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Oxtriphylline

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Chemistry

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Also known as: Choline theophyllinate, 4499-40-5, Cholinophyllin, Choledyl, Choline theophylline, Theocolin

Molecular Formula

C₁₂H₂₁N₅O₃

Molecular Weight

283.33 g/mol

InChI Key

SOELXOBIIIBLRJ-UHFFFAOYSA-M

FDA UNII

3K045XR58X

Oxtriphylline is the choline salt of theophylline with an anti-asthmatic property. Oxtriphylline appears to inhibit phosphodiesterase and prostaglandin production, regulates calcium flux and intracellular calcium distribution, and antagonizes adenosine. Physiologically, this agent causes relaxation of bronchial smooth muscle, produces vasodilation (except in cerebral vessels), stimulates cardiac muscle, as well as induces diuresis and gastric acid secretion. It may also suppress inflammation and improve contractility of the diaphragm.

1 2D Structure

Oxtriphylline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,3-dimethyl-2-oxopurin-6-olate;2-hydroxyethyl(trimethyl)azanium

2.1.2 InChI

InChI=1S/C7H8N4O2.C5H14NO/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;1-6(2,3)4-5-7/h3,12H,1-2H3;7H,4-5H2,1-3H3/q;+1/p-1

2.1.3 InChI Key

SOELXOBIIIBLRJ-UHFFFAOYSA-M

2.1.4 Canonical SMILES

CN1C(=C2C(=NC=N2)N(C1=O)C)[O-].C[N+](C)(C)CCO

2.2 Other Identifiers

2.2.1 UNII

3K045XR58X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Brondaxin

2. Brondecon

3. Choledyl

4. Choledyl-sa

5. Choline Theophyllinate

6. Cholinetheophyllinate

7. Cholinophyllin

8. Euspirax

9. Oxtripylline-sa

10. Theobret

2.3.2 Depositor-Supplied Synonyms

1. Choline Theophyllinate

2. 4499-40-5

3. Cholinophyllin

4. Choledyl

5. Choline Theophylline

6. Theocolin

7. Choline Salt With Theophylline (1:1)

8. Oxtriphylline [usp]

9. 146-71-4

10. Nsc-760431

11. Choline Theophyllinate [inn]

12. 1,3-dimethyl-2-oxopurin-6-olate;2-hydroxyethyl(trimethyl)azanium

13. 3k045xr58x

14. Oxtriphylline (usp)

15. Choline Theophylline (jan)

16. Choline Theophyllinate (inn)

17. Cholinophylline

18. Oxtrimethylline

19. Soliphylline

20. Teofilcolina

21. Theoxylline

22. Cholegyl

23. Choline Theophylline [jan]

24. Filoral

25. Sabidal

26. Teokolin

27. 2-hydroxy-n,n,n-trimethylethanaminium 1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-ide

