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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H30O16.3H2O
Molecular Weight 664.5644
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RUTOSIDE TRIHYDRATE

SMILES

C[C@@]1([H])[C@@]([H])([C@]([H])([C@]([H])([C@]([H])(OC[C@]2([H])[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])(O2)Oc3c(=O)c4c(cc(cc4oc3-c5ccc(c(c5)O)O)O)O)O)O)O)O1)O)O)O.O.O.O

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

HIDE SMILES / InChI

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

Molecular Formula C27H30O16
Molecular Weight 610.5186
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Originator

Curator's Comment:: Rutin was first isolated in 1842 by GFerman chemist AUgust Weiss from garden ruc, Ruta graveolens

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
13.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PHLOGENZYM

Approved Use

Taking 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 Use

Swelling 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 Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
89.9 μg/L
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
1017 μg × h/L
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
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
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

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Metabolism of hydroxyethylrutosides (HR): metabolism of [14C]-HR in man.
1976
Effect of o-(beta-hydroxyethyl)-rutoside in lymphangiography.
1977 Feb
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
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.
1994 Aug 3
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
Inhibitory effect of quercetin on carrageenan-induced inflammation in rats.
2003 Dec 26
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
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
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
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
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
Flavonoids suppress human glioblastoma cell growth by inhibiting cell metabolism, migration, and by regulating extracellular matrix proteins and metalloproteinases expression.
2015 Dec 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 Fri Jun 25 21:13:41 UTC 2021
Edited
by admin
on Fri Jun 25 21:13:41 UTC 2021
Record UNII
RF4N03853G
Record Status Validated (UNII)
Record Version
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Name Type Language
RUTOSIDE TRIHYDRATE
EP   WHO-DD  
Common Name English
RUTIN TRIHYDRATE
Common Name English
4H-1-BENZOPYRAN-4-ONE, 3-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-, TRIHYDRATE
Common Name English
RUTOSIDE TRIHYDRATE [WHO-DD]
Common Name English
RUTIN HYDRATE
JAN  
Common Name English
RUTIN HYDRATE [JAN]
Common Name English
RUTOSIDE TRIHYDRATE [EP MONOGRAPH]
Common Name English
Code System Code Type Description
EVMPD
SUB30642
Created by admin on Fri Jun 25 21:13:41 UTC 2021 , Edited by admin on Fri Jun 25 21:13:41 UTC 2021
PRIMARY
PUBCHEM
16218542
Created by admin on Fri Jun 25 21:13:41 UTC 2021 , Edited by admin on Fri Jun 25 21:13:41 UTC 2021
PRIMARY
CAS
250249-75-3
Created by admin on Fri Jun 25 21:13:41 UTC 2021 , Edited by admin on Fri Jun 25 21:13:41 UTC 2021
PRIMARY
EPA CompTox
250249-75-3
Created by admin on Fri Jun 25 21:13:41 UTC 2021 , Edited by admin on Fri Jun 25 21:13:41 UTC 2021
PRIMARY
FDA UNII
RF4N03853G
Created by admin on Fri Jun 25 21:13:41 UTC 2021 , Edited by admin on Fri Jun 25 21:13:41 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY