Diosmin

Clinical data
AHFS/Drugs.com| International Drug Names
Routes of
administration| By mouth
ATC code|

* C05CA03 (WHO)

Identifiers

IUPAC name

* 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|

* 520-27-4 N

PubChem CID|

* 5281613

DrugBank|

* DB08995 N

ChemSpider|

* 4444932 Y

UNII|

* 7QM776WJ5N

KEGG|

* D07858 Y

ChEBI|

* CHEBI:4631 N

ChEMBL|

* ChEMBL231884 Y

Chemical and physical data
Formula| C28H32O15
Molar mass| 608.549 g·mol−1
3D model (JSmol)|

* Interactive image

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

InChI

* 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 Y

* Key:GZSOSUNBTXMUFQ-YFAPSIMESA-N Y

NY (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]

## Contents

* 1 Uses
* 1.1 Phlebotonics
* 2 Adverse effects
* 3 Regulatory status
* 4 See also
* 5 References

## 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

* Daflon
* Venalex

## References

1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 "Diosmin". Drugs.com. 1 January 2019. https://www.drugs.com/npp/diosmin.html.
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 11: CD003229. doi:10.1002/14651858.CD003229.pub4. ISSN 1469-493X. PMID 33141449. https://pubmed.ncbi.nlm.nih.gov/33141449.
3. ↑ 3.0 3.1 "Phlebotonics for haemorrhoids". The Cochrane Database of Systematic Reviews (8): CD004322. August 2012. doi:10.1002/14651858.CD004322.pub3. PMID 22895941.
4. ↑ "Recommendations for the medical management of chronic venous disease: The role of Micronized Purified Flavanoid Fraction (MPFF)". Phlebology 32 (1_suppl): 3–19. April 2017. doi:10.1177/0268355517692221. PMID 28211296. "Only recently has a standardized formulation MPFF been available in the United States (Vasculera—Primus Pharmaceuticals, Inc.).".
5. ↑ 5.0 5.1 "Consensus statement on the symptom-based treatment of chronic venous diseases". Journal of the German Society of Dermatology 14 (6): 575–83. June 2016. doi:10.1111/ddg.13006. PMID 27240062.
6. ↑ "The American Society of Colon and Rectal Surgeons Clinical Practice Guidelines for the Management of Hemorrhoids". Diseases of the Colon and Rectum 61 (3): 284–292. March 2018. doi:10.1097/DCR.0000000000001030. PMID 29420423.
7. ↑ "Guidelines for the treatment of hemorrhoids (short report)". Journal of Visceral Surgery 153 (3): 213–8. June 2016. doi:10.1016/j.jviscsurg.2016.03.004. PMID 27209079.
8. ↑ "Treatment of hemorroïdal disease: new french guidelines" (in fr). La Revue du Praticien 67 (10): 1059–1062. December 2017. PMID 30512599.
9. ↑ "Executive Summary - The Association of Colon & Rectal Surgeons of India (ACRSI) Practice Guidelines for the Management of Haemorrhoids-2016". The Indian Journal of Surgery 79 (1): 58–61. February 2017. doi:10.1007/s12262-016-1578-7. PMID 28331268.
10. ↑ "Portuguese Society of Gastroenterology Consensus on the Diagnosis and Management of Hemorrhoidal Disease". GE - Portuguese Journal of Gastroenterology 27 (2): 90–102. 2020. doi:10.1159/000502260. PMID 32266306.
11. ↑ "Evaluation and management of hemorrhoids: Italian society of colorectal surgery (SICCR) consensus statement". Techniques in Coloproctology 19 (10): 567–75. October 2015. doi:10.1007/s10151-015-1371-9. PMID 26403234.
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. https://www.sciencedirect.com/science/article/pii/B9781437729306000550.
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". 2005. http://apps.who.int/medicinedocs/en/m/abstract/Js16780e/.

* v
* t
* e

Vasoprotectives (C05)

Antihemorrhoidals for topical use|

| corticosteroids|

* Hydrocortisone
* Prednisolone
* Betamethasone
* Fluorometholone
* Fluocortolone
* Dexamethasone
* Fluocinolone acetonide
* Fluocinonide

|

local anesthetics|

* Lidocaine
* Tetracaine
* Benzocaine
* Dibucaine
* Procaine
* Oxetacaine
* Pramocaine

other|

* Tribenoside

Antivaricose therapy|

| heparins or heparinoids for topical use|

* Organo-heparinoid
* Sodium apolate
* Heparin
* Pentosan polysulfate

|

sclerosing agents for local injection|

* Monoethanolamine oleate
* Polidocanol
* Inverted sugar syrup
* Sodium tetradecyl sulfate
* Phenol

other|

* Calcium dobesilate

Capillary stabilising agents|

| bioflavonoids|

* Rutoside
* Monoxerutin
* Diosmin
* Troxerutin
* Hidrosmin

|

other|

* Tribenoside
* Etamsylate

* v
* t
* e

Flavones and their conjugates

Aglycones|

| Monohydroxyflavone|

* 6-Hydroxyflavone

|

Dihydroxyflavones|

* Chrysin
* 4',7-Dihydroxyflavone
* 7,8-Dihydroxyflavone

Trihydroxyflavones|

* Apigenin
* Baicalein
* Norwogonin

Tetrahydroxyflavones|

* Isoscutellarein
* Luteolin
* Norartocarpetin
* Scutellarein

Pentahydroxyflavones|

* Nortangeretin
* 6-Hydroxyluteolin
* Norwightin
* Hypolaetin
* Tricetin

O-methylated flavones|

* Acacetin
* Alnetin
* Artocarpetin
* Chrysoeriol
* Cirsilineol
* Cirsiliol
* Cirsimaritin
* Diosmetin
* Eupatilin
* Genkwanin
* Hispidulin
* Nepetin
* Nobiletin
* Oroxylin A
* Pratol
* Salvigenin
* Sinensetin
* Tangeretin
* Techtochrysin
* Tricin
* Wogonin
* Zapotin

Glycosides|

| of apigenin|

* Apiin
* Apigetrin
* Isovitexin
* Rhoifolin
* Saponarin
* Schaftoside
* Vicenin-2
* Vitexin

|

of baicalein|

* Baicalin
* Tetuin

of hypolaetin|

* Hypolaetin 8-glucoside
* Hypolaetin 8-glucuronide

of luteolin|

* Cynaroside
* Isoorientin
* Orientin
* Veronicastroside
* Luteolin-7-O-glucuronide

* Giraldiin A and B
* Nepitrin
* Oroxindin
* Scutellarin

Acetylated|

* Artocarpetin A
* Artoindonesianin P

Sulfated glycosides|

Theograndin I and II

Polymers|

* Amentoflavone

Drugs|

* Diosmin
* Hidrosmin

0.00

(0 votes)

Original source: https://en.wikipedia.orghttps://handwiki.org/wiki/ Diosmin. Read more

|

Retrieved from "https://handwiki.orghttps://handwiki.org/wiki/index.php?title=Chemistry:Diosmin&oldid=2111801"
*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template