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

MedKoo CAT#: 540138

CAS#: 21679-14-1

Description: Fludarabine is an adenosine analong, DNA chain terminator, and inhibitor of ribonucleotide reductase, DNA ligase, DNA primase, and adenoside A1 receptors. It is use to treat leukemias and graft-versus host disease in transplant patients. It also induces cell cycle arrest and apoptosis in alloreactive bone marrow stromal cells.


Chemical Structure

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Fludarabine
CAS# 21679-14-1

Theoretical Analysis

MedKoo Cat#: 540138
Name: Fludarabine
CAS#: 21679-14-1
Chemical Formula: C10H12FN5O4
Exact Mass: 285.0873
Molecular Weight: 285.23
Elemental Analysis: C, 42.11; H, 4.24; F, 6.66; N, 24.55; O, 22.44

Price and Availability

Size Price Availability Quantity
100.0mg USD 150.0 2 Weeks
200.0mg USD 250.0 2 Weeks
500.0mg USD 450.0 2 Weeks
1.0g USD 650.0 2 Weeks
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Related CAS #: 75607-67-9 (phosphate)   21679-14-1    

Synonym: Fludarabine; HSDB 6964; HSDB6964; HSDB-6964; NSC 118218; NSC118218; NSC-118218

IUPAC/Chemical Name: (2R,3S,4S,5R)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

InChi Key: HBUBKKRHXORPQB-FJFJXFQQSA-N

InChi Code: InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6+,9-/m1/s1

SMILES Code: NC1=C2N=CN([C@H]3[C@H]([C@@H]([C@@H](CO)O3)O)O)C2=NC(F)=N1

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

Preparing Stock Solutions

The following data is based on the product molecular weight 285.23 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

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1: McCune JS, Mager DE, Bemer MJ, Sandmaier BM, Storer BE, Heimfeld S. Association of fludarabine pharmacokinetic/dynamic biomarkers with donor chimerism in nonmyeloablative HCT recipients. Cancer Chemother Pharmacol. 2015 Jul;76(1):85-96. doi: 10.1007/s00280-015-2768-x. Epub 2015 May 17. PubMed PMID: 25983023; PubMed Central PMCID: PMC4489995.

2: Leitch MM, Sherman WH, Brannagan TH 3rd. Fludarabine in the Treatment of Refractory Chronic Inflammatory Demyelinating Neuropathies. J Clin Neuromuscul Dis. 2015 Sep;17(1):1-5. doi: 10.1097/CND.0000000000000083. PubMed PMID: 26301372.

3: Xu Q, Jiang C, Rong Y, Yang C, Liu Y, Xu K. The effects of fludarabine on rat cerebral ischemia. J Mol Neurosci. 2015 Feb;55(2):289-96. doi: 10.1007/s12031-014-0320-9. Epub 2014 May 15. PubMed PMID: 24825839.

4: Velázquez-Sánchez-de-Cima S, Zamora-Ortiz G, Hernández-Reyes J, Rosales-Durón AD, González-Ramírez MP, Martagón-Herrera NA, Ruiz-Delgado GJ, Ruiz-Argüelles GJ. Oral versus intravenous fludarabine as part of a reduced-intensity conditioning for allogeneic stem cell transplantation. Acta Haematol. 2014;132(1):125-8. doi: 10.1159/000357108. Epub 2014 Feb 18. PubMed PMID: 24556580.

5: Nunes AA, da Silva AS, Souza KM, Koury Cde N, de Mello LM. Rituximab, fludarabine, and cyclophosphamide versus fludarabine and cyclophosphamide for treatment of chronic lymphocytic leukemia: A systematic review with meta-analysis. Crit Rev Oncol Hematol. 2015 Jun;94(3):261-9. doi: 10.1016/j.critrevonc.2015.02.013. Epub 2015 Mar 11. Review. PubMed PMID: 25797826.

6: Hanafi LA, Gauchat D, Godin-Ethier J, Possamaï D, Duvignaud JB, Leclerc D, Grandvaux N, Lapointe R. Fludarabine downregulates indoleamine 2,3-dioxygenase in tumors via a proteasome-mediated degradation mechanism. PLoS One. 2014 Jun 9;9(6):e99211. doi: 10.1371/journal.pone.0099211. eCollection 2014. PubMed PMID: 24911872; PubMed Central PMCID: PMC4050125.

7: Lorkova L, Scigelova M, Arrey TN, Vit O, Pospisilova J, Doktorova E, Klanova M, Alam M, Vockova P, Maswabi B, Klener P Jr, Petrak J. Detailed Functional and Proteomic Characterization of Fludarabine Resistance in Mantle Cell Lymphoma Cells. PLoS One. 2015 Aug 18;10(8):e0135314. doi: 10.1371/journal.pone.0135314. eCollection 2015. PubMed PMID: 26285204; PubMed Central PMCID: PMC4540412.

8: Shah N, Tam C, Seymour JF, Rule S. How applicable is fludarabine, cyclophosphamide and rituximab to the elderly? Leuk Lymphoma. 2015 Jun;56(6):1599-610. doi: 10.3109/10428194.2014.963083. Epub 2014 Nov 20. Review. PubMed PMID: 25213181.

