2337. Cladribine

Nomenclature

CAS number: 4291-63-8
2-Chloro-2′-deoxyadenosine; 2-chloro-6-amino-9-(2-deoxy-β-d-erythro-pentofuranosyl)purine; 2-chlorodeoxyadenosine; 2-CdA; CldAdo; NSC-105014-F; Leustatin (Ortho Biotech).
C10H12ClN5O3; mol wt 285.69.
C 42.04%, H 4.23%, Cl 12.41%, N 24.51%, O 16.80%.

Description and references

Substituted purine nucleoside with antileukemic activity. Prepn as intermediate in synthesis of 2-deoxynucleosides: H. Venner, Ber. 93, 140 (1960); M. Ikehara, H. Tada, J. Am. Chem. Soc. 85, 2344 (1963); eidem, ibid. 87, 606 (1965). Synthesis and biological activity: L. F. Christensen et al., J. Med. Chem. 15, 735 (1972). Stereospecific synthesis: Z. Kazimierczuk et al., J. Am. Chem. Soc. 106, 6379 (1984); R. K. Robins, G. R. Revankar, EP 173059; eidem, US 4760137 (1986, 1988 both to Brigham Young Univ.). Specific toxicity to lymphocytes: D. A. Carson et al., Proc. Natl. Acad. Sci. USA 77, 6865 (1980); eidem, Blood 62, 737 (1983). Mechanism of action: S. Seto et al., J. Clin. Invest. 75, 377 (1985). Clinical evaluation in chronic lymphocytic leukemia: L. D. Piro et al., Blood 72, 1069 (1988); in hairy cell leukemia: eidem, N. Engl. J. Med. 322, 1117 (1990).

Chemical structure

Properties

Crystals from water, softens at 210-215°, solidifies and turns brown (Christensen). Also reported as crystals from ethanol, mp 220° (softens), resolidifies, turns brown and does not melt below 300° (Kazimierczuk). [α]D25 -18.8° (c = 1 in DMF). uv max in 0.1N NaOH: 265 nm; in 0.1N HCl: 265 nm.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Antimetabolites; Purine Analogs