Fludarabine
Title: Fludarabine
CAS Registry Number: 21679-14-1
CAS Name: 9-b-D-Arabinofuranosyl-2-fluoro-9H-purin-6-amine
Additional Names: 9-b-D-arabinofuranosyl-2-fluoroadenine; 2-fluorovidarabine; 2-fluoro-9-b-D-arabinofuranosyladenine; 2-F-araA
Manufacturers' Codes: NSC-118218; NSC-118218-H
Molecular Formula: C10H12FN5O4
Molecular Weight: 285.23
Percent Composition: C 42.11%, H 4.24%, F 6.66%, N 24.55%, O 22.44%
Literature References: Adenosine deaminase-resistant purine nucleoside antimetabolite. Prepn and in vitro cytotoxicity: J. A. Montgomery, K. Hewson, J. Med. Chem. 12, 498 (1969). Improved prepn: J. A. Montgomery et al., J. Heterocycl. Chem. 16, 157 (1979); J. A. Montgomery, US 4210745 (1980 to U.S. Dept. Health, Education and Welfare). Inhibition of DNA synthesis and in vivo antileukemic activity: R. W. Brockman et al., Biochem. Pharmacol. 26, 2193 (1977). Metabolized to 5¢-monophosphate: R. W. Brockman et al., Cancer Res. 40, 3610 (1980). HPLC determn in human leukemia cells: V. Gandhi et al., J. Chromatogr. 413, 293 (1987). Prepn of 5¢-monophosphate: J. A. Montgomery, A. T. Shortnacy, US 4357324 (1982 to U.S. Dept. of Health and Human Services). Pharmacokinetics in humans: M. R. Hersh et al., Cancer Chemother. Pharmacol. 17, 277 (1986). Evaluation of therapeutic efficacy and CNS toxicity in acute refractory leukemia: R. P. Warrell, Jr., E. Berman, J. Clin. Oncol. 4, 74 (1986); H. G. Chun et al., Cancer Treat. Rep. 70, 1225 (1986). Series of articles on pharmacology and therapeutic use: Semin. Oncol. 17, Suppl. 8, 1-78 (1990).
Properties: Crystals from ethanol + water, mp 260°. [a]D25 +17 ±2.5° (c = 0.1 in ethanol). uv max (pH 1, pH 7, pH 13): 262, 261, 262 nm (e ´ 10-3 13.2, 14.8, 15.0). Sparingly sol in water, organic solvents.
Melting point: mp 260°
Optical Rotation: [a]D25 +17 ±2.5° (c = 0.1 in ethanol)
Absorption maximum: uv max (pH 1, pH 7, pH 13): 262, 261, 262 nm (e ´ 10-3 13.2, 14.8, 15.0)
 
Derivative Type: 5¢-Monophosphate
CAS Registry Number: 75607-67-9
Additional Names: 2-F-ara-AMP
Manufacturers' Codes: NSC-328002; NSC-312887
Trademarks: Fludara (Schering AG)
Molecular Formula: C10H13FN5O7P
Molecular Weight: 365.21
Percent Composition: C 32.89%, H 3.59%, F 5.20%, N 19.18%, O 30.67%, P 8.48%
Properties: Sol in water.
 
Therap-Cat: Phosphate as antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Purine Analogs.

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