CPX-351 | CAS# 1256639-86-7 | Daunonubicin/Cytarabine

MedKoo Cat#: 565357 | Name: CPX-351

Description:

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

CPX-351 is a Liposomal-encapsulated combination of daunorubicin and cytarabine for the treatment of newly diagnosed tAML or AML with myelodysplasia-related changes (AML-MRCs).

Chemical Structure

CPX-351

CAS#1256639-86-7

Theoretical Analysis

MedKoo Cat#: 565357

Name: CPX-351

CAS#: 1256639-86-7

Chemical Formula: C36H42N4O15

Exact Mass:

Molecular Weight: 770.75

Elemental Analysis: C, 56.10; H, 5.49; N, 7.27; O, 31.14

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Vyxeos; Cytarabine/daunonubicin; Daunonubicin/cytarabine; CPX351; CPX 351; CPX-351

IUPAC/Chemical Name

(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

InChi Key

HBQCEICSYDCGJG-SZXLQUARSA-N

InChi Code

InChI=1S/C27H29NO10.C9H13N3O5/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t10-,14-,16-,17-,22+,27-;4-,6-,7+,8-/m01/s1

SMILES Code

O=C1C2=C(O)C([C@@H](O[C@@H]3O[C@@H](C)[C@@H](O)[C@@H](N)C3)C[C@](O)(C(C)=O)C4)=C4C(O)=C2C(C5=CC=CC(OC)=C51)=O.O=C6N=C(N)C=CN6[C@@H]7O[C@H](CO)[C@@H](O)[C@@H]7O

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

>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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 770.75 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.

