Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H32O15 |
Molecular Weight | 608.5458 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]1([H])[C@@]([H])([C@]([H])([C@]([H])([C@]([H])(OC[C@]2([H])[C@]([H])([C@@]([H])([C@]([H])([C@]([H])(Oc3cc(c4c(=O)cc(-c5ccc(c(c5)O)OC)oc4c3)O)O2)O)O)O)O1)O)O)O
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 | 608.5458 |
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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Clinical and hemodynamic outcomes in patients with chronic venous insufficiency after oral micronized flavonoid therapy. | 2001 Nov-Dec |
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Daflon for haemorrhoids: a prospective, multi-centre observational study. | 2004 Dec |
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[Derivatives of semi-synthetic diosmine in the treatment of patients with chronic venous insufficiency. The results of a prospective study--using phlebodia 600]. | 2005 |
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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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[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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Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones. | 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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Treatment of metastatic melanoma B16F10 by the flavonoids tangeretin, rutin, and diosmin. | 2005 Aug 24 |
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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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Treatment of abnormal uterine bleeding with micronized flavonoids. | 2005 May |
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Antiradical and anti-H2O2 properties of polyphenolic compounds from an aqueous peppermint extract. | 2005 Nov-Dec |
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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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Micronized diosmin (Detralex) for vein-related trophic ulcers: European experience. | 2006 |
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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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[Risk factors of chronic venous insufficiency of the lower extremities and possibilities of its medication in therapeutic practice]. | 2006 |
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Comparison of Pycnogenol and Daflon in treating chronic venous insufficiency: a prospective, controlled study. | 2006 Apr |
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Effects of citrus flavonoids on redox homeostasis of toxin-injured liver in rat. | 2006 Dec |
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Toxicological aspects of flavonoid interaction with biomacromolecules. | 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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Venoruton vs Daflon: evaluation of effects on quality of life in chronic venous insufficiency. | 2006 Mar-Apr |
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Determination of trace levels of diosmin in a pharmaceutical preparation by adsorptive stripping voltammetry at a glassy carbon electrode. | 2006 Oct |
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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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[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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The effect of citrus flavonoids on the redox state of alimentary-induced fatty liver in rats. | 2007 Mar |
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Analgesic, anti-inflammatory and venotonic effects of Cissus quadrangularis Linn. | 2007 Mar 21 |
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Screening of various phenolic acids and flavonoid derivatives for their anticholinesterase potential. | 2007 Nov-Dec |
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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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Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones. | 2008 Apr 1 |
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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 |
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Mechanisms in experimental venous valve failure and their modification by Daflon 500 mg. | 2008 Jan |
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Flavonoid-mediated presenilin-1 phosphorylation reduces Alzheimer's disease beta-amyloid production. | 2009 Mar |
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
Fri Jun 25 21:18:53 UTC 2021
by
admin
on
Fri Jun 25 21:18:53 UTC 2021
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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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Code System | Code | Type | Description | ||
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4370
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PRIMARY | |||
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DB08995
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D004145
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3489
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7QM776WJ5N
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PRIMARY | |||
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CHEMBL231884
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5281613
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9000-18-4
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520-27-4
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1213318
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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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SUPERSEDED | |||
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3157
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PRIMARY | |||
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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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PRIMARY |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
NMT 3%
USP
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IMPURITY -> PARENT |
NMT 3%
USP
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IMPURITY -> PARENT |
NMT 3%
USP
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IMPURITY -> PARENT |
NMT 1%
USP
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IMPURITY -> PARENT |
NMT 5%
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |