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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H30O16
Molecular Weight 610.5186
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RUTIN

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

InChI

InChIKey=IKGXIBQEEMLURG-NVPNHPEKSA-N
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

HIDE SMILES / InChI

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 benzopyrone derivatives on drug activity and metabolism.
1986 Oct-Dec
[Conservative management of lymphedema of the limbs].
1991 Aug 4
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
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
Inhibitory activity of flavonoids and tannins against HIV-1 protease.
2000 Sep
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
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
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
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
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
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
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
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 Fri Jun 25 21:46:24 UTC 2021
Edited
by admin
on Fri Jun 25 21:46:24 UTC 2021
Record UNII
5G06TVY3R7
Record Status Validated (UNII)
Record Version
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Name Type Language
RUTIN
DSC   INCI   MI   USP-RS   VANDF  
INCI  
Official Name English
OSYRITRIN
Common Name English
GLOBULARIACITRIN
Common Name English
ILIXANTHIN
Common Name English
RUTIN [MI]
Common Name English
MYRTICOLORIN
Common Name English
YUNXIANGGAN
Common Name English
RUTIN (QUERCETIN-3-O-RUTINOSIDE) (CONSTITUENT OF GINKGO) [DSC]
Common Name English
RUTIN [INCI]
Common Name English
QUERCETIN 3-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOPYRANOSIDE
Systematic Name English
TANRUTIN
Common Name English
QUERCETIN 3-RUTINOSIDE
Common Name English
RUTOSIDE [WHO-DD]
Common Name English
RUTIN (QUERCETIN-3-O-RUTINOSIDE) (CONSTITUENT OF HAWTHORN LEAF WITH FLOWER) [DSC]
Common Name English
VIOLAQUERCETRIN
Common Name English
NOVARRUTINA
Common Name English
RUTIN [DSC]
Common Name English
RUTOSIDE
INN   WHO-DD  
INN  
Official Name English
C.I. 75730
Code English
2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4H-CHROMEN-4-ONE-3-YL 6-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOSIDE
Common Name English
NSC-9220
Code English
RUTOSIDE [INN]
Common Name English
PALIUROSIDE
Common Name English
RUTIN [VANDF]
Common Name English
QUERCETIN-3-O-RUTINOSIDE
Common Name English
BIRUTAN
Common Name English
SOPHORIN
Common Name English
3-RHAMNOGLUCOSIDE OF 5,7,3',4'-TETRAHYDROXYFLAVONOL
Common Name English
RUTIN [USP-RS]
Common Name English
Classification Tree Code System Code
DSLD 120 (Number of products:1322)
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
WHO-ATC C05CA01
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
WHO-VATC QC05CA01
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
DSLD 1394 (Number of products:104)
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
WHO-VATC QC05CA51
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
WHO-ATC C05CA51
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
NCI_THESAURUS C792
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
Code System Code Type Description
WIKIPEDIA
RUTIN
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
USP_CATALOG
1606503
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
3535
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
CAS
153-18-4
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-814-1
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
ChEMBL
CHEMBL226335
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
PUBCHEM
5280805
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
EVMPD
SUB10407MIG
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
INN
2213
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
MESH
D012431
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
EPA CompTox
153-18-4
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
MERCK INDEX
M9708
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY Merck Index
FDA UNII
5G06TVY3R7
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
DRUG BANK
DB01698
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
NCI_THESAURUS
C819
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY
RXCUI
9500
Created by admin on Fri Jun 25 21:46:24 UTC 2021 , Edited by admin on Fri Jun 25 21:46:24 UTC 2021
PRIMARY RxNorm
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER flavonoid
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
METABOLITE -> PARENT
IN-VIVO
URINE
METABOLITE -> PARENT
Quantity of quercetin-3-glucuronide in urine of six healthy human subjects 0-24hr (total) after consumption of tomato juice containing 176 micromoles of rutin; Unit: nmoles
IN-VIVO
URINE
METABOLITE -> PARENT
Cmax: 4.3 +/- 1.5 nM; Tmax: 5.4 +/- 0.2 hr; T1/2: 6.9 +/- 0.3 hr (n=6)
IN-VIVO
PLASMA
METABOLITE -> PARENT
IN-VIVO
PLASMA; URINE
METABOLITE -> PARENT
IN-VIVO
URINE
METABOLITE -> PARENT
Quantity of Isorhamnetin-3-glucuronide in urine of six healthy human subjects 0-24hr (total) after consumption of tomato juice containing 176 micromoles of rutin; Unit: nmoles
IN-VIVO
URINE
METABOLITE -> PARENT
Cmax: 12 +/- 2 nM; Tmax: 4.7 +/- 0.3 hr; T1/2: 5.7 +/- 0.6 hr (n=6)
IN-VIVO
PLASMA
METABOLITE -> PARENT
IN-VIVO
URINE
METABOLITE -> PARENT
Excretion of 3-Hydroxyphenylacetic acid in the urine of human subjects (n=6, 0-24hr total) after rutin (176 micromoles) supplemented tomato juice; Unit: micromoles
IN-VIVO
URINE
METABOLITE -> PARENT
Quantity of Quercetin-4'-glucuronide in urine of five healthy human subjects 0-24hr (total) after consumption of tomato juice containing 176 micromoles of rutin; Unit: nmoles
IN-VIVO
URINE
METABOLITE -> PARENT
IN-VIVO
URINE
METABOLITE -> PARENT
Excretion of 3,4-Dihydroxyphenylacetic acid in the urine of human subjects (n=6, 0-24hr total) after rutin (176 micromoles) supplemented tomato juice; Unit: micromoles
IN-VIVO
URINE
METABOLITE -> PARENT
IN-VIVO
PLASMA; URINE
METABOLITE -> PARENT
Excretion of 3-Methoxy-4-Hydroxyphenylacetic acid in the urine of human subjects (n=6, 0-24hr total) after rutin (176 micromoles) supplemented tomato juice; Unit: micromoles
IN-VIVO
URINE
METABOLITE -> PARENT
IN-VIVO
URINE
METABOLITE -> PARENT
IN-VIVO
PLASMA; URINE
METABOLITE -> PARENT
IN-VIVO
PLASMA; URINE
METABOLITE -> PARENT
Quantity of Quercetin-3'-glucuronide in urine of six healthy human subjects 0-24hr (total) after consumption of tomato juice containing 176 micromoles of rutin; Unit: nmoles
IN-VIVO
URINE
Related Record Type Details
IMPURITY -> PARENT
NMT 2%
USP
IMPURITY -> PARENT
USP
IMPURITY -> PARENT
NMT 2%
USP
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ACTIVE MOIETY