QUERCETIN

US Previously Marketed

First approved in 1953

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O7
Molecular Weight	302.2357
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C3=CC=C(O)C(O)=C3

InChI

InChIKey=REFJWTPEDVJJIY-UHFFFAOYSA-N

InChI=1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H

HIDE SMILES / InChI

Description
Sources: http://www.akspublication.com/paper05_jul-dec2007.htm | https://www.drugbank.ca/drugs/DB04216

Quercetin is a unique bioflavonoid that has been extensively studied by researchers over the past 30 years. Quercetin, the most abundant of the flavonoids (the name comes from the Latin –quercetum, meaning oak forest, quercus oak) consists of 3 rings and 5 hydroxyl groups. Quercetin is a member of the class of flavonoids called flavonoles and forms the backbone for many other flavonoids including the citrus flavonoids like rutin, hesperidins, Naringenin and tangeritin. It is widely distributed in the plant kingdom in rinds and barks. The best described property of Quercetin is its ability to act as antioxidant. Quercetin seems to be the most powerful flavonoids for protecting the body against reactive oxygen species, produced during the normal oxygen metabolism or are induced by exogenous damage [9, 10]. One of the most important mechanisms and the sequence of events by which free radicals interfere with the cellular functions seem to be the lipid peroxidation leading eventually the cell death. To protect this cellular death to happen from reactive oxygen species, living organisms have developed antioxidant line of defense systems [11]. These include enzymatic and non-enzymatic antioxidants that keep in check ROS/RNS level and repair oxidative cellular damage. The major enzymes, constituting the first line of defence, directly involved in the neutralization of ROS/RNS are: superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GPx) The second line of defence is represented by radical scavenging antioxidants such as vitamin C, vitamin A and plant phytochemicals including quercetin that inhibit the oxidation chain initiation and prevent chain propagation. This may also include the termination of a chain by the reaction of two radicals. The repair and de novo enzymes act as the third line of defence by repairing damage and reconstituting membranes. These include lipases, proteases, DNA repair enzymes and transferases. Quercetin is a specific quinone reductase 2 (QR2) inhibitor, an enzyme (along with the human QR1 homolog) which catalyzes metabolism of toxic quinolines. Inhibition of QR2 in plasmodium may potentially cause lethal oxidative stress. The inhibition of antioxidant activity in plasmodium may contribute to killing the malaria causing parasites.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
transformed cell apoptotic process 104 Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28528183	Activator 1447
reactive oxygen species metabolic process 68 Target ID: GO:0072593 Sources: http://www.akspublication.com/paper05_jul-dec2007.htm \| https://www.ncbi.nlm.nih.gov/pubmed/28431473	Modulator 846
Hyaluronidase-1 2 Target ID: CHEMBL4528 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28433637	Inhibitor 8504
Tyrosinase 41 Target ID: CHEMBL1973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28273864	Inhibitor 8504	14.29 nM [IC50]
Phospholipase A2 9 Target ID: Phospholipase A2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28256049	Inhibitor 8504	1.36 µM [IC50]
Estrogen receptor beta 113 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17724002	Agonist 2752	113.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Acute mountain sickness 5 Sources: https://clinicaltrials.gov/ct2/show/NCT02463357	Primary	Phase III 665	Unknown Approved Use Unknown
Thromboembolism 8 Sources: http://adisinsight.springer.com/drugs/800001680	Primary	Phase III 665	Unknown Approved Use Unknown
Chronic obstructive pulmonary disease 175 Sources: http://adisinsight.springer.com/drugs/800001680	Primary	Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
500 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9816216/	630 mg/m² single, intravenous dose: 630 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		QUERCETIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2077 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9816216/	630 mg/m² single, intravenous dose: 630 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		QUERCETIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
47 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9816216/	630 mg/m² single, intravenous dose: 630 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		QUERCETIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252		inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP1 116 CYP1A2 2153 CYP2C19 2057 CYP2E1 1060 CYP2C8 1057 P-gp 1741 BCRP 910 OATP1B1 1079	P-gp 2052 UGT 219 sulfotransferases 39 UGT1A1/3/8 2	CYP1A1 151 CYP1A2 832 CYP2B1 26 MRP1 74 UGT1A6 34 MRP2 146

