Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H32O15 |
Molecular Weight | 608.5447 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C=C1O)C2=CC(=O)C3=C(O2)C=C(O[C@@H]4O[C@H](CO[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)C=C3O
InChI
InChIKey=GZSOSUNBTXMUFQ-YFAPSIMESA-N
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24092244Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/diosmin.html | https://www.drugbank.ca/drugs/DB08995 | https://www.ncbi.nlm.nih.gov/pubmed/25893991 | https://clinicaltrials.gov/ct2/show/NCT02616731 |
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24092244
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/diosmin.html | https://www.drugbank.ca/drugs/DB08995 | https://www.ncbi.nlm.nih.gov/pubmed/25893991 | https://clinicaltrials.gov/ct2/show/NCT02616731 |
Diosmin is a flavone indicated for the treatment of venous disease i.e., chronic venous insufficiency (CVI) including spider and varicose veins, leg swelling (edema), stasis dermatitis and venous ulcers. Diosmin is also used as a stand-alone or surgical adjunctive therapy in hemorrhoidal disease. There are extensive clinical trials that show diosmin improves all stages of venous disease including venous ulcers and improves quality of life. Diosmin prolongs the vasoconstrictor effect of norepinephrine on the vein wall, increasing venous tone, and therefore reducing venous capacitance, distensibility, and stasis. This increases the venous return and reduces venous hyperpressure present in patients suffering from CVI. Diosmin improves lymphatic drainage by increasing the frequency and intensity of lymphatic contractions, and by increasing the total number of functional lymphatic capillaries. Furthermore, diosmin with hesperidine decreases the diameter of lymphatic capillaries and the intralymphatic pressure. Diosmin reduces the expression of endothelial adhesion molecules (ICAM1, VCAM1), and inhibits the adhesion, migration, and activation of leukocytes at the capillary level. This leads to a reduction in the release of inflammatory mediators, principally oxygen free radicals, and prostaglandins (PGE2, PGF2a). Diosmin is currently a prescription medication in some European countries (under the Dio-PP, Venotec, Daflon etc. tradenames), and is sold as a nutritional supplement in the United States.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL4026 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19766327 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Therapeutic approach to chronic venous insufficiency and its complications: place of Daflon 500 mg. | 2001 Aug |
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[Effect of daflon on the transcapillary fluid exchange in hindlimbs of anesthesized Wistar rats]. | 2001 Mar-Apr |
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Clinical and hemodynamic outcomes in patients with chronic venous insufficiency after oral micronized flavonoid therapy. | 2001 Nov-Dec |
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HR (Venoruton1000, Paroven, 0-[beta-hydroxyethyl]-rutosides) vs. Daflon 500 in chronic venous disease and microangiopathy: an independent prospective, controlled, randomized trial. | 2002 Jul |
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Effects of plant-derived phenols on rat liver cytochrome P450 2B1 activity. | 2002 May-Jun |
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Micronised purified flavonoid fraction: a review of its use in chronic venous insufficiency, venous ulcers and haemorrhoids. | 2003 |
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[Efficacy and safety of treatment with methotrexate, leflunomide, detralex, and their combination of patients with rheumatoid arthritis]. | 2003 Apr-Jun |
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Effects of Daflon on oxidative stress induced by hindlimb ischemia/reperfusion. | 2003 Jul |
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From skin disorders to venous leg ulcers: pathophysiology and efficacy of Daflon 500 mg in ulcer healing. | 2003 Jul-Aug |
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From symptoms to leg edema: efficacy of Daflon 500 mg. | 2003 Jul-Aug |
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Flavonoids detection by HPLC-DAD-MS-MS in lemon juices from Sicilian cultivars. | 2003 Jun 4 |
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Simultaneous reversed-phase high-performance liquid chromatographic method for the determination of diosmin, hesperidin and naringin in different citrus fruit juices and pharmaceutical formulations. | 2003 Sep 19 |
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[The principles of action and use of phlebotropic agents]. | 2004 |
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Flavonoid distribution during the development of leaves, flowers, stems, and roots of Rosmarinus officinalis. postulation of a biosynthetic pathway. | 2004 Aug 11 |
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The effect of diosmin hesperidin on intestinal ischaemia--reperfusion injury. | 2004 Nov-Dec |
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[PHLEBODIA (diosmine): a role in the management of bleeding nonprolapsed hemorrhoids]. | 2005 |
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[Butcher's Broom, in the treatment of venous insufficiency]. | 2005 Aug |
