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{{short description|Chemical compound}}
{{Drugbox
{{cs1 config|name-list-style=vanc}}{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| verifiedrevid = 460791226
| verifiedrevid = 460791226
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| pregnancy_category =
| pregnancy_category =
| legal_status =
| legal_status =
| routes_of_administration = oral
| routes_of_administration = [[Oral administration|By mouth]]


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
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<!--Chemical data-->
<!--Chemical data-->
| C=28 | H=32 | O=15
| C=28 | H=32 | O=15
| molecular_weight = 608.545 g/mol
| smiles = 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
| smiles = 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey = GZSOSUNBTXMUFQ-YFAPSIMESA-N
| StdInChIKey = GZSOSUNBTXMUFQ-YFAPSIMESA-N
}}
}}
'''Diosmin''' (diosmetin 7-O-rutinoside), a [[flavone]] [[glycoside]] of [[diosmetin]], is manufactured from [[peel (fruit)|citrus fruit peels]] as a [[prescription drug|non-prescription]] [[dietary supplement]] used to aid treatment of [[hemorrhoid]]s or [[chronic venous insufficiency|chronic venous diseases, mainly of the legs]].<ref name=drugs/>
'''Diosmin''' (diosmetin 7-O-rutinoside), a [[flavone]] [[glycoside]] of [[diosmetin]], is manufactured from [[peel (fruit)|citrus fruit peels]] as a phlebotonic [[prescription drug|non-prescription]] [[dietary supplement]] used to aid treatment of [[hemorrhoid]]s or [[chronic venous insufficiency|chronic venous diseases, mainly of the legs]].<ref name=drugs/>


==Uses==
==Uses==
Diosmin is a dietary supplement used to aid treatment of [[hemorrhoid]]s and venous diseases, i.e., [[chronic venous insufficiency]] including spider and varicose veins, leg swelling ([[edema]]), [[stasis dermatitis]] and [[venous ulcer]]s.<ref name="drugs">{{cite web |title=Diosmin |url=https://www.drugs.com/npp/diosmin.html |publisher=Drugs.com |access-date=7 November 2019 |date=1 January 2019}}</ref> The mechanism of action of Diosmin and other phlebotonics is undefined,<ref name=drugs/> and [[evidence-based medicine|clinical evidence]] of benefit is limited.<ref name=drugs/> Diosmin is not recommended for treating the [[rectum|rectal mucosa]], skin irritations, or wounds, and should not be used to treat [[dermatitis]], [[eczema]], or [[urticaria]].<ref name=drugs/> Diosmin is not recommended for use in children or women during [[pregnancy]].<ref name=drugs/>
Diosmin is a dietary supplement used to aid treatment of [[hemorrhoid]]s and venous diseases, i.e., [[chronic venous insufficiency]] including spider and varicose veins, leg swelling ([[edema]]), [[stasis dermatitis]] and [[venous ulcer]]s.<ref name="drugs">{{cite web |title=Diosmin |url=https://www.drugs.com/npp/diosmin.html |publisher=Drugs.com |access-date=7 November 2019 |date=1 January 2019}}</ref> The mechanism of action of Diosmin and other phlebotonics is undefined,<ref name=drugs/> and [[evidence-based medicine|clinical evidence]] of benefit is limited.<ref name=drugs/> Diosmin is not recommended for treating the [[rectum|rectal mucosa]], skin irritations, or wounds, and should not be used to treat [[dermatitis]], [[eczema]], or [[urticaria]].<ref name=drugs/> Diosmin is not recommended for use in children or women during [[pregnancy]].<ref name=drugs/> There is moderate-quality evidence that diosmin or other phlebotonics improved leg and ankle swelling and lower leg pain,<ref>{{cite journal | vauthors = Martinez-Zapata MJ, Vernooij RW, Simancas-Racines D, Uriona Tuma SM, Stein AT, Moreno Carriles RM, Vargas E, Bonfill Cosp X | display-authors = 6 | title = Phlebotonics for venous insufficiency | journal = The Cochrane Database of Systematic Reviews | volume = 2020 | issue = 11 | pages = CD003229 | date = November 2020 | pmid = 33141449 | pmc = 8094625 | doi = 10.1002/14651858.CD003229.pub4 }}</ref> and low-quality evidence for treating [[hemorrhoid]]s.<ref name="drugs" /><ref name="Perera2012">{{cite journal | vauthors = Perera N, Liolitsa D, Iype S, Croxford A, Yassin M, Lang P, Ukaegbu O, van Issum C | display-authors = 6 | title = Phlebotonics for haemorrhoids | journal = The Cochrane Database of Systematic Reviews | issue = 8 | pages = CD004322 | date = August 2012 | pmid = 22895941 | doi = 10.1002/14651858.CD004322.pub3 | s2cid = 28445593 }}</ref>


