2′-deoxy-5-fluorinated uridine

Structural formula

Business number	014B
Molecular formula	C9H11FN2O5
Molecular weight	246.19
label	5-fluoro-2′-deoxyuridine, Fluorourea deoxynucleoside, 5-fluorodeoxyuridine, Fluoride, Fluridine, 5-fluoro-2′-deoxyurea nucleoside, 5-fluorodeoxyuridine, 5-fluoro-2′-deoxyuridine, 5-fluoro-2′-deoxyuracil, 2′-Deoxyfluridine, FDUR, 1-(2-Deoxy-beta-d-ribofuranosyl)-5-fluorouracil, 5-Fluoro-2′-deoxy-beta-uridine, NSC-27640, antineoplastic drugs

Numbering system

CAS number:50-91-9

MDL number:MFCD00006530

EINECS number:200-072-5

RTECS number:YU7535000

BRN number:2645818

PubChem number:24894724

Physical property data

1. Properties: colorless crystals.

2. Density (g/mL, 25/4℃): Undetermined

3. Relative vapor density (g/mL, air=1): Undetermined

4. Melting point (ºC): 150～151

5. Boiling point (ºC, normal pressure): Undetermined

6. Boiling point (ºC, 5.2kPa): Undetermined

7. Refractive index: Undetermined

8. Flash point (ºC): Undetermined

9. Specific rotation (º): α ]_D+37° (in water), +48.6° (in dimethylformamide)

10. Autoignition point or ignition temperature ( ºC): Undetermined

11. Vapor pressure (kPa, 25ºC): Undetermined

12. Saturated vapor pressure (kPa, 60ºC): Undetermined

13. Heat of combustion (KJ/mol): Undetermined

14. Critical temperature (ºC): Undetermined

15. Critical pressure (KPa): Undetermined

16. Logarithmic value of oil-water (octanol/water) partition coefficient: Undetermined

17. Explosion upper limit (%, V/V): Undetermined

18 . Lower explosion limit (%, V/V): Undetermined

19. Solubility: Easily soluble in water and methanol, almost insoluble in chloroform and Ether.

Toxicological data

None

Ecological data

None

Molecular structure data

1. Molar refractive index: 51.94

2. Molar volume (cm³/mol): 150.0

3. Isotonic specific volume (90.2K ): 437.6

4. Surface tension (dyne/cm): 72.3

5. Polarizability (10-24cm3): 20.59

Compute chemical data

1. Reference value for hydrophobic parameter calculation (XlogP): None

2. Number of hydrogen bond donors: 3

3. Number of hydrogen bond acceptors: 6

4. Number of rotatable chemical bonds: 2

5. Number of tautomers: 3

6. Topological molecule polar surface area 99.1

7. Number of heavy atoms: 17

8. Surface charge: 0

9. Complexity: 386

10. Number of isotope atoms: 0

11. Determine the number of atomic stereocenters: 3

12. Uncertain number of atomic stereocenters: 0

13. Determine the number of chemical bond stereocenters: 0

14. Number of uncertain chemical bond stereocenters: 0

15. Number of covalent bond units: 1

Properties and stability

Rapid intravenous injection can quickly degrade into 5-fluorouracil, with the same effects and side effects as 5-fluorouracil. Continuous arterial infusion can be directly converted into 5-fluorodeoxyurea, thereby inhibiting DNA synthesis. Effective results can be obtained with a smaller dose, which is three times higher than rapid intravenous infusion.

Storage method

This product should be sealed with argon gas and stored at 0~4℃.

Synthesis method

Methyl-2-deoxy-D-ribofuranoside is p-toluoylated and hydrolyzed with acetic acid-hydrochloric acid to replace the methoxy group at position 1 with chlorine, and then combined with 1 – The condensation of mercury acetoxy-5-fluorouracil is obtained by hydrolyzing the product to remove the p-toluyl group.

Purpose

1. Biochemical research. Inhibitor of DNA synthesis. Medical antiviral agent, antitumor agent.

2.Anti-tumor drugs. It is suitable for the treatment of liver cancer, gastrointestinal cancer, breast cancer and head and neck cancer.