BO2

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

Created:	2006-01-06
Last modified:	2024-09-27

Find Related PDB Entry
2 entries where BO2 is found as a standalone ligand31 entries where BO2 is covalently linked to polymer or other heterogen groups

Help Find related ligands:
Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Help

Find related ligands:

Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Chemical Details
Formal Charge	0
Atom Count	53
Chiral Atom Count	2
Bond Count	54
Aromatic Bond Count	12

Toggle Hydrogen Toggle Labels

Chemical Component Summary
Name	N-[(1R)-1-(DIHYDROXYBORYL)-3-METHYLBUTYL]-N-(PYRAZIN-2-YLCARBONYL)-L-PHENYLALANINAMIDE
Synonyms	BORTEZOMIB
Systematic Name (OpenEye OEToolkits)	[(1R)-3-methyl-1-[[(2S)-3-phenyl-2-(pyrazin-2-ylcarbonylamino)propanoyl]amino]butyl]boronic acid
Formula	C₁₉ H₂₅ B N₄ O₄
Molecular Weight	384.237
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(NC(C(=O)NC(B(O)O)CC(C)C)Cc1ccccc1)c2nccnc2
SMILES	CACTVS	3.341	CC(C)C[CH](NC(=O)[CH](Cc1ccccc1)NC(=O)c2cnccn2)B(O)O
SMILES	OpenEye OEToolkits	1.5.0	B(C(CC(C)C)NC(=O)C(Cc1ccccc1)NC(=O)c2cnccn2)(O)O
Canonical SMILES	CACTVS	3.341	CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)c2cnccn2)B(O)O
Canonical SMILES	OpenEye OEToolkits	1.5.0	B([C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)NC(=O)c2cnccn2)(O)O
InChI	InChI	1.03	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	InChI	1.03	GXJABQQUPOEUTA-RDJZCZTQSA-N

Drug Info: DrugBank

DrugBank ID	DB00188
Name	Bortezomib
Groups	approved investigational
Description	Bortezomib 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	Bortezomib [(1R)-3-methyl-1-({(2S)-3-phenyl-2-[(pyrazin-2-ylcarbonyl)amino]propanoyl}amino)butyl]boronic acid N-[(1R)-1-(DIHYDROXYBORYL)-3-methylbutyl]-N-(pyrazin-2-ylcarbonyl)-L-phenylalaninamide
Brand Names	Bortezomib Accord Bortezomib Bortezomib Fresenius Kabi Bortezomib Hospira Bortezomib Sun Velcade
Indication	Bortezomib is indicated for the treatment of adults with multiple myeloma or mantle cell lymphoma.[L44341]
Categories	Acids Acids, Noncarboxylic Antineoplastic Agents Antineoplastic and Immunomodulating Agents Boron Compounds Boronic Acids Cardiotoxic antineoplastic agents Cytochrome P-450 CYP1A2 Inhibitors Cytochrome P-450 CYP1A2 Inhibitors (moderate) Cytochrome P-450 CYP1A2 Inhibitors (strength unknown) Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 Inhibitors (weak) Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C19 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2C9 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP2D6 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Hepatotoxic Agents Hypotensive Agents Immunosuppressive Agents Myelosuppressive Agents Narrow Therapeutic Index Drugs OATP1B3 inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Potential QTc-Prolonging Agents Proteasome Inhibitors Pyrazines QTc Prolonging Agents
ATC-Code	L01XG01
CAS number	179324-69-7

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Proteasome subunit beta type-5	MALASVLERPLPVNQRGFFGLGGRADLLDLGPGSLSDGLSLAAPGWGVPE...	unknown	inhibitor
Proteasome subunit beta type-1	MLSSTAMYSAPGRDLGMEPHRAAGPLQLRFSPYVFNGGTILAIAGEDFAI...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	substrate,inhibitor
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate,inhibitor
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate,inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate
Solute carrier organic anion transporter family member 1B3	MDQHQHLNKTAESASSEKKKTRRCNGFKMFLAALSFSYIAKALGGIIMKI...	unknown	inhibitor
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