===Phlebotonics===
===Phlebotonics===
Diosmin is included among a small class of agents called "phlebotonics" having heterogeneous composition and consisting partly of [[peel (fruit)|citrus peel]] [[extract]]s ([[flavonoid]]s, such as [[hesperidin]]) and synthetic compounds, which are used to treat [[chronic venous insufficiency]] or [[hemorrhoid]]s.<ref name=drugs/> A 2016 Cochrane review found only moderate-quality evidence that diosmin or other phlebotonics improved leg and ankle swelling and lower leg pain,<ref name="Cochrane2016">{{cite journal | vauthors = Martinez-Zapata MJ, Vernooij RW, Uriona Tuma SM, Stein AT, Moreno RM, Vargas E, Capellà D, Bonfill Cosp X | display-authors = 6 | title = Phlebotonics for venous insufficiency | journal = The Cochrane Database of Systematic Reviews | volume = 4 | pages = CD003229 | date = April 2016 | pmid = 27048768 | doi = 10.1002/14651858.CD003229.pub3 | url = https://semanticscholar.org/paper/c448caf3827acaee9c9767cac6bfd03831705f18 }}</ref> and a 2012 review indicated low-quality evidence for treating [[hemorrhoid]]s.<ref name=drugs/><ref name="Perera2012">{{cite journal | vauthors = Perera N, Liolitsa D, Iype S, Croxford A, Yassin M, Lang P, Ukaegbu O, van Issum C | display-authors = 6 | title = Phlebotonics for haemorrhoids | journal = The Cochrane Database of Systematic Reviews | issue = 8 | pages = CD004322 | date = August 2012 | pmid = 22895941 | doi = 10.1002/14651858.CD004322.pub3 | url = https://semanticscholar.org/paper/437861f6eb24981bc09e17d56cef5ce266e69f3d }}</ref>
Diosmin is included among a small class of agents called "phlebotonics" having heterogeneous composition and consisting partly of [[peel (fruit)|citrus peel]] [[extract]]s ([[flavonoid]]s, such as [[hesperidin]]) and synthetic compounds, which are used to treat [[chronic venous insufficiency]] or [[hemorrhoid]]s.<ref name=drugs/>


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 stockings|compression therapy]], concurring with the previous guidance of the International European Society for Vascular Surgery.<ref name="CVDUS2017" /> The [[Deutsche_Dermatologische_Gesellschaft|German Dermatological Society]] indicated that Diosmin may be used with other treatments for symptoms of [[chronic venous disease]]s.<ref name="Stucker2016">{{cite journal | vauthors = Stücker M, Debus ES, Hoffmann J, Jünger M, Kröger K, Mumme A, Ramelet AA, Rabe E | display-authors = 6 | title = Consensus statement on the symptom-based treatment of chronic venous diseases | journal = Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology | volume = 14 | issue = 6 | pages = 575–83 | date = June 2016 | pmid = 27240062 | doi = 10.1111/ddg.13006 | type = Professional society guidelines | doi-access = free }}</ref>
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 ulcer]]s, having "beneficial outcomes without serious adverse events", alone or combined with [[compression stockings|compression therapy]], concurring with the previous guidance of the International European Society for Vascular Surgery.<ref name="CVDUS2017">{{cite journal | vauthors = Bush R, Comerota A, Meissner M, Raffetto JD, Hahn SR, Freeman K | s2cid = 24389276 | title = Recommendations for the medical management of chronic venous disease: The role of Micronized Purified Flavanoid Fraction (MPFF) | journal = Phlebology | volume = 32 | issue = 1_suppl | pages = 3–19 | date = April 2017 | pmid = 28211296 | doi = 10.1177/0268355517692221 | type = Professional society guidelines | quote = Only recently has a standardized formulation MPFF been available in the United States (Vasculera—Primus Pharmaceuticals, Inc.). }}</ref> The [[Deutsche Dermatologische Gesellschaft|German Dermatological Society]] indicated that Diosmin may be used with other treatments for symptoms of [[chronic venous disease]]s.<ref name="Stucker2016">{{cite journal | vauthors = Stücker M, Debus ES, Hoffmann J, Jünger M, Kröger K, Mumme A, Ramelet AA, Rabe E | display-authors = 6 | title = Consensus statement on the symptom-based treatment of chronic venous diseases | journal = Journal of the German Society of Dermatology | volume = 14 | issue = 6 | pages = 575–83 | date = June 2016 | pmid = 27240062 | doi = 10.1111/ddg.13006 | type = Professional society guidelines | doi-access = free }}</ref>


