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Diosmin

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Diosmin
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
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 mass608.549 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 glycoside of diosmetin, is manufactured from citrus fruit peels as a phlebotonic non-prescription dietary supplement used to aid treatment of hemorrhoids or chronic venous diseases, mainly of the legs.[1]

Uses

Diosmin is a 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.[1] The mechanism of action of Diosmin and other phlebotonics is undefined,[1] and clinical evidence of benefit is limited.[1] Diosmin is not recommended for treating the rectal mucosa, skin irritations, or wounds, and should not be used to treat dermatitis, eczema, or urticaria.[1] Diosmin is not recommended for use in children or women during pregnancy.[1] There is moderate-quality evidence that diosmin or other phlebotonics improved leg and ankle swelling and lower leg pain,[2] and low-quality evidence for treating hemorrhoids.[1][3]

Phlebotonics

Diosmin is included among a small class of agents called "phlebotonics" having heterogeneous composition and consisting partly of citrus peel extracts (flavonoids, such as hesperidin) and synthetic compounds, which are used to treat chronic venous insufficiency or hemorrhoids.[1]

In 2017, the American Working Group in Chronic Venous Disease recommended use of micronized purified flavonoid fraction (diosmiplex) as a medical food for chronic venous disease symptoms and venous ulcers, having "beneficial outcomes without serious adverse events", alone or combined with compression therapy, concurring with the previous guidance of the International European Society for Vascular Surgery.[4] The German Dermatological Society indicated that Diosmin may be used with other treatments for symptoms of chronic venous diseases.[5]

The American Society of Colon and Rectal Surgeons mentions phlebotonics as a possible treatment for symptoms of hemorrhoid grades I to II, as there is only moderate-quality evidence of effectiveness with "expectations of minimal harm", while having no evidence of long-term benefit.[3][6] French,[7][8] Indian,[9] Portuguese,[10] and Italian[11] professional societies of coloproctology issued similar recommendations regarding phlebotonics for hemorrhoids.

Adverse effects

In some 10% of users, diosmin causes mild gastrointestinal disorders or skin irritations (hives, itching), stomach pain, nausea, heart arrhythmias, or anemia.[1] Preliminary research indicates no evidence of toxicity.[1] The US Food and Drug Administration (FDA) concluded in 2001 that there was inadequate evidence on which to base an expectation of safety.[12] As of 2013, the FDA did not revise this position.[13]

Regulatory status

Diosmin is distributed in the U.S. as a dietary supplement called Daflon.[1] Diosmin is not approved as a prescription drug in the United States or Europe.[1] Phlebotonics are not approved in Germany,[5] and are restricted in Spain only for the treatment of chronic venous diseases.[14]

See also

References

  1. ^ a b c d e f g h i j k l "Diosmin". Drugs.com. 1 January 2019. Retrieved 7 November 2019.
  2. ^ Martinez-Zapata, Maria José; Vernooij, Robin Wm; Simancas-Racines, Daniel; Uriona Tuma, Sonia Maria; Stein, Airton T.; Moreno Carriles, Rosa Maria M.; Vargas, Emilio; Bonfill Cosp, Xavier (November 3, 2020). "Phlebotonics for venous insufficiency". The Cochrane Database of Systematic Reviews. 2020 (11): CD003229. doi:10.1002/14651858.CD003229.pub4. ISSN 1469-493X. PMC 8094625. PMID 33141449.
  3. ^ a b Perera N, Liolitsa D, Iype S, Croxford A, Yassin M, Lang P, et al. (August 2012). "Phlebotonics for haemorrhoids". The Cochrane Database of Systematic Reviews (8): CD004322. doi:10.1002/14651858.CD004322.pub3. PMID 22895941. S2CID 28445593.
  4. ^ Bush R, Comerota A, Meissner M, Raffetto JD, Hahn SR, Freeman K (April 2017). "Recommendations for the medical management of chronic venous disease: The role of Micronized Purified Flavanoid Fraction (MPFF)". Phlebology (Professional society guidelines). 32 (1_suppl): 3–19. doi:10.1177/0268355517692221. PMID 28211296. S2CID 24389276. Only recently has a standardized formulation MPFF been available in the United States (Vasculera—Primus Pharmaceuticals, Inc.).
  5. ^ a b Stücker M, Debus ES, Hoffmann J, Jünger M, Kröger K, Mumme A, et al. (June 2016). "Consensus statement on the symptom-based treatment of chronic venous diseases". Journal of the German Society of Dermatology (Professional society guidelines). 14 (6): 575–83. doi:10.1111/ddg.13006. PMID 27240062.
  6. ^ Davis BR, Lee-Kong SA, Migaly J, Feingold DL, Steele SR (March 2018). "The American Society of Colon and Rectal Surgeons Clinical Practice Guidelines for the Management of Hemorrhoids". Diseases of the Colon and Rectum (Professional society guidelines). 61 (3): 284–292. doi:10.1097/DCR.0000000000001030. PMID 29420423. S2CID 4198610.
  7. ^ Higuero T, Abramowitz L, Castinel A, Fathallah N, Hemery P, Laclotte Duhoux C, et al. (June 2016). "Guidelines for the treatment of hemorrhoids (short report)". Journal of Visceral Surgery (Professional society guidelines). 153 (3): 213–8. doi:10.1016/j.jviscsurg.2016.03.004. PMID 27209079.
  8. ^ Higuero T (December 2017). "Treatment of hemorroïdal disease: new french guidelines". La Revue du Praticien (in French). 67 (10): 1059–1062. PMID 30512599.
  9. ^ Agarwal N, Singh K, Sheikh P, Mittal K, Mathai V, Kumar A (February 2017). "Executive Summary - The Association of Colon & Rectal Surgeons of India (ACRSI) Practice Guidelines for the Management of Haemorrhoids-2016". The Indian Journal of Surgery (Professional society guidelines). 79 (1): 58–61. doi:10.1007/s12262-016-1578-7. PMC 5346092. PMID 28331268.
  10. ^ Salgueiro P, Caetano AC, Oliveira AM, Rosa B, Mascarenhas-Saraiva M, Ministro P, et al. (2020). "Portuguese Society of Gastroenterology Consensus on the Diagnosis and Management of Hemorrhoidal Disease". GE - Portuguese Journal of Gastroenterology (Professional society guidelines). 27 (2): 90–102. doi:10.1159/000502260. PMC 7113592. PMID 32266306.
  11. ^ Trompetto M, Clerico G, Cocorullo GF, Giordano P, Marino F, Martellucci J, et al. (October 2015). "Evaluation and management of hemorrhoids: Italian society of colorectal surgery (SICCR) consensus statement". Techniques in Coloproctology. 19 (10): 567–75. doi:10.1007/s10151-015-1371-9. hdl:10447/208054. PMID 26403234. S2CID 30827065.
  12. ^ 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]
  13. ^ Garg, Nitin; Gloviczki, Peter (2013). "55 - Chronic Venous Insufficiency". Vascular Medicine: A Companion to Braunwald's Heart Disease (Second ed.). Elsevier Health Sciences. pp. 652–666. ISBN 9781437729306.
  14. ^ "Consolidated List of Products - Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or Not Approved by Governments, Twelfth Issue - Pharmaceuticals. United Nations - New York, 2005". apps.who.int. 2005. Archived from the original on November 8, 2014. Retrieved 7 November 2019.
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