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Doxofylline

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Also known as: 69975-86-6, Doxophylline, Ansimar, Dioxyfilline, Ventax, Maxivent

Molecular Formula

C₁₁H₁₄N₄O₄

Molecular Weight

266.25 g/mol

InChI Key

HWXIGFIVGWUZAO-UHFFFAOYSA-N

FDA UNII

MPM23GMO7Z

Doxofylline is a methylxanthine derivative with the presence of a dioxolane group in position 7. As a drug used in the treatment of asthma, doxofylline has shown similar efficacy to theophylline but with significantly fewer side effects in animal and human studies. In contrast with other xanthine derivatives, doxofylline does not significantly bind to adenosine alpha-1 or alpha-2 receptors and lacks stimulating effects. Decreased affinity for adenosine receptors may account for the better safety profile of doxofylline compared to theophylline. Unlike theophylline, doxofylline does not affect calcium influx and does not antagonize the actions of calcium channel blockers which could explain reduced cardiac adverse reactions associated with the drug. The anti-asthmatic effects of doxophylline are mediated by other mechanisms, primarily through inhibiting the activities of the phosphodiesterase (PDE) enzyme.

1 2D Structure

Doxofylline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethylpurine-2,6-dione

2.1.2 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

2.1.3 InChI Key

HWXIGFIVGWUZAO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CC3OCCO3

2.2 Other Identifiers

2.2.1 UNII

MPM23GMO7Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(7'-theophyllinemethyl)1,3-dioxolane

2. Doxophylline

3. Tmdo

2.3.2 Depositor-Supplied Synonyms

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

2.4 Create Date

2005-07-07

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₄N₄O₄
Molecular Weight	266.25 g/mol
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 Å²
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

4 Drug and Medication Information

4.1 Drug Indication

Indicated for the treatment of chronic obstructive pulmonary disease (COPD), bronchial asthma and pulmonary disease with spastic bronchial component.

5 Pharmacology and Biochemistry

5.1 Pharmacology

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.

5.2 MeSH Pharmacological Classification

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.)

5.3 ATC Code

R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03D - Other systemic drugs for obstructive airway diseases

R03DA - Xanthines

R03DA11 - Doxofylline

5.4 Absorption, Distribution and Excretion

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.

5.5 Metabolism/Metabolites

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.

5.6 Biological Half-Life

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.

5.7 Mechanism of Action

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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