pentyl N-{1-[(2R,3S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate

• ChemBase ID: 163598
• Molecular Formular: C15H22FN3O6
• Molecular Mass: 359.3500832
• Monoisotopic Mass: 359.14926366
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1cc(c(nc1=O)NC(=O)OCCCCC)F)C)O)O
• Canonical SMILES: CCCCCOC(=O)Nc1nc(=O)n(cc1F)[C@@H]1O[C@@H](C([C@@H]1O)O)C
• InChI: InChI=1S/C15H22FN3O6/c1-3-4-5-6-24-15(23)18-12-9(16)7-19(14(22)17-12)13-11(21)10(20)8(2)25-13/h7-8,10-11,13,20-21H,3-6H2,1-2H3,(H,17,18,22,23)/t8-,10?,11+,13-/m1/s1
• InChIKey: GAGWJHPBXLXJQN-IZSYJUOESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pentyl N-{1-[(2R,3S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate
• IUPAC Traditional name: pentyl N-{1-[(2R,3S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl}carbamate
• Synonyms: 5’-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine; [1-(5-Deoxy-β-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl]carbamic Acid Pentyl Ester; Capecitibine; Capecytabine; Capiibine; Captabin; Ro 09-1978; Ro 09-1978/000; Xeloda; Capecitabine

Database IDs

• CAS Number: 154361-50-9
• PubChem SID: 162257733
• PubChem CID: 46783385

CALCULATED PROPERTIES

• Acid pKa: 8.226098
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.76731384
• LogD (pH = 7.4): 0.71495193
• Log P: 0.76803607
• Molar Refractivity: 82.746 cm^3
• Polarizability: 32.438602 Å^3
• Polar Surface Area: 120.69 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White to Pale Green Solid
• Melting Point: 110-121°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C175650

Capecitabine is an antineoplastic agent. Capecitabine is a prodrug of Doxifluridine (D556750).

REFERENCES

• Muss, H., et al.: New Eng. J. Med., 360, 2055 (2009)
• Takahashi, S., et al.: Drug Metab. Disposition, 37, 956 (2009)
• Saltz, L., et al.: J. Clin. Oncol., 27, 653 (2009)
• Sanderson, H., et al.: Toxicol. Lett., 187, 84 (2009)