5-fluoro-1,2,3,4-tetrahydro(2-13C,1,3-15N2)pyrimidine-2,4-dione

• ChemBase ID: 136450
• Molecular Formular: C4H3FN2O2
• Molecular Mass: 133.05669583
• Monoisotopic Mass: 133.01528019
• SMILES: c1c(c(=O)[15nH][13c](=O)[15nH]1)F
• Canonical SMILES: Fc1c[15nH][13c](=O)[15nH]c1=O
• InChI: InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)/i4+1,6+1,7+1
• InChIKey: GHASVSINZRGABV-XZQGXACKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-fluoro-1,2,3,4-tetrahydro(2-^1^3C,1,3-^1^5N₂)pyrimidine-2,4-dione
• IUPAC Traditional name: 5-fluoro-1,3-dihydro(2-^1^3C,1,3-^1^5N₂)pyrimidine-2,4-dione
• Synonyms: 5-Fluorouracil-2-13C,15N2; 5-Fluoro-2,4(1H,3H)pyrimidinedione-13C,15N2; 2,4-Dihydroxy-5-fluoropyrimidine-13C,15N2; 5-FU-13C,15N2; 5-Fluoropyrimidine-2,4-diol-13C,15N2; Adrucil-13C,15N2; Arumel-13C,15N2; Carac-13C,15N2; Fluorouracil-13C,15N2; Queroplex-13C,15N2; Ro 2-9757-13C,15N2; Timazin-13C,15N2; U 8953-13C,15N2; 5-Fluorouracil-13C,15N2

Database IDs

• MDL Number: MFCD09840633
• PubChem SID: 162230720
• PubChem CID: 57369200

CALCULATED PROPERTIES

• Acid pKa: 7.7624574
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.65818775
• LogD (pH = 7.4): -0.810272
• Log P: -0.6558481
• Molar Refractivity: 26.1722 cm^3
• Polarizability: 9.588146 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Hot Water; Methanol
• Apperance: Beige Solid
• Melting Point: >270°C (dec.); 282-286 °C (dec)(lit.)
• Mass Shift: M+3

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Isotopic Purity: 98 atom % 15N; 99 atom % 13C
• Mol. Weight: mol wt 133.01 by atom % calculation
• Empirical Formula (Hill Notation): 13CC3H3F15N2O2

DETAILS

Sigma Aldrich - 723258

Packaging
This product may be available from bulk stock and can be packaged on demand. For information on pricing, availability and packaging, please contact Stable Isotopes Customer Service.

Toronto Research Chemicals - F596002

Labelled 5-FU, a potent antineoplastic agent in clinical use. Also an inhibitor of DNA synthesis.

REFERENCES

• Rudy, B.C., et al.: Anal. Profiles Drug Subs., 2, 221 (1973)
• Miyashita, O., et al.: Chem. Pharm. Bull., 29, 3181 (1973)
• Hansen, R.M., et al.: Cancer Invest., 9, 637 (1973)