Floxuridine

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

What is the Floxuridine?

The molecule Floxuridine presents a molecular formula of C9H11FN2O5 and its IUPAC name is 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione.

Floxuridine (5-FUDR) is an antineoplastic chemotherapy agent used in the treatment of cancer. It is a pyrimidine analog and is converted to 5-fluorouracil (5-FU) in the body. 5-FU is a thymidylate synthase inhibitor and inhibits DNA synthesis..

Floxuridine is used as a first-line treatment for metastatic colorectal cancer. It is also used in the treatment of pancreatic, gastric, and breast cancers..

5-FUDR exists as a solution for injection and is usually given by IV infusion. The infusion should be given over 30-60 minutes. The usual dose is 500-1000 mg/m2 given every other day for 2-6 weeks..

Common side effects of floxuridine include fatigue, nausea, vomiting, and diarrhea. More serious side effects include myelosuppression, mucositis, and hepatotoxicity..

Floxuridine is a pyrimidine analog that is converted to 5-fluorouracil (5-FU) in the body. 5-FU is a thymidylate synthase inhibitor and inhibits DNA synthesis..

Floxuridine is used as a first-line treatment for metastatic colorectal cancer. It is also used in the treatment of pancreatic, gastric, and breast cancers..

5-FUDR exists as a solution for injection and is usually given by IV infusion. The infusion should be given over 30-60 minutes. The usual dose is 500-1000 mg/m2 given every other day for 2-6 weeks..

Common side effects of floxuridine include fatigue, nausea, vomiting, and diarrhea. More serious side effects include myelosuppression, mucositis, and hepatotoxicity..

3D structure

Cartesian coordinates

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

2D drawing

 

Floxuridine ODKNJVUHOIMIIZ-RRKCRQDMSA-N chemical compound 2D structure molecule svg
Floxuridine

 

Molecule descriptors

 
IUPAC name5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
InChI codeInChI=1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
InChI KeyODKNJVUHOIMIIZ-RRKCRQDMSA-N
SMILESO=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1F

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.

  • (+)-5-fluoro-2'-deoxyuridine
  • (+)-5-fluorodeoxyuridine
  • 006F530
  • 039LU44I5M
  • 1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracil
  • 1-(beta-D-2-deoxy-erythro-pentofuranosyl)-5-fluorouracil
  • 1-[(4S,2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,3-dihydropyri midine-2,4-dione
  • 1-beta-D-2'-Deoxyribofuranosyl-5-flurouracil
  • 136353-77-0
  • 136353-81-6
  • 136353-85-0
  • 1beta-D-2'-Deoxyribofuranosyl-5-flurouracil
  • 2''-deoxy-5-fluorouridine
  • 2'-Deoxy-5-fluorouridine
  • 2'-deoxy-5-fluoro uridine
  • 2'-deoxy-5-fluoro-d-uridine
  • 2-deoxy-5'-fluorouridine
  • 396726-50-4
  • 5 Fluorodeoxyuridine
  • 5-FUDR
  • 5-FdUrd
  • 5-Fluor-1-(beta-2'-deoxyribofuranosyl)pyrimidin-2,4(1H,3H)-dion
  • 5-Fluoro-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
  • 5-Fluoro-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
  • 5-Fluoro-2'-deoxy-beta-uridine
  • 5-Fluoro-2'-deoxyuridine
  • 5-Fluoro-2'-deoxyuridine, thymidylate synthase inhibitor
  • 5-Fluoro-2-deoxyuridine
  • 5-Fluoro-2-desoxyuridine
  • 5-Fluoro-dUrd
  • 5-Fluorodeoxyuridine
  • 5-Fluorouracil 2'-deoxyriboside
  • 5-Fluorouracil deoxyriboside
  • 5-floxuridine
  • 5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  • 5-fluoro-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
  • 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
  • 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
  • 5-fluoro-2''-Deoxy-uridine
  • 5-fluoro-2''-deoxyuridine
  • 50-91-9
  • 5FdU
  • AC-16391
  • AI3-50691
  • BBL033765
  • BCP02871
  • BCP0726000269
  • BCP9000691
  • BDBM50340678
  • BRN 0090221
  • CCG-220965
  • CS-1827
  • D04197
  • D2235
  • DB00322
  • DSSTox_CID_3057
  • DSSTox_GSID_23057
  • DSSTox_RID_76855
  • Deoxyfluorouridine
  • EN300-52649
  • Epitope ID:138108
  • FDUR
  • FUDR
  • FdU
  • FdUrd
  • Floxiridina
  • Floxuridin
  • Floxuridine
  • Floxuridine (Fludara)
  • Floxuridine (USP/INN)
  • Floxuridine,(S)
  • Floxuridinum
  • Fluorodeoxyuridine
  • Fluoruridine deoxyribose
  • GTPL4801
  • HMS2090I12
  • HMS2230N22
  • HMS3715A11
  • HSDB 3227
  • HY-B0097
  • J-700034
  • MFCD00006530
  • MLS000069439
  • MLS002695934
  • MLS006011768
  • NCGC00023722-03
  • NCGC00023722-05
  • NCGC00023722-06
  • NCGC00023722-08
  • NSC 27640
  • NSC-27640
  • NSC27640
  • Opera_ID_1559
  • PS-7520
  • Q5462356
  • Ro 5-0360
  • SMR000059051
  • SR-01000000001
  • SR-01000000001-2
  • SRI-9246-15
  • SRI-9246_18
  • STK801909
  • Uridine, 2'-deoxy-5'-fluoro-
  • Uridine, 2'-deoxy-5-fluoro
  • Uridine, 2'-deoxy-5-fluoro-
  • Z802671482
  • beta-5-Fluoro-2'-deoxyuridine
  • floxidine
  • floxuridine
  • s1299
  • uridine, 2,5'-18O2-2'-deoxy-5-fluoro-
  • uridine, 2-18O-2'-deoxy-5-fluoro-
  • uridine, 3-15N-2'-deoxy-5-fluoro-
  • uridine, 5'-18O-2'-deoxy-5-fluoro-

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3813010
  • CAS-50-91-9
  • UNII-039LU44I5M
  • AKOS005622662
  • BRD-K47832606-001-26-9
  • BRD-K47832606-001-30-1
  • DTXSID3023057
  • CHEMBL917
  • CHEBI:60761
  • Tox21_110892
  • Tox21_110892_1
  • EINECS 200-072-5
  • SCHEMBL4424

Physico-Chemical properties

IUPAC name5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-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.