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Diosmin
Also known as: 520-27-4, Barosmin, Diosimin, Venosmine, Diosmil, Diosmine
Molecular Formula
C28H32O15
Molecular Weight
608.5  g/mol
InChI Key
GZSOSUNBTXMUFQ-YFAPSIMESA-N
FDA UNII
7QM776WJ5N

A bioflavonoid that strengthens vascular walls.
1 2D Structure

Diosmin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
2.1.2 InChI
InChI=1S/C28H32O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-8,10,19,21-30,32-37H,9H2,1-2H3/t10-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
2.1.3 InChI Key
GZSOSUNBTXMUFQ-YFAPSIMESA-N
2.1.4 Canonical SMILES
CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
2.1.5 Isomeric SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
7QM776WJ5N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Barosmin

2. Buchu Resin

3. Daflon

4. Resin, Buchu

5. Venosmine

2.3.2 Depositor-Supplied Synonyms

1. 520-27-4

2. Barosmin

3. Diosimin

4. Venosmine

5. Diosmil

6. Diosmine

7. Flebosten

8. Daflon

9. Tovene

10. Ven-detrex

11. Diovenor

12. Buchu Resin

13. Litosmil

14. Veno-v

15. Flebosmil

16. Diosminum

17. Rioven

18. Diosmetin 7-o-rutinoside

19. Diosven

20. Flebaven

21. Flebavena

22. Hemerven

23. Insuven

24. Varinon

25. Dioven

26. Diosmetin-7-o-rutinoside

27. Diosmin [inn]

28. Diosmetin 7-rutinoside

29. 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

30. 7qm776wj5n

31. Chebi:4631

32. 3',5,7-trihydroxy-4'-methoxyflavone 7-rutinoside

33. 3',5,7-trihydroxy-4'-methoxyflavone-7-rutinoside

34. Diosmin (inn)

35. Nsc-758417

36. 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-((((2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)methyl)tetrahydro-2h-pyran-2-yl)oxy)-4h-chromen-4-one

37. Diosmin, Analytical Standard

38. Dsstox_cid_25892

39. Dsstox_rid_81206

40. Dsstox_gsid_45892

41. 3',5,7-trihydroxy-4'-methoxyflavone-7-(6-o-(-deoxy-alpha-l-mannopyraonsyl)-beta-d-glucopyranoside

42. 5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one

43. 3',5,7-trihydroxy-4'-methoxyflavone 7-rhamnoglucoside

44. Cas-520-27-4

45. Diosmin [inn:ban]

46. Diosmin [inn-spanish]

47. Diosmine [inn-french]

48. Diosminum [inn-latin]

49. Sr-01000799147

50. Unii-7qm776wj5n

51. Ccris 7915

52. Ncgc00095022-01

53. 4h-1-benzopyran-4-one, 7-((6-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-

54. 4h-1-benzopyran-4-one, 7-[[6-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-

55. Einecs 208-289-7

56. Daflon (tn)

57. Mfcd00009772

58. Diosmin (8)

59. Se 4601

60. Diosmine [inci]

61. Diosmin [dsc]

62. Diosmin [mi]

63. Diosmin [mart.]

64. Diosmin [usp-rs]

65. Diosmin [who-dd]

66. Mls001304032

67. Schembl120870

68. Diosmin [ep Monograph]

69. Chembl231884

70. Dtxsid4045892

71. 3',5-dihydroxy-4'-methoxy-4-oxo-4h-chromen-7-ylrutosid

72. Bdbm153267

73. Hms2233p16

74. Hms3713l08

75. Act05288

76. Zinc4098512

77. Tox21_111392

78. 3',5-dihydroxy-4'-methoxy-4-oxo-4h-chromen-7-ylrutosid [iupac]

79. S2292

80. Akos015969767

81. Tox21_111392_1

82. Bcp9000612

83. Ccg-208570

84. Db08995

85. Nsc 758417

86. Smp1_000183

87. Ncgc00344564-01

88. 4h-1-benzopyran-4-one, 7-((6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-

89. 4h-1-benzopyran-4-one,7-[[6-o-(6-deoxy-a-l-mannopyranosyl)-b-d-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-

90. 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4h-1-benzopyran-7-yl 6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranoside

91. 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-((6-o-alpha-l-rhamnopyranosyl-beta-d-glycopyranosyl)oxy)-4-chromenon

