Arabinocytidine, 阿糖胞苷

1-(b-D-Arabinofuranosyl)cytosine

Cytarabine is also know as cytosine arabinoside (ara-C) and is a chemotherapy drug that works by inhibiting DNA synthesis. It acts as a nucleoside analogue, which is incorporated into the growing DNA chain during replication. Cytarabine combines a cytosine base with an arabinose sugar (1β-arabinofuranosylcytosine) and is an analog for human deoxycytosine. Cytarabine interferes with DNA synthesis as it is rapidly converted to cytosine arabinoside triphosphate, damaging DNA when cells are in the syntheis phase (S phase). Tumor cells which are highly mitotic and growing rapidly are therefore prefertially targeted. Cytarabine also inhibits nucleotide reductase enzymes as well as nuclear polymerases, leading to interruption and inhibition of synthesis, strand breaks and cell death.

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.

COA:

Name: Cytosine β-D-Arabinofuranoside；Arabinocytidine       

CAS: 147-94-4       M.F.: C₉H₁₃N₃O₅                      M.W._: 243.22    

References:

1. Donehower RC, et al., Cancer Treat. Rep. 1986, 70, p1059