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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
Structure of DIOSMIN

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

HIDE SMILES / InChI

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

Description
Curator's Comment:: 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

Sources: Dissert. Bern, Journal, 1925

Approval Year

PubMed

PubMed

TitleDatePubMed
Clinical and hemodynamic outcomes in patients with chronic venous insufficiency after oral micronized flavonoid therapy.
2001 Nov-Dec
Daflon for haemorrhoids: a prospective, multi-centre observational study.
2004 Dec
[Derivatives of semi-synthetic diosmine in the treatment of patients with chronic venous insufficiency. The results of a prospective study--using phlebodia 600].
2005
[PHLEBODIA (diosmine): a role in the management of bleeding nonprolapsed hemorrhoids].
2005
[Possibility of the regulation of venous outflow from deep brain structures].
2005
[Butcher's Broom, in the treatment of venous insufficiency].
2005 Aug
[Analysis of surgical procedures on the vena saphena magna in the Czech Republic and an effect of Detralex during its stripping].
2005 Aug
Flavonoids to reduce bleeding and pain after stapled hemorrhoidopexy: a randomized controlled trial.
2005 Aug
Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones.
2005 Aug
Venous leg ulcer: a meta-analysis of adjunctive therapy with micronized purified flavonoid fraction.
2005 Aug
Treatment of metastatic melanoma B16F10 by the flavonoids tangeretin, rutin, and diosmin.
2005 Aug 24
Hesperidin, a citrus bioflavonoid, decreases the oxidative stress produced by carbon tetrachloride in rat liver and kidney.
2005 Jan 31
Determination of flavonoids in citrus juices by micro-HPLC-ESI/MS.
2005 Jul
Phlebotonics for venous insufficiency.
2005 Jul 20
Venous ulcers: pathophysiology and treatment options.
2005 May
Treatment of abnormal uterine bleeding with micronized flavonoids.
2005 May
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
The effect of the flavonoid diosmin, grape seed extract and red wine on the pulmonary metastatic B16F10 melanoma.
2005 Oct
Daflon 500 mg and venous leg ulcer: new results from a meta-analysis.
2005 Sep-Oct
Daflon 500 mg: symptoms and edema clinical update.
2005 Sep-Oct
Chronic venous insufficiency and the therapeutic effects of Daflon 500 mg.
2005 Sep-Oct
Chronic venous disease, inflammation, and Daflon 500 mg.
2005 Sep-Oct
Micronized diosmin (Detralex) for vein-related trophic ulcers: European experience.
2006
[Semisynthetic Diosmin (Phlebodia 600) for therapy of lower limb chronic venous insufficiency].
2006
The effect of purified micronized flavonoid fraction on the healing of anastomoses in the colon in rats.
2006
[Risk factors of chronic venous insufficiency of the lower extremities and possibilities of its medication in therapeutic practice].
2006
Comparison of Pycnogenol and Daflon in treating chronic venous insufficiency: a prospective, controlled study.
2006 Apr
Effects of citrus flavonoids on redox homeostasis of toxin-injured liver in rat.
2006 Dec
Toxicological aspects of flavonoid interaction with biomacromolecules.
2006 Dec
The impact of micronized purified flavonoid fraction on the treatment of acute haemorrhoidal episodes.
2006 Jun
Venoruton vs Daflon: evaluation of effects on quality of life in chronic venous insufficiency.
2006 Mar-Apr
Determination of trace levels of diosmin in a pharmaceutical preparation by adsorptive stripping voltammetry at a glassy carbon electrode.
2006 Oct
Possible regulation of venous outflow from deep brain structures.
2006 Oct
[Results of administering Phlebodia 600 in fertile women with orthostasis-dependent phlebopathy].
2007
Bioavailability of diclofenac sodium after pretreatment with diosmin in healthy volunteers.
2007
[Congenital anomalies of the inferior vena cava: diagnosis and medical treatment].
2007
Effects of micronized purified flavonoid fraction (Daflon) on pelvic pain in women with laparoscopically diagnosed pelvic congestion syndrome: a randomized crossover trial.
2007
[Studies on pharmacokinetics of diosmin in rats].
2007 Mar
The effect of citrus flavonoids on the redox state of alimentary-induced fatty liver in rats.
2007 Mar
Analgesic, anti-inflammatory and venotonic effects of Cissus quadrangularis Linn.
2007 Mar 21
Screening of various phenolic acids and flavonoid derivatives for their anticholinesterase potential.
2007 Nov-Dec
[Immunological aspects of aphthous stomatitis].
2007 Oct
Effects of diosmin, a flavonoid glycoside in citrus fruits, on P-glycoprotein-mediated drug efflux in human intestinal Caco-2 cells.
2007 Sep 5
[Certain aspects of pathogenesis of hemorheological and trophic disturbances and their pharmacological correction in patients with chronic venous insufficiency].
2008
Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
2008 Apr 1
Update on uses and properties of citrus flavonoids: new findings in anticancer, cardiovascular, and anti-inflammatory activity.
2008 Aug 13
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
Identification of small molecule inhibitors of Pseudomonas aeruginosa exoenzyme S using a yeast phenotypic screen.
2008 Feb 29
Mechanisms in experimental venous valve failure and their modification by Daflon 500 mg.
2008 Jan
Flavonoid-mediated presenilin-1 phosphorylation reduces Alzheimer's disease beta-amyloid production.
2009 Mar
Patents

