Fludarabine phosphate (in stock) | CAS#75607-67-9

MedKoo Cat#: 100370 | Name: Fludarabine phosphate

Description:

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

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: 365.0537

Molecular Weight: 365.21

Elemental Analysis: C, 32.89; H, 3.59; F, 5.20; N, 19.18; O, 30.67; P, 8.48

Price and Availability

Size	Price	Availability
100mg	USD 90.00	Ready to ship
200mg	USD 150.00	Ready to ship
500mg	USD 300.00	Ready to ship
1g	USD 550.00	Ready to ship
2g	USD 950.00	Ready to ship
5g	USD 1,850.00	Ready to ship

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Related CAS #

21679-14-1 (free base) 75607-67-9 (phosphate) 107811-61-0 (diphosphate) 1169548-80-4 (F18)

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 Key

GIUYCYHIANZCFB-FJFJXFQQSA-N

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

More Info

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. OfortaÂ™ (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.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#YYP30816

QC Data

View QC data: current batch, Lot#YYP30816

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Fludarabine (phosphate) is an analogue of adenosine and deoxyadenosine, which is able to compete with dATP for incorporation into DNA and inhibit DNA synthesis.

In vitro activity:

The effect of fludarabine phosphate (FLU) on in vitro growth, gene expression and the antigenic phenotype of human glioblastoma multiforme (GBM) cells displaying a multidrug sensitive and a multidrug resistant (MDR) phenotype. FLU exhibited a marked differential toxicity toward GBM-MDR cells versus the multidrug sensitive GBM parental cell line. Growth of GBM-MDR cells for seven days in 2.5 to 7.5 muM FLU resulted in a dose-dependent reduction or elimination of growth which persisted after removal of this agent. In contrast, recovery from FLU-induced growth suppression was observed in parental multidrug sensitive GBM cells. Acquisition of increased FLU sensitivity in GBM-MDR cells did not appear to result from selection for a subset of sensitive cells or an artifact associated with the DNA-transfection process. This conclusion is supported by the similar pattern of FLU resistance in GBM-18 clones isolated after transfection with a cloned hygromycin resistance gene and selection for resistance to hygromycin. Reference: Int J Oncol. 1992 Jul;1(2):227-39. https://www.spandidos-publications.com/ijo/1/2/227

In vivo activity:

Intratumoral administration of fludarabine phosphate (F-araAMP) in human tumor xenografts expressing E. coli PNP resulted in complete regressions and/or prolonged tumor inhibition. External beam radiation significantly augmented this effect. Injection of large human tumor xenografts (human glioma, nonsmall cell lung cancer, or malignant prostate tumors) with Ad/PNP followed by intratumoral F-araAMP resulted in excellent antitumor activity superior to that observed following systemic administration of prodrug. Reference: Cancer Chemother Pharmacol. 2012 Aug;70(2):321-9. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/22760227/

	Solvent	mg/mL	mM
Solubility
	DMSO	73.0	199.88
	Water	3.0	8.21

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

1. Jiang H, Su Z, Datta S, Guarini L, Waxman S, Fisher P. Fludarabine phosphate selectively inhibits growth and modifies the antigenic phenotype of human glioblastoma-multiforme cells expressing a multidrug resistance phenotype. Int J Oncol. 1992 Jul;1(2):227-39. doi: 10.3892/ijo.1.2.227. PMID: 21584536.

In vivo protocol:

1. Sorscher EJ, Hong JS, Allan PW, Waud WR, Parker WB. In vivo antitumor activity of intratumoral fludarabine phosphate in refractory tumors expressing E. coli purine nucleoside phosphorylase. Cancer Chemother Pharmacol. 2012 Aug;70(2):321-9. doi: 10.1007/s00280-012-1908-9. Epub 2012 Jul 4. PMID: 22760227; PMCID: PMC3423194.

1: Bordonaro R, FerraÃ¹ F, Giuffrida D, CalÃ¬ 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.