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: Lin TL, Newell LF, Stuart RK, Michaelis LC, Rubenstein E, Pentikis HS, Callahan T, Alvarez D, Liboiron BD, Mayer LD, Wang Q, Banerjee K, Louie AC. A phase 2 study to assess the pharmacokinetics and pharmacodynamics of CPX-351 and its effects on cardiac repolarization in patients with acute leukemias. Cancer Chemother Pharmacol. 2019 May 16. doi: 10.1007/s00280-019-03856-9. [Epub ahead of print] PubMed PMID: 31098682. 2: Vincelette ND, Ding H, Huehls AM, Flatten KS, Kelly RL, Kohorst MA, Webster J, Hess AD, Pratz KW, Karnitz LM, Kaufmann SH. Effect of CHK1 Inhibition on CPX-351 Cytotoxicity in vitro and ex vivo. Sci Rep. 2019 Mar 5;9(1):3617. doi: 10.1038/s41598-019-40218-0. PubMed PMID: 30837643; PubMed Central PMCID: PMC6400938. 3: Wang Q, Banerjee K, Vasilinin G, Marier JF, Gibbons JA. Population Pharmacokinetics and Exposure-Response Analyses for CPX-351 in Patients With Hematologic Malignancies. J Clin Pharmacol. 2019 May;59(5):748-762. doi: 10.1002/jcph.1366. Epub 2018 Dec 19. PubMed PMID: 30566230. 4: Howell G, Oliai C, Schiller G. Liposomal Cytarabine-Daunorubicin (CPX-351) Extravasation: Case Report and Literature Review. Anticancer Res. 2018 Dec;38(12):6927-6930. doi: 10.21873/anticanres.13070. Review. PubMed PMID: 30504411. 5: Anderson E, Mehta P, Heywood J, Rees B, Bone H, Robinson G, Reynolds D, Salisbury V, Mayer L. CPX-351 exhibits hENT-independent uptake and can be potentiated by fludarabine in leukaemic cells lines and primary refractory AML. Leuk Res. 2018 Nov;74:121-129. doi: 10.1016/j.leukres.2018.08.007. Epub 2018 Aug 11. PubMed PMID: 30119908. 6: Di Y, Wasan EK, Cawthray J, Wasan KM. Scavenger receptor class BI (SR-BI) mediates uptake of CPX-351 into K562 leukemia cells. Drug Dev Ind Pharm. 2019 Jan;45(1):21-26. doi: 10.1080/03639045.2018.1513026. Epub 2018 Sep 5. PubMed PMID: 30113235. 7: Lancet JE, Uy GL, Cortes JE, Newell LF, Lin TL, Ritchie EK, Stuart RK, Strickland SA, Hogge D, Solomon SR, Stone RM, Bixby DL, Kolitz JE, Schiller GJ, Wieduwilt MJ, Ryan DH, Hoering A, Banerjee K, Chiarella M, Louie AC, Medeiros BC. CPX-351 (cytarabine and daunorubicin) Liposome for Injection Versus Conventional Cytarabine Plus Daunorubicin in Older Patients With Newly Diagnosed Secondary Acute Myeloid Leukemia. J Clin Oncol. 2018 Sep 10;36(26):2684-2692. doi: 10.1200/JCO.2017.77.6112. Epub 2018 Jul 19. PubMed PMID: 30024784; PubMed Central PMCID: PMC6127025. 8: Chen EC, Fathi AT, Brunner AM. Reformulating acute myeloid leukemia: liposomal cytarabine and daunorubicin (CPX-351) as an emerging therapy for secondary AML. Onco Targets Ther. 2018 Jun 12;11:3425-3434. doi: 10.2147/OTT.S141212. eCollection 2018. Review. PubMed PMID: 29928134; PubMed Central PMCID: PMC6003284. 9: Talati C, Lancet JE. CPX-351: changing the landscape of treatment for patients with secondary acute myeloid leukemia. Future Oncol. 2018 May;14(12):1147-1154. doi: 10.2217/fon-2017-0603. Epub 2018 Jan 30. Review. PubMed PMID: 29378418. 10: Walter RB, Othus M, Orlowski KF, McDaniel EN, Scott BL, Becker PS, Percival MM, Hendrie PC, Medeiros BC, Chiarella MT, Louie AC, Estey EH. Unsatisfactory efficacy in randomized study of reduced-dose CPX-351 for medically less fit adults with newly diagnosed acute myeloid leukemia or other high-grade myeloid neoplasm. Haematologica. 2018 Mar;103(3):e106-e109. doi: 10.3324/haematol.2017.182642. Epub 2017 Dec 14. PubMed PMID: 29242304; PubMed Central PMCID: PMC5830380. 11: Nikanjam M, Capparelli EV, Lancet JE, Louie A, Schiller G. Persistent cytarabine and daunorubicin exposure after administration of novel liposomal formulation CPX-351: population pharmacokinetic assessment. Cancer Chemother Pharmacol. 2018 Jan;81(1):171-178. doi: 10.1007/s00280-017-3484-5. Epub 2017 Nov 22. PubMed PMID: 29167924; PubMed Central PMCID: PMC5756117. 12: Wei AH, Tiong IS. Midostaurin, enasidenib, CPX-351, gemtuzumab ozogamicin, and venetoclax bring new hope to AML. Blood. 2017 Dec 7;130(23):2469-2474. doi: 10.1182/blood-2017-08-784066. Epub 2017 Oct 19. Review. PubMed PMID: 29051180. 13: Brunetti C, Anelli L, Zagaria A, Specchia G, Albano F. CPX-351 in acute myeloid leukemia: can a new formulation maximize the efficacy of old compounds? Expert Rev Hematol. 2017 Oct;10(10):853-862. doi: 10.1080/17474086.2017.1369400. Epub 2017 Aug 24. Review. PubMed PMID: 28814164. 14: Gordon MJ, Tardi P, Loriaux MM, Spurgeon SE, Traer E, Kovacsovics T, Mayer LD, Tyner JW. CPX-351 exhibits potent and direct ex vivo cytotoxicity against AML blasts with enhanced efficacy for cells harboring the FLT3-ITD mutation. Leuk Res. 2017 Feb;53:39-49. doi: 10.1016/j.leukres.2016.12.002. Epub 2016 Dec 12. PubMed PMID: 28013106. 15: Cortes JE, Goldberg SL, Feldman EJ, Rizzeri DA, Hogge DE, Larson M, Pigneux A, Recher C, Schiller G, Warzocha K, Kantarjian H, Louie AC, Kolitz JE. Phase II, multicenter, randomized trial of CPX-351 (cytarabine:daunorubicin) liposome injection versus intensive salvage therapy in adults with first relapse AML. Cancer. 2015 Jan 15;121(2):234-42. doi: 10.1002/cncr.28974. Epub 2014 Sep 15. PubMed PMID: 25223583; PubMed Central PMCID: PMC5542857. 16: Carol H, Fan MM, Harasym TO, Boehm I, Mayer LD, Houghton P, Smith MA, Lock RB. Efficacy of CPX-351, (cytarabine:daunorubicin) liposome injection, against acute lymphoblastic leukemia (ALL) xenograft models of the Pediatric Preclinical Testing Program. Pediatr Blood Cancer. 2015 Jan;62(1):65-71. doi: 10.1002/pbc.25133. Epub 2014 Sep 9. PubMed PMID: 25203866; PubMed Central PMCID: PMC4237711. 17: Lancet JE, Cortes JE, Hogge DE, Tallman MS, Kovacsovics TJ, Damon LE, Komrokji R, Solomon SR, Kolitz JE, Cooper M, Yeager AM, Louie AC, Feldman EJ. Phase 2 trial of CPX-351, a fixed 5:1 molar ratio of cytarabine/daunorubicin, vs cytarabine/daunorubicin in older adults with untreated AML. Blood. 2014 May 22;123(21):3239-46. doi: 10.1182/blood-2013-12-540971. Epub 2014 Mar 31. PubMed PMID: 24687088; PubMed Central PMCID: PMC4624448. 18: Gergis U, Roboz G, Shore T, Ritchie E, Mayer S, Wissa U, McKenna M, Christos P, Pearse R, Mark T, Scandura J, van Besien K, Feldman E. A phase I study of CPX-351 in combination with busulfan and fludarabine conditioning and allogeneic stem cell transplantation in adult patients with refractory acute leukemia. Biol Blood Marrow Transplant. 2013 Jul;19(7):1040-5. doi: 10.1016/j.bbmt.2013.04.013. Epub 2013 May 4. PubMed PMID: 23648237. 19: Feldman EJ, Kolitz JE, Trang JM, Liboiron BD, Swenson CE, Chiarella MT, Mayer LD, Louie AC, Lancet JE. Pharmacokinetics of CPX-351; a nano-scale liposomal fixed molar ratio formulation of cytarabine:daunorubicin, in patients with advanced leukemia. Leuk Res. 2012 Oct;36(10):1283-9. doi: 10.1016/j.leukres.2012.07.006. Epub 2012 Jul 26. PubMed PMID: 22840315. 20: Feldman EJ, Lancet JE, Kolitz JE, Ritchie EK, Roboz GJ, List AF, Allen SL, Asatiani E, Mayer LD, Swenson C, Louie AC. First-in-man study of CPX-351: a liposomal carrier containing cytarabine and daunorubicin in a fixed 5:1 molar ratio for the treatment of relapsed and refractory acute myeloid leukemia. J Clin Oncol. 2011 Mar 10;29(8):979-85. doi: 10.1200/JCO.2010.30.5961. Epub 2011 Jan 31. PubMed PMID: 21282541; PubMed Central PMCID: PMC4520927.