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Marizomib

Marizomib

  • CAT Number: R036162
  • CAS Number: 437742-34-2
  • Molecular Formula: C15H20ClNO4
  • Molecular Weight: 313.778
  • Purity: ≥95%
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Marizomib (CAS 437742-34-2), also known as ML 858, NPI-0052 and Salinosporamide A, is a potent and selective 20S proteasome inhibitor from natural origin. Marizomib irreversibly inhibits proteasome to overcome compensatory hyperactivation in multiple myeloma and solid tumour patients. Marizomib activity as a single agent in malignant gliomas: ability to cross the blood-brain barrier. Marizomib exhibits prolonged inhibition, attenuated efflux, and greater cytotoxicity than its reversible analogs.

Catalog Number R036162
CAS Number 437742-34-2
Molecular Formula

C15H20ClNO4

Purity 95%
Target Proteasome
Solubility Soluble in DMSO
Storage Store at -20°C
IUPAC Name (1S,2R,5R)-2-(2-chloroethyl)-5-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-1-methyl-7-oxa-4-azabicyclo[3.2.0]heptane-3,6-dione
InChI InChI=1S/C15H20ClNO4/c1-14-10(7-8-16)12(19)17-15(14,13(20)21-14)11(18)9-5-3-2-4-6-9/h3,5,9-11,18H,2,4,6-8H2,1H3,(H,17,19)/t9-,10+,11+,14+,15+/m1/s1
InChIKey NGWSFRIPKNWYAO-SHTIJGAHSA-N
SMILES CC12C(C(=O)NC1(C(=O)O2)C(C3CCCC=C3)O)CCCl
Reference

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1:Marizomib for central nervous system-multiple myeloma. Badros A, Singh Z, Dhakal B, Kwok Y, MacLaren A, Richardson P, Trikha M, Hari P.Br J Haematol. 2017 Apr;177(2):221-225. doi: 10.1111/bjh.14498. PMID: 28387460<br />
2:Marizomib irreversibly inhibits proteasome to overcome compensatory hyperactivation in multiple myeloma and solid tumour patients. Levin N, Spencer A, Harrison SJ, Chauhan D, Burrows FJ, Anderson KC, Reich SD, Richardson PG, Trikha M.Br J Haematol. 2016 Sep;174(5):711-20. doi: 10.1111/bjh.14113. Epub 2016 May 9. PMID: 27161872 Free PMC Article<br />
3:Phase I Clinical Trial of Marizomib (NPI-0052) in Patients with Advanced Malignancies Including Multiple Myeloma: Study NPI-0052-102 Final Results. Harrison SJ, Mainwaring P, Price T, Millward MJ, Padrik P, Underhill CR, Cannell PK, Reich SD, Trikha M, Spencer A.Clin Cancer Res. 2016 Sep 15;22(18):4559-66. doi: 10.1158/1078-0432.CCR-15-2616. Epub 2016 Apr 26. PMID: 27117181<br />
4:Phase 1 study of marizomib in relapsed or relapsed and refractory multiple myeloma: NPI-0052-101 Part 1. Richardson PG, Zimmerman TM, Hofmeister CC, Talpaz M, Chanan-Khan AA, Kaufman JL, Laubach JP, Chauhan D, Jakubowiak AJ, Reich S, Trikha M, Anderson KC.Blood. 2016 Jun 2;127(22):2693-700. doi: 10.1182/blood-2015-12-686378. Epub 2016 Mar 23. PMID: 27009059 Free PMC Article<br />
5:Induction of cell death by the novel proteasome inhibitor marizomib in glioblastoma in vitro and in vivo. Manton CA, Johnson B, Singh M, Bailey CP, Bouchier-Hayes L, Chandra J.Sci Rep. 2016 Jan 25;6:18953. doi: 10.1038/srep18953. PMID: 26804704 Free PMC Article<br />
6:Marizomib activity as a single agent in malignant gliomas: ability to cross the blood-brain barrier. Di K, Lloyd GK, Abraham V, MacLaren A, Burrows FJ, Desjardins A, Trikha M, Bota DA.Neuro Oncol. 2016 Jun;18(6):840-8. doi: 10.1093/neuonc/nov299. Epub 2015 Dec 17. PMID: 26681765<br />
7:Synergistic anti-myeloma activity of the proteasome inhibitor marizomib and the IMiD immunomodulatory drug pomalidomide. Das DS, Ray A, Song Y, Richardson P, Trikha M, Chauhan D, Anderson KC.Br J Haematol. 2015 Dec;171(5):798-812. doi: 10.1111/bjh.13780. Epub 2015 Oct 12. PMID: 26456076 Free PMC Article<br />
8:Efficacy of panobinostat and marizomib in acute myeloid leukemia and bortezomib-resistant models. Corrales-Medina FF, Manton CA, Orlowski RZ, Chandra J.Leuk Res. 2015 Mar;39(3):371-9. doi: 10.1016/j.leukres.2014.12.014. Epub 2015 Jan 3. PMID: 25612941 Free PMC Article<br />
9:Marizomib, a potent second generation proteasome inhibitor from natural origin. Ma L, Diao A.Anticancer Agents Med Chem. 2015;15(3):298-306. Review. PMID: 25403165<br />
10:Antileukemic activity and mechanism of drug resistance to the marine Salinispora tropica proteasome inhibitor salinosporamide A (Marizomib). Niewerth D, Jansen G, Riethoff LF, van Meerloo J, Kale AJ, Moore BS, Assaraf YG, Anderl JL, Zweegman S, Kaspers GJ, Cloos J.Mol Pharmacol. 2014 Jul;86(1):12-9. doi: 10.1124/mol.114.092114. Epub 2014 Apr 15. PMID: 24737138 Free PMC Article

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