RUTIN

US Previously Marketed

First marketed in 1921

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 Search

SMILES

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=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

Description
Sources: http://www.webmd.com/vitamins-supplements/ingredientmono-270-rutin.aspx
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Aldose reductase 45 Target ID: CHEMBL2622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12193020	Inhibitor 8504		13.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis 157 Sources: http://www.webmd.com/vitamins-supplements/ingredientmono-270-rutin.aspx?activeingredientid=270&	Primary	Approved 8583	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.
Postmastectomy lymphoedema of the arm 2 Sources: http://www.webmd.com/vitamins-supplements/ingredientmono-270-rutin.aspx?activeingredientid=270&	Primary	Approved 8583	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.
Open-angle glaucoma 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22731245	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
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
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

AUC

Value	Dose	Analyte	Population
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
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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
activator 150 supressor 22			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 725 OAT3 747 CYP1A1 132 CYP1B1 32 P-gp 1741 BCRP 910 OATP2B1 157 OATP1B3 961 OATP1B1 1079	P-gp 2052 MRP2 252 MRP3 58	CYP1A1 151

Drug as perpetrator

Target	Modality	Activity
CYP1A1 272	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/17177569/ \|https://pubmed.ncbi.nlm.nih.gov/27749250/	inconclusive
CYP1A1 272	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17177569/ \|https://pubmed.ncbi.nlm.nih.gov/16271822/	no
OAT1 730	inhibitor 4027 Sources: https://core.ac.uk/download/pdf/268419301.pdf	no
OAT3 749	inhibitor 4027 Sources: https://core.ac.uk/download/pdf/268419301.pdf	no
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22394605/	no
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22394605/	weak [IC50 111.5 uM]
OATP2B1 162	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/24285294/	yes [EC50 2.32 uM]
CYP1B1 93	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16271822/	yes [IC50 27 uM]
OATP2B1 162	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25858254/	yes [IC50 60.7 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/28752532/ \| https://pubmed.ncbi.nlm.nih.gov/27216424/	yes [IC50 7.2 uM]
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/28752532/	yes
CYP3A4 2633	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/21466223/	yes
CYP3A4 2633	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/27749250/	yes
OATP1B1 1095	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/16081670/	yes
P-gp 1932	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/21466223/	yes

Drug as victim

Target	Modality	Activity
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24198722/	yes
MRP3 58	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24198722/	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24198722/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/15710766/

