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| Other names | 5-fluoro-1-(oxolan-2-yl)pyrimidine-2,4-dione |
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| Routes of administration | Oral |
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| Elimination half-life | 3.9-11 hours |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.038.027  |
| Chemical and physical data | |
| Formula | C8H9FN2O3 |
| Molar mass | 200.169 g·mol−1 |
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Tegafur is a chemotherapeutic prodrugof5-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.[1]
It was patented in 1967 and approved for medical use in 1972.[2]
As a prodrug to 5-FU it is used in the treatment of the following cancers:[3]
It is often given in combination with drugs that alter its bioavailability and toxicity such as gimeracil, oteracil or uracil.[3] These agents achieve this by inhibiting the enzyme dihydropyrimidine dehydrogenase (uracil/gimeracil) or orotate phosphoribosyltransferase (oteracil).[3]
The major side effects of tegafur are similar to fluorouracil and include myelosuppression, central neurotoxicity and gastrointestinal toxicity (especially diarrhoea).[3] Gastrointestinal toxicity is the dose-limiting side effect of tegafur.[3] Central neurotoxicity is more common with tegafur than with fluorouracil.[3]
The dihydropyrimidine dehydrogenase (DPD) enzyme is responsible for the detoxifying metabolism of fluoropyrimidines, a class of drugs that includes 5-fluorouracil, capecitabine, and tegafur.[5] Genetic variations within the DPD gene (DPYD) can lead to reduced or absent DPD activity, and individuals who are heterozygousorhomozygous for these variations may have partial or complete DPD deficiency; an estimated 0.2% of individuals have complete DPD deficiency.[5][6] Those with partial or complete DPD deficiency have a significantly increased risk of severe or even fatal drug toxicities when treated with fluoropyrimidines; examples of toxicities include myelosuppression, neurotoxicity and hand-foot syndrome.[5][6]
It is a prodrug to 5-FU, which is a thymidylate synthase inhibitor.[3]
It is metabolised to 5-FU by CYP2A6.[7][8]
Click on genes, proteins and metabolites below to link to respective articles.[§ 1]
