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1. 2-(7'-theophyllinemethyl)1,3-dioxolane
2. Doxophylline
3. Tmdo
1. 69975-86-6
2. Doxophylline
3. Ansimar
4. Dioxyfilline
5. Ventax
6. Maxivent
7. Abc 12/3
8. Synasma
9. 7-(1,3-dioxolan-2-ylmethyl)theophylline
10. Mpm23gmo7z
11. Nsc-759645
12. Abc-12/3
13. 1h-purine-2,6-dione, 7-(1,3-dioxolan-2-ylmethyl)-3,7-dihydro-1,3-dimethyl-
14. 7-((1,3-dioxolan-2-yl)methyl)-1,3-dimethyl-1h-purine-2,6(3h,7h)-dione
15. Ncgc00159330-02
16. Dsstox_cid_2968
17. 7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-3,7-dihydro-1h-purine-2,6-dione
18. Dsstox_rid_76810
19. Dsstox_gsid_22968
20. Doxofilina
21. Doxofyllinum
22. Doxofylline [usan:inn]
23. Doxofilina [inn-spanish]
24. Doxofyllinum [inn-latin]
25. 7-((1,3-dioxolan-2-yl)methyl)-1,3-dimethyl-3,7-dihydro-1h-purine-2,6-dione
26. Cas-69975-86-6
27. Sr-01000789760
28. Einecs 274-239-6
29. Unii-mpm23gmo7z
30. Brn 0561195
31. 2-(7'-theophyllinemethyl)-1,3-dioxolane
32. Doxofylline,(s)
33. Maxivent (tn)
34. 2-(7'-teofillinmetil)-1,3-diossolano [italian]
35. Mfcd00865218
36. 2-(7'-teofillinmetil)-1,3-diossolano
37. Doxofylline [mi]
38. Doxofylline [inn]
39. Doxofylline (usan/inn)
40. Doxofylline [usan]
41. Theophylline, 7-(1,3-dioxolan-2-ylmethyl)-
42. 1h-purine-2,6-dione, 3,7-dihydro-7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-
43. 7-(1,3-dioxolon-2-ylmethyl)-1,2,3,6-tetrahydro-1,3-dimethyl-2,6-purindion
44. Doxofylline [mart.]
45. Schembl37963
46. Doxofylline [who-dd]
47. 5-26-14-00120 (beilstein Handbook Reference)
48. Mls001214637
49. Zinc3837
50. Chembl1527608
51. Dtxsid7022968
52. Chebi:94714
53. Doxofylline, >=98% (hplc)
54. 7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-purine-2,6-dione
55. Hms2090e04
56. Hms2877p10
57. Hms3652h03
58. Hms3714m21
59. Hms3885b09
60. Pharmakon1600-01502358
61. Abc-1213
62. Bcp12155
63. Hy-b0004
64. Tox21 111577
65. Tox21_111577
66. Bbl012263
67. Do-309
68. Nsc759645
69. S4164
70. Stk735429
71. 7-(1,3-dioxolan-2-ylmethyl)-3,7-dihydro-1,3-dimethyl-1h-purine-2,6-dione
72. Akos005535592
73. Tox21_111577_1
74. Ac-3492
75. Ccg-213050
76. Cs-8019
77. Db09273
78. Ds-7424
79. Nsc 759645
80. Ncgc00159330-03
81. Ncgc00159330-04
82. Ncgc00159330-10
83. Bd164389
84. Smr000543614
85. D4302
86. Ft-0630792
87. Sw199176-2
88. D03898
89. D90272
90. Ab00828111-06
91. Ab00828111_07
92. Ab00828111_08
93. 975d866
94. A836720
95. L001990
96. Q425887
97. 7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethylxanthine
98. Sr-01000789760-2
99. Sr-01000789760-3
100. 7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-1h-purine-2,6-dione
101. Doxofylline, United States Pharmacopeia (usp) Reference Standard
102. 7-[(1,3-dioxolan-2-yl)methyl]-1,3-dimethyl-2,3,6,7-tetrahydro-1h-purine-2,6-dione
| Molecular Weight | 266.25 g/mol |
|---|---|
| Molecular Formula | C11H14N4O4 |
| XLogP3 | -0.9 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Exact Mass | 266.10150494 g/mol |
| Monoisotopic Mass | 266.10150494 g/mol |
| Topological Polar Surface Area | 76.9 Ų |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Complexity | 398 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
Indicated for the treatment of chronic obstructive pulmonary disease (COPD), bronchial asthma and pulmonary disease with spastic bronchial component.
