Diosmin

Diosmin
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration		 oral
ATC code C05CA03 (WHO)
Identifiers
CAS Number 520-27-4 N
PubChem (CID) 5281613
DrugBank DB08995 N
ChemSpider 4444932 YesY
UNII 7QM776WJ5N YesY
KEGG D07858 YesY
ChEBI CHEBI:4631 N
ChEMBL CHEMBL231884 YesY
ECHA InfoCard 100.007.537
Chemical and physical data
Formula C28H32O15
Molar mass 608.545 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

Diosmin is a flavone, a member of the flavonoid family. Diosmin aglycone is diosmetin. It can be found in Teucrium gnaphalodes, a plant endemic to the Iberian Peninsula.[1]

Drug

Diosmin is a semisynthetic flavonoid molecule derived from citrus d (modified hesperidin). It is an oral phlebotropic drug used in the treatment of venous disease, i.e., chronic venous insufficiency (CVI) including spider and varicose veins, leg swelling (edema), stasis dermatitis and venous ulcers. It is also used as a stand-alone or surgical adjunctive therapy in hemorrhoidal disease (HD).

There are extensive clinical trials that show diosmin improves all stages of venous disease including venous ulcers and improves quality of life.[2] There are no prospective studies in arterial disease.

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.

Diosmin has been found to be effective in mitigating hyperglycemia in diabetic rats.[3] It is also speculated that diosmin might have potential in the treatment of neurodegenerative diseases,[4] such as Alzheimer's disease, and its anti-inflammatory and anti-apoptotic activity has been demonstrated in neuronal cells, in vitro.[5]

Mechanisms

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.

At the microcirculation level, diosmin reduces capillary hyperpermeability and increases capillary resistance by protecting the microcirculation from damaging processes.

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).

Regulatory status

Diosmin is distributed in the U.S. as a dietary supplement and as a prescription medical food.[6] The FDA concluded that there was inadequate evidence on which to base an expectation of safety.,[7] however, diosmin products have beed used in Europe for over 40 years with no safety issues. One company that markets diosmin supplements, Nutratech, has responded that diosmin can reasonably be expected to be safe on the basis of clinical trials, and has a long history of use in Europe. In the U.S., dietary supplements are regulated under Dietary Supplement Health and Education Act of 1994, which does not require proof of efficacy so long as no specific health claims are made. The enhanced version of diosmin, Vasculera, is sold as a medical food product. Under FDA regulation, medical food products must obtain GRAS (generally recognized as safe) status and have scientifically proven efficacy.[8]

See also

References

  1. ↑ Flavonoid Aglycones and Glycosides from Teucrium gnaphalodes. F. A. T. Barberán, M. I. Gil, F. Tomás, F. Ferreres and A. Arques, J. Nat. Prod., 1985, 48 (5), pages 859–860, doi:10.1021/np50041a040
  2. ↑ Jantet, G. (2002-06-01). "Chronic venous insufficiency: worldwide results of the RELIEF study. Reflux assEssment and quaLity of lIfe improvEment with micronized Flavonoids". Angiology. 53 (3): 245–256. ISSN 0003-3197. PMID 12025911.
  3. ↑ Leelavinothan Pari, Subramani Srinivasan, Antihyperglycemic effect of diosmin on hepatic key enzymes of carbohydrate metabolism in streptozotocin-nicotinamide-induced diabetic rats, Biomedicine & Pharmacotherapy, Volume 64, Issue 7, September 2010, Pages 477-481.
  4. ↑ Sirlak, Mustafa; Akar, A. Ruchan; Eryilmaz, Sadik; Cetinkanat, Elif Kuzgun; Ozcinar, Evren; Kaya, Bulent; Elhan, Atilla Halil; Ozyurda, Umit (2010-01-01). "Micronized purified flavonoid fraction in pretreating CABG patients". Texas Heart Institute Journal. 37 (2): 172–177. ISSN 1526-6702. PMC 2851420Freely accessible. PMID 20401289.
  5. ↑ Sanjay L.Dholakiya, Kenza E. Benzeroual, Protective effect of Diosmin on LPS-induced apoptosis in PC12 cells and inhibition of TNF- [alpha] expression, Toxicology in Vitro, In Press, Accepted Manuscript, Available online 6 April 2011.
  6. ↑ Public Health Service memorandum, Sept. 13, 2005
  7. ↑ New Dietary Ingredients in Dietary Supplements, U. S. Food and Drug Administration Center for Food Safety and Applied Nutrition Office of Nutritional Products, Labeling, and Dietary Supplements February 2001 (Updated September 10, 2001) , Memorandum
  8. ↑ http://www.fda.gov/Food/GuidanceRegulation/GuidanceDocumentsRegulatoryInformation/ucm054048.htm. Missing or empty |title= (help)
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