9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)-

Base Information

• Chemical Name: 9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)-
• CAS No.: 75607-67-9
• Molecular Formula: C10H13FN5O7P
• Molecular Weight: 365.215
• Hs Code.: 2934990002
• NSC Number: 312887
• DSSTox Substance ID: DTXSID80860982
• ChEMBL ID: CHEMBL1965242
• Mol file: 75607-67-9.mol

Synonyms:2-fluoro-9-(5-o-phosphonopentofuranosyl)-9h-purin-6-amine;FAMP;[(2R,3S,4S,5R)-5-(6-amino-2-fluoropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate;NSC312887;9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-.beta.-D-arabinofuranosyl)-;NSC-328002;Fludara (Berlex);SCHEMBL1650192;9-.beta.-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate);CHEMBL1965242;DTXSID80860982;GIUYCYHIANZCFB-UHFFFAOYSA-N;HMS3654F05;STL452901;STL452969;NCI60_002698;FT-0630840;AB01273950-01;9-.beta.-Arabinofuranosyl-2-fluoroadenine-5'-phosphate;Z2736093605;9-.beta.-D-Arabinofuranosyl-2-fluoroadenine 5'-monophosphate;2-Fluoro-9-(5-O-phosphono-.beta.-D-arabinofuranosyl)-9H-purin-6-amine;2-fluoro-9-(5-O-phosphonopentofuranosyl)-1,9-dihydro-6H-purin-6-imine

Chemical Property of 9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)-

Chemical Property:

• Vapor Pressure: 7.38E-32mmHg at 25°C
• Melting Point: 203°C(dec.)(lit.)
• Refractive Index: 1.878
• Boiling Point: 864.2 °C at 760 mmHg
• PKA: 1.86±0.10(Predicted)
• Flash Point: 476.4 °C
• PSA: 195.88000
• Density: 2.39 g/cm³
• LogP: -1.14270
• Storage Temp.: -20°C
• Solubility.: DMSO: soluble1mg/mL
• Water Solubility.: Soluble in DMSO or water at 5mg/ml
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 4
• Exact Mass: 365.05366293
• Heavy Atom Count: 24
• Complexity: 514

Purity/Quality:

99% ^*data from raw suppliers

Fludarabine phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)COP(=O)(O)O)O)O)F)N
• 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.
• Uses: anticonvulsant 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.
• 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).
• 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.

Technology Process of 9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)-

There total 5 articles about 9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.5%

Fludarabine (146-78-1,19768-92-4,21679-14-1,21679-15-2) + triethyl phosphate (78-40-0) → fludarabine phosphate (75607-67-9,71261-44-4)

Guidance literature:

With trichlorophosphate; at -5 - -1 ℃; for 15h; Temperature;

Reference yield: 90.0%

Fludarabine (146-78-1,19768-92-4,21679-14-1,21679-15-2) → fludarabine phosphate (75607-67-9,71261-44-4)

Guidance literature:

With triethyl phosphate; trichlorophosphate; at -10 - -5 ℃; Temperature;

Reference yield:

trimethyl phosphite (512-56-1) + Fludarabine (146-78-1,19768-92-4,21679-14-1,21679-15-2) → fludarabine phosphate (75607-67-9,71261-44-4)

Guidance literature:

With trichlorophosphate; In ethanol; water;

upstream raw materials:

Fludarabine

trimethyl phosphite

triethyl phosphate

pyrographite

Downstream raw materials:

Fludarabine

Refernces

• 1、 -. "A 9 - β - D - arabinofuranosyl -2 - fluoro adenine -5 ' - phosphate ester preparation method (by machine translation)". Paragraph 0033; 0034; 0035; 0036; 0037; 0039; 0040; 0042. . Retrieved 2018/09/26.
• 2、 Serra, Immacolata,Conti, Silvia,Piskur, Jure,Clausen, Anders R.,Munch-Petersen, Birgitte,Terreni, Marco,Ubiali, Daniela. "Immobilized Drosophila melanogaster deoxyribonucleoside kinase (DmdNK) as a high performing biocatalyst for the synthesis of purine arabinonucleotides". . p. 563 - 570. Retrieved 2014/05/20.