CAS 17199-43-8

5'-deoxy-5'fluorothymidine

Description:

5'-Deoxy-5'-fluorothymidine, commonly referred to as FTD, is a nucleoside analog of thymidine where a fluorine atom replaces the hydroxyl group at the 5' position. This modification enhances its stability and alters its biological activity, making it a valuable compound in medicinal chemistry, particularly in cancer treatment. FTD is primarily utilized as an antiviral and anticancer agent, functioning as a substrate for DNA synthesis and inhibiting the activity of thymidine kinases. Its mechanism of action involves incorporation into DNA, leading to chain termination during replication. The compound is typically administered in a phosphorylated form, which is more biologically active. In terms of physical properties, FTD is a white to off-white solid, soluble in water and organic solvents, and has a relatively low melting point. Its pharmacokinetics and metabolism are significant areas of research, as they influence its therapeutic efficacy and safety profile. Overall, 5'-deoxy-5'-fluorothymidine represents an important tool in the development of targeted therapies for various malignancies.

Formula: C₁₀H₁₃FN₂O₄

InChI: InChI=1/C10H13FN2O4/c1-5-4-13(10(16)12-9(5)15)8-2-6(14)7(3-11)17-8/h4,6-8,14H,2-3H2,1H3,(H,12,15,16)

InChI key: InChIKey=MYWVPKQWFIVGJZ-XLPZGREQSA-N

SMILES: O=C1N([C@@H]2O[C@H](CF)[C@@H](O)C2)C=C(C)C(=O)N1

Synonyms:

• 1-(2,5-dideoxy-5-fluoropentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione
• 2',5'-Dideoxy-5'-fluorothymidine
• 2′,5′-Dideoxy-5′-fluorothymidine
• 5'-Fluorodeoxythymidine
• 5′-Fluoro-5′-deoxythymidine
• Nsc 142845
• Thymidine, 5'-deoxy-5'-fluoro- (8CI)(9CI)
• Thymidine, 5′-deoxy-5′-fluoro-
• 5'-Deoxy-5'fluorothymidine
• 5'-Deoxy-5'-fluorothymidine
• 5′-Deoxy-5′-fluorothymidine

5'-Deoxy-5'-fluorothymidine

CAS: 17199-43-8

5'-Deoxy-5'-fluorothymidine is a cytotoxic agent that inhibits the synthesis of DNA by binding to the enzyme thymidylate synthase and preventing the formation of thymine nucleotide. 5'-Deoxy-5'-fluorothymidine has shown to be effective against herpes simplex virus, murine bone, and tissue culture cells. This drug also inhibits cellular proliferation in vitro and can be used in chemotherapy treatment. 5'-Deoxy-5'-fluorothymidine is synthesized from guanine by an enzyme called deoxyguanosine kinase. The biosynthesis of this drug involves two steps: conversion of guanine to xanthosine monophosphate (XMP) and conversion of XMP to 5'-deoxy-5'-fluorothymidine (dFTP).

Formula: C₁₀H₁₃FN₂O₄

Purity: Min. 95%

Molecular weight: 244.22 g/mol

Ref: 3D-ND78221