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.<ref name="Perera2012" /><ref>{{cite journal | vauthors = Davis BR, Lee-Kong SA, Migaly J, Feingold DL, Steele SR | title = The American Society of Colon and Rectal Surgeons Clinical Practice Guidelines for the Management of Hemorrhoids | journal = Diseases of the Colon and Rectum | volume = 61 | issue = 3 | pages = 284–292 | date = March 2018 | pmid = 29420423 | doi = 10.1097/DCR.0000000000001030 | url = https://semanticscholar.org/paper/b456690f2e80475bbf2d747d0b095f5dba012870 | type = Professional society guidelines }}</ref> French,<ref>{{cite journal | vauthors = Higuero T, Abramowitz L, Castinel A, Fathallah N, Hemery P, Laclotte Duhoux C, Pigot F, Pillant-Le Moult H, Senéjoux A, Siproudhis L, Staumont G, Suduca JM, Vinson-Bonnet B | display-authors = 6 | title = Guidelines for the treatment of hemorrhoids (short report) | journal = Journal of Visceral Surgery | volume = 153 | issue = 3 | pages = 213–8 | date = June 2016 | pmid = 27209079 | doi = 10.1016/j.jviscsurg.2016.03.004 | type = Professional society guidelines }}</ref><ref>{{cite journal | vauthors = Higuero T | title = Treatment of hemorroïdal disease: new french guidelines | journal = La Revue du Praticien | volume = 67 | issue = 10 | pages = 1059–1062 | date = December 2017 | pmid = 30512599 | lang = fr }}</ref> Indian,<ref>{{cite journal | vauthors = Agarwal N, Singh K, Sheikh P, Mittal K, Mathai V, Kumar A | title = Executive Summary - The Association of Colon & Rectal Surgeons of India (ACRSI) Practice Guidelines for the Management of Haemorrhoids-2016 | journal = The Indian Journal of Surgery | volume = 79 | issue = 1 | pages = 58–61 | date = February 2017 | pmid = 28331268 | pmc = 5346092 | doi = 10.1007/s12262-016-1578-7 | type = Professional society guidelines }}</ref> Portuguese,<ref>{{cite journal | vauthors = Salgueiro P, Caetano AC, Oliveira AM, Rosa B, Mascarenhas-Saraiva M, Ministro P, Amaro P, Godinho R, Coelho R, Gaio R, Fernandes S | display-authors = 6 |title=Portuguese Society of Gastroenterology Consensus on the Diagnosis and Management of Hemorrhoidal Disease |journal=GE - Portuguese Journal of Gastroenterology |volume=27 |issue=2 |pages=90–102 |doi=10.1159/000502260 |type=Professional society guidelines|year=2020 |doi-access=free }}</ref> and Italian<ref>{{cite journal | vauthors = Trompetto M, Clerico G, Cocorullo GF, Giordano P, Marino F, Martellucci J, Milito G, Mistrangelo M, Ratto C | display-authors = 6 | title = Evaluation and management of hemorrhoids: Italian society of colorectal surgery (SICCR) consensus statement | journal = Techniques in Coloproctology | volume = 19 | issue = 10 | pages = 567–75 | date = October 2015 | pmid = 26403234 | doi = 10.1007/s10151-015-1371-9 | hdl = 10447/208054 }}</ref> professional societies of [[coloproctology]] issued similar recommendations regarding phlebotonics for hemorrhoids.
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.<ref name="Perera2012" /><ref>{{cite journal | vauthors = Davis BR, Lee-Kong SA, Migaly J, Feingold DL, Steele SR | s2cid = 4198610 | title = The American Society of Colon and Rectal Surgeons Clinical Practice Guidelines for the Management of Hemorrhoids | journal = Diseases of the Colon and Rectum | volume = 61 | issue = 3 | pages = 284–292 | date = March 2018 | pmid = 29420423 | doi = 10.1097/DCR.0000000000001030 | type = Professional society guidelines }}</ref> French,<ref>{{cite journal | vauthors = Higuero T, Abramowitz L, Castinel A, Fathallah N, Hemery P, Laclotte Duhoux C, Pigot F, Pillant-Le Moult H, Senéjoux A, Siproudhis L, Staumont G, Suduca JM, Vinson-Bonnet B | display-authors = 6 | title = Guidelines for the treatment of hemorrhoids (short report) | journal = Journal of Visceral Surgery | volume = 153 | issue = 3 | pages = 213–8 | date = June 2016 | pmid = 27209079 | doi = 10.1016/j.jviscsurg.2016.03.004 | type = Professional society guidelines | doi-access = free }}</ref><ref>{{cite journal | vauthors = Higuero T | title = Treatment of hemorroïdal disease: new french guidelines | journal = La Revue du Praticien | volume = 67 | issue = 10 | pages = 1059–1062 | date = December 2017 | pmid = 30512599 | language = fr }}</ref> Indian,<ref>{{cite journal | vauthors = Agarwal N, Singh K, Sheikh P, Mittal K, Mathai V, Kumar A | title = Executive Summary - The Association of Colon & Rectal Surgeons of India (ACRSI) Practice Guidelines for the Management of Haemorrhoids-2016 | journal = The Indian Journal of Surgery | volume = 79 | issue = 1 | pages = 58–61 | date = February 2017 | pmid = 28331268 | pmc = 5346092 | doi = 10.1007/s12262-016-1578-7 | type = Professional society guidelines }}</ref> Portuguese,<ref>{{cite journal | vauthors = Salgueiro P, Caetano AC, Oliveira AM, Rosa B, Mascarenhas-Saraiva M, Ministro P, Amaro P, Godinho R, Coelho R, Gaio R, Fernandes S | display-authors = 6 |title=Portuguese Society of Gastroenterology Consensus on the Diagnosis and Management of Hemorrhoidal Disease |journal=GE - Portuguese Journal of Gastroenterology |volume=27 |issue=2 |pages=90–102 |doi=10.1159/000502260 |type=Professional society guidelines|year=2020 | pmid = 32266306 | pmc = 7113592 |doi-access=free }}</ref> and Italian<ref>{{cite journal | vauthors = Trompetto M, Clerico G, Cocorullo GF, Giordano P, Marino F, Martellucci J, Milito G, Mistrangelo M, Ratto C | s2cid = 30827065 | display-authors = 6 | title = Evaluation and management of hemorrhoids: Italian society of colorectal surgery (SICCR) consensus statement | journal = Techniques in Coloproctology | volume = 19 | issue = 10 | pages = 567–75 | date = October 2015 | pmid = 26403234 | doi = 10.1007/s10151-015-1371-9 | hdl = 10447/208054 | hdl-access = free }}</ref> professional societies of [[coloproctology]] issued similar recommendations regarding phlebotonics for hemorrhoids.


