1-[(3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride

• ChemBase ID: 120168
• Molecular Formular: C9H12ClFN2O5
• Molecular Mass: 282.6533832
• Monoisotopic Mass: 282.04187739
• SMILES: n1(C2[C@@H]([C@@H]([C@H](O2)C)O)O)c(=O)[nH]c(=O)c(c1)F.Cl
• Canonical SMILES: C[C@H]1OC([C@@H]([C@@H]1O)O)n1cc(F)c(=O)[nH]c1=O.Cl
• InChI: InChI=1S/C9H11FN2O5.ClH/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16;/h2-3,5-6,8,13-14H,1H3,(H,11,15,16);1H/t3-,5-,6-,8?;/m1./s1
• InChIKey: QLUHBFPFKMSHMP-COAGBBGMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride
• IUPAC Traditional name: 1-[(3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-3H-pyrimidine-2,4-dione hydrochloride; 1-[(3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride
• Synonyms: 1-((3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione hydrochloride; Doxifluridine Hydrochloride

Database IDs

• CAS Number: 3094-09-5
• PubChem SID: 162214521
• PubChem CID: 51052078

CALCULATED PROPERTIES

• Acid pKa: 7.6742187
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.1717542
• LogD (pH = 7.4): -1.3514775
• Log P: -1.1688893
• Molar Refractivity: 51.2248 cm^3
• Polarizability: 20.08188 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Prodrug of 5-Fluoro-2,4(1 H ,3 H) -pyrimidinedione

Product Information

• Salt Data: HCl
• Application(s): Antineoplastic agent

REFERENCES

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• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 475
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DYE415