Identification

Name
Diosmin
Accession Number
DB08995
Type
Small Molecule
Groups
Approved, Investigational
Description

Diosmin is a semisynthetic drug indicated for the treatment of venous disease. Diosmin is a flavone that can be found in the plant Teucrium gnaphalodes. Diosmin is available as a prescription medicine in several European countries, and is available as a nutritional supplement in the United States and the rest of Europe. It should be noted that clinical studies have been inconclusive and no articles have been published pertaining to its use in the treatment of vascular disease. When used in rats, diosmin has been effective at mitigating hyperglycaemia, and may also have antineurodegenerative properties.

Structure
Thumb
Synonyms
  • 3',5,7-trihydroxy-4'-methoxyflavone 7-rhamnoglucoside
  • 3',5,7-trihydroxy-4'-methoxyflavone-7-rutinoside
  • diosmetin 7-neohesperidoside
  • Diosmetin 7-O-rutinoside
  • diosmin
  • Diosmina
  • Diosmine
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Analpram AdvancedDiosmin (600 mg/1) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Hydrocortisone acetate (25 mg/1g) + Pramoxine hydrochloride (10 mg/1g)KitSebela Pharmaceuticals Inc.2015-08-072017-02-28Us
Analpram AdvancedDiosmin (600 mg/1) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Hydrocortisone acetate (25 mg/1g) + Pramoxine hydrochloride (10 mg/1g)KitOralSebela Pharmaceuticals Inc.2015-08-072016-08-31Us
Analpram AdvancedDiosmin (600 mg/1) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Hydrocortisone acetate (25 mg/1g) + Pramoxine hydrochloride (10 mg/1g)KitSebela Pharmaceuticals Inc.2015-08-072017-02-28Us
International/Other Brands
Barosmin / Dalfon (Servier) / Detralex / Diosven / Dioven / Diovenor / Flebosmil / Flebosten / Hemerven / Insuven / Litosmil / Varinon / Ven-detrex / Venosmine
Categories
UNII
7QM776WJ5N
CAS number
520-27-4
Weight
Average: 608.5447
Monoisotopic: 608.174120354
Chemical Formula
C28H32O15
InChI Key
GZSOSUNBTXMUFQ-YFAPSIMESA-N
InChI
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
IUPAC Name
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
SMILES
COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O)C=C(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C=C2O1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAryl hydrocarbon receptor
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D07858
KEGG Compound
C10039
PubChem Compound
5281613
PubChem Substance
310264956
ChemSpider
4444932
BindingDB
153267
ChEBI
4631
ChEMBL
CHEMBL231884
Drugs.com
Drugs.com Drug Page
Wikipedia
Diosmin
ATC Codes
C05CA03 — DiosminC05CA53 — Diosmin, combinations

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2RecruitingTreatmentHypermenorrhea1
2, 3CompletedPreventionInfertilities1
3CompletedTreatmentChronic Venous Disease of Lower Limbs1
3Unknown StatusTreatmentChronic Venous Insufficiency (CVI) / Diseases1
3Unknown StatusTreatmentChronic Venous Insufficiency (CVI) / Hemorrhoids1
4CompletedTreatmentIncompetent accessory saphenous veins1
4Enrolling by InvitationBasic ScienceChronic Venous Insufficiency (CVI)1
4RecruitingTreatmentDeep Vein Thrombosis (DVT) / Post Thrombotic Syndrome1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Kit
KitOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.54 mg/mLALOGPS
logP0.08ALOGPS
logP-0.44ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area234.29 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity142.39 m3·mol-1ChemAxon
Polarizability59.17 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0002-0090000000-5ba2996dd1e65cd9aef6
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0udj-0298000000-0bbbfc4f4a4f06eabd19
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-1249000000-89e125689ac3c8ab2522
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0pb9-0079000000-3ec59b6cb85bb16ee539
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0pb9-0059000000-23c28bc86f2cb99c8879

Taxonomy

Description
This compound belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Flavonoid glycosides
Direct Parent
Flavonoid-7-O-glycosides
Alternative Parents
4'-O-methylated flavonoids / 3'-hydroxyflavonoids / 5-hydroxyflavonoids / Flavones / Phenolic glycosides / O-glycosyl compounds / Chromones / Disaccharides / Methoxyphenols / Phenoxy compounds
show 15 more
Substituents
Flavonoid-7-o-glycoside / 4p-methoxyflavonoid-skeleton / 3'-hydroxyflavonoid / 5-hydroxyflavonoid / Flavone / Hydroxyflavonoid / Phenolic glycoside / Chromone / Disaccharide / Glycosyl compound
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
rutinoside, disaccharide derivative, monomethoxyflavone, glycosyloxyflavone, dihydroxyflavanone (CHEBI:4631) / flavones (C10039)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Transcription regulatory region dna binding
Specific Function
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes...
Gene Name
AHR
Uniprot ID
P35869
Uniprot Name
Aryl hydrocarbon receptor
Molecular Weight
96146.705 Da
References
  1. Zhang S, Qin C, Safe SH: Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context. Environ Health Perspect. 2003 Dec;111(16):1877-82. [PubMed:14644660]

Drug created on June 16, 2014 12:43 / Updated on November 05, 2018 17:49