Cytarabine
Title: Cytarabine
CAS Registry Number: 147-94-4
CAS Name: 4-Amino-1-b-D-arabinofuranosyl-2(1H)-pyrimidinone
Additional Names: 1-b-D-arabinofuranosylcytosine; Ara-C; b-cytosine arabinoside; aracytidine
Manufacturers' Codes: CHX-3311; U-19920
Trademarks: Alexan (Ebewe); Aracytine (Pfizer); Cytosar (Pharmacia & Upjohn); Depocyte (Pharmacia); Udicil (Pharmacia & Upjohn)
Molecular Formula: C9H13N3O5
Molecular Weight: 243.22
Percent Composition: C 44.44%, H 5.39%, N 17.28%, O 32.89%
Literature 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). 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).
Properties: Crystals from ethanol, mp 212-213°. [a]D24 +153° (c = 0.5 in water). uv max at pH 2: 281.0, 212.5 nm (e 13171, 10230); at pH 12: 272.5 nm (e 9259).
Melting point: mp 212-213°
Optical Rotation: [a]D24 +153° (c = 0.5 in water)
Absorption maximum: uv max at pH 2: 281.0, 212.5 nm (e 13171, 10230); at pH 12: 272.5 nm (e 9259)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs.

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