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{{chembox
{{DrugProjectFormSinglePage
|authorTag={{AV}}
|OTC=Yes
|genericName=rutin
|aOrAn=a
|drugClass=[[bioflavonoid]]
|indicationType=treatment
|indication=temporary relief of food and pollen sensitivities including [[rhinitis]], [[sinusitis]], nasal congestion, [[hay fever]]; [[impotence]], [[lactose intolerance]], and bladder [[infection]].
|adverseReactions=[[abdominal discomfort]], [[palpitations]], [[dizziness]], [[headache]], [[alopecia]], [[tiredness]], [[dry mouth]], [[pruritus]], [[leg edema]], [[gastritis]], [[vomiting]], [[diarrhea]], [[dyspepsia]], [[skin rash]], [[muscle stiffness]]<!--Black Box Warning-->
|blackBoxWarningTitle=Title
|blackBoxWarningBody=<i><span style="color:#FF0000;">ConditionName: </span></i>
 
* Content
 
<!--Adult Indications and Dosage-->
 
<!--FDA-Labeled Indications and Dosage (Adult)-->
|fdaLIADAdult=*For temporary relief of food and pollen sensitivities including [[rhinitis]], [[sinusitis]], nasal congestion, [[hay fever]]; [[impotence]], [[lactose intolerance]], and [[bladder infectio]]n.
 
<!--Off-Label Use and Dosage (Adult)-->
 
<!--Guideline-Supported Use (Adult)-->
|offLabelAdultGuideSupport=There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of {{PAGENAME}} in adult patients.
 
<!--Non–Guideline-Supported Use (Adult)-->
|offLabelAdultNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in adult patients.
 
<!--Pediatric Indications and Dosage-->
 
<!--FDA-Labeled Indications and Dosage (Pediatric)-->
|fdaLIADPed=There is limited information regarding <i>FDA-Labeled Use</i> of {{PAGENAME}} in pediatric patients.
 
<!--Off-Label Use and Dosage (Pediatric)-->
 
<!--Guideline-Supported Use (Pediatric)-->
|offLabelPedGuideSupport=There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.
 
<!--Non–Guideline-Supported Use (Pediatric)-->
|offLabelPedNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.
 
<!--Contraindications-->
|contraindications=<!--Warnings-->
|warnings=* Keep out of reach of children. In case of overdose, contact physician or Poison Control Center right away.
 
*If pregnant or breast-feeding, seek advice of a health professional before use.
 
*Tamper seal: "Sealed for Your Protection." Do not use if seal is broken or missing.
 
 
<!--Adverse Reactions-->
*[[Decrease in hematocrit]], [[red blood cell count]], [[beta globulin]], increase in [[prothrombin time]], abdominal discomfort, [[palpitations]], [[dizziness]], [[headache]], [[alopecia]], tiredness,  [[dry mouth]], [[pruritus]], [[leg edema]], [[gastritis]], [[vomiting]], [[diarrhea]], [[dyspepsia]], [[skin rash]], [[muscle stiffness]]
<!--Clinical Trials Experience-->
|clinicalTrials=There is limited information regarding <i>Clinical Trial Experience</i> of {{PAGENAME}} in the drug label.
 
<!--Postmarketing Experience-->
|postmarketing=There is limited information regarding <i>Postmarketing Experience</i> of {{PAGENAME}} in the drug label.
 
 
<!--Drug Interactions-->
|drugInteractions=<!--Use in Specific Populations-->
|useInPregnancyAUS=There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of {{PAGENAME}} in women who are pregnant.
|useInLaborDelivery=There is no FDA guidance on use of {{PAGENAME}} during labor and delivery.
|useInNursing=There is no FDA guidance on the use of {{PAGENAME}} with respect to nursing mothers.
|useInPed=*In case of overdose, contact physician or Poison Control Center right away.
|useInGeri=There is no FDA guidance on the use of {{PAGENAME}} with respect to geriatric patients.
|useInGender=There is no FDA guidance on the use of {{PAGENAME}} with respect to specific gender populations.
|useInRace=There is no FDA guidance on the use of {{PAGENAME}} with respect to specific racial populations.
|useInRenalImpair=There is no FDA guidance on the use of {{PAGENAME}} in patients with [[renal impairment]].
|useInHepaticImpair=There is no FDA guidance on the use of {{PAGENAME}} in patients with [[hepatic impairment]].
|useInReproPotential=There is no FDA guidance on the use of {{PAGENAME}} in women of reproductive potentials and males.
|useInImmunocomp=There is no FDA guidance one the use of {{PAGENAME}} in patients who are [[immunocompromised]].
 
