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

[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
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 44 Target ID: CHEMBL2622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12193020	Inhibitor 8297		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 8429	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 8429	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 51 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22731245	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	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	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
activator 80 supressor 21			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 599 OAT3 642 CYP1A1 110 CYP1B1 19 P-gp 1461 BCRP 699 OATP2B1 123 OATP1B3 706 OATP1B1 788	P-gp 1537 MRP2 205 MRP3 50	CYP1A1 108

Drug as perpetrator

Target	Modality	Activity
CYP1A1 218	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/17177569/ \|https://pubmed.ncbi.nlm.nih.gov/27749250/	inconclusive
CYP1A1 218	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17177569/ \|https://pubmed.ncbi.nlm.nih.gov/16271822/	no
OAT1 603	inhibitor 3277 Sources: https://core.ac.uk/download/pdf/268419301.pdf	no
OAT3 644	inhibitor 3277 Sources: https://core.ac.uk/download/pdf/268419301.pdf	no
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22394605/	no
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22394605/	weak [IC50 111.5 uM]
OATP2B1 126	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/24285294/	yes [EC50 2.32 uM]
CYP1B1 67	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16271822/	yes [IC50 27 uM]
OATP2B1 126	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25858254/	yes [IC50 60.7 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28752532/ \| https://pubmed.ncbi.nlm.nih.gov/27216424/	yes [IC50 7.2 uM]
BCRP 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28752532/	yes
CYP3A4 1925	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/21466223/	yes
CYP3A4 1925	supressor 155 Sources: https://pubmed.ncbi.nlm.nih.gov/27749250/	yes
OATP1B1 803	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/16081670/	yes
P-gp 1650	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/21466223/	yes

Drug as victim

Target	Modality	Activity
MRP2 205	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/24198722/	yes
MRP3 50	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/24198722/	yes
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/24198722/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/15710766/

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0489	http://www.3bsc.com/index/pro_info.php?id=19845
3B Scientific (Wuhan) Corp	3B1-00046	http://www.3bsc.com/index/pro_info.php?id=20258
AA Blocks	AA00HY0Q	https://www.aablocks.com/goods/Goods/detail?id=AA00HY0Q
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
Aaron Chemicals	AR00HYSI	http://www.aaronchem.com/153-18-4
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
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
BLD Pharm	BD32066	http://www.bldpharm.com/products/153-18-4.html
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
CSNpharm	CSN16175	https://www.csnpharm.com/products/rutin.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
DC Chemicals	DCL-001	http://www.dcchemicals.com//product_show-Rutin.html
Hairui	QUSA01001	http://www.hairuichem.com/en/product/153-18-4.html
Lab Network	LN00195157	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00195157
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
abcr GmbH	AB401423	http://www.abcr.com/shop/en/AB401423
eNovation Chemicals	D379048	http://www.enovationchem.com/productDetails.asp?productID=D379048
iChemical	EBD1328144	http://www.ichemical.com/products/153-18-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-7397273315	https://mcule.com/MCULE-7397273315/

PubMed

Title	Date	PubMed
Metabolism of hydroxyethylrutosides (HR): metabolism of [14C]-HR in man.	1976	989368
Effect of o-(beta-hydroxyethyl)-rutoside in lymphangiography.	1977 Feb	401613
Inhibitory effect of the flavonoid O-(beta-hydroxyethyl)-rutoside on increased microvascular permeability induced by various agents in rat skin.	1983	6088413
Effect of benzopyrone derivatives on drug activity and metabolism.	1986 Oct-Dec	3582421
[Conservative management of lymphedema of the limbs].	1991 Aug 4	1866167
Antimicrobial constituents of Gomphrena martiana and Gomphrena boliviana.	1992 Apr	1608273
Flavones are inhibitors of HIV-1 proteinase.	1992 Oct 30	1445308
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.	1994 Aug 3	7520698
Flavonoids as phospholipase A2 inhibitors: importance of their structure for selective inhibition of group II phospholipase A2.	1997 Jun	9246576
Identification and quantification of flavonoids in human urine samples by column-switching liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry.	2000 Apr 1	10763246
Steroid hormone activity of flavonoids and related compounds.	2000 Jul	10989984
Inhibitory activity of flavonoids and tannins against HIV-1 protease.	2000 Sep	10993207
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	11500931
Characterization of enzymes participating in carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human placenta.	2001 Jan 30	11306090
Flavonoids and nitric oxide synthase.	2002 Dec	12512693
A pharmacophore for human pregnane X receptor ligands.	2002 Jan	11744617
Search of antimicrobial activity of selected non-antibiotic drugs.	2002 Nov-Dec	12669766
Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans.	2003 Jun	12771321
Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids.	2005 Jan 17	15598565
Differential inhibition of oxidized LDL-induced apoptosis in human endothelial cells treated with different flavonoids.	2005 May	15975156
Antitubercular sterols from Thalia multiflora Horkel ex Koernicke.	2005 Oct	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 Sep	16304905
Inhibition of human cytochrome CYP 1 enzymes by flavonoids of St. John's wort.	2006 Jan 16	16271822
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Flavonoids inhibit histamine release and expression of proinflammatory cytokines in mast cells.	2008 Oct	18958421
Naturally occurring flavonoids attenuate high glucose-induced expression of proinflammatory cytokines in human monocytic THP-1 cells.	2009 Aug	19557821
Structural relationship and binding mechanisms of five flavonoids with bovine serum albumin.	2010 Dec 9	21150826
Bifenthrin-induced oxidative stress in human erythrocytes in vitro and protective effect of selected flavonols.	2010 Mar	19833193
Gastroprotective effect of rutin against indomethacin-induced ulcers in rats.	2010 Sep	20374237
Phenolic compounds from Achillea millefolium L. and their bioactivity.	2011	21503279
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.	2011 Dec 15	21872416
Rutin attenuates cisplatin induced renal inflammation and apoptosis by reducing NFκB, TNF-α and caspase-3 expression in wistar rats.	2011 Sep	21605616
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	21756928
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	21967610
Differential protective effects of quercetin, resveratrol, rutin and epigallocatechin gallate against mitochondrial dysfunction induced by indomethacin in Caco-2 cells.	2012 Feb 5	22214982
Antiplasmodial activity of flavonol quercetin and its analogues in Plasmodium falciparum: evidence from clinical isolates in Bangladesh and standardized parasite clones.	2012 Jun	22215188
Bioactivity-guided fractionation of Phyllanthus orbicularis and identification of the principal anti HSV-2 compounds.	2012 Oct	22318977
Toxicity of clopidogrel and ticlopidine on human myeloid progenitor cells: importance of metabolites.	2012 Sep 28	22651985
Toxicity of thienopyridines on human neutrophil granulocytes and lymphocytes.	2013 Jun 7	23499857
Dietary flavonoids fisetin and myricetin: dual inhibitors of Plasmodium falciparum falcipain-2 and plasmepsin II.	2014 Apr	24468190
Effects of resveratrol and other wine polyphenols on the proliferation, apoptosis and androgen receptor expression in LNCaP cells.	2014 Jul-Aug	24726691
Rutin ameliorates cyclophosphamide induced oxidative stress and inflammation in Wistar rats: role of NFκB/MAPK pathway.	2015 Apr 25	25753322
Flavonoids suppress human glioblastoma cell growth by inhibiting cell metabolism, migration, and by regulating extracellular matrix proteins and metalloproteinases expression.	2015 Dec 5	26408079
Synthesis, characterization and biological evaluation of Rutin-zinc(II) flavonoid -metal complex.	2015 Sep 5	26091902

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.

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

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

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)