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    Tegafur

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Ftorafur, 17902-23-7, Futraful, Sinoflurol, Fental, Fluorofur
    Molecular Formula
    C8H9FN2O3
    Molecular Weight
    200.17  g/mol
    InChI Key
    WFWLQNSHRPWKFK-UHFFFAOYSA-N
    FDA UNII
    1548R74NSZ
    Congener of FLUOROURACIL with comparable antineoplastic action. It has been suggested especially for the treatment of breast neoplasms.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-fluoro-1-(oxolan-2-yl)pyrimidine-2,4-dione
    2.1.2 InChI
    InChI=1S/C8H9FN2O3/c9-5-4-11(6-2-1-3-14-6)8(13)10-7(5)12/h4,6H,1-3H2,(H,10,12,13)
    2.1.3 InChI Key
    WFWLQNSHRPWKFK-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CC(OC1)N2C=C(C(=O)NC2=O)F
    2.2 Other Identifiers
    2.2.1 UNII
    1548R74NSZ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(2-tetrahydrofuryl)-5-fluorouracil

    2. 1-(tetrahydro-2-furanyl)-5-fluorouracil

    3. 5-fluoro-1-(tetrahydro-2-furanyl)-2,4-pyrimidinedione

    4. Florafur

    5. Fluorofur

    6. Ft 207

    7. Ft-207

    8. Ft207

    9. Ftorafur

    10. Futraful

    11. N1-(2'-tetrahydrofuryl)-5-fluorouracil

    12. Sunfural S

    13. Uftoral

    14. Utefos

    2.3.2 Depositor-Supplied Synonyms

    1. Ftorafur

    2. 17902-23-7

    3. Futraful

    4. Sinoflurol

    5. Fental

    6. Fluorofur

    7. Citofur

    8. Neberk

    9. Coparogin

    10. Furafluor

    11. Furofutran

    12. Nitobanil

    13. Exonal

    14. Fulfeel

    15. Lifril

    16. Lamar

    17. Tefsiel C

    18. Florafur

    19. Riol

    20. 5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione

    21. Ft-207

    22. Franroze

    23. Furflucil

    24. Sunfral

    25. 1-(2-tetrahydrofuryl)-5-fluorouracil

    26. Franrose

    27. Phthorafur

    28. Sunfural

    29. Fulaid

    30. 5-fluoro-1-(tetrahydro-2-furyl)uracil

    31. Mjf-12264

    32. 2,4(1h,3h)-pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-

    33. Atillon

    34. Fluorafur

    35. Nsc-148958

    36. 5-fluoro-1-(tetrahydro-2-furfuryl)uracil

    37. Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-

    38. Ft 207

    39. 5-fluoro-1-(tetrahydro-2-furanyl)-2,4-pyrimidinedione

    40. N1-(2-tetrahydrofuryl)-5-fluorouracil

    41. 1-(tetrahydrofuran-2-yl)-5-fluorouracil

    42. 5-fluoro-1-(tetrahydrofuran-2-yl)uracil

    43. Uracil, 1-(tetrahydrofuran-2-yl)-5-fluoro-

    44. 5-fluoro-1-(oxolan-2-yl)pyrimidine-2,4-dione

    45. Nsc 148958

    46. 5-fluoro-1-(tetrahydro-3-furyl)uracil

    47. 1-(tetrahydro-2-furanyl)-5-fluoro-2,4-pyrimidinedione

    48. Mls000069497

    49. Chebi:32188

    50. 1-(2-tetrahydroformyl)-5-fluorouracil

    51. 1548r74nsz

    52. 5-fluoro-1-tetrahydrofuran-2-yl-pyrimidine-2,4-dione

    53. Ncgc00159418-02

    54. Ncgc00159418-05

    55. Smr000059106

    56. 2,4(1h,3h)pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-

    57. Racemic Ftorafur

    58. Dsstox_cid_1305

    59. Dsstox_rid_76070

    60. Dsstox_gsid_21305

    61. Phthorafur [czech]

    62. Ft-207 (nsc 148958)

    63. Tegafurum

    64. Tegafurum [inn-latin]

    65. Cas-37076-68-9

    66. Ccris 2762

    67. Ft207

    68. Einecs 241-846-2

    69. Mfcd00012351

    70. Brn 0525766

    71. N1-(2'-tetrahydrofuryl)-5-fluorouracil

    72. 1-(tetrahydro-2-furanyl)-5-fluorouracil

    73. Unii-1548r74nsz

    74. N(sub 1)-(2-tetrahydrofuryl)-5-fluorouracil

    75. Tegafur [usan:inn:ban:jan]

    76. N(sub 1)-(2'-furanidyl)-5-fluouracil [czech]

    77. Atillon (tn)

    78. Tegafur ,(s)

    79. N(sub 1)-(2'-furanidyl)-5-fluouracil

    80. Ts-1 (salt/mix)

    81. Tegafur [usan]

    82. Tegafur [inn]

    83. Tegafur [jan]

    84. Tegafur [mi]

    85. Opera_id_1726

    86. Tegafur [mart.]

    87. Tegafur [who-dd]

    88. Upcmld-dp063

    89. Schembl4552

    90. Tegafur [ema Epar]

    91. 5-24-06-00285 (beilstein Handbook Reference)

    92. 79107-97-4

    93. Mls000759414

    94. Mls001076521

    95. Mls001424119

    96. Chembl20883

    97. Tegafur (jp17/usan/inn)

    98. F-5-fu

    99. Teysuno Component Tegafur

    100. Upcmld-dp063:001

    101. Gtpl10513

    102. Dtxsid001009966

    103. Hms1665i05

    104. Hms2051b15

    105. Hms2090k04

    106. Hms2232e05

    107. Hms3371h21

    108. Hms3393b15

    109. Hms3654p13

    110. Hms3715d14

    111. N1-(2'-furanidyl)-5-fluouracil

    112. 5-fluoro-1-(tetrahydro-2-furanyl)-2,4(1h,3h)-pyrimidinedione

    113. Bcp22714

    114. Tegafur Component Of Teysuno

    115. 5-fluoro-1-(tetrahydrofuran-2-yl)

