Bortezomib
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MedKoo CAT#: 100100

CAS#: 179324-69-7

Description: Bortezomib is a dipeptide boronic acid analogue with antineoplastic activity. Bortezomib reversibly inhibits the 26S proteasome, a large protease complex that degrades ubiquinated proteins. By blocking the targeted proteolysis normally performed by the proteasome, bortezomib disrupts various cell signaling pathways, leading to cell cycle arrest, apoptosis, and inhibition of angiogenesis. Specifically, the agent inhibits nuclear factor (NF)-kappaB, a protein that is constitutively activated in some cancers, thereby interfering with NF-kappaB-mediated cell survival, tumor growth, and angiogenesis. In vivo, bortezomib delays tumor growth and enhances the cytotoxic effects of radiation and chemotherapy.


Price and Availability

Size
Price

100mg
USD 150
1g
USD 750
10g
USD 2950
Size
Price

200mg
USD 250
2g
USD 1250
50g
USD 6950
Size
Price

500mg
USD 450
5g
USD 1950
200g
USD 21450

Bortezomib, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100100
Name: Bortezomib
CAS#: 179324-69-7
Chemical Formula: C19H25BN4O4
Exact Mass: 384.19689
Molecular Weight: 384.24
Elemental Analysis: C, 59.39; H, 6.56; B, 2.81; N, 14.58; O, 16.66


Synonym: PS-341; PS 341; PS341; LDP 341; LDP-341 ;LDP341; MLN341; MLN-341; MLN 341. US brand name: VELCADE.

IUPAC/Chemical Name: ((R)-3-methyl-1-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butyl)boronic acid

InChi Key: GXJABQQUPOEUTA-RDJZCZTQSA-N

InChi Code: 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

SMILES Code: CC(C)C[C@@H](B(O)O)NC([C@@H](NC(C1=NC=CN=C1)=O)CC2=CC=CC=C2)=O


Technical Data

Appearance:
white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Bortezomib is "indicated" (recommended) for single-agent use in the treatment of patients with multiple myeloma who have received at least two prior therapies and are progressing on their most recent therapy. Clinical investigations have been completed or are under way to evaluate the safety and efficacy of bortezomib alone or in combination with chemotherapy in multiple myeloma, both at relapse and presentation, as well as in other cancer types.
 
Bortezomib (VELCADE®, formerly PS-341) was approved for the treatment of patients with relapsed or refractory multiple myeloma in May 2003 by the US Food and Drug Administration and in April 2004 by the Committee for Proprietary Medicinal Products of the European Union. In December 2006 the FDA approved Bortezomib for treatment of mantle cell lymphoma.
 
Bortezomib binds to the proteasome and does so "reversibly" (this is a chemical term that means that the bortezomib molecule can come free under different micro-cellular chemical conditions.) Normal healthy (non-cancer) cells are not as prone to damage from this binding after the Bortezomib comes off, as cancer cells are. Malignant cells suffer a breakdown even after inhibition of the proteasome for a short time.
 
 
According to http://en.wikipedia.org/wiki/Bortezomib, Bortezomib was originally synthesized in 1995 (MG-341) at a company called Myogenics, which soon changed its name to ProScript. After promising preclinical results, the drug (PS-341) was tested in a small Phase I clinical trial on patients with multiple myeloma cancer. ProScript ran out of money and was bought by Leukosite in May 1999. Leukosite in turn was bought by Millennium Pharmaceuticals in October 1999. At this point in time, the project had low priority amongst other projects at the company. This changed significantly when one of the first volunteers to receive the drug in the clinical trial achieved a complete response and was still alive four years later. At the time this was a remarkable result. Later clinical experimentation indicates the possibility of a complete response in 15% of patients in a similar condition, when treated with bortezomib. In May 2003, seven years after the initial synthesis, bortezomib (Velcade) was approved in the United States by the Food and Drug Administration (FDA) for use in multiple myeloma, based on the results from the SUMMIT Phase II trial.
According to http://en.wikipedia.org/wiki/Bortezomib, Bortezomib was originally synthesized in 1995 (MG-341) at a company called Myogenics, which soon changed its name to ProScript. After promising preclinical results, the drug (PS-341) was tested in a small Phase I clinical trial on patients with multiple myeloma cancer. ProScript ran out of money and was bought by Leukosite in May 1999. Leukosite in turn was bought by Millennium Pharmaceuticals in October 1999. At this point in time, the project had low priority amongst other projects at the company. This changed significantly when one of the first volunteers to receive the drug in the clinical trial achieved a complete response and was still alive four years later. At the time this was a remarkable result. Later clinical experimentation indicates the possibility of a complete response in 15% of patients in a similar condition, when treated with bortezomib. In May 2003, seven years after the initial synthesis, bortezomib (Velcade) was approved in the United States by the Food and Drug Administration (FDA) for use in multiple myeloma, based on the results from the SUMMIT Phase II trial.


