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    Chemistry

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    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
    Diosmin
    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.

    API Reference Price

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    07-Jan-2021
    31-Aug-2024
    KGS
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