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Identification
NameQuercetin
Accession NumberDB04216  (EXPT02732)
TypeSmall Molecule
GroupsExperimental
DescriptionA flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin. [PubChem]
Structure
Thumb
Synonyms
3,5,7,3',4'-Pentahydroxyflavone
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII9IKM0I5T1E
CAS number117-39-5
WeightAverage: 302.2357
Monoisotopic: 302.042652674
Chemical FormulaC15H10O7
InChI KeyREFJWTPEDVJJIY-UHFFFAOYSA-N
InChI
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
IUPAC Name
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
SMILES
OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionQuercetin 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Tyrosine-protein kinase HCKProteinunknownNot AvailableHumanP08631 details
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoformProteinunknownNot AvailableHumanP48736 details
UDP-glucuronosyltransferase 3A1ProteinunknownNot AvailableHumanQ6NUS8 details
ATP synthase subunit alpha, mitochondrialProteinunknownNot AvailableHumanP25705 details
ATP synthase subunit beta, mitochondrialProteinunknownNot AvailableHumanP06576 details
ATP synthase subunit gamma, mitochondrialProteinunknownNot AvailableHumanP36542 details
Serine/threonine-protein kinase pim-1ProteinunknownNot AvailableHumanP11309 details
HTH-type transcriptional regulator TtgRProteinunknownNot AvailablePseudomonas putida (strain DOT-T1E)Q9AIU0 details
3-hydroxyisobutyryl-CoA hydrolase, mitochondrialProteinunknownNot AvailableHumanQ6NVY1 details
3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZProteinunknownNot AvailableHelicobacter pyloriQ5G940 details
Serine/threonine-protein kinase 17BProteinunknownNot AvailableHumanO94768 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Quercetin.Approved
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Quercetin.Approved
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Quercetin.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Quercetin.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Quercetin.Experimental
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Quercetin.Approved, Investigational
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Quercetin.Approved, Investigational
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Quercetin.Approved
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Quercetin.Approved
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Quercetin.Approved
Arsenic trioxideThe serum concentration of Arsenic trioxide can be increased when it is combined with Quercetin.Approved, Investigational
AtazanavirThe serum concentration of Atazanavir can be increased when it is combined with Quercetin.Approved, Investigational
AtenololThe serum concentration of Atenolol can be increased when it is combined with Quercetin.Approved
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Quercetin.Approved, Investigational
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Quercetin.Approved, Vet Approved
BoceprevirThe serum concentration of Boceprevir can be increased when it is combined with Quercetin.Approved
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Quercetin.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Quercetin.Approved
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Quercetin.Approved, Investigational
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Quercetin.Approved
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Quercetin.Approved
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Quercetin.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Quercetin.Approved
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Quercetin.Approved, Investigational
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Quercetin.Approved
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Quercetin.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Quercetin.Withdrawn
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Quercetin.Approved, Vet Approved
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Quercetin.Approved
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Quercetin.Approved, Investigational
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Quercetin.Approved
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Quercetin.Approved
ClarithromycinThe serum concentration of Clarithromycin can be increased when it is combined with Quercetin.Approved
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Quercetin.Approved, Illicit
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Quercetin.Approved, Investigational
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Quercetin.Approved
ClopidogrelThe serum concentration of Clopidogrel can be increased when it is combined with Quercetin.Approved, Nutraceutical
ClozapineThe serum concentration of Clozapine can be increased when it is combined with Quercetin.Approved
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Quercetin.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Quercetin.Approved
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Quercetin.Approved
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Quercetin.Approved
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Quercetin.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Quercetin.Approved
DabrafenibThe serum concentration of Dabrafenib can be increased when it is combined with Quercetin.Approved
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Quercetin.Approved
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Quercetin.Approved
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Quercetin.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Quercetin.Approved
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Quercetin.Approved
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Quercetin.Approved, Investigational, Vet Approved
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Quercetin.Approved, Illicit, Vet Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Quercetin.Approved
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Quercetin.Approved
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Quercetin.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Quercetin.Illicit
DiltiazemThe serum concentration of Diltiazem can be increased when it is combined with Quercetin.Approved
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Quercetin.Approved
DocetaxelThe serum concentration of Docetaxel can be increased when it is combined with Quercetin.Approved, Investigational
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Quercetin.Approved, Investigational, Vet Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Quercetin.Approved, Investigational
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Quercetin.Approved
