4-amino-1-[(4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

• ChemBase ID: 179696
• Molecular Formular: C9H11F2N3O4
• Molecular Mass: 263.1981464
• Monoisotopic Mass: 263.07176229
• SMILES: n1(C2C([C@@H]([C@H](O2)CO)O)(F)F)c(=O)nc(cc1)N
• Canonical SMILES: OC[C@H]1OC(C([C@@H]1O)(F)F)n1ccc(nc1=O)N
• InChI: InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7?/m1/s1
• InChIKey: SDUQYLNIPVEERB-WETFRILZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-1-[(4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
• Synonyms: Gemzar; Gemcitabine

Database IDs

• CAS Number: 95058-81-4
• PubChem SID: 164235606
• PubChem CID: 11054511

CALCULATED PROPERTIES

• Acid pKa: 11.51707
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.4665402
• LogD (pH = 7.4): -1.4665728
• Log P: -1.4665396
• Molar Refractivity: 53.2503 cm^3
• Polarizability: 20.563793 Å^3
• Polar Surface Area: 108.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Nucleoside antimetabolite

Product Information

• Application(s): Antimetabolite; Antineoplastic agent; Antineoplastic agent for treatment of lung and pancreatic tumours; Antiviral agent; Nucleoside transporter substrate

REFERENCES

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• Chou, T.S. et al., Synthesis, 1992, 565, (synth, ir, uv, cmr, bibl)
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• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 538