==Adverse effects==
==Adverse effects==
In some 10% of users, diosmin causes mild [[gastrointestinal disease|gastrointestinal disorders]] or skin irritations (hives, itching), stomach pain, nausea, heart [[arrhythmia]]s, or [[anemia]].<ref name=drugs/> Preliminary research indicates no evidence of [[toxicity]].<ref name=drugs/> The US [[Food and Drug Administration]] (FDA) concluded in 2001 that there was inadequate evidence on which to base an expectation of safety.<ref>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) [https://www.fda.gov/Food/DietarySupplements/ucm109764.htm], Memorandum [https://www.fda.gov/ohrms/dockets/dockets/95s0316/rpt0083_01.pdf]</ref> {{asof|2013}}, the FDA did not revise this position.<ref>{{cite book |last1=Garg |first1=Nitin |last2=Gloviczki |first2=Peter |title=Vascular Medicine: A Companion to Braunwald's Heart Disease (Second Edition) |date=2013 |publisher=Elsevier Health Sciences |isbn=9781437729306 |pages=652–666 |chapter-url=https://www.sciencedirect.com/science/article/pii/B9781437729306000550 |chapter=55 - Chronic Venous Insufficiency}}</ref>
In some 10% of users, diosmin causes mild [[gastrointestinal disease|gastrointestinal disorders]] or skin irritations (hives, itching), stomach pain, nausea, heart [[arrhythmia]]s, or [[anemia]].<ref name=drugs/> Preliminary research indicates no evidence of [[toxicity]].<ref name=drugs/> The US [[Food and Drug Administration]] (FDA) concluded in 2001 that there was inadequate evidence on which to base an expectation of safety.<ref>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) [https://www.fda.gov/Food/DietarySupplements/ucm109764.htm], Memorandum [https://www.fda.gov/ohrms/dockets/dockets/95s0316/rpt0083_01.pdf]</ref> {{asof|2013}}, the FDA did not revise this position.<ref>{{cite book | vauthors = Garg N, Gloviczki P |chapter=55 - Chronic Venous Insufficiency |title=Vascular Medicine: A Companion to Braunwald's Heart Disease |date=2013 |publisher=Elsevier Health Sciences |isbn=9781437729306 |pages=652–666 | doi = 10.1016/B978-1-4377-2930-6.00055-0 |edition=Second }}</ref>


