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MedKoo Cat#: 529911 | Name: Zalypsis

Description:

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

Zalypsis, also known as PM-10450, is transcription factor inhibitor potentially for the treatment of lymphoma, and cervical carcinoma.

Chemical Structure

Zalypsis
Zalypsis
CAS#308359-57-1

Theoretical Analysis

MedKoo Cat#: 529911

Name: Zalypsis

CAS#: 308359-57-1

Chemical Formula: C37H38F3N3O8

Exact Mass: 709.2600

Molecular Weight: 709.72

Elemental Analysis: C, 62.62; H, 5.40; F, 8.03; N, 5.92; O, 18.03

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
PM-00104; PM-10450; PM00104; PM10450; PM 00104; PM 10450
IUPAC/Chemical Name
2-Propenamide, N-(((6aS,7R,13S,14S,16R)-5-(acetyloxy)-6,6a,7,13,14,16-hexahydro-8,14-dihydroxy-9-methoxy-4,10,17-trimethyl-7,13-imino-12H-1,3-dioxolo(7,8)isoquino(3,2-b)(3)benzazocin-16-yl)methyl)-3-(3-(trifluoromethyl)phenyl)-, (2E)-
InChi Key
VPAHZSUNBOYNQY-DLVGLDQCSA-N
InChi Code
InChI=1S/C37H38F3N3O8/c1-17-11-21-13-25-36(47)43-24(30(42(25)4)28(21)31(46)32(17)48-5)14-23-29(35-34(49-16-50-35)18(2)33(23)51-19(3)44)26(43)15-41-27(45)10-9-20-7-6-8-22(12-20)37(38,39)40/h6-12,24-26,30,36,46-47H,13-16H2,1-5H3,(H,41,45)/b10-9+/t24-,25-,26-,30-,36-/m0/s1
SMILES Code
O=C(NC[C@H]1C2=C(C(OC(C)=O)=C(C)C3=C2OCO3)C[C@@]4([H])[C@@](N5C)([H])C6=C(O)C(OC)=C(C)C=C6C[C@@]5([H])[C@H](O)N41)/C=C/C7=CC=CC(C(F)(F)F)=C7
Appearance
Solid powder
Purity
>98% (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
>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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 709.72 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: Moneo V, Serelde BG, Blanco-Aparicio C, Diaz-Uriarte R, Avilés P, Santamaría G, Tercero JC, Cuevas C, Carnero A. Levels of active tyrosine kinase receptor determine the tumor response to Zalypsis. BMC Cancer. 2014 Apr 23;14:281. doi: 10.1186/1471-2407-14-281. PubMed PMID: 24758355; PubMed Central PMCID: PMC4023704. 2: Colado E, Paíno T, Maiso P, Ocio EM, Chen X, Alvarez-Fernández S, Gutiérrez NC, Martín-Sánchez J, Flores-Montero J, San Segundo L, Garayoa M, Fernández-Lázaro D, Vidriales MB, Galmarini CM, Avilés P, Cuevas C, Pandiella A, San-Miguel JF. Zalypsis has in vitro activity in acute myeloid blasts and leukemic progenitor cells through the induction of a DNA damage response. Haematologica. 2011 May;96(5):687-95. doi: 10.3324/haematol.2010.036400. PubMed PMID: 21330323; PubMed Central PMCID: PMC3084915. 3: Romano M, Frapolli R, Zangarini M, Bello E, Porcu L, Galmarini CM, García-Fernández LF, Cuevas C, Allavena P, Erba E, D'Incalci M. Comparison of in vitro and in vivo biological effects of trabectedin, lurbinectedin (PM01183) and Zalypsis® (PM00104). Int J Cancer. 2013 Nov;133(9):2024-33. doi: 10.1002/ijc.28213. PubMed PMID: 23588839. 4: Leal JF, García-Hernández V, Moneo V, Domingo A, Bueren-Calabuig JA, Negri A, Gago F, Guillén-Navarro MJ, Avilés P, Cuevas C, García-Fernández LF, Galmarini CM. Molecular pharmacology and antitumor activity of Zalypsis in several human cancer cell lines. Biochem Pharmacol. 