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Quercetin.Approved, Investigational
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Quercetin.Approved, Investigational
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Quercetin.Approved, Investigational
ErythromycinThe serum concentration of Erythromycin can be increased when it is combined with Quercetin.Approved, Vet Approved
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Quercetin.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Estriol can be increased when it is combined with Quercetin.Approved, Vet Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Quercetin.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Quercetin.Approved
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Quercetin.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Quercetin.Approved
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Quercetin.Approved
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Quercetin.Approved
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Quercetin.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Quercetin.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Quercetin.Approved
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Quercetin.Approved, Investigational
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Quercetin.Approved
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Quercetin.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Quercetin.Withdrawn
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Quercetin.Approved
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Quercetin.Approved, Vet Approved
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Quercetin.Approved
IdelalisibThe serum concentration of Idelalisib can be increased when it is combined with Quercetin.Approved
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Quercetin.Approved
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Quercetin.Approved
IndacaterolThe serum concentration of Indacaterol can be increased when it is combined with Quercetin.Approved
IndinavirThe serum concentration of Indinavir can be increased when it is combined with Quercetin.Approved
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Quercetin.Approved, Investigational
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Quercetin.Approved, Investigational
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Quercetin.Approved, Vet Approved
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Quercetin.Approved
KetoconazoleThe serum concentration of Ketoconazole can be increased when it is combined with Quercetin.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Quercetin.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Quercetin.Approved, Investigational
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Quercetin.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Quercetin.Approved
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Quercetin.Approved
LenvatinibThe serum concentration of Lenvatinib can be increased when it is combined with Quercetin.Approved
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Quercetin.Approved, Investigational
LevofloxacinThe serum concentration of Levofloxacin can be increased when it is combined with Quercetin.Approved, Investigational
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Quercetin.Approved
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Quercetin.Approved
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Quercetin.Approved
LosartanThe serum concentration of Losartan can be increased when it is combined with Quercetin.Approved
MannitolThe serum concentration of Mannitol can be increased when it is combined with Quercetin.Approved, Investigational
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Quercetin.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Quercetin.Approved, Vet Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Quercetin.Approved, Investigational
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Quercetin.Approved, Illicit
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Quercetin.Approved
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Quercetin.Approved, Investigational
MorphineThe serum concentration of Morphine can be increased when it is combined with Quercetin.Approved, Investigational
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Quercetin.Approved, Investigational
NadololThe serum concentration of Nadolol can be increased when it is combined with Quercetin.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Quercetin.Approved
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Quercetin.Approved, Vet Approved
NelfinavirThe serum concentration of Nelfinavir can be increased when it is combined with Quercetin.Approved
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Quercetin.Approved
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Quercetin.Approved
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Quercetin.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Quercetin.Approved
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Quercetin.Approved
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Quercetin.Approved, Investigational
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Quercetin.Approved
OsimertinibThe serum concentration of Osimertinib can be increased when it is combined with Quercetin.Approved
PaclitaxelThe serum concentration of Paclitaxel can be increased when it is combined with Quercetin.Approved, Vet Approved
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Quercetin.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Quercetin.Approved
PhenobarbitalThe serum concentration of Phenobarbital can be increased when it is combined with Quercetin.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Quercetin.Approved, Vet Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Quercetin.Approved
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Quercetin.Approved
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Quercetin.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Quercetin.Approved
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Quercetin.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Quercetin.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Quercetin.Approved, Vet Approved
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Quercetin.Approved, Vet Approved
PropranololThe serum concentration of Propranolol can be increased when it is combined with Quercetin.Approved, Investigational
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Quercetin.Approved
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Quercetin.Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Quercetin.Approved
QuinineThe serum concentration of Quinine can be increased when it is combined with Quercetin.Approved
