References of (2R,3S,5R)-5-(6-amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
Title: Cladribine
CAS Registry Number: 4291-63-8
CAS Name: 2-Chloro-2￠-deoxyadenosine
Synonyms: 2-chloro-6-amino-9-(2-deoxy-b-D-
erythro-pentofuranosyl)purine; 2-chlorodeoxyadenosine; 2-CdA; CldAdo
Manufacturers' Codes: NSC-105014-F
Trademarks: Leustatin (Ortho Biotech)
Molecular Formula: C10H12ClN5O3
Molecular Weight: 285.69
Percent Composition: C 42.04%, H 4.23%, Cl 12.41%, N 24.51%, O 16.80%
Literature 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).
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). [a]D25 -18.8° (c = 1 in DMF). uv max in 0.1
N NaOH: 265 nm; in 0.1
N HCl: 265 nm.
Melting point: mp 220° (softens), resolidifies, turns brown and does not melt below 300°
Optical Rotation: [a]D25 -18.8° (c = 1 in DMF)
Absorption maximum: uv max in 0.1
N NaOH: 265 nm; in 0.1
N HCl: 265 nm
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Purine Analogs.
