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
| Molecular Formula | C27H30O16 |
| Molecular Weight | 610.5175 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|
| Differential inhibitory effects of various flavonoids on the activities of reverse transcriptase and cellular DNA and RNA polymerases. | 1990 Jul 5 |
|
| [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 |
|
| 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 |
|
| Differential inhibition of oxidized LDL-induced apoptosis in human endothelial cells treated with different flavonoids. | 2005 May |
|
| Antitubercular sterols from Thalia multiflora Horkel ex Koernicke. | 2005 Oct |
|
| [Effect of polyphenols from the Mediterranean diet on proliferation and mediators of in vitro invasiveness of the MB-49 murine bladder cancer cell line]. | 2005 Sep |
|
| Influence of quercetin and rutin on growth and antioxidant defense system of a human hepatoma cell line (HepG2). | 2006 Feb |
|
| Inhibition of human cytochrome CYP 1 enzymes by flavonoids of St. John's wort. | 2006 Jan 16 |
|
| Antiparasitic activity of flavonoids and isoflavones against Cryptosporidium parvum and Encephalitozoon intestinalis. | 2006 Jun |
|
| 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 |
|
| Protective effect of rutin, a polyphenolic flavonoid against haloperidol-induced orofacial dyskinesia and associated behavioural, biochemical and neurochemical changes. | 2007 Oct |
|
| 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 |
|
| Flavonoids inhibit histamine release and expression of proinflammatory cytokines in mast cells. | 2008 Oct |
|
| 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 |
|
| Phenolic compounds from Achillea millefolium L. and their bioactivity. | 2011 |
|
| Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation. | 2011 Dec 15 |
|
| 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 |
|
| Plant polyphenols regulate chemokine expression and tissue repair in human keratinocytes through interaction with cytoplasmic and nuclear components of epidermal growth factor receptor system. | 2012 Feb 15 |
|
| Differential protective effects of quercetin, resveratrol, rutin and epigallocatechin gallate against mitochondrial dysfunction induced by indomethacin in Caco-2 cells. | 2012 Feb 5 |
|
| 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 |
|
| Toxicity of thienopyridines on human neutrophil granulocytes and lymphocytes. | 2013 Jun 7 |
|
| Dietary flavonoids fisetin and myricetin: dual inhibitors of Plasmodium falciparum falcipain-2 and plasmepsin II. | 2014 Apr |
|
| 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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:58:36 GMT 2023
by
admin
on
Fri Dec 15 18:58:36 GMT 2023
|
| Record UNII |
RF4N03853G
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
SUB30642
Created by
admin on Fri Dec 15 18:58:36 GMT 2023 , Edited by admin on Fri Dec 15 18:58:36 GMT 2023
|
PRIMARY | |||
|
16218542
Created by
admin on Fri Dec 15 18:58:36 GMT 2023 , Edited by admin on Fri Dec 15 18:58:36 GMT 2023
|
PRIMARY | |||
|
250249-75-3
Created by
admin on Fri Dec 15 18:58:36 GMT 2023 , Edited by admin on Fri Dec 15 18:58:36 GMT 2023
|
PRIMARY | |||
|
DTXSID50179735
Created by
admin on Fri Dec 15 18:58:36 GMT 2023 , Edited by admin on Fri Dec 15 18:58:36 GMT 2023
|
PRIMARY | |||
|
RF4N03853G
Created by
admin on Fri Dec 15 18:58:36 GMT 2023 , Edited by admin on Fri Dec 15 18:58:36 GMT 2023
|
PRIMARY | |||
|
100000115324
Created by
admin on Fri Dec 15 18:58:36 GMT 2023 , Edited by admin on Fri Dec 15 18:58:36 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE | |||
|
ANHYDROUS->SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |