Fluorouracil

• Catalog No.: DB00544
• CAS Number: 51-21-8
• M. F.: C4H3FN2O2
• M. W.: 130.0772232

SYNONYMS

• IUPAC name: 5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: fluorouracil
• Brand Name: 5 Fluorouracil; Phtoruracil; Effluderm; Queroplex; Adrucil; Carzonal; Efudex; Efudix; Efurix; FU; Fluoroblastin; Fluri; Fluro Uracil; Timazin; URF; Ulup; Arumel; Carac; Fluoroplex; Fluracil; Fluracilum; Fluril; Ftoruracil; Kecimeton; Phthoruracil

DATABASE IDS

• PubChem SID: 46508557
• CAS Number: 51-21-8
• PubChem CID: 3385

PROPERTIES

• Hydrophobicity(logP): -0.8
• Solubility: < 0.1 g/100 mL at 19 °C

DETAILS

Description (English)

• Drug Groups: approved
• Description: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the thymidylate synthetase conversion of deoxyuridylic acid to thymidylic acid. [PubChem]
• 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.
• Pharmacology: 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.
• Toxicity: LD₅₀=230mg/kg (orally in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: 28-100%
• Half Life: 10-20 minutes
• Protein Binding: 8-12%
• Elimination: Seven percent to 20% of the parent drug is excreted unchanged in the urine in 6 hours; of this over 90% is excreted in the first hour.; The remaining percentage of the administered dose is metabolized, primarily in the liver.
• References: 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]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• 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