206183 ; 144206225 ; 152049125 ; 152239004 ; 152344341 ; 160829216 ; 160968549
ChEBI ID
ChEBI:52717
CAS Number
179324-69-7
TTD Drug ID
D0SH3I
Formula
C19H25BN4O4
Canonical SMILES
B(C(CC(C)C)NC(=O)C(CC1=CC=CC=C1)NC(=O)C2=NC=CN=C2)(O)O
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
InChIKey
GXJABQQUPOEUTA-RDJZCZTQSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Bortezomib metabolite M1 DM001431
71607433
Oxidation - Oxidative Deboronation 1 [4]
Bortezomib metabolite M2 DM001434
71607434
Oxidation - Oxidation; Deboronation 1 [4]
Bortezomib metabolite M23 DM001444 N. A. Unclear 1 [4]
Bortezomib metabolite M24 DM001445 N. A. Unclear 1 [4]
Bortezomib metabolite M34 DM001443
71607432
Unclear 1 [4]
Bortezomib metabolite M25 DM001438 N. A. Oxidation - Hydoxylation 2 [4]
Bortezomib metabolite M26 DM001437
165411877
Oxidation - Hydoxylation 2 [4]
Bortezomib metabolite M27 DM001441 N. A. Oxidation - Hydoxylation 2 [4]
Bortezomib metabolite M28 DM001440 N. A. Oxidation - Hydoxylation 2 [4]
Bortezomib metabolite M3 DM001432
67121778
Hydrolysis - Hydrolysis 2 [4]
Bortezomib metabolite M5 DM001439
156028078
Oxidation - Hydoxylation 2 [4]
Bortezomib metabolite M6 DM001442 N. A. Oxidation - Hydoxylation 2 [4]
Bortezomib metabolite M8 DM001435
156028138
Oxidation - Hydoxylation 2 [4]
Bortezomib metabolite M33 DM001436 N. A. Unclear 3 [4]
Bortezomib metabolite M4 DM001433
15042559
Unclear 3 [4]
⏷ Show the Full List of 15  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000408 Bortezomib Bortezomib metabolite M1 Oxidation - Oxidative Deboronation CYP2C19 ... [4]
MR000409 Bortezomib Bortezomib metabolite M2 Oxidation - Oxidation; Deboronation CYP2C9 ... [4]
MR000410 Bortezomib Bortezomib metabolite M34 Unclear Unclear [4]
MR000411 Bortezomib Bortezomib metabolite M23 Unclear CYP3A4 ... [4]
MR000412 Bortezomib Bortezomib metabolite M24 Unclear CYP3A4 ... [4]
MR000397 Bortezomib metabolite M1 Bortezomib metabolite M3 Hydrolysis - Hydrolysis Unclear [4]
MR000398 Bortezomib metabolite M1 Bortezomib metabolite M26 Oxidation - Hydoxylation Unclear [4]
MR000399 Bortezomib metabolite M1 Bortezomib metabolite M25 Oxidation - Hydoxylation Unclear [4]
MR000400 Bortezomib metabolite M1 Bortezomib metabolite M5 Oxidation - Hydoxylation Unclear [4]
MR000402 Bortezomib metabolite M2 Bortezomib metabolite M3 Hydrolysis - Hydrolysis Unclear [4]
MR000403 Bortezomib metabolite M2 Bortezomib metabolite M8 Oxidation - Hydoxylation CYP3A4 [4]
MR000404 Bortezomib metabolite M2 Bortezomib metabolite M28 Oxidation - Hydoxylation Unclear [4]
MR000405 Bortezomib metabolite M2 Bortezomib metabolite M27 Oxidation - Hydoxylation Unclear [4]
MR000406 Bortezomib metabolite M2 Bortezomib metabolite M6 Oxidation - Hydoxylation Unclear [4]
MR000401 Bortezomib metabolite M3 Bortezomib metabolite M4 Unclear Unclear [4]
MR000407 Bortezomib metabolite M8 Bortezomib metabolite M33 Unclear Unclear [4]
⏷ Show the Full List of 16 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
References
1 Bortezomib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Human metabolism of the proteasome inhibitor bortezomib: identification of circulating metabolites. Drug Metab Dispos. 2005 Jun;33(6):771-7.
3 Investigation of drug-drug interaction potential of bortezomib in vivo in female Sprague-Dawley rats and in vitro in human liver microsomes. Drug Metab Dispos. 2006 Apr;34(4):702-8.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
5 Relative contributions of the five major human cytochromes P450, 1A2, 2C9, 2C19, 2D6, and 3A4, to the hepatic metabolism of the proteasome inhibitor bortezomib. Drug Metab Dispos. 2005 Nov;33(11):1723-8.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.