4831 T3D4776 Fluorouracil 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. 51-21-8 3385 C4H3FN2O2 White powder. 282-283°C 1.11E+004 mg/L (at 22°C) 28-100% 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. 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 LD<sub>50</sub>=230mg/kg (orally in mice) 3, not classifiable as to its carcinogenicity to humans. (L135) 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. 2014-09-11T05:16:06Z 2014-12-24T20:26:57Z Fluorouracil C07649 46345 DB00544 URF true OC1=NC=C(F)C(O)=N1 C4H3FN2O2 InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) InChIKey=GHASVSINZRGABV-UHFFFAOYSA-N 130.0772 130.017855555 Exogenous Solid -0.89 HMDB14684 CHEMBL185 3268 <p>Leroy B. Townsend, Robert A. Earl, Steven J. Manning, &#8220;Method of synthesizing 1-(tetrahydro-2-furanyl)-5-fluorouracil.&#8221; U.S. Patent US3960864, issued October, 1969.</p>