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Tegafur

PubChem CID
5386
Structure
Tegafur_small.png
Tegafur_3D_Structure.png
Molecular Formula
Synonyms
  • tegafur
  • 17902-23-7
  • Ftorafur
  • Futraful
  • Sinoflurol
Molecular Weight
200.17 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
Tegafur is an organohalogen compound and a member of pyrimidines.
Tegafur (INN, BAN, USAN) is a prodrug of [DB00544] (5-FU), an antineoplastic agent used as the treatment of various cancers such as advanced gastric and colorectal cancers. It is a pyrimidine analogue used in combination therapies as an active chemotherapeutic agent in conjunction with [DB09257] and [DB03209], or along with [DB00544] as [DB09327]. Tegafur is usually given in combination with other drugs that enhance the bioavailability of the 5-FU by blocking the enzyme responsible for its degradation, or serves to limit the toxicity of 5-FU by ensuring high concentrations of 5-FU at a lower dose of tegafur. When converted and bioactivated to 5-FU, the drug mediates an anticancer activity by inhibiting thymidylate synthase (TS) during the pyrimidine pathway involved in DNA synthesis. 5-FU is listed on the World Health Organization's List of Essential Medicines.
Tegafur is a congener of the antimetabolite fluorouracil with antineoplastic activity. Tegafur is a prodrug that is gradually converted to fluorouracil in the liver by the cytochrome P-450 enzyme. Subsequently, 5-FU is metabolized to two active metabolites, 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP) by both tumor cells and normal cells. FdUMP inhibits DNA synthesis and cell division by inhibiting thymidylate synthase and reducing normal thymidine production, while FUTP inhibits RNA and protein synthesis by competing with uridine triphosphate. (NCI04)

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Tegafur.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-fluoro-1-(oxolan-2-yl)pyrimidine-2,4-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

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)
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

WFWLQNSHRPWKFK-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C1CC(OC1)N2C=C(C(=O)NC2=O)F
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C8H9FN2O3
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

17902-23-7
82294-77-7

2.3.2 Deprecated CAS

35959-67-2, 37308-51-3, 56767-38-5, 65732-47-0, 73120-84-0, 79107-97-4

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 KEGG ID

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 PharmGKB ID

2.3.15 Wikidata

2.3.16 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1-(2-Tetrahydrofuryl)-5-fluorouracil
  • 1-(Tetrahydro-2-furanyl)-5-fluorouracil
  • 5-Fluoro-1-(tetrahydro-2-furanyl)-2,4-pyrimidinedione
  • Florafur
  • Fluorofur
  • FT 207
  • FT-207
  • FT207
  • Ftorafur
  • Futraful
  • N1-(2'-Tetrahydrofuryl)-5-fluorouracil
  • Sunfural S
  • Tegafur
  • Uftoral
  • Utefos

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
200.17 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
-0.3
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
200.05972032 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
200.05972032 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
58.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
14
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
316
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Melting Point

339.8-343.4
MSDS

3.2.2 Solubility

29.9 [ug/mL] (The mean of the results at pH 7.4)
Partly miscible
MSDS

3.2.3 Dissociation Constants

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Antineoplastic and immunomodulating agents -> Antineoplastic agents
S92 | FLUOROPHARMA | List of ~340 ATC classified fluoro-pharmaceuticals | DOI:10.5281/zenodo.5979646

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
209155
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
209155
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 13
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

71.0 99.99

43.0 40

200.0 22

41.0 21

72.0 14

Thumbnail
Thumbnail
Notes
instrument=JEOL JMS-01-SG-2
2 of 13
View All
Spectra ID
Instrument Type
CI-B
Ionization Mode
positive
Top 5 Peaks

131.0 99.99

71.0 82

202.0 8

132.0 7

201.0 0.65

Thumbnail
Thumbnail
Notes
instrument=JEOL JMS-D-300

4.2.2 MS-MS

Spectra ID
Ionization Mode
Positive
Top 5 Peaks

131.02361 100

71.05368 75

113.99843 50

71.04895 25

Thumbnail
Thumbnail

4.2.3 LC-MS

MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
201.0658
Instrument
SCIEX TripleTOF 6600
Instrument Type
LC-ESI-QTOF
Ionization Mode
positive
Collision Energy
35 eV
Retention Time
1.218683
Top 5 Peaks

131.02361 100

71.05368 75

113.99843 50

71.04895 25

113.98944 25

Thumbnail
Thumbnail

4.2.4 Other MS

1 of 4
View All
Authors
MASS SPECTROSCOPY SOC. OF JAPAN (MSSJ)
Instrument
JEOL JMS-01-SG-2
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 75 eV
Top 5 Peaks

71 999

43 400

200 220

41 210

72 140

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 4
View All
Authors
MASS SPECTROSCOPY SOC. OF JAPAN (MSSJ)
Instrument
JEOL JMS-D-300
Instrument Type
CI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 200 eV
Top 5 Peaks

131 999

71 820

202 80

132 70

201 7

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.3 UV Spectra

4.3.1 UV-VIS Spectra

Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4 IR Spectra

4.4.1 FTIR Spectra

1 of 2
Technique
FILM (CAST FROM CHCl3)
Source of Sample
MAYBRIDGE CHEMICAL COMPANY LTD., NORTH CORNWALL, ENGLAND
Catalog Number
X 13
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
209155
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
209155
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.5 Raman Spectra

Catalog Number
209155
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 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.

