Identification and Related Records
- 【Name】
- 9H-Purin-6-amine,9-b-D-arabinofuranosyl-2-fluoro-
- 【Iupac name】
- (2R,3S,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,
4-diol
- 【Registry number】
- 21679-14-1 (CAS DataBase Reference)
- 【Synonyms】
-
Adenine,9-b-D-arabinofuranosyl-2-fluoro- (8CI)
2-Fluoro Ara-A
2-Fluoro-9-b-D-arabinofuranosyladenine
2-Fluoroadenine arabinoside
9-b-D-Arabinofuranosyl-2-fluoroadenine
9-b-D-Arabinosyl-2-fluoroadenine
F-ara-A
NSC 118218
NSC 118218H
Fludarabine Base
- 【EINECS(EC#)】
- 244-525-5
- 【Molecular Formula】
- C10H12FN5O4 (Products with the same molecular formula)
- 【Molecular Weight】
- 285.23
- 【Inchi】
- InChI=1/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
- 【Canonical SMILES】
- C1=NC2=C(N1C3C(C(C(O3)CO)O)O)N=C(N=C2N)F
- 【Isomers smiles】
- C1=NC2=C(N1[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N=C(N=C2N)F
21679-14-1.mol
Chemical and Physical Properties
- 【Appearance】
- white solid
- 【Density】
- 2.17g/cm3
- 【Melting Point】
- 265-268°C
- 【Boiling Point】
- 747.3°Cat760mmHg
- 【Vapour】
- 1.86E-23mmHg at 25°C
- 【Refractive Index】
- 1.876
- 【Flash Point】
- 405.8°C
- 【Solubilities】
- Very soluble
- 【Color/Form】
- Crystals
- 【Storage temp】
- 2-8°C
- 【Spectral properties】
- UV max: 262, 261, 262 nm (epsilon X10-3 13.2, 14.8, 15.0)
- 【Computed Properties】
- Molecular Weight:285.231783 [g/mol]
Molecular Formula:C10H12FN5O4
XLogP3:-0.6
H-Bond Donor:4
H-Bond Acceptor:5
Rotatable Bond Count:2
Tautomer Count:3
Exact Mass:285.087332
MonoIsotopic Mass:285.087332
Topological Polar Surface Area:140
Heavy Atom Count:20
Formal Charge:0
Complexity:367
Isotope Atom Count:0
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:4
Feature 3D Cation Count:4
Feature 3D Ring Count:3
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:16
Safety and Handling
- 【Risk Statements】
- R23/24/25;R36/37/38;R39
- 【Safety Statements 】
- S26;S36/37;S45
- 【Formulations/Preparations】
- FLUDARA (fludarabine phosphate) injection, powder, lyophilized, for solution.
- 【Disposal Methods】
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Use and Manufacturing
- 【Usage】
-
Used as an antineoplastic
Biomedical Effects and Toxicity
- 【Biological Activity】
- Purine analog that inhibits DNA synthesis. Exhibits antiproliferative activity (IC 50 = 1.54 μ M in RPMI cells) and triggers apoptosis through increasing Bax and decreasing Bid, XIAP and survivin expression. Displays anticancer activity against hematological malignancies in vivo .
- 【Pharmacological Action】
- - Substances that inhibit or prevent the proliferation of NEOPLASMS.
- 【Therapeutic Uses】
- Fludarabine is indicated for 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. /Included in US product labeling/
Fludarabine is indicated for treatment of non-Hodgkin's lymphomas. /NOT included in US product labeling/
Fludarabine phosphate is a purine analogue now commonly used in the treatment of low-grade lymphoid malignancies. [Churn M et al; Clin Oncol (R Coll Radiol) 13 (4): 273-5 (2001)]
- 【Biomedical Effects and Toxicity】
- ... To compare the pharmacokinetics of sc & iv fludarabine in patients with lupus nephritis. ... Open-label, randomized, crossover trial conducted with a phase I-II trial. ... Government research hospital. ... Five patients with lupus nephritis. ... Fludarabine 30 mg/m2/day was administered either sc or as a 0.5-hr iv infusion for 3 consecutive days. All patients received oral cyclophosphamide 0.5 g/m2 on the first day of each cycle. ... Plasma samples were collected before & 0.5, 1, 1.5, 2, 4, 8, & 24 hrs after the first dose. Urine was collected at 6-hr intervals for 24 hrs. Plasma & urine were analyzed for fluoro-arabinofuranosyladenine (F-ara-A), fludarabine's main metabolite, using high-performance liquid chromatography. Compartmental techniques were used to determine the pharmacokinetics of F-ara-A; a linear two-compartment model best described them. Comparison of the pharmacokinetics between sc & iv admin was done by using a Wilcoxon signed rank test. No significant differences were found between sc & iv admin in median (interquartile range) maximum concns of 0.51 (0.38-0.56) & 0.75 (0.52-0.91) mg/L, respectively, or in fitted area under the concn-time curves from 0-24 hrs of 4.65 (4.17-4.98) & 4.55 (3.5-4.94) mg x hr/L, respectively. Bioavailability of F-ara-A after sc dosing was approx 105% of the bioavailability after iv admin. Differences in renal clearance & % of dose excreted in urine for sc & iv admin were nonsignificant. No injection site reactions were seen with subcutaneous dosing. ... Sc & iv admin of fludarabine appear to have similar pharmacokinetics in patients with lupus nephritis. Sc injection may offer a convenient alternative to iv admin.
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