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Diosmin

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Diosmin
Clinical data
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
ChemSpider
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
  • Key:GZSOSUNBTXMUFQ-YFAPSIMESA-N

Diosmin is a semisynthetic phlebotropic drug, a member of the flavonoid family. It is an oral phlebotropic drug used in the treatment of venous disease, i.e., chronic venous insufficiency (CVI) and hemorrhoidal disease (HD), in acute or chronic hemorrhoids, in place of rubber-band ligation, in combination with fiber supplement, or as an adjuvant therapy to hemorrhoidectomy, in order to reduce secondary bleeding.

Clinical studies have been inconclusive and no review articles on its use in vascular disease have been published.[1][2]

Diosmin is currently a prescription medication in some European countries, and is sold as a nutritional supplement in the United States and the rest of Europe.

Diosmin aglycone is diosmetin.

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.[3] The FDA concluded that there was inadequate evidence on which to base an expectation of safety.[4] 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.

References

  1. ^ Veverková L, Kalac J, Jedlicka V, Wechsler J (2005). "[Analysis of surgical procedures on the vena saphena magna in the Czech Republic and an effect of Detralex during its stripping]". Rozhl Chir (in Czech). 84 (8): 410–2, 414–6. PMID 16218350. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. ^ Danielsson G, Jungbeck C, Peterson K, Norgren L (2002). "A randomised controlled trial of micronised purified flavonoid fraction vs placebo in patients with chronic venous disease". Eur J Vasc Endovasc Surg. 23 (1): 73–6. doi:10.1053/ejvs.2001.1531. PMID 11748952. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ Public Health Service memorandum, Sept. 13, 2005
  4. ^ 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) [1], Memorandum [2]

External links

  • Diosmin, Alternative Medicine Review, Sept 2004