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[Analysis of surgical procedures on the vena saphena magna in the Czech Republic and an effect of Detralex during its stripping]. | 2005 Aug |
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Flavonoids to reduce bleeding and pain after stapled hemorrhoidopexy: a randomized controlled trial. | 2005 Aug |
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Venous leg ulcer: a meta-analysis of adjunctive therapy with micronized purified flavonoid fraction. | 2005 Aug |
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Micronized purified flavonoid fraction (MPFF): a review of its pharmacological effects, therapeutic efficacy and benefits in the management of chronic venous insufficiency. | 2005 Jan |
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Hesperidin, a citrus bioflavonoid, decreases the oxidative stress produced by carbon tetrachloride in rat liver and kidney. | 2005 Jan 31 |
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HR, 0-(beta-hydroxyethyl)-rutosides, in comparison with diosmin+hesperidin in chronic venous insufficiency and venous microangiopathy: an independent, prospective, comparative registry study. | 2005 Jan-Feb |
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Determination of flavonoids in citrus juices by micro-HPLC-ESI/MS. | 2005 Jul |
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Phlebotonics for venous insufficiency. | 2005 Jul 20 |
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Venous ulcers: pathophysiology and treatment options. | 2005 May |
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The effect of the flavonoid diosmin, grape seed extract and red wine on the pulmonary metastatic B16F10 melanoma. | 2005 Oct |
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Daflon 500 mg and venous leg ulcer: new results from a meta-analysis. | 2005 Sep-Oct |
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Daflon 500 mg: symptoms and edema clinical update. | 2005 Sep-Oct |
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Chronic venous insufficiency and the therapeutic effects of Daflon 500 mg. | 2005 Sep-Oct |
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[Semisynthetic Diosmin (Phlebodia 600) for therapy of lower limb chronic venous insufficiency]. | 2006 |
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The effect of purified micronized flavonoid fraction on the healing of anastomoses in the colon in rats. | 2006 |
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Effects of citrus flavonoids on redox homeostasis of toxin-injured liver in rat. | 2006 Dec |
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The impact of micronized purified flavonoid fraction on the treatment of acute haemorrhoidal episodes. | 2006 Jun |
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Central nervous system depressant action of flavonoid glycosides. | 2006 Jun 13 |
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Bioavailability of diclofenac sodium after pretreatment with diosmin in healthy volunteers. | 2007 |
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[Congenital anomalies of the inferior vena cava: diagnosis and medical treatment]. | 2007 |
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Effects of micronized purified flavonoid fraction (Daflon) on pelvic pain in women with laparoscopically diagnosed pelvic congestion syndrome: a randomized crossover trial. | 2007 |
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[Studies on pharmacokinetics of diosmin in rats]. | 2007 Mar |
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[Immunological aspects of aphthous stomatitis]. | 2007 Oct |
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Effects of diosmin, a flavonoid glycoside in citrus fruits, on P-glycoprotein-mediated drug efflux in human intestinal Caco-2 cells. | 2007 Sep 5 |
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[Certain aspects of pathogenesis of hemorheological and trophic disturbances and their pharmacological correction in patients with chronic venous insufficiency]. | 2008 |
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Update on uses and properties of citrus flavonoids: new findings in anticancer, cardiovascular, and anti-inflammatory activity. | 2008 Aug 13 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02616731
use diosmin oral tablets 500 mg t.d.s (three times daily) with the onset of the first day of menstrual cycle till the end of bleeding
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27890807
Human breast cancer cells MCF-7, MDA-MB-231 and SK-BR-3 were used for activity evaluation in MTT assay. Cells of an initial concentration of 5000 cells per a well of 96-well plate were incubated with 2.5, 5, 10, 20, 30 and 50 mkM diosmin for 24 h and metabolic activity (MTT test) was then analyzed.
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QC05CA53
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QC05CA03
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FDA ORPHAN DRUG |
582417
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NCI_THESAURUS |
C306
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7QM776WJ5N
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DB08995
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D004145
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m4595
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DIOSMIN
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520-27-4
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ACTIVE MOIETY