QUERCETIN DIHYDRATE

US Previously Marketed

First approved in 1953

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O7.2H2O
Molecular Weight	338.2663
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O.OC1=CC(O)=C2C(=O)C(O)=C(OC2=C1)C3=CC(O)=C(O)C=C3

InChI

InChIKey=GMGIWEZSKCNYSW-UHFFFAOYSA-N

InChI=1S/C15H10O7.2H2O/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;2*1H2

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 106 Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28528183	Activator 1404
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 817
Hyaluronidase-1 2 Target ID: CHEMBL4528 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28433637	Inhibitor 8146
Tyrosinase 41 Target ID: CHEMBL1973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28273864	Inhibitor 8146	14.29 nM [IC50]
Target ID: Phospholipase A2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28256049	Inhibitor 8146	1.36 µM [IC50]
Estrogen receptor beta 110 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17724002	Agonist 2637	113.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Acute mountain sickness 5 Sources: https://clinicaltrials.gov/ct2/show/NCT02463357	Primary	Phase III 651	Unknown Approved Use Unknown
Thromboembolism 8 Sources: http://adisinsight.springer.com/drugs/800001680	Primary	Phase III 651	Unknown Approved Use Unknown
Chronic obstructive pulmonary disease 171 Sources: http://adisinsight.springer.com/drugs/800001680	Primary	Phase I 422	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 753 inhibitor 1532		inhibitor 1789

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP1 106 CYP1A2 1463 CYP2C19 1410 CYP2E1 846 CYP2C8 869 P-gp 1401 BCRP 678 OATP1B1 770	P-gp 1491 UGT 183 sulfotransferases 35 UGT1A1/3/8 2	CYP1A1 103 CYP1A2 671 CYP2B1 24 MRP1 47 UGT1A6 33 MRP2 108

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C19 1484	inhibitor 3185 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5822518/	moderate [IC50 11.6 uM]
CYP3A4 1857	inhibitor 3185 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5822518/	moderate to strong [IC50 5.5 uM]
CYP2C8 923	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/	modest [Ki 10.1 uM]
CYP1A2 1620	inducer 1515 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2984105/	no
CYP2E1 929	inhibitor 3185 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5822518/	not significant [IC50 104 uM]
CYP1A2 1620	inhibitor 3185 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 1826	inhibitor 3185 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5822518/	potent [IC50 0.65 uM]
OATP1B1 785	inhibitor 3185 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 751	inhibitor 3185 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 1588	inhibitor 3185 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263194/	yes [IC50 8 uM]
MRP1 170	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11306701/	yes [IC50 8.1 uM]
CYP1A1 206	inducer 1515 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1220303/	yes
CYP2B1 39	inducer 1515 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2984105/	yes
CYP3A4 1857	inducer 1515 Sources: https://dmd.aspetjournals.org/content/31/5/533.short	yes
MRP1 170	inducer 1515 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0300483X01005704	yes
UGT1A6 139	inducer 1515 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295299003664	yes
MRP2 452	inducer 1515 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 1620	supressor 149 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 702	activator 208 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 1491	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263194/	no
UGT 183	substrate 3264 Sources: https://onlinelibrary.wiley.com/doi/10.1111/1541-4337.12342	yes
UGT1A1/3/8 2	substrate 3264 Sources: https://onlinelibrary.wiley.com/doi/10.1111/1541-4337.12342	yes
sulfotransferases 35	substrate 3264 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	3B2-0468	http://www.3bsc.com/index/pro_info.php?id=19824
3B Scientific (Wuhan) Corp	3B1-00047	http://www.3bsc.com/index/pro_info.php?id=20259
AA Blocks	AA0036WO	http://www.aablocks.com/goods/Goods/detail?id=AA0036WO
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
Aaron Chemicals	AR0037OG	http://www.aaronchem.com/6151-25-3
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	Quercetin dihydrate - Sophoretin	http://www.adooq.com/quercetin-dihydrate-sophoretin.html
Adooq BioScience	A10765	https://www.adooq.com/quercetin-dihydrate-sophoretin.html
Alfa Aesar	A15807	https://www.alfa.com/en/catalog/A15807/
Alfa Chemistry	AP6151253-B	https://reagents.alfa-chemistry.com/product/quercetin-cas-6151-25-3-14091.html
Alfa Chemistry	AP6151253-A	https://reagents.alfa-chemistry.com/product/quercetin-dihydrate-cas-6151-25-3-14090.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	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
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
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
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
CSNpharm	CSN13129	https://www.csnpharm.com/products/quercetin-dihydrate.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
DC Chemicals	DCAPI1284	http://www.dcchemicals.com/product_show-Quercetin dihydrate (Sophoretin).html
EMD Millipore	551600	http://www.emdbiosciences.com/product/551600
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
LGC Standards	MM0109.03	https://www.lgcstandards.com/US/en/p/MM0109.03
Lab Network	LN00193657	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00193657
Matrix Scientific	95141	https://www.matrixscientific.com/095141.html
MedChem Express	HY-N0146	https://www.medchemexpress.com/quercetin-dihydrate.html
MolMall	20746	http://www.molmall.net/product/20746
MolPort	MolPort-002-131-742	https://www.molport.com/shop/molecule-link/MolPort-002-131-742
Molcore	CS16427	https://www.molcore.com/product/6151-25-3
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
abcr GmbH	AB121197	http://www.abcr.de/shop/en/AB121197
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
iChemical	EBD49345	http://www.ichemical.com/products/6151-25-3.html