<!--Administration and Monitoring-->
|administration=* Oral
 
* Intravenous
|monitoring=There is limited information regarding <i>Monitoring</i> of {{PAGENAME}} in the drug label.
 
 
<!--IV Compatibility-->
|IVCompat=There is limited information regarding <i>IV Compatibility</i> of {{PAGENAME}} in the drug label.
 
<!--Overdosage-->
|overdose=There is limited information regarding <i>Chronic Overdose</i> of {{PAGENAME}} in the drug label.
 
<!--Pharmacology-->
 
<!--Drug box 2-->
|drugBox={{chembox2
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 455039901
| verifiedrevid = 455039901
|   Name = Rutin
| Name = Rutin
|   ImageFile = Rutin structure.png
| ImageFile = Rutin structure.png
|   ImageSize = 250px
| ImageSize = 250px
|   ImageName = Rutin structure.png
| ImageName = Rutin
|   PIN = 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[&alpha;-<small>L</small>-rhamnopyranosyl-(1→6)-&beta;-<small>D</small>-glucopyranosyloxy]-4''H''-chromen-4-one
| PIN = 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[&alpha;-<small>L</small>-rhamnopyranosyl-(1→6)-&beta;-<small>D</small>-glucopyranosyloxy]-4''H''-chromen-4-one
|   IUPACName = 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-({[(2''R'',3''R'',4''R'',5''R'',6''S'')-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4''H''-chromen-4-one
| IUPACName = 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-({[(2''R'',3''R'',4''R'',5''R'',6''S'')-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4''H''-chromen-4-one
|   IUPACName_hidden = yes
| OtherNames=Rutoside<br>Phytomelin<br>Sophorin<br>Birutan<br>Eldrin<br>Birutan Forte<br>Rutin trihydrate<br>Globularicitrin<br>Violaquercitrin
|  OtherNames=Rutoside<br>Phytomelin<br>Sophorin<br>Birutan<br>Eldrin<br>Birutan Forte<br>Rutin trihydrate<br>Globularicitrin<br>Violaquercitrin
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
|   CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
|   CASNo = 153-18-4
| CASNo = 153-18-4
|   ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4444362
| ChemSpiderID = 4444362
|   KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C05625
| KEGG = C05625
| PubChem = 5280805
| PubChem = 5280805
|   RTECS = VM2975000
| RTECS = VM2975000
|   DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
|   DrugBank = DB01698
| DrugBank = DB01698
|   UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
|   UNII = 5G06TVY3R7
| UNII = 5G06TVY3R7
|   SMILES = CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
| InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
|  InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
| ATCCode_prefix = C05
|   ATCCode_prefix = C05
| ATCCode_suffix = CA01
|   ATCCode_suffix = CA01
   }}
   }}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
|   C=27|H=30|O=16
| C=27|H=30|O=16
|   ExactMass = 610.153385 u
| ExactMass = 610.153385 u
|   Appearance = Solid
| Appearance = Solid
|   Density =  
| Density =  
|   MeltingPtC = 242
| MeltingPtC = 242
|   BoilingPtC =
| BoilingPtC =
|   Solubility = 12.5 mg/100 mL<ref>''[[Merck Index]]'', 12th Edition, '''8456'''</ref><br>13 mg/100mL<ref>{{cite journal | doi = 10.1002/jps.3030411106 | title = Some physical properties of rutin | year = 2006 | last1 = Krewson | first1 = C. F. | last2 = Naghski | first2 = J. | journal = Journal of the American Pharmaceutical Association | volume = 41 | issue = 11 | pages = 582–7 | pmid = 12999623}}</ref>
| Solubility = 12.5 mg/100 mL<ref>''[[Merck Index]]'', 12th Edition, '''8456'''</ref><br>13 mg/100mL<ref>{{cite journal | doi = 10.1002/jps.3030411106 | title = Some physical properties of rutin | year = 2006 | last1 = Krewson | first1 = C. F. | last2 = Naghski | first2 = J. | journal = Journal of the American Pharmaceutical Association | volume = 41 | issue = 11 | pages = 582–7 | pmid = 12999623}}</ref>
   }}
   }}
| Section3 = {{Chembox Hazards
| Section3 = {{Chembox Hazards
|   NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0
| NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0
   }}
   }}
}}
}}