28. Colina Teofillinato

29. Ethanaminium, 2-hydroxy-n,n,n-trimethyl-, Salt With 3,7-dihydro-1,3-dimethyl-1h-purine-2,6-dione

30. Cholini Theophyllinas

31. Choledyl Sa 400

32. Teofilinato De Colina

33. Theophylline Cholinate

34. Oxtriphylline Pediatric

35. Choline Theophylline Salt

36. Theophyllinate De Choline

37. Colina Teofillinato [dcit]

38. Theophylline Salt Of Choline

39. Unii-3k045xr58x

40. Cholintheophyllinat

41. Theophylline, Compd. With Choline

42. Cholini Theophyllinas [inn-latin]

43. Theocolin (tn)

44. Einecs 224-798-7

45. Teofilinato De Colina [inn-spanish]

46. Zy 15061

47. Choline Thieophyllinate

48. Theophyllinate De Choline [inn-french]

49. Theophyline And Choline

50. Choline, Compd. With Theophylline (1:1)

51. Schembl4629

52. Oxtriphylline [vandf]

53. Schembl152854

54. Oxtriphylline [usp-rs]

55. Chembl1200434

56. Dtxsid20894867

57. (2-hydroxyethyl)trimethylammonium Compound With Theophylline

58. Hms2094a07

59. Pharmakon1600-01505759

60. Choline Theophyllinate [mi]

61. Oxtriphylline [orange Book]

62. Hy-b1718

63. Nsc760431

64. Oxtriphylline [usp Monograph]

65. Akos025392171

66. Choline Theophyllinate [mart.]

67. Ccg-213695

68. Choline Theophyllinate [who-dd]

69. Db01303

70. Ks-1426

71. Nsc 760431

72. Ethanaminium, 2-hydroxy-n,n,n-trimethyl-, Salt With 3,7-dihydro-1,3-dimethylpurine-2,6-dione

73. 1h-purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-, Ion(1-), 2-hydroxy-n,n,n-trimethylethanaminium

74. Ethanaminium, 2-hydroxy-n,n,n-trimethyl-, Salt With 3,7-dihydro-1,3-dimethyl-1h-purine-2,6-dione (1:1)

75. Cs-0013721

76. D02017

77. Choline, Hydroxide, Compd. With Theophylline (1:1)

78. Q5104342

79. Ethanaminium, 2-hydroxy-n,n,n-trimethyl-, Salt With 3,9-dihydro-1,3-dimethyl-1h-purine-2,6-dione (1:1)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₂₁N₅O₃
Molecular Weight	283.33 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	283.16443955 g/mol
Monoisotopic Mass	283.16443955 g/mol
Topological Polar Surface Area	91.6 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	415
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	2

4 Drug and Medication Information

4.1 Drug Indication

Used to treat the symptoms of asthma, bronchitis, COPD, and emphysema.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Oxtriphylline is a bronchodilator. Oxtriphylline works in several ways: it relaxes muscles in your lungs and chest to allow more air in, decreases the sensitivity of your lungs to allergens and other substances that cause inflammation, and increases the contractions of your diaphragm to draw more air into the lungs.

5.2 MeSH Pharmacological Classification

Bronchodilator Agents

Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)

5.3 ATC Code

R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03D - Other systemic drugs for obstructive airway diseases

R03DA - Xanthines

R03DA02 - Choline theophyllinate

5.4 Absorption, Distribution and Excretion

Absorption

After ingestion, theophylline is released from oxytriphylline in the acidic environment of the stomach.

Route of Elimination

The kidneys are the main route of elimination for both theophylline and its metabolites, but some unchanged theophylline is eliminated in the feces.

Volume of Distribution

Theophylline has an apparent volume of distribution of 0.30.7 L/kg in children and adults, and the Vd is about twice that of an adult in premature infants.

Clearance

Theophylline has an average clearance in children (over 6 months) of 1.45 mL/kg per minute, and in healthy, nonsmoking adults of 0.65 mL/kg per hour.

5.5 Metabolism/Metabolites

Theophylline undergoes hepatic metabolism to 1,3-dimethyluric acid, 1-methyluric acid, and 3-methylxanthine.

5.6 Biological Half-Life

The serum half life varies greatly between patients and in age. The half life range for a healthy, nonsmoking adult is 3-12.8 hours, for children is 1.59.5 hours, and for for premature infants is 1558 hours.

5.7 Mechanism of Action

Oxtriphylline is a choline salt of theophylline. After ingestion, theophylline is released from oxytriphylline, and theophylline relaxes the smooth muscle of the bronchial airways and pulmonary blood vessels and reduces airway responsiveness to histamine, methacholine, adenosine, and allergen. Theophylline competitively inhibits type III and type IV phosphodiesterase (PDE), the enzyme responsible for breaking down cyclic AMP in smooth muscle cells, possibly resulting in bronchodilation. Theophylline also binds to the adenosine A2B receptor and blocks adenosine mediated bronchoconstriction. In inflammatory states, theophylline activates histone deacetylase to prevent transcription of inflammatory genes that require the acetylation of histones for transcription to begin.

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