2'-Fluoro-2'-deoxyuridine CAS No. 784-71-4

Product Description

2'-Fluoro-2'-deoxyuridine (FdU) is a fluorinated nucleoside analog, where a fluorine atom replaces the hydroxyl group at the 2' position of the deoxyribose sugar in deoxyuridine. It has the chemical formula C₉H₁₁FN₂O₅ and its IUPAC name is 1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione. FdU acts as an antimetabolite, interfering with DNA/RNA synthesis, and is studied for its antiviral or anticancer activity, though it is less commonly used than 5-Fluoro-2'-deoxyuridine (FdUrd, Floxuridine). Unlike FdUrd, where the fluorine is at the 5-position of the uracil base and inhibits thymidylate synthase (TS), FdU has its fluorine at the 2' position of the sugar moiety, potentially affecting RNA function or acting as a chain terminator. It is used as a research tool in studying nucleoside metabolism and has shown some antiviral potential, although it is not a major drug in this area. In cancer research, FdU is less studied than 5-FU derivatives, but modifications may alter its biological activity.

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Product Use & Characteristics

Chemical Formula: C₉H₁₁FN₂O₅
Molecular Weight: 246.19 g/mol
IUPAC Name: 1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

Structural Features:

• Pyrimidine Base: Uracil (U)

• Sugar Part: 2'-deoxyribose with a fluorine atom replacing the hydroxyl group at the 2' position (–OH → –F)

Key Features:

• Acts as an antimetabolite, interfering with DNA/RNA synthesis.

• Fluorine substitution enhances stability against enzymatic degradation and affects base pairing and DNA/RNA function.

• May inhibit thymidylate synthase (TS) after conversion to its monophosphate form.

Uses

Research Tool:

• Used in studying nucleoside metabolism.

• Utilized in the design and synthesis of aptamers, antagomirs, and siRNA, enhancing stability against enzymatic degradation and improving target affinity.

Antiviral Research:

• Shows activity against certain viruses, such as herpes simplex virus 1 (HSV-1), by inhibiting viral replication.

• Potential for developing antiviral drugs, although it is not a major drug in this area.

Cancer Research:

• Studied for its antitumor/anticancer effects, particularly as a thymidylate synthase (TS) inhibitor.

• Used in therapeutic oligonucleotides to combat certain cancers, including prostate and breast cancer.

• Less studied than 5-FU derivatives, but modifications may alter biological activity.

Biochemical Labeling and Probe Design:

• Potential use as a probe in structural biology studies such as NMR and X-ray crystallography due to the presence of fluorine atoms.

As a Prodrug or Intermediate:

• Can be used to synthesize other more complex nucleoside drugs, such as Gemcitabine and Trifluridine.

Mechanism of Action

Primary Metabolite:

• Often metabolized to 5-fluorouracil (5-FU), which is then converted into fluorodeoxyuridine monophosphate (FdUMP).

Main Mechanisms:

• Thymidylate Synthase Inhibition: FdUMP acts as a "suicide inhibitor" of thymidylate synthase (TS), preventing the production of thymidine monophosphate (dTMP) and leading to "thymine-less death" in rapidly dividing cancer cells.

• Incorporation into DNA and RNA: 5-FU and its metabolites can be incorporated into both RNA and DNA, disrupting RNA processing and function, leading to faulty mRNA translation and impaired protein synthesis, and causing DNA strand breaks and faulty repair mechanisms.

Potential Side Effects

Gastrointestinal Issues:

• Nausea, vomiting, diarrhea (which can be severe), mouth sores (stomatitis), and stomach ulcers.

Bone Marrow Suppression:

• Low blood cell counts (leukopenia, thrombocytopenia, anemia), increasing the risk of infection, bleeding, and fatigue.

Liver-Related Effects:

• Elevated liver enzymes, and in some cases, more severe hepatic dysfunction or biliary damage (sclerosing cholangitis), especially with intra-arterial administration.

Dermatological Effects:

• Hair loss (alopecia) and hand-foot syndrome (redness, swelling, and pain on the palms and soles).

Other:

• Fever, dizziness, headache, and potential for genetic defects or harm to an unborn child.

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