PubMed

Title	Date	PubMed
Heat-shock protein-73 protects against small intestinal warm ischemia-reperfusion injury in the rat.	1999 Apr	10216529
Modulation of apoptotic and inflammatory genes by bioflavonoids and angiotensin II inhibition in ureteral obstruction.	2000 Aug 1	10925121
Oxidative stress involvement in chemically induced differentiation of K562 cells.	2000 Jan 1	10656287
Effects of genistein and structurally related phytoestrogens on cell cycle kinetics and apoptosis in MDA-MB-468 human breast cancer cells.	2000 Jan-Feb	10601582
Suppression by flavonoids of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells: structure-activity relationship.	2000 Jul	10920275
The effect of mycophenolate mofetil and polyphenolic bioflavonoids on renal ischemia reperfusion injury and repair.	2000 Mar	10688038
Suppression of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells by chemopreventive agents with a resorcin-type structure.	2000 May	10783318
Differential estrogen receptor binding of estrogenic substances: a species comparison.	2000 Nov 15	11162928
Synergy between ethanol and grape polyphenols, quercetin, and resveratrol, in the inhibition of the inducible nitric oxide synthase pathway.	2000 Nov 15	11020457
Induced cytoskeletal changes in bovine pulmonary artery endothelial cells by resveratrol and the accompanying modified responses to arterial shear stress.	2001	11178103
Measurement of copper-binding sites on low density lipoprotein.	2001 Apr	11304478
Structure-activity study on the quinone/quinone methide chemistry of flavonoids.	2001 Apr	11304128
Natural therapies for ocular disorders, part two: cataracts and glaucoma.	2001 Apr	11302779
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
Activity of plant flavonoids against antibiotic-resistant bacteria.	2001 Feb	11180521
Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: glutathione oxidation and conjugation.	2001 Feb 15	11182292
Reduction of dehydroascorbic acid by homocysteine.	2001 Feb 16	11342267
Separation of kaempferols in Impatients balsamina flowers by capillary electrophoresis with electrochemical detection.	2001 Feb 16	11269529
Antibacterial action of tryptanthrin and kaempferol, isolated from the indigo plant (Polygonum tinctorium Lour.), against Helicobacter pylori-infected Mongolian gerbils.	2001 Jan	11211212
Phenolic constituents of Phenax angustifolius.	2001 Jan	11170671
Neuroprotective constituents from Hedyotis diffusa.	2001 Jan	11170670
Synthesis, characterization, antioxidative and antitumor activities of solid quercetin rare earth(III) complexes.	2001 Jan 1	11192698
Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis.	2001 Jan 22	11165029
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.	2001 Jan 22	11165023
Mut-Test to detect substances suppressing spontaneous mutation due to oxidative damage.	2001 Jan 25	11152968
Serum-dependent perinuclear accumulation of Cdc42 in mammalian cells.	2001 Jan-Feb	11115572
Noni plant may help TB.	2001 Mar	11332409
Presence of aldose reductase inhibitors in tea leaves.	2001 Mar	11325026
Enhanced antioxidant activity after chlorination of quercetin by hypochlorous acid.	2001 Mar	11290856
Flavonoids and phenylpropanoid derivatives from Campanula barbata.	2001 Mar	11281141
Treatment of interstitial cystitis with a quercetin supplement.	2001 Mar	11272677
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.	2001 Mar	11258977
Relationship between effects of phenolic compounds on the generation of free radicals from lactoperoxidase-catalyzed oxidation of NAD(P)H or GSH and their DPPH scavenging ability.	2001 Mar	11253920
Simultaneous determination of quercetin, kaempferol and (E)-cinnamic acid in vegetative organs of Schisandra chinensis Baill. by HPLC.	2001 Mar	11248500
Biochemical characterization of galloyl pedunculagin (ellagitannin) as a selective inhibitor of the beta-regulatory subunit of A-kinase in vitro.	2001 Mar	11226880
Protective effect of various antioxidants on the toxicity of sulphur mustard administered to mice by inhalation or percutaneous routes.	2001 Mar 14	11248218
Detection of drug-induced, superoxide-mediated cell damage and its prevention by antioxidants.	2001 Mar 15	11295363
Determination of phenolic acids and flavonoids of apple and pear by high-performance liquid chromatography.	2001 Mar 2	11261721
Induction of stress response proteins and experimental renal ischemia/reperfusion.	2001 May	11318950
Influence of prenylated and non-prenylated flavonoids on liver microsomal lipid peroxidation and oxidative injury in rat hepatocytes.	2001 May	11313109
Suppression of inducible cyclooxygenase and nitric oxide synthase through activation of peroxisome proliferator-activated receptor-gamma by flavonoids in mouse macrophages.	2001 May 4	11343698

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

QUERCETIN DIHYDRATE

Common Name

English

Quercetin dihydrate [WHO-DD]

Common Name

English

QUERCETIN DIHYDRATE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C306