{{CMG}}{{AE}}{{SS}}


'''Rutin''', also called '''rutoside''', '''quercetin-3-O-rutinoside''' and '''sophorin''', is the [[glycoside]] between the [[flavonol]] [[quercetin]] and the [[disaccharide]] [[rutinose]] (α-<small>L</small>-rhamnopyranosyl-(1→6))-β-<small>D</small>-glucopyranose). In the [[fava d'anta]] tree, the synthesis is done via a [[rutin synthase]] activity.<ref>{{cite journal|url=http://cat.inist.fr/?aModele=afficheN&cpsidt=21997861|title=Rutin synthase in fava d'anta: Purification and influence of stressors|author=Lucci|author2=Mazzafera|journal=Canadian journal of plant science|year=2009|volume=89|issue=5|pages=895–902|doi=10.4141/CJPS09001}}</ref>
<!--Mechanism of Action-->
|mechAction=<!--Structure-->
|structure=<!--Pharmacodynamics-->
|PD=There is limited information regarding <i>Pharmacodynamics</i> of {{PAGENAME}} in the drug label.


== Occurrences ==
<!--Pharmacokinetics-->
Rutin is one of the phenolic compounds found in the invasive plant species ''[[Carpobrotus edulis]]'' and contributes to the antibacterial<ref>Purification and identification of active antibacterial components in Carpobrotusedulis L. Elmarie van der Watt and Johan C Pretorius, Journal of Ethnopharmacology, Volume 76, Issue 1, June 2001, Pages 87–91, {{doi|10.1016/S0378-8741(01)00197-0}}</ref> and antioxidant<ref>Antioxidant and Antibacterial Properties of Mesembryanthemum crystallinum and Carpobrotus edulis Extracts. Bouftira Ibtissem, Chedly Abdelly and Souad Sfar, Advances in Chemical Engineering and Science, 2012, Vol. 2 No. 3, pages 359-365, {{doi|10.4236/aces.2012.23042}}</ref> properties of the plant.
|PK=There is limited information regarding <i>Pharmacokinetics</i> of {{PAGENAME}} in the drug label.


Its name comes from the name of ''[[Ruta graveolens]]'', a plant that also contains rutin.
<!--Nonclinical Toxicology-->
|nonClinToxic=There is limited information regarding <i>Nonclinical Toxicology</i> of {{PAGENAME}} in the drug label.


=== In food ===
<!--Clinical Studies-->
Rutin is a [[citrus]] [[flavonoid]] [[glycoside]] found in many plants including [[buckwheat]],<ref name="Kreft">{{cite journal
|clinicalStudies=There is limited information regarding <i>Clinical Studies</i> of {{PAGENAME}} in the drug label.
| author=Kreft S, Knapp M, Kreft I
| title=Extraction of rutin from buckwheat (''Fagopyrum esculentum Moench'') seeds and determination by capillary electrophoresis
| journal=J. Agric. Food Chem.
| volume=47
| issue=11
| pages=4649–52
| date=November 1999
| pmid=10552865
| doi=10.1021/jf990186p
}}</ref> the leaves and [[Petiole (botany)|petiole]]s of ''[[Rhubarb|Rheum]]'' species, and [[asparagus]].  [[Tartary buckwheat]] seeds have been found to contain more rutin (about 0.8-1.7% dry weight) than common buckwheat seeds (0.01% dry weight).<ref name="Kreft"/> Rutin is also found in the fruit of the [[Dimorphandra mollis|''fava d'anta'']] tree (from [[Brazil]]), fruits and flowers of the [[pagoda tree]], fruits and fruit rinds (especially the citrus fruits [[orange (fruit)|orange]], [[grapefruit]], [[lemon]], and [[Lime (fruit)|lime]]) and apple; berries such as [[mulberry]], [[ash tree]] fruits, [[aronia]] berries and [[Cranberry|cranberries]].<ref>[http://harvardmagazine.com/2012/09/curbing-clots ''Curbing Clots''], Sept, 2012</ref>


