6442. Nelarabine

Nomenclature

CAS number: 121032-29-9
9-β-d-Arabinofuranosyl-6-methoxy-9H-purin-2-amine; 2-amino-9-β-d-arabinofuranosyl-6-methoxy-9H-purine; GW-506U78; 506U; Arranon (GSK); Atriance (GSK).
C11H15N5O5; mol wt 297.27.
C 44.44%, H 5.09%, N 23.56%, O 26.91%.

Description and references

Purine nucleoside; prodrug of guanine arabinoside. Prepn: T. A. Krenitsky et al., EP 294114 (1988 to Wellcome Foundation); idem, D. J. T. Porter, US 5424295 (1995 to Burroughs Wellcome); D. R. Averett et al., Antimicrob. Agents Chemother. 35, 851 (1991). HPLC determn of active metabolites in leukemia cells: C. O. Rodriguez Jr. et al., J. Chromatogr. B 745, 421 (2000). Mechanism of action study: idem, et al., Blood 102, 1842 (2003). Clinical pharmacokinetics: D. F. Kisor et al., J. Clin. Oncol. 18, 995 (2000). Clinical evaluation in T-cell malignancies: S. L. Berg et al., ibid. 23, 3376 (2005). Review of pharmacology and clinical experience: D. F. Kisor, Ann. Pharmacother. 39, 1056-1063 (2005).

Chemical structure

Properties

mp 209-217° (dec). uv max (50 mM potassium phosphate buffer (pH 7.0)-ethanol (9:1, v/v)): 247.5, 279 nm (ε 9100, 9300). [α]D20 +55.9° (c = 0.27 in DMF). Slightly sol to sol in water.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Antimetabolites; Purine Analogs