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5'-deoxy-5-Fluorocytidine

Catalog No.
C3513
A cytidine analog that can interfere with DNA methyltransferase activity.
Grouped product items
SizePriceStock Qty
1g
$50.00
In stock
For scientific research use only and should not be used for diagnostic or medical purposes.

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Background

5'-deoxy-5-Fluorocytidine (CAS No.: 66335-38-4) is a cytidine analog and key intermediate metabolite in the biotransformation of the prodrug capecitabine, widely studied in the context of antimetabolite-based cancer therapeutics and epigenetic regulation. Formed in the liver via carboxylesterase-mediated conversion of capecitabine, this compound undergoes sequential enzymatic deamination by cytidine deaminase to yield 5'-deoxy-5-fluorouridine, which is further converted by thymidine phosphorylase in tumor tissues to the active cytotoxic agent 5-fluorouracil, thereby contributing to selective antitumor activity. Mechanistically, as a nucleoside analog, it can be incorporated into nucleic acids and is associated with disruption of DNA synthesis and modification processes, while also being implicated in interference with DNA methyltransferase activity and modulation of DNA methylation pathways. Its biological effects are primarily indirect, with cytotoxicity arising after metabolic activation, and activity is typically observed in the nanomolar to micromolar range depending on cellular context and enzymatic expression profiles. 5'-deoxy-5-Fluorocytidine is commonly utilized in biochemical and pharmacological studies investigating fluoropyrimidine metabolism, tumor-selective drug activation, and epigenetic regulation, as well as in in vitro cell-based assays and in vivo tumor models of colorectal, breast, and non-small cell lung cancers, where experimental concentrations and dosing regimens vary according to specific study designs and objectives.

Chemical Properties

Physical AppearanceA solid
Storage-20°C
M.Wt245.21
Cas No.66335-38-4
FormulaC9H12FN3O4
Synonyms5'-DFCR
Solubilityinsoluble in EtOH; ≥40.1 mg/mL in H2O; ≥41.3 mg/mL in DMSO
Chemical Name4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidin-2(1H)-one
Canonical SMILESC[C@H]1O[C@@H](N2C(N=C(N)C(F)=C2)=O)[C@H](O)[C@@H]1O
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

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