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C19 2141	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5822518/	moderate [IC50 11.6 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5822518/	moderate to strong [IC50 5.5 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/	modest [Ki 10.1 uM]
CYP1A2 2333	inducer 1966 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2984105/	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5822518/	not significant [IC50 104 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5822518/	not significant [IC50 151 uM]	no (pharmacogenomic study) Comment: drug inhibits caffeine metabolism, which is unrelated to CYP1A21C and 1F gene polymorphisms (https://www.hindawi.com/journals/bmri/2014/405071/) Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5822518/
CYP2D6 2546	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5822518/	potent [IC50 0.65 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3403202/	yes [IC50 15.9 uM]	weak (co-administration study) Comment: AUC increase of 24%, Cmax increase of 31% Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3403202/
BCRP 985	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7285070/	yes [IC50 4.22 uM]	yes (co-administration study) Comment: 1.8-fold increase in AUC8h and 1.5 fold increase in Cmax Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7285070/
P-gp 1932	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263194/	yes [IC50 8 uM]
MRP1 232	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11306701/	yes [IC50 8.1 uM]
CYP1A1 272	inducer 1966 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1220303/	yes
CYP2B1 41	inducer 1966 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2984105/	yes
CYP3A4 2633	inducer 1966 Sources: https://dmd.aspetjournals.org/content/31/5/533.short	yes
MRP1 232	inducer 1966 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0300483X01005704	yes
UGT1A6 171	inducer 1966 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295299003664	yes
MRP2 625	inducer 1966 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295299003664	yes	no (co-administration study) Comment: 133% induction at 50 uM of drug; see https://www.sciencedirect.com/science/article/pii/S1818087618305154#bib0013 for in vivo study Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295299003664
CYP1A2 2333	supressor 160 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1440-1681.2009.05158.x Page: 5.0	yes	weak (co-administration study) Comment: decreased enzyme activity by 10.4% Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1440-1681.2009.05158.x Page: 5.0
CYP2A6 911	activator 342 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1440-1681.2009.05158.x Page: 1.0	yes	weak (co-administration study) Comment: increased enzyme activity by 25.3% Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1440-1681.2009.05158.x Page: 1.0

