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Arabinosylcytosine

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Book cover Antineoplastic and Immunosuppressive Agents

Abstract

Arabinosyleytosine (1-β-D-arabinofuranosylcytosine; cytosine arabinoside; cytosar; ara-C; cytarabine) is a member of a class of nucleosides in which D-arabinose constitutes the pentose sugar moiety. Thus, these compounds are analogs of ribo- nucleosides in which the hydroxyl group at the 2’-position is inverted. However, in most respects the arabinosides do not behave biologically as ribonucleoside analogs. Certain arabinosides are naturally occurring, both arabinosylthymine and arabinosyluracil (ara-U) having been isolated from the sponge Cryptotethya crypta, (Bergman and Feeney, 1951; Bergman and Burke, 1955). Cohen (1963) has reviewed some aspects of the occurrence, isolation, and relevance to chemotherapy of the arabinosides, and suggested a possible role for these nucleosides in aging. The same author in a later review (Cohen, 1966) has outlined methods for chemical synthesis of these compounds, the metabolism of ara-C and ara-U in bacteria, and some effects of the arabinosides on mammalian cells. Much of the pharmacological information regarding ara-C that was available through 1968 may be found briefly reviewed in an article on cancer chemotherapy by Sartorelli and Creasey (1969). Clinical brochures that include some information about the chemistry, antitumor activity in experimental systems, and preliminary data obtained in man, have been prepared by Livingston and Carter (1968) and the Upjohn Company (1970). Notari et al. (1972) have defined the stability of the drug under various storage conditions and found that at neutral pH the drug retains 90% of its potency after 6 months at room temperature.

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  1. William A. Creasey
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  1. Department of Pharmacology, Yale University School of Medicine, 06510, New Haven, Connecticut, USA

    Alan C. Sartorelli (Professor) (Professor)

  2. Laboratory of Chemical Pharmacology, National Cancer Institute, National Institutes of Health, 20014, Bethesda, Maryland, USA

    David G. Johns M.D.

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Creasey, W.A. (1975). Arabinosylcytosine. In: Sartorelli, A.C., Johns, D.G. (eds) Antineoplastic and Immunosuppressive Agents. Handbuch der experimentellen Pharmakologie / Handbook of Experimental Pharmacology, vol 38 / 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-65806-8_13

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