Fludarabine phosphate

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MedKoo CAT#: 100370

CAS#: 75607-67-9 (phosphate)

Description: Fludarabine phosphate is t he phosphate salt of a fluorinated nucleotide antimetabolite analog of the antiviral agent vidarabine (ara-A) with antineoplastic activity. Fludarabine phosphate is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. This metabolite may inhibit DNA polymerase alpha, ribonucleotide reductase and DNA primase, thereby interrupting DNA synthesis and inhibiting tumor cell growth.

Chemical Structure

Fludarabine phosphate
CAS# 75607-67-9 (phosphate)

Theoretical Analysis

MedKoo Cat#: 100370
Name: Fludarabine phosphate
CAS#: 75607-67-9 (phosphate)
Chemical Formula: C10H13FN5O7P
Exact Mass: 365.05366
Molecular Weight: 365.21
Elemental Analysis: C, 32.89; H, 3.59; F, 5.20; N, 19.18; O, 30.67; P, 8.48

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Related CAS #: 75607-67-9 (phosphate)   21679-14-1    

Synonym: Fludara; Beneflur. 2FaraAMP.

IUPAC/Chemical Name: ((2R,3S,4S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate


InChi Code: InChI=1S/C10H13FN5O7P/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,14,15)(H2,19,20,21)/t3-,5-,6+,9-/m1/s1

SMILES Code: O=P(O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=C(F)N=C23)[C@@H](O)[C@@H]1O)O

Appearance: white 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

Preparing Stock Solutions

The following data is based on the product molecular weight 365.21 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: Bordonaro R, Ferraù F, Giuffrida D, Calì S, Priolo D, Colina P, Ursino M, Failla G. Fludarabine phosphate as an active and well tolerated salvage therapy in an elderly heavily pretreated Hodgkin's disease patient: a case report. Tumori. 1999 Jul-Aug;85(4):288-9. Review. PubMed PMID: 10587034.

2: McLaughlin P, Robertson LE, Keating MJ. Fludarabine phosphate in lymphoma: an important new therapeutic agent. Cancer Treat Res. 1996;85:3-14. Review. PubMed PMID: 9043771.

3: Rodriguez G. Fludarabine phosphate. A new anticancer drug with significant activity in patients with chronic lymphocytic leukemia and in patients with lymphoma. Invest New Drugs. 1994;12(2):75-92. Review. PubMed PMID: 7532163.

4: Keating MJ, O'Brien S, Plunkett W, Robertson LE, Gandhi V, Estey E, Dimopoulos M, Cabanillas F, Kemena A, Kantarjian H. Fludarabine phosphate: a new active agent in hematologic malignancies. Semin Hematol. 1994 Jan;31(1):28-39. Review. PubMed PMID: 7510070.

5: Binet JL. Fludarabine phosphate in chronic lymphoproliferative diseases. The French Group on CLL. Nouv Rev Fr Hematol. 1993 Feb;35(1):5-7. Review. PubMed PMID: 7685518.

Additional Information

Fludarabine is highly effective in the treatment of chronic lymphocytic leukemia, producing higher response rates than alkylating agents such as chlorambucil alone. Fludarabine is used in various combinations with cyclophosphamide, mitoxantrone, dexamethasone and rituximab in the treatment of indolent non-Hodgkins lymphomas. As part of the FLAG regimen, fludarabine is used together with cytarabine and granulocyte colony-stimulating factor in the treatment of acute myeloid leukaemia. Because of its immunosuppressive effects, fludarabine is also used in some conditioning regimens prior to non myeloablative allogeneic stem cell transplant.
Oforta™ (fludarabine phosphate tablets) for oral administration contain fludarabine phosphate, a fluorinated nucleotide analog of the antiviral agent vidarabine, 9-beta -D-arabinofuranosyladenine (ara-A) that is relatively resistant to deamination by adenosine deaminase. Each tablet contains 10 mg of the active ingredient fludarabine phosphate. The tablet core consists of microcrystalline cellulose, lactose monohydrate, colloidal anhydrous silicon dioxide, croscarmellose sodium and magnesium stearate. The film-coat contains hypromellose, talc, titanium dioxide (E171) and ferric oxide pigment (red/E172, yellow/E172).
Mechanism of Action
Fludarabine phosphate (2F-ara-AMP) is a synthetic purine nucleotide antimetabolite agent. Upon administration, 2F-ara-AMP is rapidly dephosphorylated in the plasma to 2F-ara-A, which then enters into the cell. Intracellularly, 2F-ara-A is converted to the 5'-triphosphate, 2-fluoro-ara-ATP (2F-ara-ATP). 2F-ara-ATP competes with deoxyadenosine triphosphate for incorporation into DNA. Once incorporated into DNA, 2F-ara-ATP functions as a DNA chain terminator, inhibits DNA polymerase alpha, gamma, and delta, and inhibits ribonucleoside diphosphate reductase. 2F-ara-A also inhibits DNA primase and DNA ligase I. The mechanism of action of this antimetabolite is not completely characterized and may be multi-faceted.