Drug as victim

Target	Modality	Activity
P-gp 2052	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263194/	no
UGT 219	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/10.1111/1541-4337.12342	yes
UGT1A1/3/8 2	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/10.1111/1541-4337.12342	yes
sulfotransferases 39	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/10.1111/1541-4337.12342	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	NO16427	https://www.001chemical.com/chem/6151-25-3
3B Scientific (Wuhan) Corp	3B1-00047	http://www.3bsc.com/index/pro_info.php?id=20259
3B Scientific (Wuhan) Corp	3B2-0468	http://www.3bsc.com/index/pro_info.php?id=19824
AA Blocks	AA0036WO	http://www.aablocks.com/goods/Goods/detail?id=AA0036WO
Aaron Chemicals	AR0037OG	http://www.aaronchem.com/6151-25-3
abcr GmbH	AB121197	http://www.abcr.de/shop/en/AB121197
Accela ChemBio Inc	SY061661	http://www.accelachem.com/cn/search.html?keyword=SY061661&attname=GoodsCode
Achemica	ACMC-20a8z6	http://www.achemica.com/prodinfo/?id=136987
Achemo Scientific Limited	AC-16751	http://www.achemo.com/search/?Keyword= 6151-25-3
Acorn PharmaTech	ACN-040191	http://www.acornpharmatech.com/
Adooq BioScience	A10765	https://www.adooq.com/quercetin-dihydrate-sophoretin.html
Adooq BioScience	Quercetin dihydrate - Sophoretin	http://www.adooq.com/quercetin-dihydrate-sophoretin.html
AHH Chemical co.,ltd	API-1446	http://www.ahhchemical.com/product/API-1446.html
AHH Chemical co.,ltd	MT-01104	http://www.ahhchemical.com/product/MT-01104.html
AK Scientific, Inc. (AKSCI)	H655	http://www.aksci.com/item_detail.php?cat=H655
AK Scientific, Inc. (AKSCI)	J10072	http://www.aksci.com/item_detail.php?cat=J10072
Alfa Aesar	A15807	https://www.alfa.com/en/catalog/A15807/
Alfa Chemistry	AP6151253-A	https://reagents.alfa-chemistry.com/product/quercetin-dihydrate-cas-6151-25-3-14090.html
Alfa Chemistry	AP6151253-B	https://reagents.alfa-chemistry.com/product/quercetin-cas-6151-25-3-14091.html
Ambeed	A114540	https://www.ambeed.com/products/6151-25-3.html
Ambinter	Amb18511406	http://www.ambinter.com/reference/18511406
Angene	AGN-PC-0T0NDG	http://www.angenechemical.com/productshow/AGN-PC-0T0NDG.html
Anward	ANW-62560	http://www.anward.com/pro_result/49011
Ark Pharm	AK101905	http://www.arkpharminc.com/products/6151-25-3.html
Aurora Fine Chemicals LLC	K02.121.655	http://online.aurorafinechemicals.com/info?ID=K02.121.655
Avantor Inc	200007-556	https://us.vwr.com/store/product/18599802/quercetin-hydrate-95
Avantor Inc	200026-652	https://us.vwr.com/store/product/18599802/quercetin-hydrate-95
Avantor Inc	BT212870-100G	https://us.vwr.com/store/product/16901776/quercetin-dihydrate-97
Avantor Inc	BT212870-25G	https://us.vwr.com/store/product/16901776/quercetin-dihydrate-97
Avantor Inc	BT212870-500G	https://us.vwr.com/store/product/16901776/quercetin-dihydrate-97
BioChemPartner	BCP07318	http://www.biochempartner.com/6151-25-3-BCP07318
BioCrick	BCN2967	http://www.biocrick.com/Quercetin-Dihydrate-BCN2967.html
Biopurify Phytochemicals	BP1190	http://www.phytopurify.com/QuercetinDihydrate-p-5253.html
BLD Pharm	BD233444	http://www.bldpharm.com/products/6151-25-3.html
BOC Sciences	6151-25-3	https://www.bocsci.com/quercetin-dihydrate-cas-6151-25-3-item-465575.html
Calbiochem	551600	http://www.emdbiosciences.com/product/551600
Capot Chemical	19976	http://www.capotchem.com/en/19976.htm
Capot Chemical	PubChem19976	http://www.capotchem.com/en/19976.htm
Chem Scene	CS-0007880	http://www.chemscene.com/6151-25-3.html
ChemBridge	5117235	http://www.hit2lead.com/search.asp?db=SC&ids=5117235
ChemFaces	CFN90931	http://www.chemfaces.com/natural/Quercetin-Dihydrate-CFN90931.html
ChemMol	99132522	http://www.chemmol.com/chemmol/99132522.html
ChemShuttle	151644	http://www.chemshuttle.com/catalogsearch/result/?q=6151-25-3&cat=
Chemspace	CSSB00016989917	https://chem-space.com/CSSB00016989917
Clearsynth	CS-O-11728	https://www.clearsynth.com/en/CSO11728.html
CSNpharm	CSN13129	https://www.csnpharm.com/products/quercetin-dihydrate.html
DC Chemicals	DCAPI1284	http://www.dcchemicals.com/product_show-Quercetin dihydrate (Sophoretin).html
EMD Millipore	551600	http://www.emdbiosciences.com/product/551600
eNovation Chemicals	D388597	http://www.enovationchem.com/productDetails.asp?productID=D388597
eNovation Chemicals	D605029	https://www.enovationchem.com/ProductDetails.asp?ProductID=D605029
eNovation Chemicals	D670826	https://www.enovationchem.com/ProductDetails.asp?ProductID=D670826
eNovation Chemicals	D954461	https://www.enovationchem.com/ProductDetails.asp?ProductID=D954461
Finetech	FT-0601606	http://www.finetechnology-ind.com/prod/detail/pub/6151-25-3.html
Glentham Life Sciences	GP1387	http://www.glentham.com/products/product/GP1387/
Hello Bio	HB0543	https://www.hellobio.com/quercetin-dihydrate.html
iChemical	EBD49345	http://www.ichemical.com/products/6151-25-3.html
Lab Network	LN00193657	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00193657
LGC Standards	MM0109.03	https://www.lgcstandards.com/US/en/p/MM0109.03
Matrix Scientific	95141	https://www.matrixscientific.com/095141.html
MedChem Express	HY-N0146	https://www.medchemexpress.com/quercetin-dihydrate.html
Molcore	CS16427	https://www.molcore.com/product/6151-25-3
MolMall	20746	http://www.molmall.net/product/20746
MolPort	MolPort-002-131-742	https://www.molport.com/shop/molecule-link/MolPort-002-131-742
MuseChem	R053790	https://www.musechem.com/product/R053790.html
Oakwood	3435	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=1442&ExtHyperLink=1
Selleck Chemicals	S2347	http://www.selleckchem.com/products/Quercetin-dihydrate(Sophoretin).html
Smolecule	S540825	http://www.smolecule.com/products/s540825
THE BioTek	bt-281208	https://www.thebiotek.com/product/inhibitors/bt-281208
VladaChem	VL144103	https://www.vladachem.com/product.php?products=6151-25-3