Rutin is one of the primary flavonols found in 'clingstone' [[peach]]es.<ref name=Chang>{{cite journal | pmid = 10691607 | doi = 10.1021/jf9904564 | year = 2000 | last1 = Chang | first1 = S | last2 = Tan | first2 = C | last3 = Frankel | first3 = EN | last4 = Barrett | first4 = DM | title = Low-density lipoprotein antioxidant activity of phenolic compounds and polyphenol oxidase activity in selected clingstone peach cultivars | volume = 48 | issue = 2 | pages = 147–51 | journal = Journal of agricultural and food chemistry}}</ref>
<!--How Supplied-->
|howSupplied=<!--Patient Counseling Information-->
|fdaPatientInfo=There is limited information regarding <i>Patient Counseling Information</i> of {{PAGENAME}} in the drug label.


== Chemical relatives ==
<!--Precautions with Alcohol-->
Rutin (quercetin rutinoside), like [[quercitrin]], is a glycoside of the [[flavonoid]] quercetin. As such, the chemical structures of both are very similar, with the difference existing in the [[hydroxyl]] functional group. Both quercetin and rutin are used in many countries as medications for [[blood vessel]] protection, and are ingredients of numerous multivitamin preparations and [[herbal remedy|herbal remedies]].
|alcohol=* Alcohol-{{PAGENAME}} interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.


==Role as ligand==
<!--Brand Names-->
It can combine with [[cations]],{{Which|date=June 2009}} supplying [[nutrient]]s from the [[soil]] to the cells in [[plant]]s.{{Citation needed|date=June 2009}} In humans, it attaches to the iron ion [[Iron|Fe]]<sup>2+</sup>, preventing it from binding to [[hydrogen peroxide]], which would otherwise create a highly reactive [[free radical]] that may damage cells. It is also an [[antioxidant]].
|brandNames=<!--Look-Alike Drug Names-->
|lookAlike=<!--Drug Shortage Status-->
|drugShortage=
}}
<!--Pill Image-->


Furthermore, it has been shown to inhibit ''[[in vitro]]'' the [[vascular endothelial growth factor]]<ref>{{cite journal|author=Luo|author2=et al.|title=Inhibition of Cell Growth and VEGF Expression in Ovarian Cancer Cells by Flavonoids|journal=Nutrition and Cancer|year=2008|volume=60|issue=6|pages=800–9|doi=10.1080/01635580802100851|pmid=19005980|last3=King|first3=Sarah M.|last4=Chen|first4=Yi Charlie}}</ref> in subtoxic concentrations, so acts as an inhibitor of [[angiogenesis]]. This finding may have potential relevance for the control of some [[cancer]]s.


==Health effects==
<!--Label Display Image-->
While a body of evidence for the effects of rutin and [[quercetin]] is available in mice,<ref>{{cite journal |author=Enkhmaa|author2= et al.|pmid=15795425|title=Mulberry (Morus alba L.) leaves and their major flavonol quercetin 3-(6-malonylglucoside) attenuate atherosclerotic lesion development in LDL receptor-deficient mice|journal=J Nutr|year=2005|volume=135|issue=4|pages=729–34|last3=Katsube|first3=T|last4=Kitajima|first4=K|last5=Anuurad|first5=E|last6=Yamasaki|first6=M|last7=Yamane|first7=Y}}</ref>
rats,<ref>{{cite journal |author=Santos|author2=et al.|title=HYPOLIPIDAEMIC EFFECTS OF NARINGENIN, RUTIN, NICOTINIC ACID AND THEIR ASSOCIATIONS|journal=Pharmacological Research|volume=40|issue=6|year=1999|pages=493–6|doi=10.1006/phrs.1999.0556|pmid=10660947|last3=Nagem|first3=TJ|last4=Pinto|first4=AS|last5=Oliveira|first5=MG}}</ref>
hamsters,<ref>{{cite journal |author=Auger|author2=et al.|title=Dietary wine phenolics catechin, quercetin, and resveratrol efficiently protect hypercholesterolemic hamsters against aortic fatty streak accumulation|journal=J Agric Food Chem.|year= 2005|volume=53|issue=6|pages=2015–21|pmid=15769129|doi=10.1021/jf048177q|last3=Gérain|first3=Peggy|last4=Lequeux|first4=Nadine|last5=Bornet|first5=Aurélie|last6=Serisier|first6=Samuel|last7=Besançon|first7=Pierre|last8=Caporiccio|first8=Bertrand|last9=Cristol|first9=Jean-Paul |first10=Jean-Max}}</ref>
and rabbits,<ref>{{cite journal |author=Juźwiak|author2=et al.|title=Effect of quercetin on experimental hyperlipidemia and atherosclerosis in rabbits|journal=Pharmacol Rep.|year=2005|volume=57|issue=5|pages=604–9|pmid=16227643|last3=Mokrzycki|first3=K|last4=Marchlewicz|first4=M|last5=Białecka|first5=M|last6=Wenda-Rózewicka|first6=L|last7=Gawrońska-Szklarz|first7=B|last8=Droździk|first8=M}}</ref>
as well as ''[[in vitro]]'' studies,<ref>{{cite journal|author=Shen|author2=et al.|title=In vitro and in vivo inhibitory activities of rutin, wogonin, and quercetin on lipopolysaccharide-induced nitric oxide and prostaglandin E2 production|journal=European Journal of Pharmacology|year=2002|volume=446|issue=1–3|pages=187–94|doi=10.1016/S0014-2999(02)01792-2|pmid=12098601|last3=Lin|first3=HY|last4=Huang|first4=HC|last5=Ko|first5=CH|last6=Yang|first6=LL|last7=Chen|first7=YC}}</ref>
no clinical studies directly demonstrate significant, positive effects of rutin as dietary supplement in humans.
 
