Bortezomib

Title: Bortezomib
CAS Registry Number: 179324-69-7
CAS Name: [(1R)-3-Methyl-1-[[(2S)-1-oxo-3-phenyl-2-[(pyrazinylcarbonyl)amino]propyl]amino]butyl]boronic acid
Additional Names: N-(2-pyrazine)carbonyl-L-phenylalanine-L-leucine boronic acid
Manufacturers' Codes: MG-341; PS-341
Trademarks: Velcade (Millenium)
Molecular Formula: C19H25BN4O4
Molecular Weight: 384.24
Percent Composition: C 59.39%, H 6.56%, B 2.81%, N 14.58%, O 16.66%
Literature References: Dipeptide boronic acid proteasome inhibitor. Prepn: J. Adams et al., WO 9613266; eidem, US 5780454 (1996, 1998 both to ProScript); idem et al., Bioorg. Med. Chem. Lett. 8, 333 (1998). Pharmacology and cytotoxic activity: idem et al., Cancer Res. 59, 2615 (1999). Crystal structure in complex with the yeast 20S proteasome: M. Groll et al., Structure 14, 451 (2006). Mechanism of action study: J. Codony-Servat et al., Mol. Cancer Ther. 5, 665 (2006). Clinical trial in refractory myeloma: P. G. Richardson et al., N. Engl. J. Med. 348, 2609 (2003). Review of clinical development: idem et al., Annu. Rev. Med. 57, 33-47 (2006).
Properties: Soly in water: 3.3-3.8 mg/ml (pH 2-6.5).
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic.
Boscalid Bosentan Bostrycoidin Bottromycin Botulin Toxins

Bortezomib
Bortezomib.svg
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Systematic (IUPAC) name
[(1R)-3-methyl-1-({(2S)-3-phenyl-2-[(pyrazin-2-ylcarbonyl)amino]propanoyl}amino)butyl]boronic acid
Clinical data
Trade names Velcade
AHFS/Drugs.com monograph
MedlinePlus a607007
Licence data EMA:Link, US FDA:link
Pregnancy cat. C (AU) D (US)
Legal status Prescription only
Routes Intravenous
Pharmacokinetic data
Protein binding 83%
Metabolism Hepatic, CYP extensively involved
Half-life 9 to 15 hours
Identifiers
CAS number 179324-69-7 YesY
ATC code L01XX32
PubChem CID 387447
DrugBank DB00188
ChemSpider 343402 YesY
UNII 69G8BD63PP YesY
ChEMBL CHEMBL325041 YesY
Chemical data
Formula C19H25BN4O4 
Mol. mass 384.237 g/mol
 YesY (what is this?)  (verify)

Bortezomib (BAN, INN and USAN. Originally codenamed PS-341; marketed as Velcade by Millennium Pharmaceuticals and Cytomib by Venus Remedies) is the first therapeutic proteasome inhibitor to be tested in humans. It is approved in the U.S. for treating relapsed multiple myeloma[1] and mantle cell lymphoma. In multiple myeloma, complete clinical responses have been obtained in patients with otherwise refractory or rapidly advancing disease.