PubMed

Title	Date	PubMed
Heat-shock protein-73 protects against small intestinal warm ischemia-reperfusion injury in the rat.	1999 Apr	10216529
A search for anti-viral properties in Panamanian medicinal plants. The effects on HIV and its essential enzymes.	1999 Jan	10075118
A new concept of tumor promotion by tumor necrosis factor-alpha, and cancer preventive agents (-)-epigallocatechin gallate and green tea--a review.	2000	10757128
Effects of luteolin, quercetin and baicalein on immunoglobulin E-mediated mediator release from human cultured mast cells.	2000 Apr	10718847
Effects of daily oral administration of quercetin chalcone and modified citrus pectin on implanted colon-25 tumor growth in Balb-c mice.	2000 Dec	11134977
Oxidative stress involvement in chemically induced differentiation of K562 cells.	2000 Jan 1	10656287
Differential effects of flavonoid compounds on tumor promoter-induced activation of the human CYP1A2 enhancer.	2000 Jan 1	10620351
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.	2000 Jul-Aug	10953322
Upstream regulatory elements in chick heme oxygenase-1 promoter: a study in primary cultures of chick embryo liver cells.	2000 Jun	10942197
Differential estrogen receptor binding of estrogenic substances: a species comparison.	2000 Nov 15	11162928
Anti-apoptotic effect of quercetin: intervention in the JNK- and ERK-mediated apoptotic pathways.	2000 Sep	10972672
Influence of quercetin on B16 melanotic melanoma growth in C57BL/6 mice and on activity of some acid hydrolases in melanoma tissue.	2001	11327532
Constituents of Afzelia bella stem bark.	2001 Apr	11324912
Kaempferide triglycoside: a possible factor of resistance of carnation (Dianthus caryophyllus) to Fusarium oxysporum f. sp. dianthi.	2001 Apr	11314958
Evaluation of polyphenolic and flavonoid compounds in honeybee-collected pollen produced in Spain.	2001 Apr	11308335
Ca2+-induced contraction of cat esophageal circular smooth muscle cells.	2001 Apr	11245615
Pre-clinical and clinical study of QC12, a water-soluble, pro-drug of quercetin.	2001 Feb	11300332
Polyphyenolics increase t-PA and u-PA gene transcription in cultured human endothelial cells.	2001 Feb	11236827
Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: glutathione oxidation and conjugation.	2001 Feb 15	11182292
Pharmacological interventions of cyanide-induced cytotoxicity and DNA damage in isolated rat thymocytes and their protective efficacy in vivo.	2001 Feb 3	11275422
LC coupled to ion-trap MS for the rapid screening and detection of polyphenol antioxidants from Helichrysum stoechas.	2001 Jan	11199231
Studies on the effects of lactate transport inhibition, pyruvate, glucose and glutamine on amino acid, lactate and glucose release from the ischemic rat cerebral cortex.	2001 Jan	11145998
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.	2001 Jan 22	11165023

Patents

Sample Use Guides

In Vivo Use Guide

COPD Subjects will be asked to avoid quercetin rich diet for one week and then asked to take one of the following for 1 week Quercetin 500 mg/350 mg of vitamin C and 10 mg niacin Quercetin 1000 mg/350 mg of vitamin C and 10 mg niacin Quercetin 2000 mg/350 mg of vitamin C and 10 mg niacin

Route of Administration: Oral

In Vitro Use Guide

DCs, exposed to 25uM quercetin, activate a pattern of genes that increase extracellular iron export, resulting in an overall decrease in the intracellular iron content and consequent diminished inflammatory abilities.

Name

Type

Language

CORVITIN

Preferred Name

English

QUERCETIN

Official Name

English

FLAVONE, 3,3',4',5,7-PENTAHYDROXY-

Common Name

English

Quercetin [WHO-DD]

Common Name

English

3'-HYDROXYKAEMPFEROL

Common Name

English

LDN-0052529

Code

English

3,3',4',5,7-PENTAHYDROXYFLAVONE

Systematic Name

English

KORVITIN

Brand Name

English

QUERCETIN (CONSTITUENT OF HAWTHORN LEAF WITH FLOWER) [DSC]

Common Name

English

QUERCETIN (CONSTITUENT OF GINKGO) [DSC]

Common Name

English

MELETIN

Common Name

English

QUERTINE

Common Name

English

2-(3,4-DIHYDROXYPHENYL)-3,5,7-TRIHYDROXY-4H-BENZOPYRAN-4-ONE

Systematic Name

English

4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-3,5,7-TRIHYDROXY-

Systematic Name

English

CYANIDELONON 1522

Systematic Name

English

LIPOFLAVON

Common Name

English

QUERCETINE

Common Name

English

FLAVONE, 3,4',5,5',7-PENTAHYDROXY-

Systematic Name

English

QUERCETIN [IARC]

Common Name

English

2-(3,4-DIHYDROXYPHENYL)-3,5,7-TRIHYDROXY-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

SOPHORETIN

Common Name

English

C.I. 75670

Common Name

English

CI-75670

Common Name

English

XANTHAURINE

Common Name

English

QUERTIN

Common Name

English

3,5,7-TRIHYDROXY-2-(3,4-DIHYDROXYPHENYL)-4H-CHROMEN-4-ONE

Systematic Name

English

QUERCETIN [HSDB]

Common Name

English

QUERCETOL

Common Name

English

NSC-9219

Code

English

QUERCETIN [USP-RS]

Common Name

English

3,5,7,3',4'-PENTAHYDROXYFLAVONE

Systematic Name

English

QUERCETIN [VANDF]

Common Name

English

QUERCETIN [MI]

Common Name

English

QUERCETIN [DSC]

Common Name

English

NSC-57655

Code

English

CYANIDENOLON 1522

Brand Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

664018