9: Podhorecka M, Klimek P, Chocholska S, Szymczyk A, Macheta A, Kowal M, Dmoszynska A, Hus M. The rate of in vitro fludarabine-induced peripheral blood and bone marrow cell apoptosis may predict the chemotherapy outcome in patients with chronic lymphocytic leukemia. Eur J Clin Pharmacol. 2015 Sep;71(9):1121-7. doi: 10.1007/s00228-015-1893-0. Epub 2015 Jul 5. PubMed PMID: 26141594; PubMed Central PMCID: PMC4532719.

10: Qiu L, Liu J, Wang Z, Hu W, Huang Q, Zhou Y. ZGDHu-1 and fludarabine have a synergistic effect on apoptosis of chronic lymphocytic leukemia cells. Oncol Rep. 2015 Sep;34(3):1239-48. doi: 10.3892/or.2015.4115. Epub 2015 Jul 8. PubMed PMID: 26165829.

11: Flowers CR, Brown JR, Rosenthal H, Stock W, Katzen HI, Cohen JB, Sinha R, Lakhanpal S, Leis JF, Waller EK, Jaye DL. A Phase 2 Trial of Fludarabine Combined With Subcutaneous Alemtuzumab for the Treatment of Relapsed/Refractory B-Cell Chronic Lymphocytic Leukemia. Clin Lymphoma Myeloma Leuk. 2015 Nov;15(11):694-8. doi: 10.1016/j.clml.2015.07.640. Epub 2015 Aug 5. PubMed PMID: 26385641.

12: Cividini F, Pesi R, Chaloin L, Allegrini S, Camici M, Cros-Perrial E, Dumontet C, Jordheim LP, Tozzi MG. The purine analog fludarabine acts as a cytosolic 5'-nucleotidase II inhibitor. Biochem Pharmacol. 2015 Mar 15;94(2):63-8. doi: 10.1016/j.bcp.2015.01.010. Epub 2015 Feb 2. PubMed PMID: 25656700.

13: Souchet-Compain L, Nguyen S, Choquet S, Leblond V. Fludarabine in Waldenstrom's macroglobulinemia. Expert Rev Hematol. 2013 Jun;6(3):229-37. doi: 10.1586/ehm.13.17. PubMed PMID: 23782076.

14: Park H, Youk J, Kim I, Yoon SS, Park S, Lee JO, Bang SM, Koh Y. Comparison of cladribine- and fludarabine-based induction chemotherapy in relapsed or refractory acute myeloid leukaemia. Ann Hematol. 2016 Oct;95(11):1777-86. doi: 10.1007/s00277-016-2774-z. Epub 2016 Aug 19. PubMed PMID: 27539617.

15: Leblond V, Johnson S, Chevret S, Copplestone A, Rule S, Tournilhac O, Seymour JF, Patmore RD, Wright D, Morel P, Dilhuydy MS, Willoughby S, Dartigeas C, Malphettes M, Royer B, Ewings M, Pratt G, Lejeune J, Nguyen-Khac F, Choquet S, Owen RG. Results of a randomized trial of chlorambucil versus fludarabine for patients with untreated Waldenström macroglobulinemia, marginal zone lymphoma, or lymphoplasmacytic lymphoma. J Clin Oncol. 2013 Jan 20;31(3):301-7. doi: 10.1200/JCO.2012.44.7920. Epub 2012 Dec 10. PubMed PMID: 23233721.

16: Tsybulskaya I, Kulak T, Kalinichenko E, Baranovsky A, Bogushevich S, Golubeva M, Kuzmitsky B. Phospholipid derivatives of cladribine and fludarabine: synthesis and biological properties. Bioorg Med Chem. 2015 Jul 1;23(13):3287-96. doi: 10.1016/j.bmc.2015.04.059. Epub 2015 Apr 25. PubMed PMID: 25960323.

17: Lozano-Santos C, Amigo-Jiménez I, Nova-Gurumeta S, Pérez-Sanz N, García-Pardo A, García-Marco JA. Arsenic trioxide synergistically potentiates the cytotoxic effect of fludarabine in chronic lymphocytic leukemia cells by further inactivating the Akt and ERK signaling pathways. Biochem Biophys Res Commun. 2015 May 29;461(2):243-8. doi: 10.1016/j.bbrc.2015.04.007. Epub 2015 Apr 11. PubMed PMID: 25869069.

18: Tsukasaki K. [Chemoimmunotherapy with fludarabine, cyclophosphamide, and rituximab]. Nihon Rinsho. 2015 Feb;73 Suppl 2:632-5. Japanese. PubMed PMID: 25831837.

19: Lee JH, Lee JH, Kim DY, Seol M, Lee YS, Kang YA, Jeon M, Lee KH. A Phase II Trial of Fludarabine/Melphalan 100 Conditioning Therapy Followed by Allogeneic Hematopoietic Cell Transplantation for Patients With Lymphoma. Clin Lymphoma Myeloma Leuk. 2015 Nov;15(11):655-63. doi: 10.1016/j.clml.2015.08.087. Epub 2015 Sep 3. PubMed PMID: 26428486.

20: Yoon JY, Ishdorj G, Graham BA, Johnston JB, Gibson SB. Valproic acid enhances fludarabine-induced apoptosis mediated by ROS and involving decreased AKT and ATM activation in B-cell-lymphoid neoplastic cells. Apoptosis. 2014 Jan;19(1):191-200. doi: 10.1007/s10495-013-0906-7. PubMed PMID: 24057147.