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Fludarabine phosphate

Product Name
Fludarabine phosphate
CAS No.
75607-67-9
Chemical Name
Fludarabine phosphate
Synonyms
FAMP;Fludura;F-ara-AMP;-F-ara-AMP;2-fluoro-araamp;5-Monophosphate;fludarabine hcl;fludara Phosphate;Fludarabin Phosphate;Fludarbine Phopshate
CBNumber
CB7347825
Molecular Formula
C10H13FN5O7P
Formula Weight
365.21
MOL File
75607-67-9.mol
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Fludarabine phosphate Property

Melting point:
203°C(dec.)(lit.)
alpha 
[α]D20 +10～+14゜(c=0.5,H2O)
Boiling point:
864.2±75.0 °C(Predicted)
Density 
2.39±0.1 g/cm3(Predicted)
RTECS 
UO7440900
storage temp. 
2-8°C
solubility 
DMSO: soluble1mg/mL
form 
Powder
pka
1.86±0.10(Predicted)
color 
white
Water Solubility 
Soluble in DMSO or water at 5mg/ml
Merck 
14,4126
Stability:
Hygroscopic
InChIKey
GIUYCYHIANZCFB-GFRUICAKSA-N
CAS DataBase Reference
75607-67-9(CAS DataBase Reference)
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Safety

WGK Germany 
3
HS Code 
2934990002
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H341Suspected of causing genetic defects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0002256
Product name
Fludarabine for peak identification
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
Y0002256
Price
$161
Updated
2024/03/01
Sigma-Aldrich
Product number
F9813
Product name
Fludarabine phosphate
Packaging
5mg
Price
$78.2
Updated
2024/03/01
Sigma-Aldrich
Product number
1272204
Product name
Fludarabine phosphate
Packaging
300mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
F0913
Product name
Fludarabine Monophosphate
Purity
>98.0%(HPLC)(T)
Packaging
25mg
Price
$30
Updated
2024/03/01
TCI Chemical
Product number
F0913
Product name
Fludarabine Monophosphate
Purity
>98.0%(HPLC)(T)
Packaging
100mg
Price
$84
Updated
2024/03/01
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Fludarabine phosphate Chemical Properties,Usage,Production

Description

Fludarabine phosphate is an antimetabolite indicated for the treatment of B cell lymphocytic leukemia. It is reportedly effective in patients refractory to other therapies. Fludarabine phosphate acts by inhibiting primer RNA synthesis. Its side effects include bone marrow suppression, anemia, thrombocytopenia and neutropenia.

Chemical Properties

White or almost white, crystalline powder, hygroscopic.

Originator

Southern Research Institute (U.S.A.)

Uses

Fludarabine phosphate is used for the treatment of chronic lymphatic leukemia and low-grade lymphoma. In the circulation,fludarabine phosphate is immediately dephosphorylated to the nucleoside fludarabine. About 30-40% of nucleoside fludarabine is excreted into the urine. In addition, fludarabine is metabolized into a hypoxanthine metabolite also excreted in the urine.Intracellularly,fludarabine is stepwise rephosphorylated to the active triphosphate. Deoxycytidine kinase is the dominant, if not the exclusive,enzyme for the formation of the monophosphate. Adenylate kinase and nucleoside diphosphate kinase are believed to be involved in the formation of the diphosphate and triphosphate,respectively.

Uses

anticonvulsant

Definition

ChEBI: Fludarabine phosphate is a purine arabinonucleoside monophosphate having 2-fluoroadenine as the nucleobase. A prodrug, it is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. Once incorporated into DNA, 2-fluoro-ara-ATP functions as a DNA chain terminator. It is used for the treatment of adult patients with B-cell chronic lymphocytic leukemia (CLL) who have not responded to, or whose disease has progressed during, treatment with at least one standard alkylating-agent containing regimenas. It has a role as an antimetabolite, an antineoplastic agent, an immunosuppressive agent, an antiviral agent, a prodrug and a DNA synthesis inhibitor. It is an organofluorine compound, a nucleoside analogue and a purine arabinonucleoside monophosphate. It derives from a 2-fluoroadenine.

brand name

Fludara (Berlex), Benefluor (Schering AG).

