2784. Cytarabine

Nomenclature

CAS number: 147-94-4
4-Amino-1-β-d-arabinofuranosyl-2(1H)-pyrimidinone; 1-β-d-arabinofuranosylcytosine; Ara-C; β-cytosine arabinoside; aracytidine; CHX-3311; U-19920; Alexan (Ebewe); Aracytine (Pfizer); Cytosar (Pharmacia & Upjohn); Depocyte (Pharmacia); Udicil (Pharmacia & Upjohn).
C9H13N3O5; mol wt 243.22.
C 44.44%, H 5.39%, N 17.28%, O 32.89%.

Description and references

Nucleoside analog; converted by cellular kinases into the active metabolite, AraCTP. Prepn: J. H. Hunter, US 3116282 (1963 to Upjohn); T. Y. Shen et al., J. Org. Chem. 30, 835 (1965). NMR soln structure of Ara-C within a DNA dodecamer: B. I. Schweitzer et al., Biochemistry 33, 11460 (1994). Crystal structure of complex with human topoisomerase I: J. E. Chrencik et al., J. Biol. Chem. 278, 12461 (2003). Clinical pharmacology and toxicology: R. C. Donehower et al., Cancer Treat. Rep. 70, 1059 (1986). Symposium on clinical pharmacology, pharmacokinetics and efficacy in leukemia: Scand. J. Haematol. 36, Suppl. 44, 1-74 (1986). Clinical pharmacokinetics of lipsomal formulations: A. Hamada et al., Clin. Pharmacokinet. 41, 705 (2002). Review of development of a high dose treatment for acute myeloid leukemia: R. L. Capizzi, Invest. New Drugs 14, 249-256 (1996); of cellular metabolism and mechanism of action: S. Grant, Adv. Cancer Res. 72, 197-233 (1998).

Chemical structure

Properties

Crystals from ethanol, mp 212-213°. [α]D24 +153° (c = 0.5 in water). uv max at pH 2: 281.0, 212.5 nm (ε 13171, 10230); at pH 12: 272.5 nm (ε 9259). Freely sol in water; slightly sol in alcohol, chloroform.

Therapeutic Category

Antineoplastic.

Therapeutic Category (Veterinary)

Antineoplastic.

Keywords

Antineoplastic; Antimetabolites; Pyrimidine Analogs