7.2 Clinical Trials

7.2.1 ClinicalTrials.gov

7.2.2 EU Clinical Trials Register

7.2.3 NIPH Clinical Trials Search of Japan

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

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.

8.2 MeSH Pharmacological Classification

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

8.3 ATC Code

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

8.4 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.

8.5 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

8.6 Biological Half-Life

The elimination half life of tegafur is approximately 11 hours.

8.7 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.

8.8 Transformations

9 Use and Manufacturing

9.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-: INACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Signal
Danger
GHS Hazard Statements

H301 (95.1%): Toxic if swallowed [Danger Acute toxicity, oral]

H311 (95.1%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H331 (95.1%): Toxic if inhaled [Danger Acute toxicity, inhalation]

Precautionary Statement Codes

P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 3 (95.1%)

Acute Tox. 3 (95.1%)

Acute Tox. 3 (95.1%)

10.2 Other Safety Information

Chemical Assessment

IMAP assessments - 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-: Environment tier I assessment

IMAP assessments - 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-: Human health tier I assessment

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

11.1.2 Protein Binding

Tegafur is 52.3% bound to serum proteins and 5-FU is 18.4% protein bound.

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Chemical Co-Occurrences in Literature

13.7 Chemical-Gene Co-Occurrences in Literature

13.8 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

15.2 Drug-Drug Interactions

15.3 Drug-Food Interactions

  • Drink plenty of fluids. Drinking water is important to prevent dehydration when taking Teysuno.
  • Take on an empty stomach. Food does not impact the bioavailability of tegafur. Food does affect other ingredients in the combination product Teysuno. Take Teysuno at least 1 hour before or after eating.

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 KEGG: ATC

17.5 KEGG: Target-based Classification of Drugs

17.6 KEGG: JP15

17.7 KEGG: Drug Groups

17.8 WHO ATC Classification System

17.9 ChemIDplus

17.10 ChEMBL Target Tree

17.11 UN GHS Classification

17.12 NORMAN Suspect List Exchange Classification

17.13 EPA DSSTox Classification

17.14 EPA TSCA and CDR Classification

17.15 PFAS and Fluorinated Organic Compounds in PubChem

17.16 EPA Substance Registry Services Tree

17.17 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-
    https://services.industrialchemicals.gov.au/search-assessments/
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-, didehydroderiv.
    https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0082294777
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  5. EPA Chemicals under the TSCA
    2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  8. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  9. Burnham Center for Chemical Genomics
  10. ChEBI
  11. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  12. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  13. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  14. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  15. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  16. Therapeutic Target Database (TTD)
  17. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Tegafur
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  18. EU Clinical Trials Register
  19. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
    2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-, (R)-
    http://www.hmdb.ca/metabolites/HMDB0246215
  20. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  21. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  22. SpectraBase
    1-(Tetrahydro-2-furanyl)-5-fluorouracil
    https://spectrabase.com/spectrum/JrTNPYUglxw
    2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-
    https://spectrabase.com/spectrum/Z3sOIXqD8I
    5-fluoro-1-(tetrahydro-2-furyl)uracil
    https://spectrabase.com/spectrum/1YPJoibv32g
    Ftorafur (5-fluoro-1-(tetrahydro-2-furyl)uracil)
    https://spectrabase.com/spectrum/7aaw7lqJsid
    5-FLUORO-1-(TETRAHYDRO-2-FURYL)URACIL
    https://spectrabase.com/spectrum/JZLl29dXlTD
    Ftorafur (5-fluoro-1-(tetrahydro-2-furyl)uracil)
    https://spectrabase.com/spectrum/ElZtu0jyNRS
    5-fluoro-1-(tetrahydro-2-furyl)uracil
    https://spectrabase.com/spectrum/ElSboHq80Ci
    Ftorafur (5-fluoro-1-(tetrahydro-2-furyl)uracil)
    https://spectrabase.com/spectrum/4f2q9EXFf8u
    Ftorafur (5-fluoro-1-(tetrahydro-2-furyl)uracil)
    https://spectrabase.com/spectrum/2szY0czk9yx
    Ftorafur (5-fluoro-1-(tetrahydro-2-furyl)uracil)
    https://spectrabase.com/spectrum/BkLTL0puIk1
  23. IUPAC Digitized pKa Dataset
    pyrimidine-2,4(1H,3H)-dione, 5-fluoro-1-(2-oxolanyl)-
    https://github.com/IUPAC/Dissociation-Constants
  24. Japan Chemical Substance Dictionary (Nikkaji)
  25. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
    Drugs listed in the Japanese Pharmacopoeia
    http://www.genome.jp/kegg-bin/get_htext?br08311.keg
  26. MassBank Europe
  27. Metabolomics Workbench
  28. NIPH Clinical Trials Search of Japan
  29. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
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    https://www.whocc.no/copyright_disclaimer/
  30. PharmGKB
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    https://www.pharmgkb.org/page/policies
  31. Springer Nature
  32. Thieme Chemistry
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    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
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  33. Wikidata
  34. Wikipedia
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  36. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
    Antimetabolites, Antineoplastic
    https://www.ncbi.nlm.nih.gov/mesh/68000964
  37. PubChem
  38. GHS Classification (UNECE)
  39. EPA Substance Registry Services
  40. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  41. PATENTSCOPE (WIPO)
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