MedKoo Cat#: 565251 | Name: Bortezomib-pinanediol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bortezomib-pinanediol is a prodrug of Bortezomib, as well as a proteasome inhibitor. 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.

Chemical Structure

Bortezomib-pinanediol
Bortezomib-pinanediol
CAS#205393-22-2

Theoretical Analysis

MedKoo Cat#: 565251

Name: Bortezomib-pinanediol

CAS#: 205393-22-2

Chemical Formula: C29H39BN4O4

Exact Mass: 518.3064

Molecular Weight: 518.47

Elemental Analysis: C, 67.18; H, 7.58; B, 2.09; N, 10.81; O, 12.34

Price and Availability

Size Price Availability Quantity
250mg USD 350.00 2 Weeks
1g USD 750.00 2 Weeks
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Related CAS #
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Synonym
Bortezomib-pinanediol
IUPAC/Chemical Name
N-((S)-1-(((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)amino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide
InChi Key
HZCSTPSWJFWZHP-GQABWHEGSA-N
InChi Code
InChI=1S/C29H39BN4O4/c1-18(2)13-25(30-37-24-16-20-15-23(28(20,3)4)29(24,5)38-30)34-26(35)21(14-19-9-7-6-8-10-19)33-27(36)22-17-31-11-12-32-22/h6-12,17-18,20-21,23-25H,13-16H2,1-5H3,(H,33,36)(H,34,35)/t20-,21-,23-,24+,25-,29-/m0/s1
SMILES Code
O=C(N[C@@H](CC1=CC=CC=C1)C(N[C@@H](CC(C)C)B2O[C@]([C@@H]3C(C)(C)[C@@H](C3)C4)(C)[C@@H]4O2)=O)C5=NC=CN=C5
Appearance
Solid powder
Purity
>97% (or refer to the Certificate of Analysis)
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
Shelf Life
>3 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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 518.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Cengiz Seval G, Beksac M. The safety of bortezomib for the treatment of multiple myeloma. Expert Opin Drug Saf. 2018 Sep;17(9):953-962. doi: 10.1080/14740338.2018.1513487. Epub 2018 Aug 30. PMID: 30118610. 2: Yamamoto S, Egashira N. Pathological Mechanisms of Bortezomib-Induced Peripheral Neuropathy. Int J Mol Sci. 2021 Jan 17;22(2):888. doi: 10.3390/ijms22020888. PMID: 33477371; PMCID: PMC7830235. 3: Tan CRC, Abdul-Majeed S, Cael B, Barta SK. Clinical Pharmacokinetics and Pharmacodynamics of Bortezomib. Clin Pharmacokinet. 2019 Feb;58(2):157-168. doi: 10.1007/s40262-018-0679-9. PMID: 29802543. 4: Scott K, Hayden PJ, Will A, Wheatley K, Coyne I. Bortezomib for the treatment of multiple myeloma. Cochrane Database Syst Rev. 2016 Apr 20;4:CD010816. doi: 10.1002/14651858.CD010816.pub2. PMID: 27096326. 5: Mateos MV, Sonneveld P, Hungria V, Nooka AK, Estell JA, Barreto W, Corradini P, Min CK, Medvedova E, Weisel K, Chiu C, Schecter JM, Amin H, Qin X, Ukropec J, Kobos R, Spencer A. Daratumumab, Bortezomib, and Dexamethasone Versus Bortezomib and Dexamethasone in Patients With Previously Treated Multiple Myeloma: Three- year Follow-up of CASTOR. Clin Lymphoma Myeloma Leuk. 2020 Aug;20(8):509-518. doi: 10.1016/j.clml.2019.09.623. Epub 2019 Oct 9. PMID: 32482541. 6: Chen M, Juengpanich S, Li S, Topatana W, Lu Z, Zheng Q, Cao J, Hu J, Chan E, Hou L, Chen J, Chen F, Liu Y, Jiansirisomboon S, Gu Z, Tongpeng S, Cai X. Bortezomib-Encapsulated Dual Responsive Copolymeric Nanoparticles for Gallbladder Cancer Targeted Therapy. Adv Sci (Weinh). 2022 Mar;9(7):e2103895. doi: 10.1002/advs.202103895. Epub 2022 Jan 23. PMID: 35068071; PMCID: PMC8895115. 7: Shah N, Meouchy J, Qazi Y. Bortezomib in kidney transplantation. Curr Opin Organ Transplant. 