Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H30O16.3H2O |
| Molecular Weight | 664.5633 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C3=O)C(O)=CC(O)=C4)C5=CC=C(O)C(O)=C5)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
InChI
InChIKey=NLLBWFFSGHKUSY-JPRRWYCFSA-N
InChI=1S/C27H30O16.3H2O/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;3*1H2/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-;;;/m0.../s1
DescriptionCurator's Comment: http://phenol-explorer.eu/contents/polyphenol/296 | https://www.ncbi.nlm.nih.gov/pubmed/22731245
Curator's Comment: http://phenol-explorer.eu/contents/polyphenol/296 | https://www.ncbi.nlm.nih.gov/pubmed/22731245
Rutin, also called rutoside, is the glycoside flavonoid found in a certain fruits and vegetables. Most rutine-rich foods are capers, olives, buckwheat (whole grain flour), asparagus, raspberry.In a clinical trial, rutin was found to aid control of intraocular pressure in patients with primary open angle glaucoma. As a component of dietary supplement Phlogenzym, rutin is used for treatment of osteoarthritis. Rutin is also used for treatment of post-surgical swelling of the arm after breast cancer surgery. Traditionally, rutin is used to prevent mucositis due to cancer treatment, to treat blood vessel disease such as varicose veins, bleeding, hemorrhoids.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2622 |
13.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | PHLOGENZYM Approved UseTaking rutin by mouth in combination with trypsin and bromelain seems to be about as effective as the medication diclofenac (Voltaren) in relieving pain and improving knee function in people with osteoarthritis. |
|||
| Primary | WOBENZYM Approved UseSwelling in the arm after breast surgery (post-surgical lymphedema). Some early research suggests that taking a specific product (Wobenzym) containing rutin, pancreatin, papain, trypsin, and chymotrypsin daily for 7 weeks reduces swelling in the arm due to breast removal surgery. |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
89.9 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11151743/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUERCETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
23.5 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11151743/ |
16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUERCETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
47.6 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11151743/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUERCETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1017 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11151743/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUERCETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
381 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11151743/ |
16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUERCETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
636 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11151743/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUERCETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| inconclusive | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| weak [IC50 111.5 uM] | ||||
| yes [EC50 2.32 uM] | ||||
| yes [IC50 27 uM] | ||||
| yes [IC50 60.7 uM] | ||||
| yes [IC50 7.2 uM] | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Metabolism of hydroxyethylrutosides (HR): metabolism of [14C]-HR in man. | 1976 |
|
| Effect of o-(beta-hydroxyethyl)-rutoside in lymphangiography. | 1977 Feb |
|
| Inhibitory effect of the flavonoid O-(beta-hydroxyethyl)-rutoside on increased microvascular permeability induced by various agents in rat skin. | 1983 |
|
| Effect of benzopyrone derivatives on drug activity and metabolism. | 1986 Oct-Dec |
|
| [Conservative management of lymphedema of the limbs]. | 1991 Aug 4 |
|
| Antimicrobial constituents of Gomphrena martiana and Gomphrena boliviana. | 1992 Apr |
|
| Flavones are inhibitors of HIV-1 proteinase. | 1992 Oct 30 |
|
| Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds. | 1994 Aug 3 |
|
| Flavonoids as phospholipase A2 inhibitors: importance of their structure for selective inhibition of group II phospholipase A2. | 1997 Jun |
|
| Identification and quantification of flavonoids in human urine samples by column-switching liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry. | 2000 Apr 1 |
|
| Inhibitory activity of flavonoids and tannins against HIV-1 protease. | 2000 Sep |
|
| Inhibition of nitric oxide synthase inhibitors and lipopolysaccharide induced inducible NOS and cyclooxygenase-2 gene expressions by rutin, quercetin, and quercetin pentaacetate in RAW 264.7 macrophages. | 2001 |
