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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:: 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

Sources: Dissert. Bern, Journal, 1925

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Clinical benefits of Daflon 500 mg in the most severe stages of chronic venous insufficiency.
2001 Aug
Selection of hybrids and edible citrus species with a high content in the diosmin functional compound. Modulating effect of plant growth regulators on contents.
2001 Jul
[Clinical practice guidelines for the treatment of hemorrhoid disease].
2001 Jun-Jul
A randomised controlled trial of micronised purified flavonoid fraction vs placebo in patients with chronic venous disease.
2002 Jan
Effects of plant-derived phenols on rat liver cytochrome P450 2B1 activity.
2002 May-Jun
Diosmin pretreatment affects bioavailability of metronidazole.
2003 Apr
[Efficacy and safety of treatment with methotrexate, leflunomide, detralex, and their combination of patients with rheumatoid arthritis].
2003 Apr-Jun
Effects of selected flavonoids and caffeic acid derivatives on hypoxanthine-xanthine oxidase-induced toxicity in cultivated human cells.
2003 Dec
Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context.
2003 Dec
A new flavonoid derivative, dosmalfate, attenuates the development of dextran sulphate sodium-induced colitis in mice.
2003 Dec
From skin disorders to venous leg ulcers: pathophysiology and efficacy of Daflon 500 mg in ulcer healing.
2003 Jul-Aug
From symptoms to leg edema: efficacy of Daflon 500 mg.
2003 Jul-Aug
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
Benzo-pyrones for reducing and controlling lymphoedema of the limbs.
2004
A validated HPLC determination of the flavone aglycone diosmetin in human plasma.
2004 Dec
Micronization enhances the protective effect of purified flavonoid fraction against postischaemic microvascular injury in the hamster cheek pouch.
2004 Mar
The effect of diosmin hesperidin on intestinal ischaemia--reperfusion injury.
2004 Nov-Dec
Semisynthesis of linarin, acacetin, and 6-iodoapigenin derivatives from diosmin.
2004 Sep
[Derivatives of semi-synthetic diosmine in the treatment of patients with chronic venous insufficiency. The results of a prospective study--using phlebodia 600].
2005
Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones.
2005 Aug
Venous ulcers: pathophysiology and treatment options.
2005 May
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
[Semisynthetic Diosmin (Phlebodia 600) for therapy of lower limb chronic venous insufficiency].
2006
[Certain aspects of pathogenesis of hemorheological and trophic disturbances and their pharmacological correction in patients with chronic venous insufficiency].
2008
Update on uses and properties of citrus flavonoids: new findings in anticancer, cardiovascular, and anti-inflammatory activity.
2008 Aug 13
Identification of small molecule inhibitors of Pseudomonas aeruginosa exoenzyme S using a yeast phenotypic screen.
2008 Feb 29
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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