CAS 17902-23-7|5-fluoro-1-(oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione|5-FLUORO-1-(TETRAHYDRO-2-FURFURYL)URACIL|tegafur|Ftorafur|5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione|...

General Information

Structure

Molecular Formula

C₈H₉FN₂O₃

Molecular Mass

200.1670632

Exact Mass

200.05972038

Charge

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)

InChIKey

WFWLQNSHRPWKFK-UHFFFAOYSA-N

Canonic Smiles

O=c1[nH]c(=O)n(cc1F)C1CCCO1

Isomeric Smiles

Fc1cn(C2CCCO2)c(=O)[nH]c1=O

Calculated Properties

JChem

Acid pKa

7.678831

H Acceptors

H Donor

LogD (pH = 5.5)

0.020991746

LogD (pH = 7.4)

-0.1571928

Log P

0.023826538

Molar Refractivity

44.5014

Polarizability

16.845354

Polar Surface Area

58.64

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

5-fluoro-1-(oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Synonyms

5-FLUORO-1-(TETRAHYDRO-2-FURFURYL)URACILFtorafur5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dioneTegafur5-Fluoro-1-(tetrahydro-2-furyl)uracilTegafur5-Fluoro-1-(tetrahydro-2-furyl)uracilTegafurFulaidCitofurFluaidNeberkFutrafulFental5-Fluoro-1-(tetrahydro-2'-furyl)uracilFurflucil1-(2-Tetrahydrofuryl)-5-fluorouracilFulfeelFT 207ExonalFluorofurSinoflurolFranrose5-Fluoro-1-(tetrahydro-2-furanyl)-2,4(1H,3H)-pyrimidinedioneCoparogin-Fluorafur

IUPAC Traditional name

tegafur 5-fluoro-1-(oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Names and Identifiers

Registration numbers

PubChem SID

MDL Number

CAS Number

EC Number

PubChem CID

Registration numbers

Properties

Product Information

Certificate of Analysis

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Purity

≥98% (HPLC)

Empirical Formula (Hill Notation)

C8H9FN2O3

Application(s)

Cytostatic

Antineoplastic agent

Pharmacology Properties

Mechanism of Action

Thymidylate synthetase inhibitor

RNA synthesis inhibitor

Fluorouracil prodrug

DNA synthesis inhibitor

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

T7205

Biochem/physiol Actions
Tegafur is a pro-drug of 5-fluorouracil, an antimetabolite used as an antineoplastic agent. It has been used as adjuvant chemotherapy for curatively resected colorectal cancer therapy.

TRC

T013900

Used as an antineoplastic.

Molecule Details

References

PubChem Literature

From Data Sources

• Buroker, T., et al.: Cancer, 44, 48 (1979)

• Au., J.L., et al.: Cancer Treat. Rep., 63, 343 (1979)

• Fujimoto, S., Drugs of Today (Barcelona), 1985, 21, 125, (rev, pharmacol)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 878

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 502

• Loo, T.L. et al., Drug Metab. Rev., 1978, 8, 137, (metab, rev)

• Au, J. et al., Cancer Chemother. Pharmacol., 1981, 7, 55, (metab)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 366A, (nmr)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 811D, (ir)

• Yamamoto, S. et al., Arzneim.-Forsch., 1981, 31, 1268, (pharmacol)

• Ozaki, S. et al., Chem. Pharm. Bull., 1986, 34, 150, (synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, FMB000; UNJ810

• Yasumoto, M. et al., J. Med. Chem., 1977, 20, 1592, (synth, resoln)

• Uchida, T. et al., Chem. Pharm. Bull., 1993, 41, 1632, (polymorphism)

• Nakai, Y. et al., Chem. Pharm. Bull., 1982, 30, 2629; 1986, 34, 1242, (cryst struct, bibl)

References

Bioactivity

PubChem BioAssay

Bioactivity