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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
Structure of Diosmin

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

HIDE SMILES / InChI

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
Antiallergic effect of flavonoid glycosides obtained from Mentha piperita L.
2002 Feb
A randomised controlled trial of micronised purified flavonoid fraction vs placebo in patients with chronic venous disease.
2002 Jan
Further investigation of the modifying effect of various chemopreventive agents on apoptosis and cell proliferation in human colon cancer cells.
2002 Oct
[Microcirculation end effect of detralex in patients with chronic venous insufficiency of the lower extremities].
2003
[The theory of lymphangion and current approaches to the pathogenesis, diagnosis and treatment of lymphedema of the lower extremities].
2003
Diosmin pretreatment affects bioavailability of metronidazole.
2003 Apr
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
Effects of Daflon on oxidative stress induced by hindlimb ischemia/reperfusion.
2003 Jul
From skin disorders to venous leg ulcers: pathophysiology and efficacy of Daflon 500 mg in ulcer healing.
2003 Jul-Aug
Flavonoids detection by HPLC-DAD-MS-MS in lemon juices from Sicilian cultivars.
2003 Jun 4
Flavonoid treatment in patients with healed venous ulcer: flow cytometry analysis suggests increased CD11b expression on neutrophil granulocytes in the circulation.
2003 May
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
[The principles of action and use of phlebotropic agents].
2004
Benzo-pyrones for reducing and controlling lymphoedema of the limbs.
2004
Study on the influence of silymarin pretreatment on metabolism and disposition of metronidazole.
2004
Flavonoid distribution during the development of leaves, flowers, stems, and roots of Rosmarinus officinalis. postulation of a biosynthetic pathway.
2004 Aug 11
Daflon for haemorrhoids: a prospective, multi-centre observational study.
2004 Dec
A validated HPLC determination of the flavone aglycone diosmetin in human plasma.
2004 Dec
Effect of the rootstock and interstock grafted in lemon tree (Citrus limon (L.) Burm.) on the flavonoid content of lemon juice.
2004 Jan 28
Micronization enhances the protective effect of purified flavonoid fraction against postischaemic microvascular injury in the hamster cheek pouch.
2004 Mar
Monograph. Diosmin.
2004 Sep
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
[Possibility of the regulation of venous outflow from deep brain structures].
2005
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
Micronized purified flavonoid fraction (MPFF): a review of its pharmacological effects, therapeutic efficacy and benefits in the management of chronic venous insufficiency.
2005 Jan
Determination of flavonoids in citrus juices by micro-HPLC-ESI/MS.
2005 Jul
Venous ulcers: pathophysiology and treatment options.
2005 May
Treatment of abnormal uterine bleeding with micronized flavonoids.
2005 May
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
Chronic venous disease, inflammation, and Daflon 500 mg.
2005 Sep-Oct
[Semisynthetic Diosmin (Phlebodia 600) for therapy of lower limb chronic venous insufficiency].
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
Central nervous system depressant action of flavonoid glycosides.
2006 Jun 13
Possible regulation of venous outflow from deep brain structures.
2006 Oct
Surgical correction of varicose vein disease under micronized diosmin protection (results of the Russian multicenter controlled trial DEFANS).
2007
Bioavailability of diclofenac sodium after pretreatment with diosmin in healthy volunteers.
2007
Effects of micronized purified flavonoid fraction (Daflon) on pelvic pain in women with laparoscopically diagnosed pelvic congestion syndrome: a randomized crossover trial.
2007
Analgesic, anti-inflammatory and venotonic effects of Cissus quadrangularis Linn.
2007 Mar 21
[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
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
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.
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
Diosmin [WHO-DD]
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
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 Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
WHO-ATC C05CA03
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
WHO-VATC QC05CA53
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
DSLD 1394 (Number of products:104)
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
WHO-ATC C05CA53
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
WHO-VATC QC05CA03
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
FDA ORPHAN DRUG 582417
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
NCI_THESAURUS C306
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
Code System Code Type Description
INN
4370
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
DAILYMED
7QM776WJ5N
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
DRUG BANK
DB08995
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
MESH
D004145
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
CHEBI
4631
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
SMS_ID
100000092048
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
RXCUI
3489
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY RxNorm
FDA UNII
7QM776WJ5N
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
ChEMBL
CHEMBL231884
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
PUBCHEM
5281613
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
CAS
9000-18-4
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
SUPERSEDED
EPA CompTox
DTXSID4045892
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
NSC
758417
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-289-7
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
EVMPD
SUB07198MIG
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
NCI_THESAURUS
C81663
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
CAS
28680-33-3
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
SUPERSEDED
DRUG CENTRAL
3157
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
RS_ITEM_NUM
1213318
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
MERCK INDEX
M4595
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
DIOSMIN
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY
CAS
520-27-4
Created by admin on Wed Jul 05 23:03:50 UTC 2023 , Edited by admin on Wed Jul 05 23:03:50 UTC 2023
PRIMARY