Description
A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.
Chemical properties
| Chemical formula | Net charge | Average mass |
|---|---|---|
| C4H3FN2O2 | 0 | 130.07730 |
Nomenclature
| IUPAC | SMILES | InChI | InChIKey | Synonyms |
|---|---|---|---|---|
| 5-fluoropyrimidine-2,4(1H,3H)-dione, 5-fluorouracil | Fc1c[nH]c(=O)[nH]c1=O | InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) | GHASVSINZRGABV-UHFFFAOYSA-N |
|
Citations
- Glavas-Dodov, M, et al. 2004. 5-Fluorouracil in topical liposome gels for anticancer treatment--formulation and evaluation. Acta Pharmaceutica (Zagreb, Croatia). 53(4).
- Lawrence, TS, et al. 2003. The mechanism of action of radiosensitization of conventional chemotherapeutic agents. Seminars in Radiation Oncology. 13(1).
- Yasumatsu, R, et al. 2008. Correlations between thymidylate synthase expression and chemosensitivity to 5-fluorouracil, cell proliferation and clinical outcome in head and neck squamous cell carcinoma. Chemotherapy. 55(1).
- Yoshisue, K, et al. 2001. Effects of 5-fluorouracil on the drug-metabolizing enzymes of the small intestine and the consequent drug interaction with nifedipine in rats. The Journal of Pharmacology and Experimental Therapeutics. 297(3).