Fluorouracil

CAS No:
51-21-8 Category:
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Product Details:

  • CAS No: 51-21-8
  • AHFC code: 84:92.00 10:00.00
  • Synonyms:
  • ATC Code: L01BC02
  • Chemical Formula: C21H28O4
  • Molecular Weight: 130.0772
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00544 (APRD00516, EXPT03204)
  • SMILES: FC1=CNC(=O)NC1=O
  • InChl: GHASVSINZRGABV-UHFFFAOYSA-N
  • PubChem: 3385
  • IUPAC: 5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione

Additional Details

Indication:
For the topical treatment of multiple actinic or solar keratoses. In the 5% strength it is also useful in the treatment of superficial basal cell carcinomas when conventional methods are impractical, such as with multiple lesions or difficult treatment sites. Fluorouracil injection is indicated in the palliative management of some types of cancer, including colon, esophageal, gastric, rectum, breast, biliary tract, stomach, head and neck, cervical, pancreas, renal cell, and carcinoid.
Pharmacodynamics:
Fluorouracil is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine – which become the building blocks of DNA. They prevent these substances from becoming incorporated into DNA during the "S" phase (of the cell cycle), stopping normal development and division. Fluorouracil blocks an enzyme which converts the cytosine nucleotide into the deoxy derivative. In addition, DNA synthesis is further inhibited because Fluorouracil blocks the incorporation of the thymidine nucleotide into the DNA strand.
Mode of Action:
The precise mechanism of action has not been fully determined, but the main mechanism of fluorouracil is thought to be the binding of the deoxyribonucleotide of the drug (FdUMP) and the folate cofactor, N5_10-methylenetetrahydrofolate, to thymidylate synthase (TS) to form a covalently bound ternary complex. This results in the inhibition of the formation of thymidylate from uracil, which leads to the inhibition of DNA and RNA synthesis and cell death. Fluorouracil can also be incorporated into RNA in place of uridine triphosphate (UTP), producing a fraudulent RNA and interfering with RNA processing and protein synthesis.
Metabolism:
Hepatic
Toxicity:
LD50=230mg/kg (orally in mice)
General Reference:
Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. Pubmed Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. Pubmed
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