Doxifluridine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Doxifluridine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Doxifluridine?

The molecule Doxifluridine presents a molecular formula of C9H11FN2O5 and its IUPAC name is 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione.

Doxifluridine is a nucleoside analogue that is used as an antineoplastic and antiviral agent. It is a fluorinated pyrimidine derivative and is structurally similar to cytidine. Doxifluridine is metabolized to its active 5′-triphosphate form, which is a nucleotide analogue of cytidine. The 5′-triphosphate form of doxifluridine inhibits thymidylate synthase, which is an enzyme that is required for DNA synthesis. Doxifluridine is active against a variety of neoplastic and viral cells in vitro and in vivo. It has been used to treat patients with viral diseases such as hepatitis B and human papillomavirus (HPV) infections. Doxifluridine has also been used as a radiosensitizer in the treatment of cancer..

3D structure

Cartesian coordinates

Geometry of Doxifluridine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Doxifluridine ZWAOHEXOSAUJHY-ZIYNGMLESA-N chemical compound 2D structure molecule svg
Doxifluridine

 

Molecule descriptors

 
IUPAC name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione
InChI codeInChI=1S/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6-,8-/m1/s1
InChI KeyZWAOHEXOSAUJHY-ZIYNGMLESA-N
SMILESC[C@H]1O[C@@H](n2cc(F)c(=O)[nH]c2=O)[C@H](O)[C@@H]1O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 094F095
  • 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione
  • 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione
  • 1-((2R,5R)-3,4-Dihydroxy-5-methyl-tetrahydro-furan-2-yl)-5-fluoro-1H-pyrimidine-2,4-dione
  • 1-((4S,2R,3R,5R)-3,4-Dihydroxy-5-methyloxolan-2-yl)-5-fluoro-1,3-dihydropyrimidine-2,4-dione
  • 1-(.BETA.-D-5-DESOXYRIBOFURANOXYL)-5-FLUORURACIL
  • 1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoropyrimidine-2,4(1H,3H)-dione (5'-Deoxy-5-fluorouridine)
  • 1-(beta-D-5-Desoxyribofuranoxyl)-5-fluoruracil
  • 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione
  • 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione
  • 3094-09-5
  • 5''-Deoxy-5-Fluorouridine (5''-Dfur)
  • 5'-DFUR (5'-Deoxy-5-fluorouridine, Doxifluridine)
  • 5'-Deoxy-5-fluorouridine
  • 5'-Dfur
  • 5'-Doxifluridine
  • 5'-dFUrd
  • 5'FDUR
  • 5'dFUrd
  • 5-DFUR
  • 5-Deoxy-5-fluorouridine
  • 5-Fluoro-5`-deoxyuridine
  • 5-fluoro-5'-deoxyuridine
  • AMC 0101
  • AMY13408
  • BDBM50132295
  • CCG-204627
  • CS-1270
  • Capecitabine related compound b
  • D01309
  • DB12947
  • DSSTox_CID_2967
  • DSSTox_GSID_22967
  • DSSTox_RID_76809
  • Doxifluridina
  • Doxifluridine
  • Doxifluridine (5-Fluoro-5'-deoxyuridine)
  • Doxifluridine (JP17/INN)
  • Doxifluridinum
  • EU-0100537
  • F 8791
  • Flutron
  • Fulturon
  • Furtulon
  • HMS2090C22
  • HMS2231I05
  • HMS3261L15
  • HY-B0021
  • KS-5065
  • LP00537
  • Lopac0_000537
  • MFCD00866530
  • MLS001332579
  • MLS001332580
  • MLS002172440
  • MLS002207077
  • NCGC00093926-01
  • NCGC00093926-02
  • NCGC00093926-03
  • NCGC00093926-05
  • NCGC00093926-11
  • NCGC00261222-01
  • NSC 758890
  • NSC-758890
  • Q1253473
  • RO-219738
  • Ro 21-9738
  • Ro 219738
  • Ro-21-9738
  • SDCCGSBI-0050520.P002
  • SMR000326811
  • SR-01000075886
  • SR-01000075886-1
  • SR-01000075886-5
  • SRI-11552-08
  • SRI-11552_09
  • Uridine, 5'-deoxy-5-fluoro-
  • Uridine-5'-deoxy-5-fluoro-
  • V1JK16Y2JP
  • doxifluridine
  • s2045

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1319177
  • CAS-3094-09-5
  • UNII-V1JK16Y2JP
  • AKOS015852921
  • AKOS015896821
  • BRD-K58262659-001-09-7
  • DTXSID2022967
  • CHEMBL1130
  • CHEBI:31521
  • Tox21_111231
  • Tox21_500537
  • Tox21_111231_1
  • EINECS 221-440-1
  • SCHEMBL8094

Physico-Chemical properties

IUPAC name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione
Molecular formulaC9H11FN2O5
Molecular weight246.192
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity53.07
LogP-1.7
Topological polar surface area104.6

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.