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Quercetin.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Quercetin.Approved, Investigational
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Quercetin.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Quercetin.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Quercetin.Approved, Investigational
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Quercetin.Approved, Investigational
RitonavirThe serum concentration of Ritonavir can be increased when it is combined with Quercetin.Approved, Investigational
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Quercetin.Approved
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Quercetin.Approved, Investigational
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Quercetin.Approved, Vet Approved
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Quercetin.Approved, Investigational
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Quercetin.Approved
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Quercetin.Approved
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Quercetin.Approved
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Quercetin.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Quercetin.Approved
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Quercetin.Approved, Investigational
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Quercetin.Approved
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Quercetin.Experimental
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Quercetin.Approved, Investigational
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Quercetin.Approved
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Quercetin.Experimental
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Quercetin.Approved
TelaprevirThe serum concentration of Telaprevir can be increased when it is combined with Quercetin.Approved
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Quercetin.Approved
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Quercetin.Approved
TimololThe serum concentration of Timolol can be increased when it is combined with Quercetin.Approved
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Quercetin.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Quercetin.Approved, Investigational
ToremifeneThe serum concentration of Toremifene can be increased when it is combined with Quercetin.Approved, Investigational
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Quercetin.Approved
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Quercetin.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Quercetin.Approved
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Quercetin.Approved
VenetoclaxThe serum concentration of Venetoclax can be increased when it is combined with Quercetin.Approved
VenlafaxineThe serum concentration of Venlafaxine can be increased when it is combined with Quercetin.Approved
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Quercetin.Approved
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Quercetin.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Quercetin.Approved, Investigational
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Quercetin.Approved
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Quercetin.Approved
Food InteractionsNot Available
References
Synthesis Reference

Miguel M. Taya, Dionisio M. Aedo, Rene Ricard, “Quercetin pentamethyl carbamate and a process for its preparation.” U.S. Patent US4202825, issued October, 1975.

US4202825
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.965
Blood Brain Barrier-0.5711
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.5629
P-glycoprotein inhibitor INon-inhibitor0.9297
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.931
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.653
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.5823
CYP450 2D6 inhibitorNon-inhibitor0.9287
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.6951
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5822
Ames testNon AMES toxic0.722
CarcinogenicityNon-carcinogens0.945
BiodegradationNot ready biodegradable0.8672
Rat acute toxicity3.0200 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9781
hERG inhibition (predictor II)Non-inhibitor0.8161
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
  • V Sab Medical Labs Inc.
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point316.5 °CPhysProp
water solubility60 mg/L (at 16 °C)SEIDELL,A (1941)
Predicted Properties
PropertyValueSource
Water Solubility0.261 mg/mLALOGPS
logP1.81ALOGPS
logP2.16ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.44ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.86 m3·mol-1ChemAxon
Polarizability28.54 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0bt9-2611390000-f8e98c928a7ed82acda4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0009000000-d4689b76f41c73487399View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0967000000-613e61ec0c69ed0ee630View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0uy0-5910000000-ee816015eec26c8621b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-0udi-0009000000-ec1cab852ed9f9f78fa4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-1907000000-6f36df2733dadae380c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0309000000-976a99c106ceca16d73bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0pi0-1900000000-b2e286366d41e47dd8fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0209000000-e891863ec110aeb660b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0940000000-aa52db00c1defe3ccf75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0219000000-5ef285c4b6bfd220b8b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0219000000-547c83bb70e7da007d6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-1907000000-a59602c09f66e9656068View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-0udi-0009000000-4416f39adf6c9b919bfaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0udi-0019000000-eb14ec62fc2fb2f1da88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0ufr-0910000000-0730bca525c17aac75c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavonols. These are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3-hydroxyflavone
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Resorcinol
  • 1,2-diphenol
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Receptor binding
Specific Function:
Non-receptor tyrosine-protein kinase found in hematopoietic cells that transmits signals from cell surface receptors and plays an important role in the regulation of innate immune responses, including neutrophil, monocyte, macrophage and mast cell functions, phagocytosis, cell survival and proliferation, cell adhesion and migration. Acts downstream of receptors that bind the Fc region of immuno...
