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

• ChemBase ID: 105021
• Molecular Formular: C8H9FN2O3
• Molecular Mass: 200.1670632
• Monoisotopic Mass: 200.05972038
• SMILES: Fc1cn(C2CCCO2)c(=O)[nH]c1=O
• Canonical SMILES: O=c1[nH]c(=O)n(cc1F)C1CCCO1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-fluoro-1-(oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 5-fluoro-1-(oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione; tegafur
• Synonyms: 5-Fluoro-1-(tetrahydro-2-furyl)uracil; Tegafur; Furflucil; Futraful; Neberk; Sinoflurol; 5-FLUORO-1-(TETRAHYDRO-2-FURFURYL)URACIL; Ftorafur; Tegafur; 5-Fluoro-1-(tetrahydro-2-furyl)uracil; 5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione; 5-Fluoro-1-(tetrahydro-2-furanyl)-2,4(1H,3H)-pyrimidinedione; 1-(2-Tetrahydrofuryl)-5-fluorouracil; 5-Fluoro-1-(tetrahydro-2'-furyl)uracil; Citofur; Coparogin-; Exonal; FT 207; Fental; Fluaid; Fluorafur; Fluorofur; Franrose; Fulaid; Fulfeel; Tegafur

Database IDs

• CAS Number: 17902-23-7
• EC Number: 241-846-2
• MDL Number: MFCD00012351
• PubChem SID: 24894905; 162091846
• PubChem CID: 5386

CALCULATED PROPERTIES

• H Donor: 1
• LogD (pH = 5.5): 0.020991746
• LogD (pH = 7.4): -0.1571928
• Log P: 0.023826538
• Molar Refractivity: 44.5014 cm^3
• Polarizability: 16.845354 Å^3
• Polar Surface Area: 58.64 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 7.678831
• H Acceptors: 3

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: >50 mg/mL; Methanol
• Apperance: White SOlid; white to off-white powder
• Melting Point: 164-165°C; 171-173 °C(lit.)

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C
• RTECS: YR0450000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 23/24/25; R:22
• Safety Statements: 22-36/37/39-45; S:36/37/39
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C; room temp

Pharmacology Properties

• Mechanism of Action: DNA synthesis inhibitor; Fluorouracil prodrug; RNA synthesis inhibitor; Thymidylate synthetase inhibitor

Product Information

• Purity: ≥98% (HPLC)
• Application(s): Antineoplastic agent; Cytostatic
• Empirical Formula (Hill Notation): C8H9FN2O3

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.

Toronto Research Chemicals - T013900

Used as an antineoplastic.

REFERENCES

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