(RS)-tegafur

Also known as MJF-12264, 1-(2-tetrahydrofuryl)-5-fluorouracil, tegafur

Tegafur is a chemotherapeutic prodrug of 5-fluorouracil (5-FU) used in the treatment of cancers. It is a component of the combination drug tegafur/uracil. When metabolised, it becomes 5-FU.

Chemical data

Formula: C8H9FN2O3
Molecular weight: 200.17 g/mol
IUPAC name: 5-fluoro-1-(oxolan-2-yl)pyrimidine-2,4-dione
SMILES: C1CC(OC1)N2C=C(C(=O)NC2=O)F
InChIKey: WFWLQNSHRPWKFK-UHFFFAOYSA-N
XLogP: -0.3
Polar surface area: 58.6 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
Indications: neoplasm, head and neck squamous cell carcinoma, hepatocellular carcinoma, colorectal adenocarcinoma

via ChEMBL · EBI

Research

21 papers

Efficacy and safety of RS plus bevacizumab versus RS plus fruquintinib as the third-line therapy in patients with refractory metastatic colorectal cancer: A real-world propensity score matching study.Journal of evidence-based medicine · 2024
The pharmacology of ftorafur (R, S-1-(tetrahydro-2-furanyl)-5-fluorouracil.Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer · 1981
Effect of CYP2A6 genetic polymorphism on the metabolic conversion of tegafur to 5-fluorouracil and its enantioselectivity.Drug metabolism and disposition: the biological fate of chemicals · 2014
Stereoselective metabolism of ftorafur (R,S-1-(tetrahydro-2-furanyl)-5-fluorouracil).Cancer chemotherapy and pharmacology · 1981
Real‑world treatment outcomes among patients with metastatic pancreatic cancer in Japan: The Tokushukai real‑world data project.Molecular and clinical oncology · 2023

via PubMed

Wikidata facts

Subclass of: medication
Mass: 200.05972

Show 6 more facts

chemical formula: C₈H₉FN₂O₃
route of administration: topical medication
World Health Organisation international non-proprietary name: tegafur
canonical SMILES: C1CC(OC1)N2C=C(C(=O)NC2=O)F
Commons category: Tegafur
significant drug interaction: acenocoumarol

Sources (3)

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Encyclopedic overview

8 sections

Contents

Medical uses
Adverse effects
Pharmacogenetics
Mechanism of action
Pharmacokinetics
Interactive pathway map
See also
References

Tegafur is a chemotherapeutic prodrug of 5-fluorouracil (5-FU) used in the treatment of cancers. It is a component of the combination drug tegafur/uracil. When metabolised, it becomes 5-FU.

It was patented in 1967 and approved for medical use in 1972.

Excerpted from Wikipedia’s “(RS)-tegafur” article, available under the CC BY-SA 4.0 licence.

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