Mechanism of action

Fludarabine phosphate is a cytotoxic purine antimetabolite that acts by inhibiting DNA synthesis. Fludarabine and its soluble derivatives interfere with phosphorylation, e.g., in L 1210 cells. Fludarabine behaves more like an analog of deoxycytidine than adenine or deoxyadenine as indicated by reports demonstrating that the presence of fluorine in the 2-position of the adenine ring alters its function as a substrate for deaminase and nucleoside kinases. This results in differences in biological activity and metabolism. Halogenation does not simply block deamination, but also influences the enzyme that carries out the phosphorylation, as a result cytotoxicity is increased. Fludarabine phosphate may selectively inhibit the incorporation of thymidine and uridine into the DNA molecule by inhibiting both ribonucleotide reductase and DNA polymerase. The maximum tolerated dose (MTD) in heavily pretreated patients with advanced malignancy/solid tumors on the daily regimen was about 15 mg/m2. Granulocytopenia and thrombocytopenia were dose-limiting.

Pharmacology

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 appears to act by inhibiting DNA polymerase alpha, ribonucleotide reductase and DNA primase, thus inhibiting DNA synthesis. The mechanism of action of this antimetabolite is not completely characterized and may be multi-faceted.
Phase I studies in humans have demonstrated that fludarabine phosphate is rapidly converted to the active metabolite, 2-fluoro-ara-A, within minutes after intravenous infusion.
Consequently, clinical pharmacology studies have focused on 2-fluoro-ara-A pharmacokinetics. After the five daily doses of 25 mg 2-fluoro-ara-AMP/m2 to cancer patients infused over 30 minutes, 2-fluoro-ara-A concentrations show a moderate accumulation. During a 5-day treatment schedule, 2-fluoro-ara-A plasma trough levels increased by a factor of about 2. The terminal half-life of 2-fluoro-ara-A was estimated as approximately 20 hours. In vitro, plasma protein binding of fludarabine ranged between 19% and 29%.

Clinical Use

Fludarabine phosphate (Fludara ® ), is a fluorinated nucleotide analog of the antiviral agent vidarabine, 9-β-D-arabinofuranosyladenine(ara-A), which differs only by the presence of a fluorine atom at position 2 of the purine moiety and a phosphate group at position 5 of the arabinose moiety (Plunkett et al., 1993). These structural modifications result in increased aqueous solubility and resistance to enzymatic degradation by adenosine deaminases compared to vidarabine (Brockman et al., 1977; Plunkett et al., 1990). Fludarabine phosphate is indicated for the treatment of patients with B-cell chronic lymphocytic leukemia (CLL) who have not responded to or whose disease has progressed during treatment with at least one standard alkylating agent containing regimen (Boogaerts et al., 2001; Rossi et al., 2004).

target

DNA synthesis

Drug interactions

Potentially hazardous interactions with other drugs
Antipsychotics: avoid concomitant use with clozapine, increased risk of agranulocytosis.
Cytotoxics: increased pulmonary toxicity with pentostatin (unacceptably high incidence of fatalities); increases intracellular concentration of cytarabine.

Metabolism

Intravenous fludarabine phosphate is rapidly dephosphorylated to fludarabine which is taken up by lymphocytes and rephosphorylated via the enzyme deoxycytidine kinase to the active triphosphate nucleotide. Clearance of fludarabine from the plasma is triphasic; elimination is mostly via renal excretion: 40-60% of an intravenous dose is excreted in the urine. The pharmacokinetics of fludarabine show considerable inter-individual variation

Fludarabine phosphate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Fludarabine phosphate manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Fludarabine phosphate 75607-67-9
Price
US $99.00-80.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-21
Hangzhou Hyper Chemicals Limited
Product
Fludarabine phosphate 75607-67-9
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
EP, USP
Supply Ability
100ton
Release date
2024-09-14
Hebei Chuanghai Biotechnology Co,.LTD
Product
Fludarabine Phosphate 75607-67-9
Price
US $2.70/kg
Min. Order
10kg
Purity
99.7%
Supply Ability
10000kg
Release date
2024-08-20

75607-67-9, Fludarabine phosphateRelated Search:

Compound phosphate Calcium phosphate Creatine phosphate DICALCIUM PHOSPHATE DIHYDRATE Clindamycin phosphate sodium hexametaphosphate FERRIC PHOSPHATE Trisodium phosphate Pentasodium triphosphate hexhydrate SULPHOSUCCINIC ACID ESTER Phytic acid Alkaline Phosphatase Sodium Phosphate Monobasic Monohydrate Fludarabine phosphate ester starch Ammonium dihydrogen phosphate Zinc phosphate phosphate

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