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=C(O)C=C(C=C1)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 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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2.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30158431/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIOSMETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
397.17 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19800189/ |
450 mg single, oral dose: 450 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIOSMETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
31.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30158431/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIOSMETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7163.54 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19800189/ |
450 mg single, oral dose: 450 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIOSMETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
70.34 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19800189/ |
450 mg single, oral dose: 450 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIOSMETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
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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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Antiallergic effect of flavonoid glycosides obtained from Mentha piperita L. | 2002 Feb |
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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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[Microcirculation end effect of detralex in patients with chronic venous insufficiency of the lower extremities]. | 2003 |
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The social and economic burden of venous leg ulcers: focus on the role of micronized purified flavonoid fraction adjuvant therapy. | 2003 |
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[The theory of lymphangion and current approaches to the pathogenesis, diagnosis and treatment of lymphedema of the lower extremities]. | 2003 |
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Diosmin pretreatment affects bioavailability of metronidazole. | 2003 Apr |
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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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Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context. | 2003 Dec |
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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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Effects of Daflon on oxidative stress induced by hindlimb ischemia/reperfusion. | 2003 Jul |
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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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Efficacy of a 6-month treatment with Daflon 500 mg in patients with venous leg ulcers associated with chronic venous insufficiency. | 2003 Mar |
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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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[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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[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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[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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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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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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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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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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Possible regulation of venous outflow from deep brain structures. | 2006 Oct |
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[Results of administering Phlebodia 600 in fertile women with orthostasis-dependent phlebopathy]. | 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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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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Different flavonoids present in the micronized purified flavonoid fraction (Daflon 500 mg) contribute to its anti-hyperpermeability effect in the hamster cheek pouch microcirculation. | 2008 Feb |
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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
Mon Mar 31 18:01:37 GMT 2025
by
admin
on
Mon Mar 31 18:01:37 GMT 2025
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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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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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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 |
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 |