Doxofylline is a methylxanthine bronchodilator with potent bronchodilator activity comparable to that of theophylline. In animal studies, doxofylline demonstrated to attenuate bronchoconstriction, inflammatory actions and the release of thromboxane A2 (TXA2) when challenged with platelet-activating factor. Doxofylline does not demonstrate direct inhibition of any histone deacetylase (HDAC) enzymes or known PDE enzyme isoforms and did not act as an antagonist at A2 or A2 receptors. The affinity for adenosine A1, A2A and A2B receptors are reported to be all higher than 100 M. It only displays an inhibitory action against PDE2A1 and antagonism at adenosine A(2A) at high concentrations. A study demonstrated that doxofylline interacts with 2-adrenoceptors to induce blood vessel relaxation and airway smooth muscle relaxation. In dog studies, doxofylline decreased airway responsiveness at a dose that did not affect heart rate and respiratory rate.
Antitussive Agents
Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally. (See all compounds classified as Antitussive Agents.)
Bronchodilator Agents
Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)
Phosphodiesterase Inhibitors
Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases. (See all compounds classified as Phosphodiesterase Inhibitors.)
R - Respiratory system
R03 - Drugs for obstructive airway diseases
R03D - Other systemic drugs for obstructive airway diseases
R03DA - Xanthines
R03DA11 - Doxofylline
Absorption
After repeated administrations doxofylline reaches the steady-state in about 4 days. Following oral administration of 400 mg doxofylline twice daily for 5 days in adults with chronic bronchitis, the peak plasma concentrations (Cmax) at steady state ranged from 5.78 to 20.76 mcg/mL. The time to reach maximum concentration (Tmax) was 1.19 0.19 hours. The absolute bioavailability of doxofylline in healthy subjects was 63 25%.
Route of Elimination
Less than 4% of an orally administered dose is excreted unchanged in the urine due to extensive hepatic metabolism.
Volume of Distribution
Doxofylline demonstrates a short distribution phase following intravenous administration of 100 mg given in adults with chronic bronchitis. As methylxanthines are distributed to all body compartments, doxofylline may be detected in breast milk and placenta.
Clearance
Following oral administration of 400 mg doxofylline twice daily for 5 days, the total clearance was 555.2 180.6 mL/min.
Doxofylline is thought to undergo hepatic metabolism which accounts for 90% of total drug clearance. -hydroxymethyltheophylline was detected in the serum and urine after oral administration of 400 mg given in healthy subjects. The circulating metabolite was devoid of any significant pharmacological activity.
Following administration of a single intravenous dose of 100 mg over 10 minutes in adults with chronic bronchitis, the elimination half life of doxofylline was 1.83 0.37 hours. Following oral administration of 400 mg twice daily for 5 days in adults with chronic bronchitis, the mean elimination half life was 7.01 0.80 hours.
The main mechanism of action of doxofylline is unclear. One of the mechanisms of action of is thought to arise from the inhibition of phosphodiesterase activity thus increasing the levels of cAMP and promoting smooth muscle relaxation. The interaction of doxofylline with beta-2 adrenoceptors was demonstrated by a study using nonlinear chromatography, frontal analysis and molecular docking. Serine 169 and serine 173 residues in the receptor are thought to be critical binding sites for doxofylline where hydrogen bonds are formed. Via mediating the actions of beta-2 adrenoceptors, doxofylline induces blood vessel relaxation and airway smooth muscle relaxation. There is also evidence that doxofylline may exert anti-inflammatory actions by reducing the pleurisy induced by the inflammatory mediator platelet activating factor (PAF) according to a rat study. It is suggested that doxofylline may play an important role in attenuating leukocyte diapedesis, supported by mouse preclinical studies where doxofylline administration was associated with inhibited leukocyte migration across vascular endothelial cells in vivo and in vitro.Unlike theophylline, doxofylline does not inhibit tumor necrosis factor-induced interleukin (IL)-8 secretion in ASM cells.
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