5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 207
• Molecular Formular: C9H11FN2O5
• Molecular Mass: 246.1924432
• Monoisotopic Mass: 246.06519968
• SMILES: Fc1cn([C@@H]2O[C@@H]([C@@H](O)C2)CO)c(=O)[nH]c1=O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1cc(F)c(=O)[nH]c1=O
• InChI: InChI=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
• InChIKey: ODKNJVUHOIMIIZ-RRKCRQDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: floxuridine
• Brand Name: FUDR
• Synonyms: 2′-Deoxy-5-fluorouridine; FUDR; Floxuridine; 5-Fluoro-2′-deoxyuridine; 5-Fluoro-2'-deoxyuridine; 5 Fluorodeoxyuridine; 5FDU; Deoxyfluorouridine; FDUR; FDURD; Floxiridina [INN-Spanish]; Floxuridinum [INN-Latin]; Floxuridin; Fluorodeoxyuridine; Fluoruridine Deoxyribose; 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)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

Database IDs

• CAS Number: 50-91-9
• EC Number: 200-072-5
• MDL Number: MFCD00006530
• Beilstein Number: 90221
• PubChem SID: 46508645; 160963670; 24894724
• PubChem CID: 5790

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.6786437
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.3427026
• LogD (pH = 7.4): -2.0867264
• Log P: -1.3151612
• Molar Refractivity: 51.2578 cm^3
• Polarizability: 20.081879 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.15
• LOG S: -0.78
• Solubility (Water): 4.08e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1.19E+004 mg/L
• Melting Point: 148 °C(lit.); 148-150 °C; 149 - 151°C
• Optical Rotation: [α]20/D +38±1°, c = 1% in H2O
• Hydrophobicity(logP): -1.4; -1.405

Safety Information

• RTECS: YU7525000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• Safety Statements: 22-36
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: mouse ... Tyms(22171)

Product Information

• Purity: ≥98.0% (HPLC); 95%; 97%; 98%
• Empirical Formula (Hill Notation): C9H11FN2O5
• Classification: Rare Derivatives of Natural Compounds

DETAILS

DrugBank - DB00322

• Drug Groups: approved
• Description: An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection. Floxuridine is available as a sterile, nonpyrogenic, lyophilized powder for reconstitution. When administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract. [PubChem]
• Indication: For palliative management of gastrointestinal adenocarcinoma metastatic to the liver, when given by continuous regional intra-arterial infusion in carefully selected patients who are considered incurable by surgery or other means. Also for the palliative management of liver cancer (usually administered by hepatic intra-arterial infusion).
• Pharmacology: Floxuridine is a pyrimidine analog that acts as an inhibitor of the S-phase of cell division. This selectively kills rapidly dividing cells. Floxuridine is an anti-metabolite. Anti-metabolites masquerade as pyramidine-like molecules which prevents normal pyrimidines from being incorporated into DNA during the S phase of the cell cycle. Flurouracil (the end-product of catabolism of floxuridine) blocks an enzyme which converts cytosine nucleosides into the deoxy derivative. In addition, DNA synthesis is further inhibited because fluoruracil blocks the incorporation of the thymdine nucleotide into the DNA strand.
• Toxicity: Oral, rat LD₅₀: 215 mg/kg. Signs of overdose include nausea, vomiting, diarrhea, gastrointestinal ulceration and bleeding, and bone marrow depression (including thrombocytopenia, leukopenia and agranulocytosis).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Elimination: The drug is excreted intact and as urea, fluorouracil, a-fluoro-bureidopropionic acid, dihydrofluorouracil, a-fluoro-b-guanidopropionic acid and a-fluoro-b-alanine in the urine; it is also expired as respiratory carbon dioxide.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - F0503

Biochem/physiol Actions
Antineoplastic drug that acts as a potent inhibitor of thymidylate synthetase1 Resistance to FUdR can develop in cancer cell cultures, among other means, by low-level Mycoplasma infection.2
Packaging
1 g in poly bottle
100, 250 mg in poly bottle

Sigma Aldrich - 46875

Biochem/physiol Actions
Antineoplastic drug that acts as a potent inhibitor of thymidylate synthetase1 Resistance to FUdR can develop in cancer cell cultures, among other means, by low-level Mycoplasma infection.2
Other Notes
Inhibits DNA synthesis by prior inhibition of thymidylate synthetase3