diosmetine
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. — NCATS
Clinical trial activity
34 trials · 31 clinical orgs · 0 marketing orgs
Earliest trial started Jan 1, 2012 (NCT01532882)
Timeline
Indications
Approved for
Studied for
- Arthritis, Rheumatoid · Phase 3
- Breast Neoplasms · Phase 3
- Colitis, Ulcerative · Phase 3
- Colorectal Neoplasms · Phase 2
- Coronavirus Infections · Early Phase 1
- Disease · Phase 3
- Drug-Related Side Effects and Adverse Reactions · Phase 3
- Esophageal and Gastric Varices · Phase 4
- Helicobacter pylori · Phase 1/Phase 2
- Hemorrhage · Phase 3
- Infertility · Phase 2/Phase 3
- Lymphedema · Phase 4
- Menorrhagia · Phase 2
- Myalgia · Phase 1
- Non-alcoholic Fatty Liver Disease · Phase 3
- Pelvic Floor Disorders · Phase 3
- Pelvis · Phase 4
- Polycystic Ovary Syndrome · Phase 4
- Postthrombotic Syndrome · Phase 4
- Proctitis · Phase 3
- Therapeutic Equivalency · Phase 1
- Venous Cutdown · Phase 4
- Venous Insufficiency · Phase 4
- Venous Thrombosis · Phase 4
Mechanism of action
- Unspecified targetOTHER
Unknown
Diosmin (diosmetin 7-O-rutinoside), is a natural flavone glycoside which is indicated for the treatment of hemorrhoids, lymphedema and varicose veins. It is well known to possess antiinflammatory, antioxidant, antimutagenic and anti-hyperlipidemic properties. It has been reported that diosmin significantly increased the transport of digoxin and cellular accumulation of rhodamine-123 in Caco-2 cells by inhibition of P-gp-mediated efflux. It has also been reported a protective mechanisms on LPS-induced lung injury through inhibition of T cell receptors, pro-inflammatory cytokines and NF-kB activation.
Chemistry & pharmacology
SMILES
COC1=C(O)C=C(C=C1)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- Mol. weight
- 608.5447 g/mol
- Lipinski Ro5
- 3 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- WikipediaDiosmin ↗
- NCATS7QM776WJ5N ↗
- ChEMBLCHEMBL90568 ↗
- ChEMBLCHEMBL231884 ↗
Also known as
- 3',5,7-trihydroxy-4'-methoxyflavone 7-rhamnoglucoside
- 3',5,7-trihydroxy-4'-methoxyflavone 7-rhamnoglucoside
- 3',5,7-trihydroxy-4'-methoxyflavone-7-rutinoside
- 3',5,7-trihydroxy-4'-methoxyflavone-7-rutinoside
- barosmin
- daflon
- daflon
- diosmetin
- diosmetin
- diosmetin 7-neohesperidoside
- diosmetin 7-neohesperidoside
- diosmetin 7-o-rutinoside
- diosmetin 7-o-rutinoside
- diosmetine
- diosmetine
- diosmetine
- diosmil
- diosmin
- diosmin
- diosmin
- diosmin
- diosmin
- diosmin
- diosmin
- diosmin
- diosmine
- diosmine
- diosmine
- diovenor
- diovenor
- flebosmil
- flebosten
- vasculera
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07176182 | Phase 2 | Nov 1, 2025 | Sun Yat-Sen University |
| NCT07185386 | N/A | May 28, 2025 | Ekalab S.r.l. |
| NCT07300735 | N/A | Mar 1, 2025 | Alexandria University |
| NCT06811220 | Phase 3 | Jan 27, 2025 | Alexandria University |
| NCT06256575 | N/A | Dec 15, 2024 | KGK Science Inc., Primus Pharmaceuticals |
| NCT07293767 | N/A | Nov 16, 2024 | Ain Shams University |
| NCT06546111 | Phase 1/Phase 2 (Phase 2) | Oct 1, 2024 | Sadat City University |
| NCT06584799 | Phase 3 | Sep 30, 2024 | Pirogov Russian National Research Medical University |
| NCT06560294 | N/A | Aug 17, 2024 | Tanta University |
| NCT06125002 | Phase 1 | Jan 31, 2024 | Universidade Estadual de Londrina, Universidade Norte do Paraná |
| NCT06083935 | Phase 4 | Nov 1, 2023 | Ain Shams University |
| NCT05756179 | Phase 3 | Jul 18, 2023 | Alexandria University |
| NCT05942547 | Phase 3 | Jul 10, 2023 | Tanta University |
| NCT06367166 | N/A | Apr 1, 2023 | Ryazan State Medical University |
| NCT05626166 | Phase 3 | Nov 30, 2022 | Tanta University |
| NCT05670457 | Phase 3 | Jun 30, 2022 | Tanta University |
| NCT05243706 | Phase 3 | Mar 1, 2022 | Ain Shams University |
| NCT05158192 | Phase 1 | Nov 4, 2021 | Grunenthal |
| NCT04358497 | Phase 4 | Oct 1, 2020 | Centro Cardiovascular Universitario, Hospital de Clínicas Dr. Manuel Quintela, Hospital Pereyra Rossell, Montevideo, University of the Republic, Uruguay |
| NCT04933591 | N/A | Sep 1, 2020 | Pirogov Russian National Research Medical University |
Organizations
Research & Development (31)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Tanta University | Academic/Hospital | 5 | 5 | 3 | 2020 |
| Ain Shams University | Academic/Hospital | 4 | 4 | 4 | 2015 |
| Alexandria University | Academic/Hospital | 3 | 3 | 2 | 2023 |
| Pirogov Russian National Research Medical University | Academic/Hospital | 3 | 3 | 3 | 2018 |
| Primus Pharmaceuticals | For profit | 3 | 3 | 1 | 2015 |
| Opera CRO | For profit | 2 | 0 | 2 | 2016 |
| Ryazan State Medical University | Academic/Hospital | 2 | 2 | 2 | 2019 |
| Servier | For profit | 2 | 0 | 2 | 2012 |
| Albert Einstein Israelite Hospital | Academic/Hospital | 1 | 0 | 1 | 2017 |
| Benha University | Academic/Hospital | 1 | 1 | 1 | 2014 |
| Centro Cardiovascular Universitario | Academic/Hospital | 1 | 0 | 1 | 2020 |
| Ekalab S.r.l. | For profit | 1 | 1 | 1 | 2025 |
| Fundação Educacional Serra dos Órgãos | Academic/Hospital | 1 | 1 | 1 | 2017 |
| Giellepi S.p.A | For profit | 1 | 1 | 1 | 2019 |
| Grunenthal | For profit | 1 | 1 | 1 | 2021 |
| Hospital de Clínicas Dr. Manuel Quintela | Academic/Hospital | 1 | 1 | 1 | 2020 |
| Hospital Pereyra Rossell, Montevideo | Academic/Hospital | 1 | 0 | 1 | 2020 |
| KGK Science Inc. | For profit | 1 | 0 | 1 | 2024 |
| Laboratoire Innotech International | For profit | 1 | 1 | 1 | 2012 |
| Laboratório Teuto Brasileiro S/A | For profit | 1 | 1 | 1 | 2012 |