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
Molecular Formula | C28H32O15 |
Molecular Weight | 608.5447 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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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[Clinical practice guidelines for the treatment of hemorrhoid disease]. | 2001 Jun-Jul |
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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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Flavonoids with epidermal growth factor-receptor tyrosine kinase inhibitory activity stimulate PEPT1-mediated cefixime uptake into human intestinal epithelial cells. | 2001 Oct |
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Efficacy of Daflon in the treatment of hemorrhoids. | 2002 Dec |
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Antiallergic effect of flavonoid glycosides obtained from Mentha piperita L. | 2002 Feb |
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Comparison of the absorption of micronized (Daflon 500 mg) and nonmicronized 14C-diosmin tablets after oral administration to healthy volunteers by accelerator mass spectrometry and liquid scintillation counting. | 2002 Jan |
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A randomised controlled trial of micronised purified flavonoid fraction vs placebo in patients with chronic venous disease. | 2002 Jan |
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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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Chronic venous insufficiency: worldwide results of the RELIEF study. Reflux assEssment and quaLity of lIfe improvEment with micronized Flavonoids. | 2002 May-Jun |
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[Microcirculation end effect of detralex in patients with chronic venous insufficiency of the lower extremities]. | 2003 |
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Diosmin pretreatment affects bioavailability of metronidazole. | 2003 Apr |
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A new flavonoid derivative, dosmalfate, attenuates the development of dextran sulphate sodium-induced colitis in mice. | 2003 Dec |
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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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Flavonoids detection by HPLC-DAD-MS-MS in lemon juices from Sicilian cultivars. | 2003 Jun 4 |
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Benzo-pyrones for reducing and controlling lymphoedema of the limbs. | 2004 |
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Study on the influence of silymarin pretreatment on metabolism and disposition of metronidazole. | 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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A validated HPLC determination of the flavone aglycone diosmetin in human plasma. | 2004 Dec |
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[The flavonoids effect against vinblastine, cyclophosphamide and paracetamol toxicity by inhibition of lipid-peroxydation and increasing liver glutathione concentration]. | 2004 Jul |
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Monograph. Diosmin. | 2004 Sep |
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Semisynthesis of linarin, acacetin, and 6-iodoapigenin derivatives from diosmin. | 2004 Sep |
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[PHLEBODIA (diosmine): a role in the management of bleeding nonprolapsed hemorrhoids]. | 2005 |
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[Possibility of the regulation of venous outflow from deep brain structures]. | 2005 |
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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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Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones. | 2005 Aug |
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Treatment of metastatic melanoma B16F10 by the flavonoids tangeretin, rutin, and diosmin. | 2005 Aug 24 |
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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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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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Re: Meshikhes A-W. N. Daflon for haemorrhoids: a prospective, multi-centre observational study. Surg JR Coll Surg Edinb Irel 2004;2(6): 355-38. | 2005 Oct |
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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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Chronic venous disease, inflammation, and Daflon 500 mg. | 2005 Sep-Oct |
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[Risk factors of chronic venous insufficiency of the lower extremities and possibilities of its medication in therapeutic practice]. | 2006 |
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Venoruton vs Daflon: evaluation of effects on quality of life in chronic venous insufficiency. | 2006 Mar-Apr |
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Possible regulation of venous outflow from deep brain structures. | 2006 Oct |
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Surgical correction of varicose vein disease under micronized diosmin protection (results of the Russian multicenter controlled trial DEFANS). | 2007 |
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Bioavailability of diclofenac sodium after pretreatment with diosmin in healthy volunteers. | 2007 |
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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 |
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Identification of small molecule inhibitors of Pseudomonas aeruginosa exoenzyme S using a yeast phenotypic screen. | 2008 Feb 29 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:03:50 UTC 2023
by
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on
Wed Jul 05 23:03:50 UTC 2023
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Record UNII |
7QM776WJ5N
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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DSLD |
226 (Number of products:24)
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WHO-ATC |
C05CA03
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WHO-VATC |
QC05CA53
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DSLD |
1394 (Number of products:104)
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WHO-ATC |
C05CA53
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WHO-VATC |
QC05CA03
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FDA ORPHAN DRUG |
582417
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NCI_THESAURUS |
C306
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4370
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7QM776WJ5N
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DB08995
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D004145
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4631
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100000092048
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3489
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7QM776WJ5N
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CHEMBL231884
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5281613
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9000-18-4
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DTXSID4045892
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758417
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208-289-7
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SUB07198MIG
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C81663
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28680-33-3
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3157
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1213318
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M4595
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PRIMARY | Merck Index | ||
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DIOSMIN
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520-27-4
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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IMPURITY -> PARENT |
NMT 3%
USP
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IMPURITY -> PARENT |
NMT 3%
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IMPURITY -> PARENT |
NMT 3%
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IMPURITY -> PARENT |
NMT 1%
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IMPURITY -> PARENT |
NMT 5%
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ACTIVE MOIETY |