[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl hypofluorite

• ChemBase ID: 72616
• Molecular Formular: C9H11FN2O5
• Molecular Mass: 246.1924432
• Monoisotopic Mass: 246.06519968
• SMILES: [C@H]1([C@H](O[C@H](C1)n1ccc(=O)[nH]c1=O)COF)O
• Canonical SMILES: FOC[C@H]1O[C@H](C[C@@H]1O)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C9H11FN2O5/c10-16-4-6-5(13)3-8(17-6)12-2-1-7(14)11-9(12)15/h1-2,5-6,8,13H,3-4H2,(H,11,14,15)/t5-,6+,8+/m0/s1
• InChIKey: VBNMRFARUUMMNM-SHYZEUOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl hypofluorite
• IUPAC Traditional name: [(2R,3S,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl hypofluorite
• Synonyms: Fluorodeoxyuridine; Floxuridine

Database IDs

• CAS Number: 50-91-9
• PubChem SID: 162037541
• PubChem CID: 22824722

CALCULATED PROPERTIES

• Acid pKa: 9.455745
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.58750916
• LogD (pH = 7.4): -0.59122115
• Log P: -0.58746165
• Molar Refractivity: 51.3418 cm^3
• Polarizability: 20.150097 Å^3
• Polar Surface Area: 88.1 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: Antimetabolites

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1299

Research Area: Colorectal cancer
Biological Activity:
Floxuridine (Fludara) is a prodrugs of floxuridine and an oncology agent with an GI50 of 5.1 μM for the inhibition of MDCK/PEPT1. Floxuridine (Fludara) belongs to the class known as antimetabolites. Floxuridine (Fludara) is most often used in the treatment of colorectal cancer. Floxuridine, an analog of 5-fluorouracil, is a fluorinated pyrimidine. Floxuridine (Fludara) works because it is broken down by the body into its active form, which is the same as a metabolite of 5-Fluorouracil. [1][2][3]

REFERENCES

• http://en.wikipedia.org/wiki/Floxuridine