92. As-13224

93. Bp-12422

94. Smr000718616

95. Bcp0726000067

96. C10039

97. D07858

98. 520d274

99. 3',5,7-trihydroxy-4'-methoxy Flavone-7-rutinoside

100. Q2607865

101. Sr-01000799147-4

102. Sr-01000799147-5

103. Sr-01000799147-6

104. Diosmin, European Pharmacopoeia (ep) Reference Standard

105. Diosmin, United States Pharmacopeia (usp) Reference Standard

106. Diosmin For System Suitability, European Pharmacopoeia (ep) Reference Standard

107. 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(((2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)methyl)tetrahydro-2h-pyran-2-yloxy)-4h-chromen-4-one

108. 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(o6-alpha-l-rhamnopyranosyl-beta-d-glucopyranosyloxy)chromen-4-one

109. 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

110. 7-((6-o-(6-deoxy-ga-l-mannopyranosyl)-.beta.-d-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4h-1-benzopyran-4-one

111. 7-((6-o-(6-deoxy-ga-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4h-1-benzopyran-4-one

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 608.5 g/mol
Molecular Formula C28H32O15
XLogP3-0.8
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count15
Rotatable Bond Count7
Exact Mass608.17412031 g/mol
Monoisotopic Mass608.17412031 g/mol
Topological Polar Surface Area234 Ų
Heavy Atom Count43
Formal Charge0
Complexity995
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Diosmin is used over-the-counter alone or with ingredients such as [hesperidin] and [diosmetin] to support vein and capillary function.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Diosmin is a venoactive drug supporting circulatory health through various actions on blood vessels; it supports lymphatic drainage and improves microcirculation while increasing venous tone and elasticity. For these reasons, diosmin is frequently taken by individuals with chronic venous disease to support vascular health and has been demonstrated to improve quality of life. In addition to the above effects, diosmin exerts antioxidant activity and scavenges oxygen free radicals, reducing levels of oxidative stress normally detected through biomarkers such as prostaglandins isoprostane precursors. In one clinical study, mean content of TNF alpha, VEGF-C, VEGF-A IL-6, in addition to FGF2 were decreased by after the therapy with diosmin; findings were statistically significant. Additionally, a decrease in edema and mean leg circumference of patients taking diosmin for three months was observed in a clinical study. Diosmin has been demonstrated to enhance the metabolism of glucose in diabetic disorders.


5.2 ATC Code

C - Cardiovascular system

C05 - Vasoprotectives

C05C - Capillary stabilizing agents

C05CA - Bioflavonoids

C05CA03 - Diosmin


5.3 Absorption, Distribution and Excretion

Absorption

Diosmin is rapidly absorbed in the gastrointestinal tract. After a 900 mg single oral dose in a study using liquid chromatography with tandem mass spectrometry (LC-MS/MS) method, Cmax was 4.23.8 ngmL-1, Tmax was 18.79.9 hours, and AUC0~96 was 185.4166.2 ngmL-1 in healthy volunteers. Another pharmacokinetic study of 5 adults revealed a Cmax of 41794.1 ng/dL.


Route of Elimination

Pharmacokinetic data show absence of urinary elimination for diosmin and its aglycone diosmetin. Minor metabolites are found to be eliminated in the urine as glucuronic acid conjugates.


Volume of Distribution

A pharmacokinetic study of 5 adults revealed a volume of distribution of 62.17.9 L.


5.4 Metabolism/Metabolites

Degradation products of diosmin such as alkyl-phenolic acids confirm a metabolic pattern similar to that of other flavonoids.


5.5 Biological Half-Life

Diosmin half-life ranges from 26 to 43 hours. One study using a liquid chromatography with tandem mass spectrometry (LC-MS/MS) method after a single 900 mg dose of diosmin demonstrated a half-life of 60.285.7 hours in healthy volunteers.


5.6 Mechanism of Action

Diosmin helps to maintain circulatory system structure and function, particularly vein strength and competence. The molecular mechanism of action of diosmin has not been established. Several resources indicate that diosmin binds to the aryl hydrocarbon receptor, however clinical relevance to vascular function is unknown. One study demonstrates that oral diosmin exerts effects on the in vitro metabolism of noradrenaline by varicose veins, potentially benefitting vascular health.


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