5-fluorouracil   Click here for help

GtoPdb Ligand ID: 4789

Synonyms: Adrucil® | Carac®
Approved drug PDB Ligand
5-fluorouracil is an approved drug (FDA (1962))
Compound class: Synthetic organic
Comment: Fluoroacil is the active metabolite of the prodrugs capecitabine and floxuridine.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 65.72
Molecular weight 130.02
XLogP -0.02
No. Lipinski's rules broken 0
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Canonical SMILES Fc1c[nH]c(=O)[nH]c1=O
Isomeric SMILES Fc1c[nH]c(=O)[nH]c1=O
InChI InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
No information available.
Summary of Clinical Use Click here for help
Fluorouracil may be used topically to treat actinic or solar keratoses and certain superficial basal cell carcinomas. Fluorouracil is given by injection as palliative therapy for various cancers of the digestive system.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
5-fluorouracil intereferes with DNA and RNA synthesis. The primary effect is on DNA synthesis, where the fluoroacil mimics normal pyrimidines, and prevents their incorporation into DNA during the S phase of the cell cycle, thus initiating cell death.