5-Fluorouracil
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Category | Enzyme inhibitors |
Catalog number | BBF-04068 |
CAS | 51-21-8 |
Molecular Weight | 130.08 |
Molecular Formula | C4H3FN2O2 |
Purity | >98% |
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Description
Fluorouracil (5-Fluoracil, 5-FU) is a DNA/RNA synthesis inhibitor, which interrupts nucleotide synthetic by inhibiting thymidylate synthase (TS).
Specification
Synonyms | 5-FU; Fluorouracil; Adrucil |
Storage | Store at RT |
IUPAC Name | 5-fluoro-1H-pyrimidine-2,4-dione |
Canonical SMILES | C1=C(C(=O)NC(=O)N1)F |
InChI | InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) |
InChI Key | GHASVSINZRGABV-UHFFFAOYSA-N |
Properties
Appearance | White Crystalline Powder |
Boiling Point | 401.4±48.0 °C at 760 mmHg |
Melting Point | 282-286°C (dec.)(lit.) |
Flash Point | 196.5±29.6 °C |
Density | 1.53 g/cm3 |
Solubility | Soluble in DMF, DMSO, methanol |
LogP | -0.89 |
Toxicity
Carcinogenicity | 3, not classifiable as to its carcinogenicity to humans. |
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, 5,10-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. |
Toxicity | LD50 = 230mg/kg (orally in mice). |
Reference Reading
Spectrum
GC-MS Spectrum - EI-B (Non-derivatized)
Experimental Conditions
Ionization Mode: positive
Chromatography Type: GC
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C4H3FN2O2
Molecular Weight (Monoisotopic Mass): 130.0179 Da
Molecular Weight (Avergae Mass): 130.0772 Da
LC-MS/MS Spectrum - LC-ESI-ITFT , negative
Experimental Conditions
Ionization Mode: negative
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C4H3FN2O2
Molecular Weight (Monoisotopic Mass): 130.0179 Da
Molecular Weight (Avergae Mass): 130.0772 Da
Mass Spectrum (Electron Ionization)
1H NMR Spectrum
Experimental Conditions
Instrument Type: JEOL
Nucleus: 1H
Frequency: 300 MHz
Chemical Shift Reference: TMS
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2