2015 Dec;20(6):652-6. doi: 10.1097/MOT.0000000000000252. PMID: 26536428. 8: Mahmoudian M, Valizadeh H, Löbenberg R, Zakeri-Milani P. Bortezomib-loaded lipidic-nano drug delivery systems; formulation, therapeutic efficacy, and pharmacokinetics. J Microencapsul. 2021 May;38(3):192-202. doi: 10.1080/02652048.2021.1876175. Epub 2021 Feb 2. PMID: 33530812. 9: Xia J, He Y, Meng B, Chen S, Zhang J, Wu X, Zhu Y, Shen Y, Feng X, Guan Y, Kuang C, Guo J, Lei Q, Wu Y, An G, Li G, Qiu L, Zhan F, Zhou W. NEK2 induces autophagy-mediated bortezomib resistance by stabilizing Beclin-1 in multiple myeloma. Mol Oncol. 2020 Apr;14(4):763-778. doi: 10.1002/1878-0261.12641. Epub 2020 Jan 29. PMID: 31955515; PMCID: PMC7138399. 10: Syed YY. Selinexor-Bortezomib-Dexamethasone: A Review in Previously Treated Multiple Myeloma. Target Oncol. 2023 Mar;18(2):303-310. doi: 10.1007/s11523-022-00945-3. Epub 2023 Jan 9. PMID: 36622630. 11: Vora PA, Patel R, Dharamsi A. Bortezomib - First Therapeutic Proteasome Inhibitor for Cancer Therapy: A Review of Patent Literature. Recent Pat Anticancer Drug Discov. 2020;15(2):113-131. doi: 10.2174/1574892815666200401113805. PMID: 32234004. 12: Robak T. Bortezomib in the treatment of mantle cell lymphoma. Future Oncol. 2015;11(20):2807-18. doi: 10.2217/fon.15.191. Epub 2015 Sep 8. PMID: 26347482. 13: Liu J, Zhao R, Jiang X, Li Z, Zhang B. Progress on the Application of Bortezomib and Bortezomib-Based Nanoformulations. Biomolecules. 2021 Dec 30;12(1):51. doi: 10.3390/biom12010051. PMID: 35053199; PMCID: PMC8773474. 14: Guerrero-Garcia TA, Mogollon RJ, Castillo JJ. Bortezomib in plasmablastic lymphoma: A glimpse of hope for a hard-to-treat disease. Leuk Res. 2017 Nov;62:12-16. doi: 10.1016/j.leukres.2017.09.020. Epub 2017 Sep 27. PMID: 28963907. 15: Robak P, Robak T. Bortezomib for the Treatment of Hematologic Malignancies: 15 Years Later. Drugs R D. 2019 Jun;19(2):73-92. doi: 10.1007/s40268-019-0269-9. PMID: 30993606; PMCID: PMC6544598. 16: Mutluay D, Tenekeci GY, Monsef YA. Bortezomib-Induced Ovarian Toxicity in Mice. Toxicol Pathol. 2022 Apr;50(3):381-389. doi: 10.1177/01926233221083527. Epub 2022 Mar 30. PMID: 35352576. 17: de Arriba de la Fuente F, Durán MS, Álvarez MÁ, Sanromán IL, Dios AM, Ríos Tamayo R, García R, González MS, Prieto E, Bárez A, Escalante F, Tejedor A, Ballesteros M, Cabañas V, Capote FJ, Couto C, Garzón S, González-Pardo M, Mateos Manteca MV. Subcutaneous bortezomib in newly diagnosed patients with multiple myeloma nontransplant eligible: Retrospective evaluation. Semin Hematol. 2018 Oct;55(4):189-196. doi: 10.1053/j.seminhematol.2017.09.002. Epub 2017 Oct 13. PMID: 30502846. 18: Eskazan AE. Bortezomib therapy in patients with relapsed/refractory acquired thrombotic thrombocytopenic purpura. Ann Hematol. 2016 Oct;95(11):1751-6. doi: 10.1007/s00277-016-2804-x. Epub 2016 Sep 3. PMID: 27590601. 19: Migkou M, Gavriatopoulou M, Terpos E, Dimopoulos MA. Optimizing therapy in bortezomib-exposed patients with multiple myeloma. Expert Rev Hematol. 2018 Jun;11(6):463-469. doi: 10.1080/17474086.2018.1479637. Epub 2018 May 28. PMID: 29788798. 20: Parlakpinar H, Gunata M. Transplantation and immunosuppression: a review of novel transplant-related immunosuppressant drugs. Immunopharmacol Immunotoxicol. 2021 Dec;43(6):651-665. doi: 10.1080/08923973.2021.1966033. Epub 2021 Aug 20. PMID: 34415233.