Multitargeted pyrimidine nucleoside carbamates, substituted with fluorine at both the base and the sugar moieties, are disclosed (see Formula I): where R=linear or branched alkyl (C1-7); R′=H, hydroxy protecting group; R″=H, phosphate ester, amino acid alkyl (C1-7) ester phoshoramidate, or phosphorodiamidate. The disclosed compounds are fluoropyrimidine prodrugs that are characterized by a novel combination of structural components that provide intracellular metabolites capable of 1) inhibiting several cellular enzymes required for the synthesis and proper functioning of DNA, and 2) causing DNA damage by misincorporation into DNA. By acting on multiple targets with different mechanisms of action, compounds of Formula I reduce the likelihood of the emergence of drug resistance, a major drawback of the use of nucleoside-based anticancer and antiviral drugs. Due to the metabolic activation profile of compounds of Formula I, characteristic adverse effects and potential lethality of the fluoropyrimidine class of anticancer drugs may be alleviated. Compounds and compositions of the present disclosure can be used in treatment of cancer and viral infections.