2009 Jul 15;78(2):162-70. doi: 10.1016/j.bcp.2009.04.003. PubMed PMID: 19427997. 5: Ocio EM, Maiso P, Chen X, Garayoa M, Alvarez-Fernández S, San-Segundo L, Vilanova D, López-Corral L, Montero JC, Hernández-Iglesias T, de Alava E, Galmarini C, Avilés P, Cuevas C, San-Miguel JF, Pandiella A. Zalypsis: a novel marine-derived compound with potent antimyeloma activity that reveals high sensitivity of malignant plasma cells to DNA double-strand breaks. Blood. 2009 Apr 16;113(16):3781-91. doi: 10.1182/blood-2008-09-177774. Erratum in: Blood. 2010 Jul 8;116(1):151. PubMed PMID: 19020308. 6: Petek BJ, Jones RL. PM00104 (Zalypsis®): a marine derived alkylating agent. Molecules. 2014 Aug 15;19(8):12328-35. doi: 10.3390/molecules190812328. Review. PubMed PMID: 25153860. 7: Ocio EM, Oriol A, Bladé J, Teruel AI, Martín J, de la Rubia J, Gutiérrez NC, Rodríguez Díaz-Pavón J, Martínez González S, Coronado C, Fernández-García EM, Siguero Gómez M, Fernández-Teruel C, San Miguel J. Phase I/II study of weekly PM00104 (Zalypsis®) in patients with relapsed/refractory multiple myeloma. Br J Haematol. 2016 Feb;172(4):625-8. doi: 10.1111/bjh.13515. PubMed PMID: 26033438. 8: Castellano DE, Bellmunt J, Maroto JP, Font-Pous A, Morales-Barrera R, Ghanem I, Suarez C, Martín Lorente C, Etxaniz O, Capdevila L, Coronado C, Alfaro V, Siguero M, Fernández-Teruel C, Carles J. Phase II clinical trial of PM00104 (Zalypsis(®)) in urothelial carcinoma patients progressing after first-line platinum-based regimen. Cancer Chemother Pharmacol. 2014 Apr;73(4):857-67. doi: 10.1007/s00280-014-2419-7. PubMed PMID: 24570330. 9: Massard C, Margetts J, Amellal N, Drew Y, Bahleda R, Stephens P, Armand JP, Calvert H, Soria JC, Coronado C, Kahatt C, Alfaro V, Siguero M, Fernández-Teruel C, Plummer R. Phase I study of PM00104 (Zalypsis®) administered as a 1-hour weekly infusion resting every fourth week in patients with advanced solid tumors. Invest New Drugs. 2013 Jun;31(3):623-30. doi: 10.1007/s10637-012-9843-5. Erratum in: Invest New Drugs. 2013 Jun;31(3):799. Stevens, Peter [corrected to Stephens, Peter]. PubMed PMID: 22688291. 10: Capdevila J, Clive S, Casado E, Michie C, Piera A, Sicart E, Carreras MJ, Coronado C, Kahatt C, Soto Matos-Pita A, Fernandez Teruel C, Siguero M, Cullell-Young M, Tabernero J. A phase I pharmacokinetic study of PM00104 (Zalypsis) administered as a 24-h intravenous infusion every 3 weeks in patients with advanced solid tumors. Cancer Chemother Pharmacol. 2013 May;71(5):1247-54. doi: 10.1007/s00280-013-2119-8. PubMed PMID: 23455428. 11: Martin LP, Krasner C, Rutledge T, Ibañes ML, Fernández-García EM, Kahatt C, Gómez MS, McMeekin S. Phase II study of weekly PM00104 (ZALYPSIS(®)) in patients with pretreated advanced/metastatic endometrial or cervical cancer. Med Oncol. 2013;30(3):627. doi: 10.1007/s12032-013-0627-3. PubMed PMID: 23771800. 