For research use only. Not for therapeutic Use.
Elacytarabine (CAT: I006455), also known as CP-4055, is an antineoplastic prodrug with potential therapeutic benefits. It is the lipophilic 5′-elaidic acid ester of cytarabine (cytosine arabinoside; Ara-C), a deoxycytidine analog. Within cells, CP-4055 is converted into cytarabine triphosphate by the enzyme deoxycytidine kinase. It competes with cytidine for incorporation into DNA, resulting in the inhibition of DNA synthesis. Compared to cytarabine, CP-4055 demonstrates enhanced cellular uptake and retention, increased activation by deoxycytidine kinase, reduced deamination and deactivation by deoxycytidine deaminase, and enhanced inhibition of DNA synthesis.
| Catalog Number | I006455 |
| CAS Number | 188181-42-2 |
| Synonyms | CP4055; CP 4055; CP-4055; Elacytarabine. ELACYT.;(E)-((2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl octadec-9-enoate. |
| Molecular Formula | C27H45N3O6 |
| Purity | ≥95% |
| Target | Nucleoside Antimetabolite/Analog |
| Solubility | Soluble in DMSO, not in water |
| Storage | 0 - 4°C for short term or -20 °C for long term |
| IUPAC Name | [(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (E)-octadec-9-enoate |
| InChI | 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 |
| InChIKey | FLFGNMFWNBOBGE-FNNZEKJRSA-N |
| SMILES | CCCCCCCCC=CCCCCCCCC(=O)OCC1C(C(C(O1)N2C=CC(=NC2=O)N)O)O |
| Reference | </br>1:Clinical potential of elacytarabine in patients with acute myeloid leukemia. Rein LA, Rizzieri DA.Ther Adv Hematol. 2014 Dec;5(6):211-20. doi: 10.1177/2040620714552615. Review. PMID: 25469211 Free PMC Article</br>2:International randomized phase III study of elacytarabine versus investigator choice in patients with relapsed/refractory acute myeloid leukemia. 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.J Clin Oncol. 2014 Jun 20;32(18):1919-26. doi: 10.1200/JCO.2013.52.8562. Epub 2014 May 19. PMID: 24841975 </br>3:Elacytarabine in relapsed/refractory acute myeloid leukaemia: an evaluation of clinical efficacy, pharmacokinetics, cardiac safety and effects on lipid profile. Knapper S, Chevassut T, Duarte R, Bergua JM, Salamero O, Johansen M, Jacobsen TF, Hals PA, Rasch W, Gianella-Borradori A, Smith M.Leuk Res. 2014 Mar;38(3):346-51. doi: 10.1016/j.leukres.2013.12.011. Epub 2013 Dec 25. PMID: 24433865 </br>4: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. 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.Leuk Lymphoma. 2014 Sep;55(9):2114-9. doi: 10.3109/10428194.2013.867489. Epub 2014 Jan 24. PMID: 24255981 </br>5:Antitumor activity of elacytarabine combined with bevacizumab, cetuximab and trastuzumab in human NSCLC xenografts. Bruheim S, Sandvold ML, Mælandsmo GM, Fodstad O.Anticancer Res. 2013 Sep;33(9):3615-21. PMID: 24023287 </br>6:Elacytarabine (CP-4055) in the treatment of acute myeloid leukemia. DiNardo CD, O/’Brien S, Gandhi VV, Ravandi F.Future Oncol. 2013 Aug;9(8):1073-82. doi: 10.2217/fon.13.130. Erratum in: Future Oncol. 2015;11(10):1584. PMID: 23902239 </br>7:Elacytarabine: lipid vector technology under investigation in acute myeloid leukemia. Keane N, Freeman C, Swords R, Giles FJ.Expert Rev Hematol. 2013 Feb;6(1):9-24. doi: 10.1586/ehm.12.68. Review. PMID: 23373775 </br>8:Elacytarabine has single-agent activity in patients with advanced acute myeloid leukaemia. 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.Br J Haematol. 2012 Sep;158(5):581-8. doi: 10.1111/j.1365-2141.2012.09186.x. Epub 2012 Jun 15. PMID: 22702906 Free PMC Article</br>9:Elacytarabine, a novel 5/’-elaidic acid derivative of cytarabine, and idarubicin combination is active in refractory acute myeloid leukemia. Giles F, Rizzieri D, Ravandi F, Swords R, Jacobsen TF, O/’Brien S.Leuk Res. 2012 Apr;36(4):e71-3. doi: 10.1016/j.leukres.2011.12.010. Epub 2012 Jan 9. No abstract available. PMID: 22226018 Free PMC Article</br>10:Phase I and pharmacokinetic study of elacytarabine, a novel 5/’-elaidic acid derivative of cytarabine, in adults with refractory hematological malignancies. Giles FJ, Vey N, Rizzieri D, Ravandi F, Prebet T, Borthakur G, Jacobsen TF, Hagen S, Nilsson B, O/’Brien S.Leukemia. 2012 Jul;26(7):1686-9. doi: 10.1038/leu.2012.1. Epub 2012 Jan 6. No abstract available. PMID: 22222600 |
