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Arabinosylcytosine

  • Chapter
Modes and Mechanisms of Microbial Growth Inhibitors

Part of the book series: Antibiotics ((ANTIBIOTICS,volume 6))

Abstract

Arabinosylcytosine (l-β-D-arabinofuranosylcytosine; cytosine arabinoside; cytarabine; ara C) belongs to a class of nucleosides with D-arabinose as the pentose sugar moiety. The inversion of the 2′-hydroxyl group as compared with ribonucleosides (Fig. 1) conveys markedly different properties, and in many respects the arabinosides are biologically more akin to 2′-deoxyribonucleosides. Several arabinosides, including arabinosylthymine and arabinosyluracil (ara U), occur naturally in the sponge Cryptotethya crypta(Bergmann and Feeney, 1951; Bergmann and Burke, 1955), and Cohen (1963) has reviewed the possible biological significance of such nucleosides. The arabinosides that have shown antitumor activity, however, have been obtained synthetically, beginning with ara C in 1959 (Walwick et al., 1959). Ara C is now the most active antimetabolite for inducing remissions in nonlymphocytic leukemia (Ellison1968), and in combination with anthracyclines, such as daunorubicin, leads to complete remission rates in the range of 60% to 70% (Kremer, 1975). Arabinosyladenine (vidarabine; ara A) was originally synthesized as an anticancer drug (Leeet al., 1960), but has since acquired a more important role as an antiviral agent, particularly for viruses of the herpes group (Pavan-Langston, 1975).

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  1. W. A. Creasey
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  1. Division of Communicable Diseases and Immunology, Walter Reed Army Institute of Research, 20307, Washington, D.C., USA

    Fred E. Hahn Ph.D.

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Creasey, W.A. (1983). Arabinosylcytosine. In: Hahn, F.E. (eds) Modes and Mechanisms of Microbial Growth Inhibitors. Antibiotics, vol 6. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68946-8_2

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