Gene Name:
HCK
Uniprot ID:
P08631
Molecular Weight:
59599.355 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein serine/threonine kinase activity
Specific Function:
Phosphoinositide-3-kinase (PI3K) that phosphorylates PtdIns(4,5)P2 (Phosphatidylinositol 4,5-bisphosphate) to generate phosphatidylinositol 3,4,5-trisphosphate (PIP3). PIP3 plays a key role by recruiting PH domain-containing proteins to the membrane, including AKT1 and PDPK1, activating signaling cascades involved in cell growth, survival, proliferation, motility and morphology. Links G-protein...
Gene Name:
PIK3CG
Uniprot ID:
P48736
Molecular Weight:
126452.625 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Udp-glycosyltransferase activity
Specific Function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds (By similarity).
Gene Name:
UGT3A1
Uniprot ID:
Q6NUS8
Molecular Weight:
59150.34 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Transmembrane transporter activity
Specific Function:
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core, and F(0) - containing the membrane proton channel, linked toget...
Gene Name:
ATP5A1
Uniprot ID:
P25705
Molecular Weight:
59750.06 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Transporter activity
Specific Function:
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core, and F(0) - containing the membrane proton channel, linked toget...
Gene Name:
ATP5B
Uniprot ID:
P06576
Molecular Weight:
56559.42 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Transmembrane transporter activity
Specific Function:
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core, and F(0) - containing the membrane proton channel, linked toget...
Gene Name:
ATP5C1
Uniprot ID:
P36542
Molecular Weight:
32995.665 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Transcription factor binding
Specific Function:
Proto-oncogene with serine/threonine kinase activity involved in cell survival and cell proliferation and thus providing a selective advantage in tumorigenesis. Exerts its oncogenic activity through: the regulation of MYC transcriptional activity, the regulation of cell cycle progression and by phosphorylation and inhibition of proapoptotic proteins (BAD, MAP3K5, FOXO3). Phosphorylation of MYC ...
Gene Name:
PIM1
Uniprot ID:
P11309
Molecular Weight:
45411.905 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Pseudomonas putida (strain DOT-T1E)
Pharmacological action
unknown
General Function:
Dna binding
Specific Function:
Represses expression from the ttgABC operon promoter and its own expression. Binds to a promoter region between the divergently transcribed ttgR and ttgABC genes/operons; in the presence of chloramphenicol or tetracycline this binding no longer occurs and ttgR and ttgABC are derepressed. This suggests that TtgR binds these antibiotics.
Gene Name:
ttgR
Uniprot ID:
Q9AIU0
Molecular Weight:
23854.075 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Hydro-lyase activity
Specific Function:
Hydrolyzes 3-hydroxyisobutyryl-CoA (HIBYL-CoA), a saline catabolite. Has high activity toward isobutyryl-CoA. Could be an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Also hydrolyzes 3-hydroxypropanoyl-CoA.
Gene Name:
HIBCH
Uniprot ID:
Q6NVY1
Molecular Weight:
43481.935 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Helicobacter pylori
Pharmacological action
unknown
General Function:
3-hydroxyoctanoyl-[acyl-carrier-protein] dehydratase activity
Specific Function:
Involved in unsaturated fatty acids biosynthesis. Catalyzes the dehydration of short chain beta-hydroxyacyl-ACPs and long chain saturated and unsaturated beta-hydroxyacyl-ACPs.Involved in unsaturated fatty acids biosynthesis. Catalyzes the dehydration of short chain beta-hydroxyacyl-ACPs and long chain saturated and unsaturated beta-hydroxyacyl-ACPs (By similarity).