References

1: Bockorny M, Chakravarty S, Schulman P, Bockorny B, Bona R. Severe heart failure after bortezomib treatment in a patient with multiple myeloma: a case report and review of the literature. Acta Haematol. 2012;128(4):244-7. doi: 10.1159/000340050. Epub 2012 Sep 4. Review. PubMed PMID: 22964848.

2: Broyl A, Jongen JL, Sonneveld P. General aspects and mechanisms of peripheral neuropathy associated with bortezomib in patients with newly diagnosed multiple myeloma. Semin Hematol. 2012 Jul;49(3):249-57. doi: 10.1053/j.seminhematol.2012.04.001. Review. PubMed PMID: 22726548.

3: Kapoor P, Ramakrishnan V, Rajkumar SV. Bortezomib combination therapy in multiple myeloma. Semin Hematol. 2012 Jul;49(3):228-42. doi: 10.1053/j.seminhematol.2012.04.010. Review. PubMed PMID: 22726546.

4: Sekiguchi Y, Shirane S, Imai H, Sugimoto K, Wakabayashi M, Sawada T, Chigira N, Ichikawa K, Komatsu N, Noguchi M. Response to low-dose bortezomib in plasma cell leukemia patients with malignant pleural effusion and ascites: a case report and a review of the literature. Intern Med. 2012;51(11):1393-8. Epub 2012 Jun 1. Review. PubMed PMID: 22687849.

5: Barosi G, Merlini G, Billio A, Boccadoro M, Corradini P, Marchetti M, Massaia M, Tosi P, Palumbo A, Cavo M, Tura S. SIE, SIES, GITMO evidence-based guidelines on novel agents (thalidomide, bortezomib, and lenalidomide) in the treatment of multiple myeloma. Ann Hematol. 2012 Jun;91(6):875-88. doi: 10.1007/s00277-012-1445-y. Epub 2012 Apr 4. Review. PubMed PMID: 22476884.

6: Sureshkumar KK, Hussain SM, Marcus RJ, Ko TY, Khan AS, Tom K, Vivas CA, Parris G, Jasnosz KM, Thai NL. Proteasome inhibition with bortezomib: an effective therapy for severe antibody mediated rejection after renal transplantation. Clin Nephrol. 2012 Mar;77(3):246-53. Review. PubMed PMID: 22377258.

7: Zangari M, Terpos E, Zhan F, Tricot G. Impact of bortezomib on bone health in myeloma: a review of current evidence. Cancer Treat Rev. 2012 Dec;38(8):968-80. doi: 10.1016/j.ctrv.2011.12.007. Epub 2012 Jan 9. Review. PubMed PMID: 22226939.

8: Mujtaba T, Dou QP. Advances in the understanding of mechanisms and therapeutic use of bortezomib. Discov Med. 2011 Dec;12(67):471-80. Review. PubMed PMID: 22204764.

9: Picot J, Cooper K, Bryant J, Clegg AJ. The clinical effectiveness and cost-effectiveness of bortezomib and thalidomide in combination regimens with an alkylating agent and a corticosteroid for the first-line treatment of multiple myeloma: a systematic review and economic evaluation. Health Technol Assess. 2011 Dec;15(41):1-204. doi: 10.3310/hta15410. Review. PubMed PMID: 22146234.

10: Delforge M. Bortezomib for previously untreated multiple myeloma. Expert Opin Pharmacother. 2011 Nov;12(16):2553-64. doi: 10.1517/14656566.2011.622266. Epub 2011 Sep 23. Review. PubMed PMID: 21942881.