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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 (diosmetin 7-O-rutinoside), a flavone derivative also known as venosmine, is a glycoside of diosmetin, which in turn is the 4'-methoxy derivative of luteolin. Diosmin is naturally occurring, mainly in the citrus family rutaceae, but also in herbs such as Teucrium gnaphalodes.[1]

Synthetic

Diosmin has 10 stereocenters. It is a non-prescription dietary supplement used to aid treatment of hemorrhoids and venous diseases, i.e., chronic venous insufficiency including spider and varicose veins, leg swelling (edema), stasis dermatitis and venous ulcers.[2]

Its mechanism of action is undefined,[2] and clinical evidence of benefit is limited.[2] Diosmin is not recommended for treating the rectal mucosa, skin irritations, or wounds, and should not be used to treat dermatitis, eczema, or urticaria.[2] Diosmin is not recommended for use in children. Phlebotonics are not approved drugs in the United States or Europe.[2]

Regulatory status

Diosmin is distributed in the U.S. as a dietary supplement and as a prescription medical food.[3] The German Dermatological Society recommends the use of phlebotonics[4] following a 2016 Cochrane review which found that diosmin significantly reduced leg and ankle swelling and lower leg pain,[5] even though phlebotonics are not approved in Germany.[4] The FDA concluded in 2001 that there was inadequate evidence on which to base an expectation of safety.[6] As of 2013, the FDA did not revise this position, and all phlebotonics remained unapproved.[7] 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.[8]

Diosminplex

Micronized purified flavonoid fraction (generic name "diosminplex", commercial name "Vasculera") is a 2nd-generation phlebotonic drug, subsequent to diosmin. Under FDA regulation, medical food products must obtain GRAS (Generally Recognized As Safe) status.[8] Diosminplex is the only phlebotonic as of 2017 sold as a medical food product with GRAS status and recognized efficiency in the management of chronic venous insufficiency.[9] Indeed, the American Working Group in Chronic Venous Disease recommends the use of diosminplex as a medical therapy for chronic venous disease and venous ulcers, having "beneficial outcomes without serious adverse events", mirroring the previous guidance of the International European Society for Vascular Society.[10]

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. ^ a b c d e "Diosmin". Drugs.com. 1 January 2019. Retrieved 7 November 2019.
  3. ^ Public Health Service memorandum, Sept. 13, 2005
  4. ^ a b Stücker, M; Debus, ES; Hoffmann, J; Jünger, M; Kröger, K; Mumme, A; Ramelet, AA; Rabe, E (June 2016). "Consensus statement on the symptom-based treatment of chronic venous diseases". Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology : JDDG (Professional society guidelines). 14 (6): 575–83. doi:10.1111/ddg.13006. PMID 27240062.
  5. ^ Martinez-Zapata, Maria José; Vernooij, Robin WM; Uriona Tuma, Sonia Maria; Stein, Airton T; Moreno, Rosa M; Vargas, Emilio; Capellà, Dolors; Bonfill Cosp, Xavier (6 April 2016). "Phlebotonics for venous insufficiency". Cochrane Database of Systematic Reviews. doi:10.1002/14651858.CD003229.pub3. PMID 27048768. {{cite journal}}: Unknown parameter |lay-url= ignored (help)
  6. ^ 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]
  7. ^ Garg, Nitin; Gloviczki, Peter (2013). "55 - Chronic Venous Insufficiency". Vascular Medicine: A Companion to Braunwald's Heart Disease (Second Edition). Elsevier Health Sciences. pp. 652–666. ISBN 9781437729306.
  8. ^ a b "Guidance for Industry: Frequently Asked Questions About Medical Foods - Second Edition". fda.gov. May 2007. Retrieved 2019. {{cite web}}: Check date values in: |access-date= (help)
  9. ^ "Vasculera - diosmiplex 630mg". dailymed.nlm.nih.gov.
  10. ^ Martinez-Zapata, Maria José; Vernooij, Robin WM; Uriona Tuma, Sonia Maria; Stein, Airton T; Moreno, Rosa M; Vargas, Emilio; Capellà, Dolors; Bonfill Cosp, Xavier (6 April 2016). "Phlebotonics for venous insufficiency". Cochrane Database of Systematic Reviews (Professional society guidelines). doi:10.1002/14651858.CD003229.pub3. PMID 27048768. {{cite journal}}: Unknown parameter |lay-url= ignored (help)
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