7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 121647
• Molecular Formular: C11H14N4O4
• Molecular Mass: 266.25326
• Monoisotopic Mass: 266.10150495
• SMILES: c12c(c(=O)n(c(=O)n1C)C)n(cn2)CC1OCCO1
• Canonical SMILES: Cn1c(=O)n(C)c2c(c1=O)n(cn2)CC1OCCO1
• InChI: InChI=1S/C11H14N4O4/c1-13-9-8(10(16)14(2)11(13)17)15(6-12-9)5-7-18-3-4-19-7/h6-7H,3-5H2,1-2H3
• InChIKey: HWXIGFIVGWUZAO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: doxofylline; 7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• Synonyms: 7-((1,3-dioxolan-2-yl)methyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione; Doxofylline; Ansimar; Maxivent; Doxofylline

Database IDs

• CAS Number: 69975-86-6
• PubChem SID: 162216000
• PubChem CID: 50942

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.48524362
• LogD (pH = 7.4): -0.48524347
• Log P: -0.48524347
• Molar Refractivity: 64.6868 cm^3
• Polarizability: 24.134043 Å^3
• Polar Surface Area: 76.9 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Target: Others
• Mechanism of Action: Increase in cyclic AMP inhibits activation of inflammatory cells in addition to bronchodilation; The bronchodilatory effect is due to their ability to inhibit phosphodiesterase (PDE) and thus inhibit breakdown of cAMP (cyclic adenosine monophosphate)

Product Information

• Salt Data: Free Base
• Application(s): Antitussive agent used for treatment of bronchospasm

REFERENCES

• U.K. Pat., 1978, Instituto Biologico Chemioterapico ABC, 1 582 510; CA, 90, 197858y, (pharmacol)
• Franzone, J.S. et al., Farmaco, Ed. Sci., 1981, 36, 220, (metab)
• Badini, C. et al., Farmaco, Ed. Sci., 1982, 37, 320, (hplc)
• Bologna, E. et al., J. Int. Med. Res., 1990, 18, 282, (pharmacokinet)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1317
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TEQ175