Elacytarabine
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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.

Chemical Structure

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Elacytarabine
CAS# 188181-42-2
Instruction

Theoretical Analysis

MedKoo Cat#: 201195
Name: Elacytarabine
CAS#: 188181-42-2
Chemical Formula: C27H45N3O6
Exact Mass: 507.33
Molecular Weight: 507.663
Elemental Analysis: C, 63.88; H, 8.93; N, 8.28; O, 18.91

Price and Availability

Size Price Availability Quantity
50mg USD 550 2 weeks
100mg USD 950 2 weeks
200mg USD 1650 2 weeks
500mg USD 2650 2 weeks
1g USD 3350 2 weeks
2g USD 5950 2 weeks
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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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 507.66 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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. PMID: 23373775.


2: 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. PMID: 25469211; PMCID: PMC4250268.


3: Burke AC, Giles FJ. Elacytarabine--lipid vector technology overcoming drug resistance in acute myeloid leukemia. Expert Opin Investig Drugs. 2011 Dec;20(12):1707-15. doi: 10.1517/13543784.2011.625009. Epub 2011 Nov 1. PMID: 22040175.


4: 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. Erratum in: Future Oncol. 2015;11(10):1584. PMID: 23902239.


5: 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. PMID: 24433865.


6: 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. PMID: 22702906; PMCID: PMC4191720.


7: 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. PMID: 24023287.


8: Adema AD, Smid K, Losekoot N, Honeywell RJ, Verheul HM, Myhren F, Sandvold ML, Peters GJ. Metabolism and accumulation of the lipophilic deoxynucleoside analogs elacytarabine and CP-4126. Invest New Drugs. 2012 Oct;30(5):1908-16. doi: 10.1007/s10637-011-9756-8. Epub 2011 Oct 15. PMID: 22002019; PMCID: PMC3432794.


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. PMID: 22226018; PMCID: PMC4104110.


10: 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. PMID: 24841975.


11: Adema AD, Losekoot N, Smid K, Kathmann I, Myhren F, Sandvold ML, Peters GJ. Induction of resistance to the lipophilic cytarabine prodrug elacytarabine (CP-4055) in CEM leukemic cells. Nucleosides Nucleotides Nucleic Acids. 2010 Jun;29(4-6):394-9. doi: 10.1080/15257771003741166. PMID: 20544525.


12: Sandvold ML, Galmarini C, Myhren F, Peters G. The activity of the lipophilic nucleoside derivatives elacytarabine and CP-4126 in a panel of tumor cell lines resistant to nucleoside analogues. Nucleosides Nucleotides Nucleic Acids. 2010 Jun;29(4-6):386-93. doi: 10.1080/15257771003729625. PMID: 20544524.


13: 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. PMID: 24255981.


14: Pignata S, Amant F, Scambia G, Sorio R, Breda E, Rasch W, Hernes K, Pisano C, Leunen K, Lorusso D, Cannella L, Vergote I. A phase I-II study of elacytarabine (CP-4055) in the treatment of patients with ovarian cancer resistant or refractory to platinum therapy. Cancer Chemother Pharmacol. 2011 Nov;68(5):1347-53. doi: 10.1007/s00280-011-1735-4. Epub 2011 Sep 10. PMID: 21909644.


15: 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. PMID: 22222600.


16: Zhu X, Ma Y, Liu D. Novel agents and regimens for acute myeloid leukemia: 2009 ASH annual meeting highlights. J Hematol Oncol. 2010 Apr 23;3:17. doi: 10.1186/1756-8722-3-17. PMID: 20416083; PMCID: PMC2880983.


17: Peters GJ. Novel developments in the use of antimetabolites. Nucleosides Nucleotides Nucleic Acids. 2014;33(4-6):358-74. doi: 10.1080/15257770.2014.894197. PMID: 24940694.


18: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Sep;30(7):543-88. PMID: 18985183.


19: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Jan-Feb;31(1):47-57. PMID: 19357798.


20: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Apr;30(3):231-51. PMID: 18597009.