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    Subjects/Pharmacology/Antimetabolites
    Antimetabolites
    medium
    pill Pharmacology

    Which feature best distinguishes 5-fluorouracil (5-FU) from methotrexate among antimetabolite chemotherapy agents?

    A. Requires dihydrofolate reductase inhibition as primary mechanism
    B. Requires intracellular phosphorylation by deoxycytidine kinase for activation
    C. Causes selective toxicity by targeting purine synthesis exclusively
    D. Acts as a thymidylate synthase inhibitor after conversion to active metabolite

    Explanation

    ## Mechanism Comparison: 5-FU vs Methotrexate ### 5-Fluorouracil (5-FU) Mechanism **Key Point:** 5-FU is a **pyrimidine antimetabolite** that requires metabolic activation to its active forms: FdUMP and FUTP. 1. Converted to FdUMP (fluorodeoxyuridine monophosphate) via multiple enzymatic steps 2. FdUMP inhibits **thymidylate synthase** — the enzyme that converts dUMP to dTMP 3. This blocks DNA synthesis by depleting thymidine nucleotides 4. Also incorporates into RNA (FUTP form), disrupting transcription ### Methotrexate (MTX) Mechanism **Key Point:** Methotrexate is a **folate antagonist** that directly inhibits **dihydrofolate reductase (DHFR)**. 1. Binds competitively to DHFR with high affinity 2. Blocks conversion of dihydrofolate → tetrahydrofolate (THF) 3. Depletes the THF cofactor pool needed for one-carbon transfer reactions 4. Inhibits both purine and pyrimidine synthesis (broader effect) ### Discriminating Feature Table | Feature | 5-FU | Methotrexate | |---------|------|---------------| | **Primary Target** | Thymidylate synthase | Dihydrofolate reductase | | **Nucleotide Affected** | Pyrimidines (primarily dTMP) | Both purines and pyrimidines | | **Mechanism** | Inhibits dUMP → dTMP | Blocks THF regeneration | | **Activation Required** | Yes (multiple steps) | No (active as given) | | **Cell Cycle Phase** | S-phase dependent | All phases | **High-Yield:** The **thymidylate synthase inhibition** is the hallmark and distinguishing feature of 5-FU among antimetabolites. This is tested frequently because it explains why 5-FU causes selective DNA synthesis block. **Clinical Pearl:** 5-FU toxicity (mucositis, diarrhea) is often managed with **leucovorin (folinic acid)** rescue, which bypasses the DHFR block — this is why 5-FU is often given with leucovorin in clinical practice, despite having a different primary target than MTX. [cite:KD Tripathi 8e Ch 65]

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