*Rutin inhibits [[platelet]] aggregation,<ref>{{cite journal|author=Navarro-Núñez|author2=et al.|doi=10.1021/jf0723209|title=Apigenin Inhibits Platelet Adhesion and Thrombus Formation and Synergizes with Aspirin in the Suppression of the Arachidonic Acid Pathway|journal=J. Agric. Food Chem.|year=2008|volume=56|issue=9|pages=2970–6|last3=Palomo|first3=M.|last4=Martínez|first4=C.|last5=Vicente|first5=V.|last6=Castillo|first6=J.|last7=Benavente-García|first7=O.|last8=Diaz-Ricart|first8=M.|last9=Escolar|first9=G.|pmid=18410117|first10=J.}}</ref> as well as decreases capillary permeability, making the blood thinner and improving circulation.{{Citation needed|date=October 2010}}
*Rutin shows [[anti-inflammatory]] activity in some animal and ''in vitro'' models.<ref>{{cite journal|author=Guardia|author2=et al.|title=Anti-inflammatory properties of plant flavonoids. Effects of rutin, quercetin and hesperidin on adjuvant arthritis in rat|journal=Il Farmaco|volume=56|issue=9|year=2001|pages=683–7|doi=10.1016/S0014-827X(01)01111-9|pmid=11680812|last3=Juarez|first3=AO|last4=Pelzer|first4=LE}}</ref><ref>{{cite journal|author=Chan Hun Jung|author2=et al.|title=Anti-asthmatic action of quercetin and rutin in conscious guinea-pigs challenged with aerosolized ovalbumin|journal=Arch. Pharmacal Research|volume=30|issue=12|pages=1599–1607|url=http://www.springerlink.com/content/3265v57604507v87|doi=10.1007/BF02977330|year=2007|last3=Cho|first3=Chul Hyung|last4=Kim|first4=Chang Jong}}</ref>
*Rutin inhibits [[aldose reductase]] activity.<ref>{{cite journal|author=G. Bhanuprakash Reddy1,*, P. Muthenna1, C. Akileshwari1, Megha Saraswat1 and J. Mark Petrash2.|title=Inhibition of aldose reductase and sorbitol accumulation by dietary rutin|journal=Current Science|volume=101|issue=9|pages=1191–1197}}</ref> Aldose reductase is an enzyme normally present in the eye and elsewhere in the body. It helps change glucose into the sugar alcohol [[sorbitol]].
* Recent studies show rutin could help prevent [[blood clots]], so could be used to treat patients at risk of [[heart attacks]] and [[strokes]].<ref>{{cite news|last=Reporter|first=Daily Mail|title=Chemical found in apples, onions and green tea can help beat blood clots|url=http://www.dailymail.co.uk/health/article-2141602/Chemical-apples-onions-green-tea-help-beat-blood-clots.html|publisher=Mail Online|accessdate=11 May 2012|location=London|date=9 May 2012}}</ref>
*Some evidence also shows rutin can be used to treat [[hemorrhoids]], [[Varicose veins|varicosis]], and [[microangiopathy]].<ref name="naturalstandard">http://www.naturalstandard.com/index-abstract.asp?create-abstract=/monographs/herbssupplements/patient-rutin.asp</ref>
*Rutin increases thyroid iodide uptake in rats without raising serum T3 or T4.<ref>http://www.plosone.org/article/info%3Adoi%2F10.1371%2Fjournal.pone.0073908</ref>
* Rutin is also an antioxidant;<ref>{{cite journal | doi = 10.1080/15216549700202141 | title = Evidence for antiradical and antioxidant properties of four biologically active N,N-Diethylaminoethyl ethers of flavaone oximes: A comparison with natural polyphenolic flavonoid rutin action | year = 1997 | last1 = Metodiewa | first1 = Diana | last2 = Kochman | first2 = Agata | last3 = Karolczak | first3 = Stefan | journal = IUBMB Life | volume = 41 | issue = 5 | pages = 1067}}</ref> compared to quercetin, acacetin, morin, hispidulin, hesperidin, and naringin, it was found to be the strongest.<ref>http://www.diet-and-health.net/Supplements/Rutin.html</ref>{{verify credibility|date=October 2012}} However, in other trials, the effects of rutin were lower or negligible compared to those of [[quercetin]].<ref>{{cite journal | doi = 10.1002/mnfr.200900329 | title = Ingested quercetin but not rutin increases accumulation of hepatic β-carotene in BALB/c mice | year = 2010 | last1 = Bando | first1 = Noriko | last2 = Muraki | first2 = Naomi | last3 = Murota | first3 = Kaeko | last4 = Terao | first4 = Junji | last5 = Yamanishi | first5 = Rintaro | journal = Molecular Nutrition & Food Research | volume = 54 | pages = S261}}</ref><ref>{{cite journal | doi = 10.1016/j.bcp.2005.03.017 | title = Quercetin, but not rutin and quercitrin, prevention of H2O2-induced apoptosis via anti-oxidant activity and heme oxygenase 1 gene expression in macrophages | year = 2005 | last1 = Chow | first1 = Jyh-Ming | last2 = Shen | first2 = Shing-Chuan | last3 = Huan | first3 = Steven K. | last4 = Lin | first4 = Hui-Yi | last5 = Chen | first5 = Yen-Chou | journal = [[Biochemical Pharmacology]] | volume = 69 | issue = 12 | pages = 1839–51 | pmid = 15876423}}</ref>
[[Hydroxyethylrutoside]]s, synthetic hydroxyethyl acetylations of rutin, are used in the treatment of chronic venous insufficiency.
 
