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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H30O16
Molecular Weight 610.5175
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RUTIN

SMILES

[H][C@@]5(OC[C@H]1O[C@@H](OC2=C(OC3=C(C2=O)C(O)=CC(O)=C3)C4=CC=C(O)C(O)=C4)[C@H](O)[C@@H](O)[C@@H]1O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O

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 610.5175
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
Inhibitory effect of the flavonoid O-(beta-hydroxyethyl)-rutoside on increased microvascular permeability induced by various agents in rat skin.
1983
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
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
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
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
[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 inhibit histamine release and expression of proinflammatory cytokines in mast cells.
2008 Oct
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
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
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 Dec 15 15:02:14 GMT 2023
Edited
by admin
on Fri Dec 15 15:02:14 GMT 2023
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
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
Rutoside [WHO-DD]
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 Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
WHO-ATC C05CA01
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
WHO-VATC QC05CA01
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
DSLD 1394 (Number of products:104)
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
WHO-VATC QC05CA51
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
WHO-ATC C05CA51
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
NCI_THESAURUS C792
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
Code System Code Type Description
WIKIPEDIA
RUTIN
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
CHEBI
28527
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
SMS_ID
100000090310
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
DRUG CENTRAL
3535
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
CAS
153-18-4
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
DAILYMED
5G06TVY3R7
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-814-1
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
CHEBI
61606
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
RS_ITEM_NUM
1606503
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL226335
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
PUBCHEM
5280805
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
EVMPD
SUB10407MIG
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
INN
2213
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
MESH
D012431
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID3022326
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
MERCK INDEX
m9708
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY Merck Index
FDA UNII
5G06TVY3R7
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
CHEBI
4055
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
DRUG BANK
DB01698
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
NCI_THESAURUS
C819
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
RXCUI
9500
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY RxNorm
NSC
9220
Created by admin on Fri Dec 15 15:02:14 GMT 2023 , Edited by admin on Fri Dec 15 15:02:14 GMT 2023
PRIMARY
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
SOLVATE->ANHYDROUS
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
Related Record Type Details
ACTIVE MOIETY