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B1-00046	http://www.3bsc.com/index/pro_info.php?id=20258
3B Scientific (Wuhan) Corp	3B2-0489	http://www.3bsc.com/index/pro_info.php?id=19845
AA Blocks	AA00HY0Q	https://www.aablocks.com/goods/Goods/detail?id=AA00HY0Q
Aaron Chemicals	AR00HYSI	http://www.aaronchem.com/153-18-4
abcr GmbH	AB401423	http://www.abcr.com/shop/en/AB401423
AbMole Bioscience	M3894	http://www.abmole.com/products/rutin.html
Achemo Scientific Limited	AC-16750	http://www.achemo.com/search/?Keyword= 153-18-4
Achemtek	0104-056448	http://www.achemtek.com/153-18-4
Acorn PharmaTech	ACN-035502	http://www.acornpharmatech.com/
Acros Organics	AC132390050	https://www.fishersci.com/shop/products/rutin-97-acros-organics/AC132390050
Acros Organics	AC132391000	https://www.fishersci.com/shop/products/rutin-97-acros-organics/AC132391000
Acros Organics	AC132395000	https://www.fishersci.com/shop/products/rutin-97-acros-organics/AC132395000
Adooq BioScience	A10815	https://www.adooq.com/rutin-rutoside.html
AHH Chemical co.,ltd	API-1467	http://www.ahhchemical.com/product/API-1467.html
AHH Chemical co.,ltd	MT-00022	http://www.ahhchemical.com/product/MT-00022.html
AHH Chemical co.,ltd	NP-0725	http://www.ahhchemical.com/product/NP-0725.html
AK Scientific, Inc. (AKSCI)	J10274	http://www.aksci.com/item_detail.php?cat=J10274
Allbio Pharm Co., Ltd	AD09741	http://www.allbiopharm.com/product/n/AD09741
Ambinter	Amb20243158	http://www.ambinter.com/reference/20243158
Angene	AGN-PC-0Q6IJL	http://www.angenechemical.com/productshow/AGN-PC-0Q6IJL.html
Aurora Fine Chemicals LLC	K04.629.876	http://online.aurorafinechemicals.com/info?ID=K04.629.876
AvaChem Scientific	3345	http://www.avachem.com/productSearch.asp?3345
Avantor Inc	101096-102	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101096-102
BenchChem	B542089	https://www.benchchem.com/product/b542089
BioSynth	Q-201691	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-201691.html
BLD Pharm	BD32066	http://www.bldpharm.com/products/153-18-4.html
Chem Scene	CS-5573	http://www.chemscene.com/153-18-4.html
ChemFaces	CFN99642	http://www.chemfaces.com/natural/Rutin-CFN99642.html
ChemMol	49426787	http://www.chemmol.com/chemmol/49426787.html
ChemProbes	Fla-A2	https://chemprobes.com/products/fla-a2
ChemProbes	Libr-A3-Fla-A2	https://chemprobes.com/products/libr-a3
Chemspace	CSSB00016992675	https://chem-space.com/CSSB00016992675
CSNpharm	CSN16175	https://www.csnpharm.com/products/rutin.html
DC Chemicals	DCL-001	http://www.dcchemicals.com//product_show-Rutin.html
eNovation Chemicals	D379048	http://www.enovationchem.com/productDetails.asp?productID=D379048
Hairui	QUSA01001	http://www.hairuichem.com/en/product/153-18-4.html
iChemical	EBD1328144	http://www.ichemical.com/products/153-18-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00195157	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00195157
mcule	MCULE-7397273315	https://mcule.com/MCULE-7397273315/
MedChem Express	HY-N0148	https://www.medchemexpress.com/Rutin.html
MuseChem	I001916	https://www.musechem.com/product/I001916.html
Oakwood	99508	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=164762&ExtHyperLink=1
R&D Chemicals	1139	http://www.rdchemicals.com/chemicals.php?mode=details&mol_id=8213
Shanghai Tauto Biotech Co., Ltd	E-0124	http://www.tautobiotech.com/BRM/eProductShow.asp?ArticleID=166
Smolecule	S542089	http://www.smolecule.com/products/s542089
TCI (Tokyo Chemical Industry)	R0035	http://www.tcichemicals.com/eshop/en/us/commodity/R0035/index.html
THE BioTek	bt-280611	https://www.thebiotek.com/product/inhibitors/bt-280611
VladaChem	VL264874-100G	https://www.vladachem.com/product.php?products=153-18-4