|
| Characterization of enzymes participating in carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human placenta. | 2001 Jan 30 |
|
| Flavonoids and nitric oxide synthase. | 2002 Dec |
|
| A pharmacophore for human pregnane X receptor ligands. | 2002 Jan |
|
| Search of antimicrobial activity of selected non-antibiotic drugs. | 2002 Nov-Dec |
|
| Inhibitory effect of quercetin on carrageenan-induced inflammation in rats. | 2003 Dec 26 |
|
| Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. | 2003 Jun |
|
| Dietary rutin, but not its aglycone quercetin, ameliorates dextran sulfate sodium-induced experimental colitis in mice: attenuation of pro-inflammatory gene expression. | 2005 Feb 1 |
|
| Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids. | 2005 Jan 17 |
|
| Antitubercular sterols from Thalia multiflora Horkel ex Koernicke. | 2005 Oct |
|
| Influence of quercetin and rutin on growth and antioxidant defense system of a human hepatoma cell line (HepG2). | 2006 Feb |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
| Comparative studies of some phenolic compounds (quercetin, rutin, and ferulic acid) affecting hepatic fatty acid synthesis in mice. | 2006 Oct 18 |
|
| In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
|
| In vitro anti-HIV and -HSV activity and safety of sodium rutin sulfate as a microbicide candidate. | 2007 Sep |
|
| Flavonoids as inhibitors of human carbonyl reductase 1. | 2008 Jul 30 |
|
| Naturally occurring flavonoids attenuate high glucose-induced expression of proinflammatory cytokines in human monocytic THP-1 cells. | 2009 Aug |
|
| Structural relationship and binding mechanisms of five flavonoids with bovine serum albumin. | 2010 Dec 9 |
|
| Vitamin E and rutin synergistically inhibit expression of vascular endothelial growth factor through down-regulation of binding activity of activator protein-1 in human promyelocytic leukemia (HL-60) cells. | 2010 Feb 12 |
|
| Bifenthrin-induced oxidative stress in human erythrocytes in vitro and protective effect of selected flavonols. | 2010 Mar |
|
| Gastroprotective effect of rutin against indomethacin-induced ulcers in rats. | 2010 Sep |
|
| Rutin attenuates cisplatin induced renal inflammation and apoptosis by reducing NFκB, TNF-α and caspase-3 expression in wistar rats. | 2011 Sep |
|
| Plant polyphenols differentially modulate inflammatory responses of human keratinocytes by interfering with activation of transcription factors NFκB and AhR and EGFR-ERK pathway. | 2011 Sep 1 |
|
| Antiplasmodial activity of flavonol quercetin and its analogues in Plasmodium falciparum: evidence from clinical isolates in Bangladesh and standardized parasite clones. | 2012 Jun |
|
| Bioactivity-guided fractionation of Phyllanthus orbicularis and identification of the principal anti HSV-2 compounds. | 2012 Oct |
|
| Toxicity of clopidogrel and ticlopidine on human myeloid progenitor cells: importance of metabolites. | 2012 Sep 28 |
|
| Effects of resveratrol and other wine polyphenols on the proliferation, apoptosis and androgen receptor expression in LNCaP cells. | 2014 Jul-Aug |
|
| Rutin ameliorates cyclophosphamide induced oxidative stress and inflammation in Wistar rats: role of NFκB/MAPK pathway. | 2015 Apr 25 |
|
| Flavonoids suppress human glioblastoma cell growth by inhibiting cell metabolism, migration, and by regulating extracellular matrix proteins and metalloproteinases expression. | 2015 Dec 5 |
|
| Synthesis, characterization and biological evaluation of Rutin-zinc(II) flavonoid -metal complex. | 2015 Sep 5 |
Patents
Sample Use Guides
As a dietary supplement and natural nutrient, rutin is administered orally. For osteoarthritis: 2 tablets of a combination product (Phlogenzym), which contains 100 mg of rutin, 48 mg of trypsin, and 90 mg of bromelain, 3 times daily.
Route of Administration:
Oral
Inhibition of aldose reductase from rat lens homogenate was measured using DL-glyceraldehyde as a substrate. The reaction was initiated by addition of NADPH at 30°C. After 30 min the reaction was stopped, and 10mM imidazole was added to convert NADP to a fluorescent product. IC50 for rutin was 13 uM.
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SUB30642
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16218542
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250249-75-3
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DTXSID50179735
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RF4N03853G
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100000115324
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ACTIVE MOIETY
SUBSTANCE RECORD