12: Salazar R, Calles A, Gil M, Durán I, García M, Hidalgo M, Coronado C, Alfaro V, Siguero M, Fernández-Teruel C, Prados R, Calvo E. Phase I study of carboplatin in combination with PM00104 (Zalypsis®) in patients with advanced solid tumors. Invest New Drugs. 2014 Aug;32(4):644-52. doi: 10.1007/s10637-014-0072-y. PubMed PMID: 24535315. 13: González-Sales M, Valenzuela B, Pérez-Ruixo C, Fernández Teruel C, Miguel-Lillo B, Soto-Matos A, Pérez-Ruixo JJ. Population pharmacokinetic-pharmacodynamic analysis of neutropenia in cancer patients receiving PM00104 (Zalypsis(®)). Clin Pharmacokinet. 2012 Nov;51(11):751-64. doi: 10.1007/s40262-012-0011-z. PubMed PMID: 23055348. 14: Pérez-Ruixo C, Valenzuela B, Fernández Teruel C, González-Sales M, Miguel-Lillo B, Soto-Matos A, Pérez-Ruixo JJ. Population pharmacokinetics of PM00104 (Zalypsis(®)) in cancer patients. Cancer Chemother Pharmacol. 2012 Jan;69(1):15-24. doi: 10.1007/s00280-011-1644-6. PubMed PMID: 21590449. 15: Yap TA, Cortes-Funes H, Shaw H, Rodriguez R, Olmos D, Lal R, Fong PC, Tan DS, Harris D, Capdevila J, Coronado C, Alfaro V, Soto-Matos A, Fernández-Teruel C, Siguero M, Tabernero JM, Paz-Ares L, de Bono JS, López-Martin JA. First-in-man phase I trial of two schedules of the novel synthetic tetrahydroisoquinoline alkaloid PM00104 (Zalypsis) in patients with advanced solid tumours. Br J Cancer. 2012 Apr 10;106(8):1379-85. doi: 10.1038/bjc.2012.99. PubMed PMID: 22491421; PubMed Central PMCID: PMC3326684. 16: Duan Z, Choy E, Harmon D, Yang C, Ryu K, Schwab J, Mankin H, Hornicek FJ. ZNF93 increases resistance to ET-743 (Trabectedin; Yondelis) and PM00104 (Zalypsis) in human cancer cell lines. PLoS One. 2009 Sep 9;4(9):e6967. doi: 10.1371/journal.pone.0006967. PubMed PMID: 19742314; PubMed Central PMCID: PMC2734182. 17: Guirouilh-Barbat J, Antony S, Pommier Y. Zalypsis (PM00104) is a potent inducer of gamma-H2AX foci and reveals the importance of the C ring of trabectedin for transcription-coupled repair inhibition. Mol Cancer Ther. 2009 Jul;8(7):2007-14. doi: 10.1158/1535-7163.MCT-09-0336. PubMed PMID: 19584237. 18: López-Iglesias AA, González-Méndez L, San-Segundo L, Herrero AB, Hernández-García S, Martín-Sánchez M, Gutiérrez NC, Paíno T, Avilés P, Mateos MV, San-Miguel JF, Garayoa M, Ocio EM. Synergistic DNA-damaging effect in multiple myeloma with the combination of zalypsis, bortezomib and dexamethasone. Haematologica. 2017 Jan;102(1):168-175. doi: 10.3324/haematol.2016.146076. PubMed PMID: 27540138; PubMed Central PMCID: PMC5210247. 19: Martínez S, Pérez L, Galmarini CM, Aracil M, Tercero JC, Gago F, Albella B, Bueren JA. Inhibitory effects of marine-derived DNA-binding anti-tumour tetrahydroisoquinolines on the Fanconi anaemia pathway. Br J Pharmacol. 2013 Oct;170(4):871-82. doi: 10.1111/bph.12331. PubMed PMID: 23937566; PubMed Central PMCID: PMC3799600. 20: Feuerhahn S, Giraudon C, Martínez-Díez M, Bueren-Calabuig JA, Galmarini CM, Gago F, Egly JM. XPF-dependent DNA breaks and RNA polymerase II arrest induced by antitumor DNA interstrand crosslinking-mimetic alkaloids. Chem Biol. 2011 Aug 26;18(8):988-99. doi: 10.1016/j.chembiol.2011.06.007. PubMed PMID: 21867914.