PubMed

Title	Date	PubMed
Flavonoids suppress human glioblastoma cell growth by inhibiting cell metabolism, migration, and by regulating extracellular matrix proteins and metalloproteinases expression.	2015-12-05	26408079
Synthesis, characterization and biological evaluation of Rutin-zinc(II) flavonoid -metal complex.	2015-09-05	26091902
Rutin ameliorates cyclophosphamide induced oxidative stress and inflammation in Wistar rats: role of NFκB/MAPK pathway.	2015-04-25	25753322
Dietary flavonoids fisetin and myricetin: dual inhibitors of Plasmodium falciparum falcipain-2 and plasmepsin II.	2014-04	24468190
Effects of resveratrol and other wine polyphenols on the proliferation, apoptosis and androgen receptor expression in LNCaP cells.	2014-02-10	24726691
Toxicity of thienopyridines on human neutrophil granulocytes and lymphocytes.	2013-06-07	23499857
Bioactivity-guided fractionation of Phyllanthus orbicularis and identification of the principal anti HSV-2 compounds.	2012-10	22318977
Toxicity of clopidogrel and ticlopidine on human myeloid progenitor cells: importance of metabolites.	2012-09-28	22651985
Antiplasmodial activity of flavonol quercetin and its analogues in Plasmodium falciparum: evidence from clinical isolates in Bangladesh and standardized parasite clones.	2012-06	22215188
Plant polyphenols regulate chemokine expression and tissue repair in human keratinocytes through interaction with cytoplasmic and nuclear components of epidermal growth factor receptor system.	2012-02-15	21967610
Differential protective effects of quercetin, resveratrol, rutin and epigallocatechin gallate against mitochondrial dysfunction induced by indomethacin in Caco-2 cells.	2012-02-05	22214982
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.	2011-12-15	21872416
Plant polyphenols differentially modulate inflammatory responses of human keratinocytes by interfering with activation of transcription factors NFκB and AhR and EGFR-ERK pathway.	2011-09-01	21756928
Rutin attenuates cisplatin induced renal inflammation and apoptosis by reducing NFκB, TNF-α and caspase-3 expression in wistar rats.	2011-09	21605616
Phenolic compounds from Achillea millefolium L. and their bioactivity.	2011	21503279
Structural relationship and binding mechanisms of five flavonoids with bovine serum albumin.	2010-12-09	21150826
Gastroprotective effect of rutin against indomethacin-induced ulcers in rats.	2010-09	20374237
Bifenthrin-induced oxidative stress in human erythrocytes in vitro and protective effect of selected flavonols.	2010-03	19833193
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.	2010-02-12	20015448
Naturally occurring flavonoids attenuate high glucose-induced expression of proinflammatory cytokines in human monocytic THP-1 cells.	2009-08	19557821
Flavonoids inhibit histamine release and expression of proinflammatory cytokines in mast cells.	2008-10	18958421
Flavonoids as inhibitors of human carbonyl reductase 1.	2008-07-30	18579125
Protective effect of rutin, a polyphenolic flavonoid against haloperidol-induced orofacial dyskinesia and associated behavioural, biochemical and neurochemical changes.	2007-10	17868205
In vitro anti-HIV and -HSV activity and safety of sodium rutin sulfate as a microbicide candidate.	2007-09	17459492
In silico prediction of pregnane X receptor activators by machine learning approaches.	2007-01	17003167
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Comparative studies of some phenolic compounds (quercetin, rutin, and ferulic acid) affecting hepatic fatty acid synthesis in mice.	2006-10-18	17032037
Antiparasitic activity of flavonoids and isoflavones against Cryptosporidium parvum and Encephalitozoon intestinalis.	2006-06	16684116
Influence of quercetin and rutin on growth and antioxidant defense system of a human hepatoma cell line (HepG2).	2006-02	15782287
Inhibition of human cytochrome CYP 1 enzymes by flavonoids of St. John's wort.	2006-01-16	16271822
Antitubercular sterols from Thalia multiflora Horkel ex Koernicke.	2005-10	16261518
[Effect of polyphenols from the Mediterranean diet on proliferation and mediators of in vitro invasiveness of the MB-49 murine bladder cancer cell line].	2005-09	16304905
Differential inhibition of oxidized LDL-induced apoptosis in human endothelial cells treated with different flavonoids.	2005-05	15975156
Dietary rutin, but not its aglycone quercetin, ameliorates dextran sulfate sodium-induced experimental colitis in mice: attenuation of pro-inflammatory gene expression.	2005-02-01	15652231
Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids.	2005-01-17	15598565
Inhibitory effect of quercetin on carrageenan-induced inflammation in rats.	2003-12-26	14654164
Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans.	2003-06	12771321
Search of antimicrobial activity of selected non-antibiotic drugs.	2003-04-03	12669766
Flavonoids and nitric oxide synthase.	2002-12	12512693
A pharmacophore for human pregnane X receptor ligands.	2002-01	11744617
Flavonoids as phospholipase A2 inhibitors: importance of their structure for selective inhibition of group II phospholipase A2.	1997-06	9246576
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.	1994-08-03	7520698
Flavones are inhibitors of HIV-1 proteinase.	1992-10-30	1445308
Antimicrobial constituents of Gomphrena martiana and Gomphrena boliviana.	1992-04	1608273
[Conservative management of lymphedema of the limbs].	1991-08-04	1866167
Differential inhibitory effects of various flavonoids on the activities of reverse transcriptase and cellular DNA and RNA polymerases.	1990-07-05	1695572
Effect of benzopyrone derivatives on drug activity and metabolism.	1986-10-01	3582421
Inhibitory effect of the flavonoid O-(beta-hydroxyethyl)-rutoside on increased microvascular permeability induced by various agents in rat skin.	1983	6088413
Effect of o-(beta-hydroxyethyl)-rutoside in lymphangiography.	1977-02	401613
Metabolism of hydroxyethylrutosides (HR): metabolism of [14C]-HR in man.	1976	989368

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Name

Type

Language

RUTIN

Official Name

English

RUTOSIDE

Preferred 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

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

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)