== In veterinary medicine ==
Rutin may have a [[veterinary]] use in the management of [[chylothorax]] in dogs and cats.<ref>{{Cite pmid |16187718}}</ref>
 
== Metabolism ==
The enzyme [[quercitrinase]] can be found in ''[[Aspergillus flavus]]''.<ref>[http://www.brenda-enzymes.org/php/result_flat.php4?ecno=3.2.1.66 ''quercitrinase'' on www.brenda-enzymes.org]</ref> It is an enzyme in the rutin catabolic pathway.<ref>{{cite journal | doi = 10.1007/s10532-010-9359-7 | title = The rutin catabolic pathway with special emphasis on quercetinase | year = 2010 | last1 = Tranchimand | first1 = Sylvain | last2 = Brouant | first2 = Pierre | last3 = Iacazio | first3 = Gilles | journal = Biodegradation | volume = 21 | issue = 6 | pages = 833–59 | pmid = 20419500}}</ref>
 
== References ==
{{reflist|2}}
 
{{Flavonol}}
{{Vasoprotectives}}
 
[[Category:Quercetin glycosides]]
[[Category:Flavonol rutinosides]]
[[Category:Flavonoid antioxidants]]
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{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Rutin''' <!-- replace if not identical with the article name -->
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Rutin.png|200px|Rutin]] <!-- replace if not identical with the pagename -->
|-
| [[IUPAC nomenclature|Systematic name]]
|  2-(3,4-dihydroxyphenyl)-<br>4,5-dihydroxy-3-[3,4,5-<br>trihydroxy-6-[(3,4,5-<br>trihydroxy-6-methyl-<br>oxan-2-yl)oxymethyl]<br>oxan-2-yl]oxy-chromen-<br>7-one
|-
| [[Chemical formula]]
| C<sub>27</sub>H<sub>30</sub>O<sub>16</sub>
|-
| [[Molecular mass]]
| 610.52 g/mol
|-
| [[Density]]
| x.xxx g/cm<sup>3</sup>
|-
| [[Melting point]]
| xx.x °C
|-
| [[Boiling point]]
| xx.x °C
|-
| [[CAS registry number|CAS number]]
| [153-18-4]
|-
| [[Simplified molecular input line entry specification|SMILES]]
| <small>xxxxx</small>
|-
| {{chembox header}} | <small>[[wikipedia:Chemical infobox|Disclaimer and references]]</small>
|-
|}
'''Rutin''', also called '''rutoside''', '''quercetin-3-rutinoside''' and '''sophorin''', is a [[citrus]] [[flavonoid]] [[glycoside]] found in [[buckwheat]], the leaves and petioles of ''[[Rhubarb|Rheum]]'' species,  and  the fruit of the [[Fava D'Anta]] tree (from [[Brazil]]), as well as other sources. Rutin is the glycoside between the [[flavonol]] [[quercetin]] and the [[disaccharide]] [[rutinose]].
 
It can combine with [[cations]], supplying [[nutrient]]s from the [[soil]] to the cells in [[plant]]s. In humans, it attaches to the iron ion [[Iron|Fe]]<sup>2+</sup>, preventing it from binding to [[hydrogen peroxide]] which would otherwise create a highly reactive [[free radical]] that may damage cells. It is also an [[antioxidant]], and therefore plays a role in inhibiting some [[cancer]]s.
 
