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TEGAFUR

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Skeletal formula of tegafur

Tegafur

CAS 17902-23-7

2,​4(1H,​3H)​-​Pyrimidinedione, 5-​fluoro-​1-​(tetrahydro-​2-​furanyl)​-
Molecular Weight,200.17, MF C8 H9 F N2 O3
172-173 °C

Miyashita, Osamu; Chemical & Pharmaceutical Bulletin 1981, 29(11), PG 3181-90

Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-
Utefos
Venoterpine
WY1559000
YR0450000
5-fluoro-1-tetrahydrofuran-2-ylpyrimidine-2,4(1H,3H)-dione
Carzonal
N1-(2′-Furanidyl)-5-fluorouracil
  • Synonyms:Ftorafur
  • ATC:L01BC03
  • EINECS:241-846-2
  • LD50:800 mg/kg (M, i.v.); 775 mg/kg (M, p.o.);
    685 mg/kg (R, i.v.); 930 mg/kg (R, p.o.);
    34 mg/kg (dog, p.o.)

Derivatives, monosodium salt

  • Formula:C8H8FN2NaO3
  • MW:222.15 g/mol
  • CAS-RN:28721-46-2

Tegafur (INN, BAN, USAN) is a chemotherapeutic prodrug of 5-flourouracil (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]

Medical uses

As a prodrug to 5-FU it is used in the treatment of the following cancers:[2]

It is often given in combination with drugs that alter its bioavailability and toxicity such as gimeracil, oteracil or uracil.[2] These agents achieve this by inhibiting the enzyme dihydropyrimidine dehydrogenase (uracil/gimeracil) or orotate phosphoribosyltransferase (oteracil).[2]

Image result for tegafur

Adverse effects

The major side effects of tegafur are similar to fluorouracil and include myelosuppression, central neurotoxicity and gastrointestinal toxicity (especially diarrhoea).[2] Gastrointestinal toxicity is the dose-limiting side effect of tegafur.[2] Central neurotoxicity is more common with tegafur than with fluorouracil.[2]

Image result for tegafur

Pharmacogenetics

The dihydropyrimidine dehydrogenase (DPD) enzyme is responsible for the detoxifying metabolism of fluoropyrimidines, a class of drugs that includes 5-fluorouracil, capecitabine, and tegafur.[4] Genetic variations within the DPD gene (DPYD) can lead to reduced or absent DPD activity, and individuals who are heterozygous or homozygous for these variations may have partial or complete DPD deficiency; an estimated 0.2% of individuals have complete DPD deficiency.[4][5] 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.[4][5]

Mechanism of action

It is a prodrug to 5-FU, which is a thymidylate synthase inhibitor.[2]

Pharmacokinetics

It is metabolised to 5-FU by CYP2A6.[6][7]

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles.[§ 1]

FluoropyrimidineActivity_WP1601

go to article go to article go to article go to pathway article go to pathway article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to PubChem Compound go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to pathway article go to pathway article go to article go to article go to article go to article go to article go to WikiPathways go to article go to article go to article go to article go to article go to article go to article go to article go to article

The interactive pathway map can be edited at WikiPathways: “FluoropyrimidineActivity_WP1601”.

Image result for tegafur

Image result for tegafur SYNTHESIS

Image result for tegafur SYNTHESIS

MASS SPECTRUM

STR2

1H NMR

str3 str4

IR

str5

13C NMR

STR2 str3

RAMAN

str4

STR2