== Regulatory status ==
== Regulatory status ==
Diosmin is distributed in the U.S. as a dietary supplement called [[Daflon]].<ref name=drugs/> Diosmin is not approved as a [[prescription drug]] in the United States or Europe.<ref name=drugs/> Phlebotonics are not approved in Germany,<ref name="Stucker2016" /> and are restricted in Spain only for the treatment of chronic venous diseases.<ref>{{cite web |title=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 |url=http://apps.who.int/medicinedocs/en/m/abstract/Js16780e/ |website=apps.who.int |access-date=7 November 2019 |date=2005}}</ref>
Diosmin is distributed in the U.S. as a dietary supplement called [[Daflon]].<ref name=drugs/> Diosmin is not approved as a [[prescription drug]] in the United States,<ref name=drugs/> although it is available as over-the-counter or prescription-only drug in Europe sold under name Detralex<ref>{{cite web|title=Detralex |url=https://www.sukl.sk/hlavna-stranka/slovenska-verzia/pomocne-stranky/detail-lieku?page_id=386&lie_id=40159 |publisher=Štátny ústav pre kontrolu liečiv |access-date=1 April 2024}}</ref> among others. Phlebotonics are not approved in Germany,<ref name="Stucker2016" /> and are restricted in Spain only for the treatment of chronic venous diseases.<ref>{{cite web |title=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 |url=http://apps.who.int/medicinedocs/en/m/abstract/Js16780e/ |archive-url=https://web.archive.org/web/20141108234228/http://apps.who.int/medicinedocs/en/m/abstract/Js16780e/ |url-status=dead |archive-date=November 8, 2014 |website=apps.who.int |access-date=7 November 2019 |date=2005}}</ref>

== Diosmiplex ==
Micronized purified flavonoid fraction (generic name diosmiplex, commercial name ''Vasculera'')<ref name="CVDUS2017">{{cite journal | vauthors = Bush R, Comerota A, Meissner M, Raffetto JD, Hahn SR, Freeman K | title = Recommendations for the medical management of chronic venous disease: The role of Micronized Purified Flavanoid Fraction (MPFF) | journal = Phlebology | volume = 32 | issue = 1_suppl | pages = 3–19 | date = April 2017 | pmid = 28211296 | doi = 10.1177/0268355517692221 | type = Professional society guidelines | quote = Only recently has a standardized formulation MPFF been available in the United States (Vasculera—Primus Pharmaceuticals, Inc.). }}</ref> is a 2nd generation diosmin classified as a [[medical food]] by the FDA in the United States for the potential treatment of [[chronic venous insufficiency]].<ref name="dailymed-diosmiplex">{{cite web |title= Vasculera- diosmiplex tablet |url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=563d3d34-a547-471e-aecd-f4a4a57cbf1d |work = DailyMed |publisher= U.S. National Institutes of Health |access-date=8 November 2019 |date=26 April 2012}}</ref><ref name="vasc">{{cite web |title=Vasculera |url=https://www.drugs.com/mtm/vasculera.html |publisher=Drugs.com |access-date=7 November 2019 |date=3 December 2018}}</ref> Diosmiplex is the only phlebotonic, {{asof|2017|lc=y}}, sold as a medical food product purported for the management of [[chronic venous insufficiency]].<ref name="CVDUS2017" /> Diosmiplex is recommended by the American Working Group in Chronic Venous Disease as a medical therapy, alone or combined with compressive therapy, for chronic venous disease symptoms and venous ulcers, having "beneficial outcomes without serious adverse events", concurring with the previous guidance of the International European Society for Vascular Surgery.<ref name="CVDUS2017" />


== See also ==
== See also ==

Latest revision as of 12:49, 5 April 2024

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[edit]

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[edit]

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[edit]

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[edit]

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,[1] although it is available as over-the-counter or prescription-only drug in Europe sold under name Detralex[14] among others. Phlebotonics are not approved in Germany,[5] and are restricted in Spain only for the treatment of chronic venous diseases.[15]

See also[edit]

References[edit]

  1. ^ a b c d e f g h i j k l "Diosmin". Drugs.com. 1 January 2019. Retrieved 7 November 2019.
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  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.).
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  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.
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  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]
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  14. ^ "Detralex". Štátny ústav pre kontrolu liečiv. Retrieved 1 April 2024.
  15. ^ "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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