Patents

Sample Use Guides

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
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 Fri Jun 25 21:18:53 UTC 2021
Edited
by admin
on Fri Jun 25 21:18:53 UTC 2021
Record UNII
7QM776WJ5N
Record Status Validated (UNII)
Record Version
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Name Type Language
DIOSMIN
DSC   EP   INN   MART.   MI   USP-RS   WHO-DD  
INN  
Official Name English
VARINON
Common Name English
DIOSMIN [EP MONOGRAPH]
Common Name English
DIOSMIN [DSC]
Common Name English
DIOSVEN
Common Name English
HEMERVEN
Common Name English
FLEBAVENA
Brand Name English
FLEBAVEN
Brand Name English
VEN-DETREX
Common Name English
INSUVEN
Common Name English
DIOVENOR
Common Name English
BUCHU RESIN
Common Name English
DIOSMIN [MART.]
Common Name English
DIOSMIN [USP-RS]
Common Name English
DIOVEN
Common Name English
TOVENE
Common Name English
DIOSMETIN 7-RUTINOSIDE
Common Name English
7-((6-O-(6-DEOXY-GA-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Common Name English
DIOSMIN [WHO-DD]
Common Name English
VENOSMINE
Common Name English
LITOSMIL
Common Name English
FLEBOSMIL
Common Name English
DIOSMINE [INCI]
Common Name English
FLEBOSTEN
Brand Name English
DAFLON
Brand Name English
NSC-758417
Code English
DIOSMINE
INCI  
INCI  
Official Name English
DIOSMIN [INN]
Common Name English
DIOSMIN [MI]
Common Name English
BAROSMIN
Common Name English
Classification Tree Code System Code
DSLD 226 (Number of products:24)
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
WHO-ATC C05CA03
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
WHO-VATC QC05CA53
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
DSLD 1394 (Number of products:104)
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
WHO-ATC C05CA53
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
WHO-VATC QC05CA03
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
FDA ORPHAN DRUG 582417
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
NCI_THESAURUS C306
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
Code System Code Type Description
INN
4370
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
DRUG BANK
DB08995
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
MESH
D004145
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
RXCUI
3489
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY RxNorm
FDA UNII
7QM776WJ5N
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
ChEMBL
CHEMBL231884
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
PUBCHEM
5281613
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
CAS
9000-18-4
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
SUPERSEDED
EPA CompTox
520-27-4
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
USP_CATALOG
1213318
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
208-289-7
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
EVMPD
SUB07198MIG
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
NCI_THESAURUS
C81663
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
CAS
28680-33-3
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
SUPERSEDED
DRUG CENTRAL
3157
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
MERCK INDEX
M4595
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
DIOSMIN
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
CAS
520-27-4
Created by admin on Fri Jun 25 21:18:53 UTC 2021 , Edited by admin on Fri Jun 25 21:18:53 UTC 2021
PRIMARY
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