Gene Name:
fabZ
Uniprot ID:
Q5G940
Molecular Weight:
18184.08 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein serine/threonine kinase activity
Specific Function:
Phosphorylates myosin light chains (By similarity). Acts as a positive regulator of apoptosis.
Gene Name:
STK17B
Uniprot ID:
O94768
Molecular Weight:
42343.595 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitorinducer
General Function:
Transporter activity
Specific Function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency.
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular Weight:
171589.5 Da
References
  1. Kauffmann HM, Pfannschmidt S, Zoller H, Benz A, Vorderstemann B, Webster JI, Schrenk D: Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression. Toxicology. 2002 Feb 28;171(2-3):137-46. [PubMed:11836020 ]
  2. Leslie EM, Mao Q, Oleschuk CJ, Deeley RG, Cole SP: Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids. Mol Pharmacol. 2001 May;59(5):1171-80. [PubMed:11306701 ]
  3. Nguyen H, Zhang S, Morris ME: Effect of flavonoids on MRP1-mediated transport in Panc-1 cells. J Pharm Sci. 2003 Feb;92(2):250-7. [PubMed:12532374 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Organic anion transmembrane transporter activity
Specific Function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular Weight:
174205.64 Da
References
  1. Bock KW, Eckle T, Ouzzine M, Fournel-Gigleux S: Coordinate induction by antioxidants of UDP-glucuronosyltransferase UGT1A6 and the apical conjugate export pump MRP2 (multidrug resistance protein 2) in Caco-2 cells. Biochem Pharmacol. 2000 Mar 1;59(5):467-70. [PubMed:10660112 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. Functions as high-affinity pyruvate transporter.
Gene Name:
SLC16A7
Uniprot ID:
O60669
Molecular Weight:
52199.745 Da
References
  1. Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. [PubMed:10417314 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name:
SLCO2B1
Uniprot ID:
O94956
Molecular Weight:
76709.98 Da
References
  1. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. [PubMed:15640378 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Shapiro AB, Ling V: Effect of quercetin on Hoechst 33342 transport by purified and reconstituted P-glycoprotein. Biochem Pharmacol. 1997 Feb 21;53(4):587-96. [PubMed:9105411 ]
  2. Eagling VA, Profit L, Back DJ: Inhibition of the CYP3A4-mediated metabolism and P-glycoprotein-mediated transport of the HIV-1 protease inhibitor saquinavir by grapefruit juice components. Br J Clin Pharmacol. 1999 Oct;48(4):543-52. [PubMed:10583025 ]
  3. Choi CH, Kim JH, Kim SH: Reversal of P-glycoprotein-mediated MDR by 5,7,3',4',5'-pentamethoxyflavone and SAR. Biochem Biophys Res Commun. 2004 Jul 30;320(3):672-9. [PubMed:15240100 ]
  4. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
  5. Youdim KA, Qaiser MZ, Begley DJ, Rice-Evans CA, Abbott NJ: Flavonoid permeability across an in situ model of the blood-brain barrier. Free Radic Biol Med. 2004 Mar 1;36(5):592-604. [PubMed:14980703 ]
  6. Borska S, Sopel M, Chmielewska M, Zabel M, Dziegiel P: Quercetin as a potential modulator of P-glycoprotein expression and function in cells of human pancreatic carcinoma line resistant to daunorubicin. Molecules. 2010 Feb 9;15(2):857-70. doi: 10.3390/molecules15020857. [PubMed:20335952 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. Depending on the tissue and on cicumstances, mediates the import or export of lactic acid and ketone bod...
Gene Name:
SLC16A1
Uniprot ID:
P53985
Molecular Weight:
53943.685 Da
References
  1. Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. [PubMed:10417314 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular Weight:
72313.47 Da
References
  1. Zhang S, Yang X, Morris ME: Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport. Mol Pharmacol. 2004 May;65(5):1208-16. [PubMed:15102949 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:24