    116. N1-(2'-furanidyl)-5-fluorouracil

    117. Tox21_111649

    118. Tox21_301812

    119. Bbl027795

    120. Ccg-50110

    121. Stk528044

    122. Tegafur, >=98% (hplc), Powder

    123. 5-fluoro-1-(2-tetrahydrofuryl)uracil

    124. Akos000121279

    125. Tox21_111649_1

    126. Ac-2112

    127. Ccg-100959

    128. Cs-1128

    129. Db09256

    130. Nc00209

    131. 1-(tetrahydro-2-furyl)-5-fluorouracil

    132. 2,4(1h,3h)-pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-, Didehydroderiv.

    133. 5-fluoro-1-(2-tetrahydrofuranyl)uracil

    134. 5-fluoro-1-(tetrahydro-2-furyl)-uracil

    135. N1 -(2-tetrahydrofuryl)-5-fluorouracil

    136. Ncgc00159418-04

    137. Ncgc00255222-01

    138. 82294-77-7

    139. As-13528

    140. Hy-17400

    141. Tegafur (ft-207; Nsc 148958)

    142. Ft-0653732

    143. Ft-0654170

    144. Ft-0674829

    145. Ft-0693965

    146. D01244

    147. Ab00572620-15

    148. 902t237

    149. A812417

    150. Q413370

    151. Sr-01000639511

    152. Q-201784

    153. Sr-01000639511-1

    154. Sr-01000639511-4

    155. 5-fluoro-1-tetrahydro-furan-2-yl-1h-pyrimidine-2,4-dione

    156. 5-fluoro-1-tetrahydro-2-furanyl-2,4(1h,3h)-pyrimidinedione

    157. 2, 4(1h,3h)-pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-, (r)-

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 200.17 g/mol
    Molecular Formula C8H9FN2O3
    XLogP3-0.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count1
    Exact Mass200.05972032 g/mol
    Monoisotopic Mass200.05972032 g/mol
    Topological Polar Surface Area58.6 Ų
    Heavy Atom Count14
    Formal Charge0
    Complexity316
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Indicated for the treatment of cancer usually in combination with other biochemically modulating drugs. Indicated in adults for the treatment of advanced gastric cancer when given in combination with [DB00515]. Indicated for the first-line treatment of metastatic colorectal cancer with [DB03419] and calcium folinate.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Tegafur is an antineoplastic agent that belongs in the class of pyrimidine analogues. It interferes with the 2'-deoxythymidylate (DTMP) synthesis in the pyrimidine pathway, resulting in inhibition of DNA synthesis. In a phase III trial investigating the clinical efficacy of S-1 (tegafur/gimeracil/oteracil) in patients with advanced or recurrent gastric cancer, treatment resulted in a high response rate and was associated with a longer overall survival and longer progression-free survival rate when used in combination with cisplatin. In a meta analysis, triple combination therapy consisting of tegafur, gimeracil and oteracil showed longer survival times and well tolerance in patients with advanced gastric cancer. Tegafur and its active metabolites are potent myleosuppressive agents.

    5.2 MeSH Pharmacological Classification

    Antimetabolites, Antineoplastic

    Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)

    5.3 ATC Code

    L01BC53

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01B - Antimetabolites

    L01BC - Pyrimidine analogues

    L01BC03 - Tegafur

    5.4 Absorption, Distribution and Excretion

    Absorption

    Tegafur displays a dose-proportional pharmacokinetic properties. Tegafur is rapidly and well absorbed into the systemic circulation, reaching the peak plasma concentration within 1 to 2 hours of administration.

    Route of Elimination

    Following oral administration, about less 20% of total tegafur is excreted unchanged in the urine.

    Volume of Distribution

    The volume of distribution based on apparent volume of distribution and urinary excretion data of tegafur is 16 L/m^2.

    Clearance

    No pharmacokinetic data available.

    5.5 Metabolism/Metabolites

    Hepatic CYP2A6 is the predominant enzyme that mediates 5-hydroxylation of tegafur to generate 5'-hydroxytegafur. This metabolite is unstable and undergoes spontaneous degradation to form 5-FU, which is an active antineoplastic agent that exerts a pharmacological action on tumours. 5-FU is rapidly metabolised by the liver enzyme dihydropyrimidine dehydrogenase (DPD).

    Tegafur has known human metabolites that include 5-Fluorouracil.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.6 Biological Half-Life

    The elimination half life of tegafur is approximately 11 hours.

    5.7 Mechanism of Action

    The transformation of 2'-deoxyurindylate (dUMP) to 2'-deoxythymidylate (dTMP) is essential in driving the synthesis of DNA and purines in cells. Thymidylate synthase catalyzes the conversion of dUMP to dTMP, which is a precursor of thymidine triphosphate (TTP), one of the four deoxyribonucleotides required for DNA synthesis. After administration into the body, tegafur is converted into the active antineoplastic metabolite, fluorouracil (5-FU). In tumour cells, 5-FU undergoes phosphorylation to form the active anabolites, including 5-fluorodeoxyuridine monophosphate (FdUMP). FdUMP and reduced folate are bound to thymidylate synthase leading to formation of a ternary complex which inhibits DNA synthesis. In addition, 5-fluorouridine-triphosphate (FUTP) is incorporated into RNA causing disruption of RNA functions.