Rutin also strengthens the [[capillary|capillaries]], and therefore can reduce the symptoms of [[haemophilia]]. It also may help to prevent a common unpleasant-looking venous [[edema]] of the legs. Rutin, as [[ferulic acid]], can reduce the cytotoxicity of oxidized [[LDL cholesterol]] and lower the risk of [[heart disease]].
 
 
 
 
==External links==


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[[Category:Flavonoids]]
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[[Category:Glycosides]]
[[Category:Cardiovascular Drugs]][[Category:Drugs]]
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{{Glycosides}}


[[de:Rutin]]
[[Category:Drug]]
[[he:רוטין]]
[[it:Rutina]]
[[ja:ルチン]]
[[pl:Rutyna]]
[[pt:Rutina]]
[[ru:Рутин]]
[[sk:Rutín]]

Latest revision as of 17:07, 20 August 2015

Rutin
Adult Indications & Dosage
Pediatric Indications & Dosage
Contraindications
Warnings & Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Administration & Monitoring
Overdosage
Pharmacology
Clinical Studies
How Supplied
Images
Patient Counseling Information
Precautions with Alcohol
Brand Names
Look-Alike Names

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Aparna Vuppala, M.B.B.S. [2]

Disclaimer

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NOTE: Most over the counter (OTC) are not reviewed and approved by the FDA. However, they may be marketed if they comply with applicable regulations and policies. FDA has not evaluated whether this product complies.

Overview

Rutin is a bioflavonoid that is FDA approved for the treatment of temporary relief of food and pollen sensitivities including rhinitis, sinusitis, nasal congestion, hay fever; impotence, lactose intolerance, and bladder infection.. Common adverse reactions include abdominal discomfort, palpitations, dizziness, headache, alopecia, tiredness, dry mouth, pruritus, leg edema, gastritis, vomiting, diarrhea, dyspepsia, skin rash, muscle stiffness.

Adult Indications and Dosage

FDA-Labeled Indications and Dosage (Adult)

Off-Label Use and Dosage (Adult)

Guideline-Supported Use

There is limited information regarding Off-Label Guideline-Supported Use of Rutin in adult patients.

Non–Guideline-Supported Use

There is limited information regarding Off-Label Non–Guideline-Supported Use of Rutin in adult patients.

Pediatric Indications and Dosage

FDA-Labeled Indications and Dosage (Pediatric)

There is limited information regarding FDA-Labeled Use of Rutin in pediatric patients.

Off-Label Use and Dosage (Pediatric)

Guideline-Supported Use

There is limited information regarding Off-Label Guideline-Supported Use of Rutin in pediatric patients.

Non–Guideline-Supported Use

There is limited information regarding Off-Label Non–Guideline-Supported Use of Rutin in pediatric patients.

