WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 201195
CAS#: 188181-42-2
Description: Elacytarabine, also known as CP-4055, is the lipophilic 5'-elaidic acid ester of the deoxycytidine analog cytosine arabinoside (cytarabine; Ara-C) with potential antineoplastic activity. As a prodrug, CP-4055 is converted intracellularly into cytarabine triphosphate by deoxycytidine kinase and subsequently competes with cytidine for incorporation into DNA, thereby inhibiting DNA synthesis. Compared to cytarabine, CP-4055 shows increased cellular uptake and retention, resulting in increased activation by deoxycytidine kinase to cytarabine triphosphate, decreased deamination and deactivation by deoxycytidine deaminase, and increased inhibition of DNA synthesis. This agent also inhibits RNA synthesis, an effect not seen with cytarabine.
MedKoo Cat#: 201195
Name: Elacytarabine
CAS#: 188181-42-2
Chemical Formula: C27H45N3O6
Exact Mass: 507.33084
Molecular Weight: 507.6627
Elemental Analysis: C, 63.88; H, 8.93; N, 8.28; O, 18.91
Synonym: CP4055; CP 4055; CP-4055; Elacytarabine. ELACYT.
IUPAC/Chemical Name: (E)-((2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl octadec-9-enoate.
InChi Key: FLFGNMFWNBOBGE-FNNZEKJRSA-N
InChi Code: InChI=1S/C27H45N3O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(31)35-20-21-24(32)25(33)26(36-21)30-19-18-22(28)29-27(30)34/h9-10,18-19,21,24-26,32-33H,2-8,11-17,20H2,1H3,(H2,28,29,34)/b10-9+/t21-,24-,25+,26-/m1/s1
SMILES Code: CCCCCCCC/C=C/CCCCCCCC(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@@H](O)[C@@H]1O)=O
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, 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).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 507.6627 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: Rein LA, Rizzieri DA. Clinical potential of elacytarabine in patients with acute myeloid leukemia. Ther Adv Hematol. 2014 Dec;5(6):211-20. doi: 10.1177/2040620714552615. Review. PubMed PMID: 25469211; PubMed Central PMCID: PMC4250268.
2: Roboz GJ, Rosenblat T, Arellano M, Gobbi M, Altman JK, Montesinos P, O'Connell C, Solomon SR, Pigneux A, Vey N, Hills R, Jacobsen TF, Gianella-Borradori A, Foss Ø, Vetrhusand S, Giles FJ. International randomized phase III study of elacytarabine versus investigator choice in patients with relapsed/refractory acute myeloid leukemia. J Clin Oncol. 2014 Jun 20;32(18):1919-26. doi: 10.1200/JCO.2013.52.8562. Epub 2014 May 19. PubMed PMID: 24841975.
3: Knapper S, Chevassut T, Duarte R, Bergua JM, Salamero O, Johansen M, Jacobsen TF, Hals PA, Rasch W, Gianella-Borradori A, Smith M. Elacytarabine in relapsed/refractory acute myeloid leukaemia: an evaluation of clinical efficacy, pharmacokinetics, cardiac safety and effects on lipid profile. Leuk Res. 2014 Mar;38(3):346-51. doi: 10.1016/j.leukres.2013.12.011. Epub 2013 Dec 25. PubMed PMID: 24433865.
4: Rizzieri D, Vey N, Thomas X, Huguet-Rigal F, Schlenk RF, Krauter J, Kindler T, Gjertsen BT, Blau IW, Jacobsen TF, Johansen M, Bergeland T, Gianella-Borradori A, Krug U. A phase II study of elacytarabine in combination with idarubicin and of human equilibrative nucleoside transporter 1 expression in patients with acute myeloid leukemia and persistent blasts after the first induction course. Leuk Lymphoma. 2014 Sep;55(9):2114-9. doi: 10.3109/10428194.2013.867489. Epub 2014 Jan 24. PubMed PMID: 24255981.
5: Bruheim S, Sandvold ML, Mælandsmo GM, Fodstad O. Antitumor activity of elacytarabine combined with bevacizumab, cetuximab and trastuzumab in human NSCLC xenografts. Anticancer Res. 2013 Sep;33(9):3615-21. PubMed PMID: 24023287.
6: DiNardo CD, O'Brien S, Gandhi VV, Ravandi F. Elacytarabine (CP-4055) in the treatment of acute myeloid leukemia. Future Oncol. 2013 Aug;9(8):1073-82. doi: 10.2217/fon.13.130. PubMed PMID: 23902239.
7: Keane N, Freeman C, Swords R, Giles FJ. Elacytarabine: lipid vector technology under investigation in acute myeloid leukemia. Expert Rev Hematol. 2013 Feb;6(1):9-24. doi: 10.1586/ehm.12.68. Review. PubMed PMID: 23373775.
8: O'Brien S, Rizzieri DA, Vey N, Ravandi F, Krug UO, Sekeres MA, Dennis M, Venditti A, Berry DA, Jacobsen TF, Staudacher K, Bergeland T, Giles FJ. Elacytarabine has single-agent activity in patients with advanced acute myeloid leukaemia. Br J Haematol. 2012 Sep;158(5):581-8. doi: 10.1111/j.1365-2141.2012.09186.x. Epub 2012 Jun 15. PubMed PMID: 22702906; PubMed Central PMCID: PMC4191720.
9: Giles F, Rizzieri D, Ravandi F, Swords R, Jacobsen TF, O'Brien S. Elacytarabine, a novel 5'-elaidic acid derivative of cytarabine, and idarubicin combination is active in refractory acute myeloid leukemia. Leuk Res. 2012 Apr;36(4):e71-3. doi: 10.1016/j.leukres.2011.12.010. Epub 2012 Jan 9. PubMed PMID: 22226018; PubMed Central PMCID: PMC4104110.
10: Giles FJ, Vey N, Rizzieri D, Ravandi F, Prebet T, Borthakur G, Jacobsen TF, Hagen S, Nilsson B, O'Brien S. Phase I and pharmacokinetic study of elacytarabine, a novel 5'-elaidic acid derivative of cytarabine, in adults with refractory hematological malignancies. Leukemia. 2012 Jul;26(7):1686-9. doi: 10.1038/leu.2012.1. Epub 2012 Jan 6. PubMed PMID: 22222600.
(Last update: 4/21/2016).
