Record Information |
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Version | 2.0 |
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Creation Date | 2014-09-11 05:16:06 UTC |
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Update Date | 2014-12-24 20:26:57 UTC |
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Accession Number | T3D4776 |
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Identification |
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Common Name | Fluorouracil |
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Class | Small Molecule |
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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. |
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Compound Type | - Amide
- Antimetabolite
- Antimetabolite, Antineoplastic
- Drug
- Immunosuppressive Agent
- Metabolite
- Organic Compound
- Organofluoride
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 5-Fluoracil | 5-Fluoropyrimidine-2,4-dione | 5-Fluorouracil | 5-Fluracil | 5-FU | Adrucil | Carac | Carzonal | Efudex | Efudix | Efurix | Fluoro Uracil | Fluoroplex | Fluorouracilo | Fluorouracilum | Fluouracil | Ftoruracil | FU |
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Chemical Formula | C4H3FN2O2 |
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Average Molecular Mass | 130.077 g/mol |
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Monoisotopic Mass | 130.018 g/mol |
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CAS Registry Number | 51-21-8 |
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IUPAC Name | 5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione |
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Traditional Name | fluorouracil |
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SMILES | OC1=NC=C(F)C(O)=N1 |
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InChI Identifier | InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) |
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InChI Key | InChIKey=GHASVSINZRGABV-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Diazines |
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Sub Class | Pyrimidines and pyrimidine derivatives |
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Direct Parent | Halopyrimidines |
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Alternative Parents | |
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Substituents | - Hydroxypyrimidine
- Halopyrimidine
- Aryl halide
- Aryl fluoride
- Heteroaromatic compound
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organofluoride
- Organohalogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | |
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Pathways | Name | SMPDB Link | KEGG Link |
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Capecitabine Pathway | Not Available | Not Available | Fluorouracil Pathway | Not Available | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 282-283°C | Boiling Point | Not Available | Solubility | 1.11E+004 mg/L (at 22°C) | LogP | -0.89 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-001i-9800000000-a3301f9fea9145d07480 | View in MoNA |
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GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-001i-0900000000-76691bd3cba2765d3687 | View in MoNA |
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GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-001i-0900000000-d801d8209e9a5aa4830b | View in MoNA |
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GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-0002-0900000000-7521695ae4a96b4a5a98 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-001i-9800000000-a3301f9fea9145d07480 | View in MoNA |
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GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-001i-0900000000-76691bd3cba2765d3687 | View in MoNA |
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GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-001i-0900000000-d801d8209e9a5aa4830b | View in MoNA |
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GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-0002-0900000000-7521695ae4a96b4a5a98 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-9600000000-8c2b278c2716f3e6b27c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-c639ed1b5365f368b59c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-1a7a70df49a360e1458c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-d89f2d944fe1cac39f55 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-50b33770c08680863cf6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-cd5bef421a05073cb1f3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-3900000000-ec9c9e1dfc9a16f625a2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-df98a4532ca49a0a0436 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-50b33770c08680863cf6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-50b33770c08680863cf6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-df98a4532ca49a0a0436 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-b117f5fa58c8f98b5c15 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-9000000000-f3e71a41b6d4417d33fd | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-001i-9200000000-29362607b7c48b82973c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-001i-0900000000-693d492f316b0c7d5ed5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-001i-1900000000-0c0ee9469bf49688c5d2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-001i-1900000000-0cecca0d265e958e19d7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-03e9-1900000000-46f20f71dbc96630cee7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-03di-1900000000-4330f38956afe6c47636 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-03di-2900000000-f935071622b89177697b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-1900000000-3fa9b91447db7dc7ba77 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-9800000000-32bf878787078ce9d817 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-9000000000-3ef559051a5b99c94b29 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-4900000000-82764fbca3290816328d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000f-9100000000-2da5eb3c925c027b5022 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-1cf432837297c55833a5 | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-001i-9400000000-b8247c8f5c45b12efaa6 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | 28-100% |
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Mechanism of Toxicity | 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, N5дус10-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. |
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Metabolism | Hepatic. The catabolic metabolism of fluorouracil results in degradation products ( e.g., CO2, urea and alpha-fluoro-beta-alanine) which are inactive.
Route of 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.
Half Life: 10-20 minutes |
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Toxicity Values | LD50=230mg/kg (orally in mice) |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. (3) |
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Uses/Sources | 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. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00544 |
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HMDB ID | HMDB14684 |
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PubChem Compound ID | 3385 |
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ChEMBL ID | CHEMBL185 |
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ChemSpider ID | 3268 |
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KEGG ID | C07649 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 46345 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | URF |
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ACToR ID | Not Available |
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Wikipedia Link | Fluorouracil |
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References |
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Synthesis Reference | Leroy B. Townsend, Robert A. Earl, Steven J. Manning, “Method of synthesizing 1-(tetrahydro-2-furanyl)-5-fluorouracil.” U.S. Patent US3960864, issued October, 1969. |
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MSDS | Link |
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General References | - Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. [12724731 ]
- Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. [15032669 ]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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