Contraindications

There is limited information regarding Rutin Contraindications in the drug label.

Warnings

  • Keep out of reach of children. In case of overdose, contact physician or Poison Control Center right away.
  • If pregnant or breast-feeding, seek advice of a health professional before use.
  • Tamper seal: "Sealed for Your Protection." Do not use if seal is broken or missing.


Adverse Reactions

Clinical Trials Experience

There is limited information regarding Clinical Trial Experience of Rutin in the drug label.

Postmarketing Experience

There is limited information regarding Postmarketing Experience of Rutin in the drug label.

Drug Interactions

There is limited information regarding Rutin Drug Interactions in the drug label.

Use in Specific Populations

Pregnancy

Pregnancy Category (FDA): There is no FDA guidance on usage of Rutin in women who are pregnant.
Pregnancy Category (AUS): There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Rutin in women who are pregnant.

Labor and Delivery

There is no FDA guidance on use of Rutin during labor and delivery.

Nursing Mothers

There is no FDA guidance on the use of Rutin with respect to nursing mothers.

Pediatric Use

  • In case of overdose, contact physician or Poison Control Center right away.

Geriatic Use

There is no FDA guidance on the use of Rutin with respect to geriatric patients.

Gender

There is no FDA guidance on the use of Rutin with respect to specific gender populations.

Race

There is no FDA guidance on the use of Rutin with respect to specific racial populations.

Renal Impairment

There is no FDA guidance on the use of Rutin in patients with renal impairment.

Hepatic Impairment

There is no FDA guidance on the use of Rutin in patients with hepatic impairment.

Females of Reproductive Potential and Males

There is no FDA guidance on the use of Rutin in women of reproductive potentials and males.

Immunocompromised Patients

There is no FDA guidance one the use of Rutin in patients who are immunocompromised.

Administration and Monitoring

Administration

  • Oral
  • Intravenous

Monitoring

There is limited information regarding Monitoring of Rutin in the drug label.

IV Compatibility

There is limited information regarding IV Compatibility of Rutin in the drug label.

Overdosage

There is limited information regarding Chronic Overdose of Rutin in the drug label.

Pharmacology

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Template:Chembox header2 | Rutin
Identifiers
ChemSpider
DrugBank
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KEGG
UNII
Properties
C27H30O16
Molar mass 610.52 g·mol−1
Hazards
Template:Chembox header2 | Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Mechanism of Action

There is limited information regarding Rutin Mechanism of Action in the drug label.

Structure

There is limited information regarding Rutin Structure in the drug label.

Pharmacodynamics

There is limited information regarding Pharmacodynamics of Rutin in the drug label.

Pharmacokinetics

There is limited information regarding Pharmacokinetics of Rutin in the drug label.

Nonclinical Toxicology

There is limited information regarding Nonclinical Toxicology of Rutin in the drug label.

Clinical Studies

There is limited information regarding Clinical Studies of Rutin in the drug label.

How Supplied

There is limited information regarding Rutin How Supplied in the drug label.

Storage

There is limited information regarding Rutin Storage in the drug label.

Images

Drug Images

{{#ask: Page Name::Rutin |?Pill Name |?Drug Name |?Pill Ingred |?Pill Imprint |?Pill Dosage |?Pill Color |?Pill Shape |?Pill Size (mm) |?Pill Scoring |?NDC |?Drug Author |format=template |template=DrugPageImages |mainlabel=- |sort=Pill Name }}

Package and Label Display Panel

{{#ask: Label Page::Rutin |?Label Name |format=template |template=DrugLabelImages |mainlabel=- |sort=Label Page }}

Patient Counseling Information

There is limited information regarding Patient Counseling Information of Rutin in the drug label.

Precautions with Alcohol

  • Alcohol-Rutin interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.

Brand Names

There is limited information regarding Rutin Brand Names in the drug label.

Look-Alike Drug Names

There is limited information regarding Rutin Look-Alike Drug Names in the drug label.

Drug Shortage Status

Price

References

The contents of this FDA label are provided by the National Library of Medicine.

  1. ↑ Merck Index, 12th Edition, 8456
  2. ↑ Krewson, C. F.; Naghski, J. (2006). "Some physical properties of rutin". Journal of the American Pharmaceutical Association. 41 (11): 582–7. doi:10.1002/jps.3030411106. PMID 12999623.



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