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
1.Irinotecan Plus Gemcitabine and Fluorouracil in Advanced Biliary Tract Cancer: A Retrospective Study.
Endlicher E1, Schnoy E, Troppmann M, Rogler G, Messmann H, Klebl F, Gelbmann C, Kullmann F. Digestion. 2016 Apr 19;93(3):229-233. [Epub ahead of print]
BACKGROUND: Since 2010, combination therapy with gemcitabine and cisplatin is the standard treatment for patients with biliary tract cancer (BTC) based on the ABC-02 trial. However, treatment after first-line progression is less clearly defined. We therefore retrospectively analyzed the efficacy of a 3-drug chemotherapy regimen in patients with advanced BTC.
2.Rapid Extracorporeal Membrane Oxygenation Overcomes Fulminant Myocarditis Induced by 5‑Fluorouracil.
Amraotkar AR, Pachika A, Grubb KJ, DeFilippis AP. Tex Heart Inst J. 2016 Apr 1;43(2):178-82. doi: 10.14503/THIJ-15-5100. eCollection 2016.
Fulminant myocarditis is a rare but potentially life-threatening illness caused by 5-fluorouracil cardiotoxicity. Data supporting the use of extracorporeal membrane oxygenation for the treatment of fulminant myocarditis are limited. A 49-year-old, previously healthy white man, recently diagnosed with anal squamous cell carcinoma, developed severe chest pain hours after completing his first 96-hour intravenous 5-fluorouracil treatment. Over a period of 3 days from onset of symptoms, the patient developed cardiogenic shock secondary to fulminant myocarditis induced by 5-fluorouracil cardiotoxicity. This required emergency initiation of extracorporeal membrane oxygenation. The patient's systolic function recovered by day 5, and on the 17th day he was discharged in hemodynamically stable condition, without symptoms of heart failure. This case shows the importance of prompt recognition of cardiogenic shock secondary to 5-fluorouracil-induced myocarditis and how the immediate initiation of extracorporeal membrane oxygenation can restore adequate tissue perfusion, leading to myocardial recovery and ultimately the survival of the patient.
3.Combination of Two Targeted Medications (Bevacizumab Plus Cetuximab) Improve the Therapeutic Response of Pancreatic Carcinoma.
Tai CJ1, Huang MT, Wu CH, Wang CK, Tai CJ, Chang CC, Hsieh CI, Chang YJ, Wu CJ, Kuo LJ, Wei PL, Chen RJ, Chiou HY. Medicine (Baltimore). 2016 Apr;95(15):e3259. doi: 10.1097/MD.0000000000003259.
The objective of this study is to evaluate the efficacy and safety profiles of the targeted medications, bevacizumab and cetuximab, in combination with cytostatic drugs in patients with locally advanced or metastatic pancreatic cancer.In this retrospective phase 2 study, a total of 59 patients with pancreatic cancer were recruited and received conventional (gemcitabine, cisplatin, and fluorouracil) or targeted regimen (conventional plus bevacizumab and cetuximab for the first cycle) in 2-week intervals for four cycles. The primary end-point for this study was the overall response rate. Secondary end-points were progression-free survival and the safety profiles of the combined therapy.The median time-to-progression and overall survival were 3 and 7 months, respectively, in the conventional treatment group as well as 11 and 13 months, respectively, in the targeted medications treatment group. The most common adverse events in both treatment groups were nausea and vomiting.
4.Cytotoxicity and Cellular uptake of 5-Fluorouracil loaded methylcellulose nanohydrogel for treatment of oral cancer.
Dalwadi C1, Patel G2. Curr Drug Deliv. 2016 Apr 17. [Epub ahead of print]
The objective of the study was to investigate the cytotoxicity and cellular uptake of prepared 5-Fluorouracil (5-FU) nanohydrogel formulation using KB oral cancer cell line and VERO fibroblast cell line. The biodegradable thermoresponsive modified methylcellulose (MMC) polymer was used for the preparation of nanohydrogel whereas it shows sol-gel phase transition at 36˚C to 40˚C. The physical crosslinking method was used followed by probe sonication for the preparation of 5-FU loaded MMC nanohydrogel. Mechanism of crosslinking was studied by FT-IR and SEM. These experimental techniques explained physical crosslinking viz. H-bonding phenomenon with the interconnected porous structure of nanoscale pore size. Cytotoxicity assay in the concentration range from 1 µg/ml to 2000µg/ml shows IC50 value at around 250µg/ml. This nanohydrogel shows concentration dependent toxicity to the cancer cells while they were less toxic to normal fibroblast VERO cells.
Spectrum
GC-MS Spectrum - EI-B (Non-derivatized)
Experimental Conditions
Instrument Type: EI-B
Ionization Mode: positive
Chromatography Type: GC
Ionization Mode: positive
Chromatography Type: GC
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
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
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
Instrument Type: LC-ESI-ITFT
Ionization Mode: negative
Ionization Mode: negative
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
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
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
Solvent: DMSO-d6+HCl
Instrument Type: JEOL
Nucleus: 1H
Frequency: 300 MHz
Chemical Shift Reference: TMS
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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
