Diosmin
Identification
- Name
- Diosmin
- Accession Number
- DB08995
- 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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Diosmin (DB08995)
- Weight
- Average: 608.5447
Monoisotopic: 608.174120354 - Chemical Formula
- C28H32O15
- 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
- Diosminum
- External IDs
- SE 4601
Pharmacology
- Indication
- Not Available
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Target Actions Organism UAryl hydrocarbon receptor agonistHumans - 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
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Take with or without food.
Products
- International/Other Brands
- Barosmin / Dalfon (Servier) / Detralex / Diosven / Dioven / Diovenor / Flebosmil / Flebosten / Insuven / Litosmil / Ven-Detrex / Venosmine
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Analpram Advanced Diosmin (600 mg/1) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Hydrocortisone acetate (25 mg/1g) + Pramoxine hydrochloride (10 mg/1g) Kit Topical Sebela Pharmaceuticals Inc. 2015-08-07 2016-08-31 US 
Analpram Advanced Diosmin (600 mg/1) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Hydrocortisone acetate (25 mg/1g) + Pramoxine hydrochloride (10 mg/1g) Kit Oral; Topical Sebela Pharmaceuticals Inc. 2015-08-07 2017-02-28 US Analpram Advanced Diosmin (600 mg/1) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Hydrocortisone acetate (25 mg/1g) + Pramoxine hydrochloride (10 mg/1g) Kit Oral; Topical Sebela Pharmaceuticals Inc. 2015-08-07 2017-02-28 US
Categories
- ATC Codes
- C05CA03 — Diosmin
- C05CA — Bioflavonoids
- C05C — CAPILLARY STABILIZING AGENTS
- C05 — VASOPROTECTIVES
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 3'-hydroxyflavonoid / 4p-methoxyflavonoid-skeleton / 5-hydroxyflavonoid / Acetal / Alcohol / Alkyl aryl ether / Anisole show 31 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- rutinoside, disaccharide derivative, monomethoxyflavone, glycosyloxyflavone, dihydroxyflavanone (CHEBI:4631) / flavones (C10039)
Chemical Identifiers
- UNII
- 7QM776WJ5N
- CAS number
- 520-27-4
- 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[[email protected]@H]3O[[email protected]](CO[[email protected]@H]4O[[email protected]@H](C)[[email protected]](O)[[email protected]@H](O)[[email protected]]4O)[[email protected]@H](O)[[email protected]](O)[[email protected]]3O)C=C2O1
References
- General References
- Not Available
- External Links
- KEGG Drug
- D07858
- KEGG Compound
- C10039
- PubChem Compound
- 5281613
- PubChem Substance
- 310264956
- ChemSpider
- 4444932
- BindingDB
- 153267
- 3489
- ChEBI
- 4631
- ChEMBL
- CHEMBL231884
- ZINC
- ZINC000004098512
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Diosmin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Lower Extremity Lymphedema 1 4 Completed Basic Science Chronic Venous Insufficiency (CVI) 1 4 Completed Treatment Deep Vein Thrombosis / Post Thrombotic Syndrome 1 4 Completed Treatment Incompetent accessory saphenous veins 1 4 Not Yet Recruiting Treatment Pelvic Congestive Syndrome / Pelvic Varices / Venous Disease 1 3 Completed Treatment Chronic Venous Disease of Lower Limbs 1 3 Unknown Status Treatment Chronic Venous Insufficiency (CVI) / Diseases 1 3 Unknown Status Treatment Chronic Venous Insufficiency (CVI) / Hemorrhoids 1 2, 3 Completed Prevention Infertility 1 1, 2 Unknown Status Treatment Hypermenorrhea 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Oral; Topical Kit Topical Tablet, film coated 500 mg Cream 5 % Cream Topical 5 g/100g Granule, for solution Oral 450 MG Tablet 150 MG Tablet 300 MG Tablet, film coated Oral 600 mg Tablet, coated Oral 150 mg Tablet Oral Tablet, coated Oral 450 mg Tablet, coated Oral 900 mg Tablet Oral 450 mg Powder, for suspension Oral 900 mg Tablet 600 mg Tablet, coated Oral 500 mg Capsule 300 MG Cream 4 % Granule, for solution Oral 300 mg Powder, for suspension Oral 300 MG Powder, for suspension Oral 450 MG Tablet 450 MG - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.54 mg/mL ALOGPS logP 0.08 ALOGPS logP -0.44 ChemAxon logS -2.6 ALOGPS pKa (Strongest Acidic) 8.48 ChemAxon pKa (Strongest Basic) -3.6 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 15 ChemAxon Hydrogen Donor Count 8 ChemAxon Polar Surface Area 234.29 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 142.39 m3·mol-1 ChemAxon Polarizability 59.17 Å3 ChemAxon Number of Rings 5 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
- Kind
- Protein
- Organism
- Humans
- 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
- 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 June 12, 2020 10:52
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