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Diosmin

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Diosmin
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		oral
ATC code
Identifiers
  • 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]oxymethyl]oxan-2-yl]oxychromen-4-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.537 Edit this at Wikidata
Chemical and physical data
FormulaC28H32O15
Molar mass608.545 g/mol g·mol−1
3D model (JSmol)
  • O=C\4c5c(O)cc(O[C@@H]2O[C@H](CO[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@H]1O)C)[C@@H](O)[C@H](O)[C@H]2O)cc5O/C(c3ccc(OC)c(O)c3)=C/4
  • 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 checkY
  • Key:GZSOSUNBTXMUFQ-YFAPSIMESA-N checkY
 ☒NcheckY (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, Diovenor, etc. tradenames), and is sold as a nutritional supplement in the United States.

Several medication containing diosmin only are available in France, among which several are generics[3].

Diosmin has been found to be effective in mitigating hyperglycemia in diabetic rats.[4] It is also speculated that diosmin might have potential in the treatment of neurodegenerative diseases,[5] such as Alzheimer's disease.

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).

Society and culture

Diosmin is distributed in the U.S. as a dietary supplement.[6][7]

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. ^ "VIDAL - Médicaments contenant la substance active seule - diosmine". www.vidal.fr (in French). Retrieved 2018-02-17.
  4. ^ 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.
  5. ^ 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 2851420. PMID 20401289.
  6. ^ "Nutratech dietary supplement notification" (PDF). FDA. November 3, 2000. Archived from the original (PDF) on December 9, 2006.
  7. ^ "Stragen Pharma dietary supplement notification" (PDF). FDA. September 6, 2005.
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